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The compounds, 3-amino-9H-pyrido left bracket 3,4-b right bracket indole and 3-amino-1-methyl-9H-pyrido left bracket 3,4-b right bracket indole, which are effectors in induction of sister chromatid exchangers in human cells, were isolated from pyrolysis products of L-tryptophan and characterized by HPLC and UV techniques.
- Tada,Saeki,Oikawa
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- N2,N9-Bis(Substituted benzyl)-β-Carbolineum Bromides as Potential Anticancer Therapeutics: Design, Synthesis, Cytotoxicity, Drug-DNA Intercalation and In-Silico Binding Properties
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The present study reports a series of novel N2,N9-bis(substituted benzyl)-β-carbolineum bromides (4a-f) synthesized from L-tryptophan in three steps with excellent yields (>80%). The structures of synthesized compounds 4a-f were confirmed by 1H- and 13C-NMR, FT-IR, LC-MS (ESI-MS) spectrum and elemental analysis. Meanwhile, the crystal structure for compound 4f was determined by X-ray single-crystal diffraction. The crystal belongs in monoclinic space group in P121/c1 space group with a = 13.253(6) ?, b = 20.809(10) ?, c = 9.116(6) ?, β = 107.215(13)°, V = 2401.4(19) ?3 and Z = 4, F(000) = 1048, Dc = 1.403 Mg/m3 and μ = 1.743 mm?1. Compounds 4a-f were evaluated for their in-vitro anticancer activity against selected human cancer cell lines, such as HT-29 (colorectal adenocarcinoma), HeLa (cervical carcinoma), HepG2 (hepatocellular carcinoma) and K562 (chronic myelogenous leukaemia, CML). Results showed that compounds 4a-f exerted excellent cytotoxicity effect with IC50 values ranging from 0.36-1.08 μM against K562 human CML cell line. It was found that synthesized β-carbolines are much less toxic towards non-cancer cell lines BALB/c3T3 and Hs-27, in comparison to cisplatin and doxorubicin, which were employed as positive controls. To investigate the binding mode of these compounds against DNA, spectroscopic studies were conducted. Subsequent UV-Visible and in-silico (molecular docking) studies revealed that compound 4f interacts with DNA through intercalation. Based on the present findings, it was suggested that compound 4f has a great potential to be developed as a novel anticancer agent.
- Hamali, Muhamad Azwan,Kamaruzaman, Nur Azzalia,Mansor, Sharif Mahsufi,Mohideen, Mazlin,Mordi, Mohd Nizam,Rahman, A. F. M. Motiur
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- Naturally-occurring tetrahydro-β-carboline alkaloids derived from tryptophan are oxidized to bioactive β-carboline alkaloids by heme peroxidases
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β-Carbolines are indole alkaloids that occur in plants, foods, and endogenously in mammals and humans, and which exhibit potent biological, psychopharmacological and toxicological activities. They form from naturally-occurring tetrahydro-β-carboline alkaloids arising from tryptophan by still unknown way and mechanism. Results in this research show that heme peroxidases catalyzed the oxidation of tetrahydro-β-carbolines (i.e. 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid) into aromatic β-carbolines (i.e. norharman and harman, respectively). This oxidation followed a typical catalytic cycle of peroxidases through redox intermediates I, II, and ferric enzyme. Both, plant peroxidases (horseradish peroxidase, HRP) and mammalian peroxidases (myeloperoxidase, MPO and lactoperoxidase, LPO) catalyzed the oxidation in an efficient manner as determined by kinetic parameters (VMAX and KM). Oxidation of tetrahydro-β-carbolines was inhibited by peroxidase inhibitors such as sodium azide, ascorbic acid, hydroxylamine and excess of H2O 2. The formation of aromatic β-carbolines by heme peroxidases can help to explain the presence and activity of these compounds in biological systems.
- Herraiz, Tomás,Galisteo, Juan
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- Preparation and a novel rearrangement reaction of 1,2,3,4-tetrahydro-9- hydroxy-β-carboline, and their applications for the total synthesis of (±)- coerulescine
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Novel 9-hydroxy-β-carboline derivatives were produced for the first time. A novel rearrangement reaction of 1,2,3,4-tetrahydro-9-hydroxy-β- carbolines was discovered to give 3,3-disubstituted oxindoles, which was successfully applied to the total synthesis of (±)-coerulescine.
- Somei,Noguchi,Yamagami,Kawada,Yamada,Yamada
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- Effect of the position of nitrogen in pyridoindole on photophysical properties and device performances of α-, β-, γ-carboline based high triplet energy host materials for deep blue devices
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Three carboline derivatives with nitrogen at different positions of the pyridoindole unit were synthesized and the effect of the position of nitrogen on the photophysical properties and device performances was investigated. β-Carboline was effective in obtaining high triplet energy and stabilizing energy levels, while α-carboline was better than other carbolines in terms of quantum efficiency. However, γ-carboline could not stabilize the LUMO level and low quantum efficiency was obtained.
- Im, Yirang,Lee, Jun Yeob
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- Synthesis method of 9H-pyrido [3, 4-b] indole
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The invention discloses a synthesis method of 9H-pyrido [3, 4-b] indole. The method comprises the following steps: taking tryptophan and chloroform as basic reaction raw materials, taking ferric salt as a catalyst, then adding alkali, carrying out cyclization aromatization reaction through free radical series connection, and finally carrying out post-treatment to obtain the 9H-pyrido [3, 4-b] indole product. According to the method, only commercially available tryptophan is used as a substrate, chloroform is used as a C1 source, a reaction precursor does not need to be prepared in advance, [5 + 1] cyclization aromatization is realized in a free radical series connection mode; and after C-C bond and C-N bond construction as well as decarboxylic acid and dehydrogenation aromatization process, without prior modification, addition of oxidizer, pre-preparation and separation of tetrahydrocarboline compounds, direct construction of pyridine heterocyclic slices can be realized througha one-pot method.
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Paragraph 0027-0050
(2021/11/03)
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- A convenient synthesis of β-carbolines by iron-catalyzed aerobic decarboxylative/dehydrogenative aromatization of tetrahydro-β-carbolines under air
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A convenient synthesis for the conversion of various substituted tetrahydro-β-carbolines has been developed by iron-catalyzed decarboxylative/dehydrogenative aromatization to construct aromatic β-carbolines under air atmosphere. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce corresponding β-carbolines in good yields in the absence of any additive. Additionally, the utility of the method was highlighted in the gram-scale synthesis of important natural β-carboline synthons norharmane (2a) and harmane (2b), which the latter provide practical access towards eudistomin N and nostocarboline.
- Mohamad Arshad, Ahmad Saifuddin,Meesala, Ramu,Hanapi, Nur Aziah,Mordi, Mohd Nizam
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- Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles
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Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.
- Abinaya, R.,Balasubramaniam, K. K.,Baskar, B.,Divya, P.,Mani Rahulan, K.,Rahman, Abdul,Sridhar, R.,Srinath, S.
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p. 5990 - 6007
(2021/08/24)
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- Reusable, homogeneous water soluble photoredox catalyzed oxidative dehydrogenation of N-heterocycles in a biphasic system: Application to the synthesis of biologically active natural products
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Herein, a simple and efficient method for the oxidative dehydrogenation (ODH) of tetrahydro-β-carbolines, indolines and tetrahydro-(iso)quinolines is described using a reusable, homogeneous cobalt-phthalocyanine photoredox catalyst in a biphasic medium. A biphasic system offers an advantage of easy separation of the product and an efficient reusability of the homogeneous photoredox catalyst. Also, the current system significantly helps to overcome the solubility issue of the substrate and catalyst at room temperature. Its potential applications to organic transformations are demonstrated by the synthesis of various biologically active N-heterocycles such as indoles, (iso)quinolines and β-carbolines and natural products such as eudistomin U, norharmane, and harmane and precursors to perlolyrine and flazin. Without isolation and purification, the catalyst solution can be reused up to 5 times with almost comparable reactivity. Furthermore, the efficiency of the reaction was demonstrated on a gram scale. To the best of our knowledge, this is the first report on ODH reactions using a non noble, reusable and homogeneous cobalt photoredox catalyst under environmentally friendly conditions.
- Abinaya, R.,Baskar, B.,Mariappan, M.,Prasanth, Arun,Sridhar, R.,Srinath, S.
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p. 2575 - 2587
(2020/05/13)
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- Method for synthesizing heterocyclic amine risk substance norharman and analogues thereof in food
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The invention provides a method for synthesizing a heterocyclic amine risky substance, namely norharman and analogues thereof in food. The synthesis method comprises the following steps: (1) with a compound (II) as a raw material, adding alkali under magnetic stirring, then adding a solvent under a nitrogen atmosphere, carrying out heating to 100-200 DEG C under a closed condition, and performingreacting for 1-24 hours; and (2) after the reacting is completed, cooling a reaction system to room temperature, conducting diluting with water, performing extracting three times, combining organic phases, carrying out drying with anhydrous sodium sulfate, performing filtering, carrying out spin-drying, and conducting separating with a chromatographic column to obtain a crystalline solid, namely the heterocyclic amine risky substance norharman. The synthesis method provided by the invention has the advantages that a C-N bond is simply and efficiently synthesized, heavy metals are not introduced in the reaction, operation is simple, the yield of the obtained heterocyclic amine is 60% or above, and the production requirements of scientific research work on heterocyclic amine compounds can bewell met. The structural formula of the heterocyclic amine risky substance norharman is as shown in a formula (I) which is described in the specification, and the structural formula (II) of the compound (II) is as defined in the specification.
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Paragraph 0027-0034
(2020/12/14)
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- Simultaneous generation of acrylamide, β-carboline heterocyclic amines and advanced glycation ends products in an aqueous Maillard reaction model system
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The simultaneous formation of acrylamide; β-carboline heterocyclic amines (HAs): harmane and norharmane; and advanced glycation end products (AGEs) (Nε-(carboxymethyl)lysine (CML) and Nε-(carboxyethyl)lysine (CEL)) was analyzed based on an aqueous model system. The model systems included lysine–glucose (Lys/Glu), asparagine–glucose (Asn/Glu), tryptophan–glucose (Trp/Glu), and a mixture of these amino acids (Mix/Glu). Only AGEs were generated when heated at 100 °C, Asn and Trp competed with Lys for glucose and methylglyoxal (MGO), and glyoxal (GO) decreased AGE content. The k value of CML, CEL, and acrylamide decreased when heated at 130 °C, whereas that of harmane increased in the Mix/Glu, owing to the competition between Lys and Asn for glucose, GO, and MGO. Harmane preferably formed via the Pictet–Spengler condensation between Trp and acetaldehyde, which further reduced acrylamide formation via the acrolein pathway.
- Chen, Jie,He, Zhiyong,Jiao, Ye,Li, Yong,Liu, Guoping,Qin, Fang,Quan, Wei,Wang, Zhaojun,Xue, Chaoyi,Zeng, Maomao
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- TRICYCLIC CRBN LIGANDS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.
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- Synthesis and biological evaluation of novel N9-heterobivalent β-carbolines as angiogenesis inhibitors
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A series of novel N9-heterobivalent β-carbolines has been synthesized. All the novel compounds were tested for their anticancer activity against six tumour cell lines in vitro. Among these molecules, compounds 5b, and 5w exhibited strong cytotoxic activities with IC50 value of lower than 20 μM. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, compounds 5b and 5w exhibited that tumour inhibition rate of over 40% in the Sarcoma 180 and Lewis lung cancer animal models. Preliminary structure–activity relationships (SARs) analysis indicated that: (1) C1-methylation and C7-methoxylation were favorable for increased activities; (2) 3-Pyridyl or 2-thienyl group substituent into position-1 of the β-carboline core, and the aryl substituent into another β-carboline ring might be detrimental to cytotoxic effects of this class compounds. Investigation of the preliminary mechanism of action demonstrated that compound 5b had obvious angiogenesis inhibitory effects in the chicken chorioallantoic membrane (CAM) assay.
- Guo, Liang,Ma, Qin,Chen, Wei,Fan, Wenxi,Zhang, Jie,Dai, Bin
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p. 375 - 387
(2019/01/10)
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- Iodine-catalyzed chemoselective dehydrogenation and aromatization of tetrahydro-β-carbolines: A short synthesis of Kumujian-C, Eudistomin-U, Norharmane, Harmane Harmalan and Isoeudistomine-M
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Temperature controlled chemoselective dehydrogenation and aromatization of tetrahydro-β-carbolines, using molecular I2 and H2O2, in DMSO solvent affords a practical access to a series of corresponding 3,4-dihydro-β-carbolines and β-carbolines respectively. This method has been successfully employed in the short synthesis of Kumujian-C, Eudistomin-U, Norharmane Harmane Harmalan and Isoeudistomin-M.
- Gaikwad, Sunil,Kamble, Dayanand,Lokhande, Pradeep
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supporting information
p. 2387 - 2392
(2018/05/24)
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- Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer
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Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.
- Huang, Yuan-Qiong,Song, Hong-Jian,Liu, Yu-Xiu,Wang, Qing-Min
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supporting information
p. 2065 - 2069
(2018/01/27)
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- CO2-Catalyzed Efficient Dehydrogenation of Amines with Detailed Mechanistic and Kinetic Studies
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CO2-catalyzed dehydrogenation of amines has been achieved under photocatalytic conditions. With this concept, various amines have been selectively dehydrogenated to the corresponding imines in the presence of different functional groups such as nitrile, nitro, ester, halogen, ether, thioether, and carbonyl or carboxylic acid moieties. At the end, the CO2-catalyzed synthesis of pharmaceutical drugs has been achieved. The CO2 radical has been detected by EPR spectroscopy using DMPO, and the mechanism of this reaction is proposed on the basis of DFT calculations and experimental evidence.
- Riemer, Daniel,Schilling, Waldemar,Goetz, Anne,Zhang, Yu,Gehrke, Sascha,Tkach, Igor,Hollóczki, Oldamur,Das, Shoubhik
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p. 11679 - 11687
(2018/11/23)
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- ORGANIC ELECTROLUMINESCENT MATERIALS CONTAINING CARBOLINE GROUP AND ORGANIC ELECTROLUMINESCENT DEVICE BY USING THE SAME
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An organic electroluminescent material is shown in General Formula (1), wherein R3 is a carboline group, R13 is a carbazole group or a carboline group, R1 to R2, R4 to R12 and R14 to R20 are each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group and an alkenyl group.
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Paragraph 0076
(2018/04/17)
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- A pure red luminescent β-carboline-substituted biphenylmethyl radical: Photophysics, stability and OLEDs
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Luminescent radicals, whose emission comes from the doublet exited state, have potential application in the field of organic optoelectronics. However, few radicals show luminescence at room temperature. Herein, a new pure red-emissive biphenyl-type (N-pyrido[3,4-b]indolyl)bis(2,4,6-trichlorophenyl)methyl radical (PyID-BTM) is designed and synthesized, in which the carbazole moiety of CzBTM (a previously reported biphenylmethyl radical by our group) is successfully replaced by β-carboline. Its photophysical properties, including the ground and excited states, and the radiative and non-radiative processes are systematically investigated. The photoluminescence quantum efficiency ( = 19.5%) of PyID-BTM is ten times higher than that of CzBTM ( = 2.0%) in cyclohexane. The crystal structure, magnetic properties, photostability and electroluminescence performance of PyID-BTM are studied. An optimized OLED device using PyID-BTM as an emissive dopant showed pure red emission with CIE coordinates of (0.649,0.317) and a maximum EQE of 2.8%, and the formation ratio of doublet excitons was up to 70%. This study provides a new approach for designing high-performance luminescence biphenylmethyl radicals for applications in organic electroluminescence.
- Abdurahman, Alim,Chen, Yingxin,Ai, Xin,Ablikim, Obolda,Gao, Yu,Dong, Shengzhi,Li, Bao,Yang, Bing,Zhang, Ming,Li, Feng
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p. 11248 - 11254
(2018/11/20)
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- Synthesis and structure-activity relationships of asymmetric dimeric β-carboline derivatives as potential antitumor agents
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A series of newly asymmetric dimeric β-carbolines with a spacer of 4–6 methylene units between the indole nitrogen and the harmine oxygen were synthesized. Structures of all the novel synthesized compounds were confirmed by their spectral and analytical studies. All of the synthesized compounds were screened for their in vitro cytotoxic activity against nine cancer cell lines. The results revealed that compounds 7c, 7o and 7s exhibited the highest cytotoxic activities with IC50 values of less than 20 μM against the tumor cell lines tested. Acute toxicities and antitumor efficacies of the selected compounds in mice were also evaluated, and compound 7o exhibited potent antitumor activities with the tumor inhibition rate of over 40%. The wound healing assay displayed a specific impairment in the motility of the HT-29 cells, which suggested the anti-metastatic potential of compound 7o. Moreover, compound 7o had obvious angiogenesis inhibitory effects in the chicken chorioallantoic membrane (CAM) assay. Preliminary structure-activity relationship (SAR) analysis indicated that: (1) 3-phenylpropyl substituent at the N9-position of the indole ring was the most suitable group giving rise to potent cytotoxic agents; (2) the spacer length affected the antitumor potencies, and four methylene units were more favorable.
- Guo, Liang,Chen, Wei,Cao, Rihui,Fan, Wenxi,Ma, Qin,Zhang, Jie,Dai, Bin
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p. 253 - 265
(2018/02/15)
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- Direct Biomimetic Synthesis of β-Carboline Alkaloids from Two Amino Acids
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The increasing importance of enzyme mimics in organic synthesis inspired us to design a novel biomimetic synthesis of β-carboline alkaloids directly from tryptophan and a second amino acid. This novel one-pot protocol utilizes abundant and readily available starting materials and thus presents a green and user-friendly alternative to conventional methods that rely on stepwise synthesis. Driven by molecular iodine and TFA, decarboxylation, deamination, Pictet-Spengler reaction, and oxidation reactions proceeded sequentially, transforming biomass amino acids into value-added alkaloid motifs.
- Wang, Zi-Xuan,Xiang, Jia-Chen,Cheng, Yan,Ma, Jin-Tian,Wu, Yan-Dong,Wu, An-Xin
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p. 12247 - 12254
(2018/09/21)
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- ORGANIC ELECTROLUMINESCENT MATERIALS CONTAINING N-PHENYLCARBOLINE AND ORGANIC ELECTROLUMINESCENT DEVICE BY USING THE SAME
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An organic electroluminescent material is shown in General Formula (1), wherein one of X1, X2, and X3 is an independent nitrogen atom, and R1 to R14 are each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a thioalkyl group, a silyl group, and an alkenyl group.
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Paragraph 0067
(2017/08/24)
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- 2 - substituted β - carbolines compound and its used for preparation for preventing or treating tumor drug application
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The invention provides 2-substituted-beta-carboline compounds and application thereof in preparing drugs for preventing or treating tumors. The structural general formula of the compounds is disclosed as Formula I. The compounds have high inhibiting actions on growth of tumor cells, and have approximate activity to the positive control paclitaxel. Part of the compounds have obviously better antitumor activity than the paclitaxel; the IC50 value is less than 1 mu M; and thus, the compounds can become efficient drugs for treating tumors.
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Paragraph 0031-0033
(2017/04/29)
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- COMPOUNDS FOR ORGANIC LIGHT EMITTING DIODE MATERIALS
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Described herein are molecules for use in organic light emitting diodes comprising at least one moiety A, at least one moiety D, and at least one moiety B.
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Paragraph 00129
(2017/12/29)
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- A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts
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A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-α-carboline that is itself readily aromatized to give α-carboline (1).
- Yan, Qiao,Gin, Emma,Banwell, Martin G.,Willis, Anthony C.,Carr, Paul D.
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p. 4328 - 4335
(2017/04/28)
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- Design, synthesis and in vitro cytotoxicity studies of novel β-carbolinium bromides
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A series of novel β-carbolinium bromides has been synthesized from easily accessible β-carbolines and 1-aryl-2-bromoethanones. The newly synthesized compounds were evaluated for their in vitro anticancer activity. Among the synthesized derivatives, compounds 16l, 16o and 16s exhibited potent anticancer activity with IC50values of 50= 3.16–7.93 μM). In order to test the mechanism of cell death, we exposed castration resistant prostate cancer cell line (C4-2) to compounds 16l and 16s, which resulted in increased levels of cleaved PARP1 and AO/EB staining, indicating that β-carbolinium salts induce apoptosis in these cells. Additionally, the most potent β-carbolines 16l and 16s were found to inhibit tubulin polymerization.
- Venkataramana Reddy,Mishra, Shriprada,Tantak, Mukund P.,Nikhil, Kumar,Sadana, Rachna,Shah, Kavita,Kumar, Dalip
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p. 1379 - 1384
(2017/03/08)
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- Synthesis of β-carbolines via a silver-mediated oxidation of tetrahydro-β-carbolines
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The oxidation of tetrahydro-β-carbolines to β-carbolines using silver carbonate was developed as an alternative to current methods. The oxidation is extremely mild and provides the products in modest to good yields after purification. A number of functional groups are tolerated by this methodology, including reduction-sensitive groups which are often cleaved with other methods. Though the mechanism is not fully understood, the reaction proceeds in an open flask, is not sensitive to light or moisture, and provides a viable synthetic route to compounds that are not easily prepared via other methodologies.
- Durham, Sierra D.,Sierra, Brianna,Gomez, Maximillian J.,Tran, Jennifer K.,Anderson, Marc O.,Whittington-Davis, Nick A.,Eagon, Scott
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supporting information
p. 2747 - 2750
(2017/06/23)
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- Iodine-catalyzed one-pot decarboxylative aromatization of tetrahydro-β-carbolines
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A synthetic strategy was developed for the preparation of β-carbolines by one-pot decarboxylation and aromatization of tetrahydro-β-carboline-3-carboxylic acids by employing 10?mol% of iodine in presence of oxidant aqueous H2O2. The method was also successfully extended for the aromatization of tetrahydro-β-carboline-3-methyl esters. The utility of the method was demonstrated in the synthesis of β-carboline alkaloids norharmane, harmane and eudistomin N.
- Meesala, Ramu,Arshad, Ahmad Saifuddin Mohamad,Mordi, Mohd Nizam,Mansor, Sharif Mahsufi
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p. 8537 - 8541
(2016/12/09)
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- An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins
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A facile method for the synthesis of a variety of β-carbolines and their natural products such as norharmane (2a), harmane (2b), eudistomins I, N, T, and U (6, 7, 9 and 10, respectively) has been successfully developed via a decorboxylative aromatization tool by employing N-chlorosuccinimide (NCS) as a mild and efficient reagent. Gratifyingly, this reagent system proceeds in a one-pot manner and converted all the tetrahydro-β-carboline acids into their corresponding decorboxylative aromatic products with good to excellent yields. Additionally, this system works well in the case of tetrahydro-β-carboline esters to produce their aromatic partners in high yields.
- Kamal, Ahmed,Sathish, Manda,Prasanthi,Chetna, Jadala,Tangella, Yellaiah,Srinivasulu, Vunnam,Shankaraiah, Nagula,Alarifi, Abdullah
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p. 90121 - 90126
(2015/11/10)
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- β-Carboline-functionalized dithioacetal as Hg2+-selective fluorescence probe in water
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A novel sensing system based on the β-carboline core has been designed and synthesized for Hg2+ detection in water. We have demonstrated that a straight forward methodology can provide rapid, sensitive and selective recognition (cross-contamination experiments) for Hg2+ over a wide pH range. The vivid fluorescence change from blue to colorless can be clearly discriminated by the naked eye. Furthermore, there is a good negative correlation between the fluorescent intensity and the concentration of Hg2+ in the range 1.0 × 10-6 M-7.0 × 10-6 M. β-Carboline as a fluorophore synthesized via this route also provides a new strategy for the design of novel fluorescence probes and fluorochromes.
- Li, Na,Dai, Jiang-Kun,Du, Hong-Tao,Yuan, Mao-Sen,Zhang, Ji-Wen,Wang, Jun-Ru
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p. 900 - 905
(2015/02/19)
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- PhI(OAc)2-mediated one-pot oxidative decarboxylation and aromatization of tetrahydro-β-carbolines: Synthesis of norharmane, harmane, eudistomin U and eudistomin i
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Iodobenzene diacetate was employed as a mild and efficient reagent for one-pot oxidative decarboxylation of tetrahydro-β-carboline acids and dehydrogenation of tetrahydro-β-carbolines to access the corresponding aromatic β-carbolines. To the best of our knowledge this is the first synthesis of β-carbolines via a one-pot oxidative decarboxylation at ambient temperature. The utility of this protocol has been demonstrated in the synthesis of β-carboline alkaloids norharmane (2o), harmane (2p), eudistomin U (9) and eudistomin I (12).
- Kamal, Ahmed,Tangella, Yellaiah,Manasa, Kesari Lakshmi,Sathish, Manda,Srinivasulu, Vunnam,Chetna, Jadala,Alarifi, Abdullah
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p. 8652 - 8662
(2015/08/24)
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- Beta and gamma carboline derivatives as potential anti-Alzheimer agents: A comparison
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Nine novel β2- and 3-carboline derivatives bearing either methyl-, propargyl- or phenethyl-residues at the indole nitrogen were synthesized and tested as potential anti-Alzheimer drugs. Antagonism of recombinantly expressed NMDA receptors, inhibition of cholinesterases, and radical scavenging properties were determined for all compounds. Some were additionally tested in vivo for their ability to reverse scopolamine-induced cognitive impairment in an 8-arm radial maze experiment with rats. For the most promising candidates, the interaction with muscarinic M1receptors was also investigated. With this set of compounds assays the influence of the scaffold itself and the substituents can be investigated separately. 5-Methyl-β3-carboline (6) was the most potent (0.25 1/4mol/100 g b.w.) compound in the in vivo test and might be a good starting point for the development of novel anti-Alzheimer drugs.
- Otto, Robert,Penzis, Robert,Gaube, Friedemann,Winckler, Thomas,Appenroth, Dorothea,Fleck, Christian,Tr?nkle, Christian,Lehmann, Jochen,Enzensperger, Christoph
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- Microwave-Assisted Synthesis of Tetrahydro-β-carbolines and β-Carbolines
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A microwave-mediated Pictet-Spengler procedure utilizing 1,2-dichloroethane (DCE) and trifluoroacetic acid (TFA) was developed to provide tetrahydro-β-carboline salts in high yields. Reactions are complete in 20 minutes or less and the product precipitates from solution in high yields and purity, negating the need for liquid-liquid extraction or column chromatography. This method tolerates a wide range of functionality and can be performed on milligram to gram scales. A subsequent microwave-mediated aromatization of the synthesized tetrahydro-β-carbolines to β-carbolines was also developed utilizing catalytic Pd/C. The aromatization is complete in 60 min or less with most substrates requiring minimal purification. A microwave-assisted Pictet-Spengler procedure was developed to afford tetrahydro-β-carboline salts in high yields with no liquid-liquid extraction or chromatography required. A subsequent microwave-assisted aromatization procedure was also developed to provide β-carbolines in high yields requiring limited purification.
- Eagon, Scott,Anderson, Marc O.
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p. 1653 - 1665
(2015/10/05)
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- Copper-catalyzed protodecarboxylation and aromatization of tetrahydro-β-carboline-3-carboxylic acids
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An efficient synthetic methodology has been developed to construct aromatic β-carbolines from tetrahydro-β-carboline-3-carboxylic acids by copper-promoted sequential decarboxylation and oxidative aromatization. Georg Thieme Verlag Stuttgart · New York.
- Meesala, Ramu,Mordi, Mohd Nizam,Mansor, Sharif Mahsufi
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p. 120 - 122
(2014/01/06)
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- Direct vicinal disubstitution of diaryliodonium salts by pyridine N-oxides and N-amidates by a 1,3-radical rearrangement
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Paired off: The title reaction leads to a series of o-pyridinium phenols (1) and anilines (2). The experimental and computational studies indicate that the key step involves homolytic cleavage to give a radical pair, which undergoes solvent-cage recombination to give the product. Copyright
- Peng, Jing,Chen, Chao,Wang, Yong,Lou, Zhenbang,Li, Ming,Xi, Chanjuan,Chen, Hui
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supporting information
p. 7574 - 7578
(2013/07/26)
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- BETA-CARBOLINES FOR USE IN THE TREATMENT OF HEARING LOSS AND VERTIGO
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The present invention is directed at β-carbolines, preferred 9-alkyl-β-carbolines (9-alkyl-β-BC), their manufacture as well as their use in prophylaxis and treatment of hearing damages, tinnitus, acute acoustic trauma, vertigo and vestibular disorder as well as pharmaceutical compositions containing theses β-carbolines.
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Paragraph 0096; 0097; 0098
(2013/03/26)
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- Total syntheses of eudistomins Y1-Y7 by an efficient one-pot process of tandem benzylic oxidation and aromatization of 1-benzyl-3,4-dihydro-β-carbolines
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The first total synthesis of eudistomin Y7 (7) and total syntheses of eudistomins Y1-Y6 (1-6) are described. An efficient room-temperature conversion of 1-benzyl-3,4-dihydro-β-carbolines (11) into 1-benzoyl-β-carbolines (14) by a one-pot process of tandem benzylic oxidation and aromatization as the key step of these total syntheses was also studied in detail. The first total synthesis of eudistomin Y 7 (7) and total syntheses of eudistomins Y1-Y6 (1-6) are described. An efficient room-temperature conversion of 1-benzyl-3,4-dihydro-β-carbolines (11) into 1-benzoyl-β-carbolines (14) by a one-pot process of tandem benzylic oxidation and aromatization as the key step of these total syntheses was also studied in detail. Copyright
- Trieu, Tien Ha,Dong, Jing,Zhang, Qiang,Zheng, Bo,Meng, Tian-Zhuo,Lu, Xia,Shi, Xiao-Xin
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supporting information
p. 3271 - 3277
(2013/07/05)
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- Design, synthesis and biological evaluation of β-carboline derivatives as novel inhibitors targeting B-Raf kinase
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β-Carboline family of compounds is a large group of alkaloids widely distributed in nature and exhibits broad-spectrum anti-tumor activities. We designed and synthesized two series of novel 1-carboxamide- and 6-sulfonamide-substituted β-carboline derivatives 7a-p and 12a-b, and their wild type B-Raf kinase inhibitory activities were described. Most compounds showed moderate to excellent inhibitory activities. Among them, 1-carboxamide-6-(N-(3-(dimethylamino)propyl)-sulfamoyl)-β-carboline, 7e exhibited potent activity (IC50 = 1.62 μM), showing the potential for further investigation as a lead compound.
- Xin, Botao,Tang, Weifang,Wang, Yue,Lin, Guowu,Liu, Haichun,Jiao, Yu,Zhu, Yong,Yuan, Haoliang,Chen, Yadong,Lu, Tao
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scheme or table
p. 4783 - 4786
(2012/08/13)
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- Synthesis of carbolines by photostimulated cyclization of anilinohalopyridines
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A general synthetic route to prepare all four carboline regioisomers by photostimulated cyclization of anilinohalopyridines is described. The methodology affords various substituted carbolines in good to excellent yields. In the case of α-carbolines, the SRN1 methodology complements previously reported palladium-catalyzed cyclization approaches.
- Laha, Joydev K.,Barolo, Silvia M.,Rossi, Roberto A.,Cuny, Gregory D.
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experimental part
p. 6421 - 6425
(2011/09/15)
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- A facile synthesis of 3-substituted 9H-pyrido[3,4-b]indol- 1(2H)-one derivatives from 3-substituted β-carbolines
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A mild and efficient two-step synthesis of 3-substituted β-carbolinone derivatives from 3-substituted β-carboline in good yields is described. A possible reaction mechanism for the formation of the skeleton of β-carbolin-1-one is proposed. The structures of these compounds were established by IR, 1H-NMR, 13C-NMR, mass spectrometry and elemental analysis, as well as X-ray crystallographic analysis of 4-2 and 6-2.
- Lin, Guowu,Wang, Yue,Zhou, Qingfa,Tang, Weifang,Wang, Jian,Lu, Tao
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scheme or table
p. 5680 - 5691
(2010/12/19)
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- Facile synthesis of isoquinolines, β-carbolines, and 3-deazapurines
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Isoquinoline, β-carbolines, and 3-deazapurines were prepared in 52-81% yields via oxidative decarboxylation of cyclic α-amino acids using ammonium persulfate as an oxidant in the presence of catalytic silver. Copyright Taylor & Francis Group, LLC.
- Huang, Wenhua,Li, Jingyi,Ou, Lihua
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p. 2137 - 2143
(2008/02/07)
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- Heterocyclic compounds and their use as antifouling agents
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The present invention relates to a nostocarboline compound of the formula (I) and its use as a biocidal agent. In this formula R1, R3, R4 and R6 are selected from the group consisting of H, F, Cl, Br, I, a C1-C20 aliphatic residue, and a C1-C20 aliphatic residue comprising a carbocyclic or heterocyclic residue; R2 is selected from the group consisting of H and Cl; R5 is selected from the group consisting of H, a C1-C20 aliphatic residue, and a C1-C20 aliphatic residue comprising a carbocyclic or heterocyclic residue; R7 is selected from the group consisting of a C1-C20 aliphatic residue, a C1-C20 aliphatic residue comprising a carbocyclic or heterocyclic residue, and a linker bound to a bioactive factor; R8 is selected from the group consisting of H, a C1-C6 aliphatic carboxylic acid, ester, or amide, and a C3-C20 carbocyclic residue; and X- is a negatively charged ion.
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Page/Page column 10
(2008/06/13)
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- HARMINE DERIVATIVES, INTERMEDIATES USED IN THEIR PREPARATION, PREPARATION PROCESSES AND USE THEREOF
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This invention relates to compounds of general formula (I), wherein R1, R2, R3, R4 and R5 are as defined specification; intermediates used in their preparation, preparation processes and use thereof. The present invention produce harmine derivatives with enhanced antihumour activity and lower nervous system toxicity by structurally modification parent structure of β-carboline of harmines at position 1, 2, 3, 7 and 9, The compounds of the present invention can be pre easily with high yield. They can be used in manufacture of a variety of antitumour medicines and medicines used in treatm tumour diseases in combination of light or radiation therapy.
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Page/Page column 47; 96
(2008/06/13)
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- Synthesis of C-14-labeled novel IKK inhibitor: 2-[14C]-N-(6- chloro-9H-pyrido [3,4-b]indol-8-yl)-3-pyridinecarboxamide
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2-[14C]-N-(6-Chloro-9H-pyrido [3,4-b]indol-8-yl)-3- pyridinecarboxamide (9A, also referred to as [14C]-PS-1145) was synthesized from [14C]-paraformaldehyde in five steps in an overall radiochemical yield of 15%. The key intermediate 1-[14C]-6-chloro-1, 2,3,4-tetrahydro-β-carboline was obtained by Pictet-Spengler cyclization of chlorotryptamine with [14C]-paraformaldehyde. Similar reactions were conducted with tryptamine to address the generality of the methodology. Copyright
- Li, Yuexian,Prakash, Shimoga R.
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p. 323 - 330
(2007/10/03)
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- An efficient procedure for the deprotection of N-pivaloylindoles, carbazoles and β-carbolines with LDA
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Treatment of variously substituted indoles with 2 equivalents of LDA at 40-45 °C led to their fast and efficient deprotection. This method was also extended to N-pivaloylcarbazoles and β-carbolines.
- Avenda?o, Carmen,Sánchez, J. Domingo,Menéndez, J. Carlos
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p. 107 - 110
(2007/10/03)
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- Microwave-enhanced cadogan cyclization: An easy access to the 2-substituted carbazoles and other fused heterocyclic systems
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A microwave-enhanced Suzuki-Miyaura cross-coupling reaction in combination with a microwave-assisted Cadogan reductive cyclization is presented as an easy access to a variety of 2-substituted carbazoles and other fused heterocyclic systems. Microwave irradiation was found very useful in minimizing the proto-deboronation issues in the cross-coupling reaction, and enhances the rate of reductive cyclization in a dramatic manner.
- Appukkuttan, Prasad,Van Der Eycken, Erik,Dehaen, Wim
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p. 127 - 133
(2007/10/03)
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- A new synthesis of 4-oxygenated β-carboline derivatives by Fischer indolization
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A new and short synthetic route to the 4-methoxy-β-carboline skeleton is described. The route involves Fischer indolization of enehydrazine of 1-tosylpiperidine-3,5-dione and successive acetalization-elimination for aromatization of 1,2,3,4-tetrahydro-2-tosyl-9H-β-carbolin-4-one. This method is efficiently applicable to synthesis of the benzene-part substituted 4-oxygenated β-carboline derivatives.
- Suzuki, Hideharu,Tsukakoshi, Yoshiyuki,Tachikawa, Takuya,Miura, Yuusuke,Adachi, Makoto,Murakami, Yasuoki
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p. 3831 - 3834
(2007/10/03)
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- A versatile route to benzocanthinones
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Benzocanthinone (1) and five analogs (10, 12-15) were prepared by radical-induced cyclizations of halo N-aroyl derivatives of β-carboline and carbazole.
- Markgraf, J. Hodge,Dowst, Adrian A.,Hensley, Laurel A.,Jakobsche, Charles E.,Kaltner, Cindy J.,Webb, Peter J.,Zimmerman, Patrick W.
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p. 9102 - 9110
(2007/10/03)
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- A novel palladium-catalyzed synthesis of β-carbolines: Application in total synthesis of naturally occurring alkaloids
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Two naturally occurring β-carbolines, 6-methoxy-2-methyl-1,2,3,4-tetrahydro-β-carboline and bauerine A, have been prepared using a Stille-type coupling, followed by a palladium-phosphine catalyzed N-heteroannulation as the key steps.
- Dantale, Shubhada W.,S?derberg, Bj?rn C. G.
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p. 5507 - 5514
(2007/10/03)
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- The first method for protection-deprotection of the indole 2,3-π bond
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(Matrix presented) The scope and generality of a new reaction of indoles with MTAD is discussed. In most cases the ene-type reaction proceeds within seconds or minutes at 0°C to provide the urazole adducts in high yield. This reaction provides the first method for protecting the indole 2,3-double bond since the urazole adducts can be reconverted to the starting indole (retro-ene) simply by heating.
- Baran, Phil S.,Guerrero, Carlos A.,Corey
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p. 1999 - 2001
(2007/10/03)
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- Chemical compounds
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Compounds of the general structural formula (I) and use of the compounds and salts and solvates thereof, as therapeutic agents.
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- Novel synthetic strategy of carbolines via palladium-catalyzed amination and arylation reaction
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Four parent carbolines and the corresponding 5- or 9-methylsulfonyl derivatives were synthesized by the palladium-catalyzed intramolecular arylation reaction of ortho-bromo-substituted anilinopyridines which were prepared by the palladium-catalyzed amination reaction of iodobenzenes with aminopyridines. Carbazole and its 9-methylsulfonyl derivative were also synthesized by the same method.
- Iwaki, Takehiko,Yasuhara, Akito,Sakamoto, Takao
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p. 1505 - 1510
(2007/10/03)
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