- Synthesis and investigations into the anticancer and antibacterial activity studies of β-carboline chalcones and their bromide salts
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A series of sixteen β-carbolines, bearing chalcone moiety at C-1 position, were prepared from easily accessible 1-acetyl-β-carboline and various aldehydes under basic conditions followed by N2-alkylation using different alkyl bromides. The prepared compounds were evaluated for in vitro cytotoxicity against a panel of human tumor cell lines. N2-Alkylated-β-carboline chalcones 13a-i represented the interesting anticancer activities compared to N2-unsubstituted β-carboline chalcones 12a-g. Off the prepared β-carbolines, 13g exhibited broad spectrum of activity with IC50 values lower than 22.5 μM against all the tested cancer cell lines. Further, the N2-alkylated-β-carboline chalcone 13g markedly induced cell death in MDA-MB-231 cells by AO/EB staining assay. The most cytotoxic compound 13g possessed a relatively high drug score of 0.48. Additionally, the prepared β-carboline chalcones displayed moderate antibacterial activities against tested bacterial strains.
- Venkataramana Reddy,Hridhay,Nikhil, Kumar,Khan, Shahid,Jha,Shah, Kavita,Kumar, Dalip
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- β-carboline alkaloids, Part 8. Regioselective homolytic acetylation of β-carbolines
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Homolytic acetylation of 3-ethoxycarbonyl-β-carboline and norharmane occurs selectively at 1-position. Better yields are obtained by generation of the acetyl radical from acetyldehyde than by oxidative decarboxylation of pyruvic acid.
- Bracher,Daab
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- Discovery of McbB, an enzyme catalyzing the β-carboline skeleton construction in the marinacarboline biosynthetic pathway
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Three genes, mcbABC, that drive the biosynthesis of marinacarbolines, have been elucidated through genome mining, gene inactivation, heterologous expression, feeding, and site-directed mutagenesis experiments. McbB is highlighted as a novel enzyme for the β-carboline core construction, which involves a Pictet-Spengler cyclization process and requiring E97 for biochemical activity.
- Chen, Qi,Ji, Changtao,Song, Yongxiang,Huang, Hongbo,Ma, Junying,Tian, Xinpeng,Ju, Jianhua
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- Synthesis and characterization of new fluorescent boro-β-carboline dyes
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The first representatives of the new fluorescent boro-β-carboline family were synthesized by the insertion of the difluoroboranyl group into the oxaza or diaza core. The resulting compounds showed good photophysical properties with fine Stokes-shifts in the range of 38-85 nm with blue and green emission. The energetics of the excitation states and molecular orbitals of two members were investigated by quantum chemical computations suggesting effects for the improved properties of diazaborinino-carbolines over oxazaborolo-carbolines. These properties nominated this chemotype as a new fluorophore for the development of fluorescent probes. As an example, diazaborinino-carbolines were used for the specific labeling of anti-Her2 antibody trastuzumab. The fluorescent conjugate showed a high fluorophore-antibody ratio and was confirmed as a useful tool for labeling and confocal microscopy imaging of tumour cellsin vitrotogether with theex vivotwo-photon microscopy imaging of tumour slices.
- Szepesi Kovács, Dénes,Hajdu, Imre,Mészáros, Gergely,Wittner, Lucia,Meszéna, Domokos,Tóth, Estilla Zsófia,Heged?s, Zita,Ran?elovi?, Ivan,Tóvári, József,Szabó, Tímea,Szilágyi, Bence,Milen, Mátyás,Keser?, Gy?rgy Miklós,ábrányi-Balogh, Péter
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p. 12802 - 12807
(2021/04/14)
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- Preparation method of 1-carbonyl-beta-carboline compound
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The invention discloses a preparation method of a 1-carbonyl-beta-carboline compound. The preparation method comprises the following step: in an air or oxygen atmosphere, in the presence of an additive and under the condition of illumination, performing oxidation reaction on tetrahydrocarboline compound as shown in a formula II to obtain the 1-carbonyl-beta-carboline compound as shown in a formula I, wherein the additive is tetrabutyl quaternary ammonium salt selected from any one of tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium chloride, tetrabutylammonium acetate and tetrabutylammonium fluoride; and the molar ratio of the tetrahydrocarboline compound as shown in the formula II to the additive is 1:(0.2-2). The preparation method provided by the invention is high in yield, wherein most of the yield is between 60% and 90%. When R3 is an aromatic group, the variety and the position of a substituent group on an aromatic ring do not have substantial influence on the yield of the reaction. In addition, the R3 group has wider applicability and also comprises an alkyl R3 group besides the aromatic R3 group, and in this aspect, the preparation method provided by the invention is substantially improved compared with the existing synthesis.
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Paragraph 0095-0098
(2017/06/13)
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- Structural Basis for β-Carboline Alkaloid Production by the Microbial Homodimeric Enzyme McbB
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Summary The β-carboline (βC) alkaloids occur throughout nature and exhibit diverse biological activities. In contrast to βC alkaloid synthesis in plants, the biosynthesis in microorganisms remains poorly understood. The recently reported McbB from Marinactinospora thermotolerans is a novel enzyme proposed to catalyze the Pictet-Spengler (PS) reaction of L-tryptophan and oxaloacetaldehyde to produce the βC scaffold of marinacarbolines. In this study, we solved the crystal structure of McbB complexed with L-tryptophan at 2.48 ? resolution, which revealed the novel protein folding of McbB and the totally different structure from those of other PS condensation catalyzing enzymes, such as strictosidine synthase and norcoclaurine synthase from plants. Structural analysis and site-directed mutagenesis confirmed that the previously proposed catalytic Glu97 at the active-site center functions as an acid and base catalyst. Remarkably, the structure-based mutants R72A and H87A, with expanded active-site cavities, newly accepted bulky phenylglyoxal as the aldehyde substrate, to produce 1-benzoyl-3-carboxy-β-carboline.
- Mori, Takahiro,Hoshino, Shotaro,Sahashi, Shusaku,Wakimoto, Toshiyuki,Matsui, Takashi,Morita, Hiroyuki,Abe, Ikuro
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p. 898 - 906
(2015/08/03)
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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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- Synthesis, in vitro anti-inflammatory and cytotoxic evaluation, and mechanism of action studies of 1-benzoyl-β-carboline and 1-benzoyl-3-carboxy-β-carboline derivatives
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In the present study, various 1-substituted and 1,3-disubstituted β-carboline derivatives were synthesized by a modified single-step Pictet-Spengler reaction. The compounds were examined for cytotoxicity and anti-inflammatory activity, as measured by the
- Yang, Mei-Lin,Kuo, Ping-Chung,Hwang, Tsong-Long,Chiou, Wen-Fei,Qian, Keduo,Lai, Chin-Yu,Lee, Kuo-Hsiung,Wu, Tian-Shung
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experimental part
p. 1674 - 1682
(2011/04/16)
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- A facile synthesis of 1-substituted βcarboline derivatives via minisci-reaction
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A mild and efficient one-pot reaction for the synthesis of 1-substituted βcarboline derivatives via the Minisci reaction has been developed with good yields and selectivity. In addition, the mechanism of the 1-substituted βcarboline derivatives by means of the nucleophilic radical is described.
- Lin, Guowu,Wang, Yue,Zhou, Qingfa,Tang, Weifang,Wang, Jian,Lu, Tao
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experimental part
p. 3541 - 3550
(2011/09/16)
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- The role of methylglyoxal in the non-enzymatic conversion of tryptophan, its methyl ester and tryptamine to 1-acetyl-β-carbolines
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Non-enzymatic modification of l-tryptophan (1) and its metabolites and derivatives with aldehydes, via the Pictet-Spengler reaction, affords β-carbolines. Here we demonstrate that methylglyoxal (2) generates 1-acetyl-β-carbolines from tryptophan (1), from its methyl ester (6) and from tryptamine (4); however, 2 did not generate 1-(1-hydroxyethyl)-β-carboline derivates. HPLC analysis of model reaction systems showed formation of 1-acetyl-β-carboline (3) and 1-acetyl-β-carboline-3-carboxylic acid (5) during incubation of 1 and 2, at pH 5.7 and 7.4, at 100 °C, and only 5 at 37 °C, at the same pH values, with limited access of oxygen. Aerobic conditions caused higher formation of 3 at 37 °C at both pH values, while, at higher temperature, the same effect was only observed at pH 5.7. Lack of oxygen did not much influence the formation of 3 or 5 at both pH and temperature values, in comparison with the formation at limited access of oxygen. Incubation of 2 and 6 generated methyl-1-acetyl-β-carboline-3-carboxylate (7) together with 3 and 5 as a result of hydrolysis of 6 into 1 and, partially, 7 into 5, while in incubation mixtures of 2 and 4 only unstable 1-acetyl-3,4-dihydro-β-carboline (8) was observed. Incubation of 1 with d-glucose as well as incubation of tryptophan with Amadori product 18 under similar conditions did not generate carbolines 3 or 5. For the first time, we were able to demonstrate the presence of 1-acetyl-β-carboline-3-carboxylic acid (5) in some commercially available ketchups and in previously heated tomato concentrate.
- Nemet, Ina,Varga-Defterdarovic, Lidija
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p. 4551 - 4562
(2008/12/20)
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- A versatile route to the synthesis of 1-substituted β-carbolines by a single step Pictet-Spengler cyclization
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A one-step conversion of l-tryptophan and activated aldehydes (1,2-dicarbonyl compounds) directly to 1-substituted β-carbolines without formation of the tetrahydro derivatives under modified Pictet-Spengler conditions was described. Moreover, a practical
- Yang, Mei-Lin,Kuo, Ping-Chung,Damu, Amooru G.,Chang, Ren-Jie,Chiou, Wen-Fei,Wu, Tian-Shung
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p. 10900 - 10906
(2007/10/03)
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- Synthesis of cytotoxic 1-polyhydroxyalkyl-β-carboline derivatives
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dl-1-(1-Oxo-3,4-threo-3,4,5-trihydroxy-1-pentyl)-β- carboline 16a was synthesized from 1-formyl-β-carboline in 13 steps. The prepared compound is one of the diastereomers of an alkaloid 3 produced by the inter-generic somatic hybrid cell culture of Rauwolfia serpentina Benth and Rhazya stricta Decaisne (family: Apocynaceae). The N9-benzyl and N9-methyl derivatives 16b,c were also prepared. The final compounds and some of the intermediates showed cytotoxic activity against human promyelocytic leukemia cells HL 60 and/or human diploid embryonic lung fibroblast cells.
- Abdel-Moty,Sakai,Aimi,Takayama,Kitajima,El-Shorbagi,Ahmed,Omar
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p. 1009 - 1017
(2007/10/03)
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- β-Carboline Alkaloids, II. - Tributyl(1-ethoxyvinyl)stannane as a C2-Building Block in the Syntheses of β-Carboline Alkaloids
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1-Acetyl-β-carboline (4) is prepared by palladium-catalyzed coupling of 1-chloro-β-carboline (1) with tributyl(1-ethoxyvinyl)stannane (2) and subsequent hydrolysis with aqueous acid.Reduction of 4 with NaBH4 gives the alkaloid 5.Nitramarine (7) and annomontine (9) are prepared from 4 by one-pot conversions of the acetyl group to a quinoline or an aminopyrimidine ring, respectively. Key Words: β-Carbolines / Alkaloids / Annomontine / Nitramarine / Stannanes / Tin compounds
- Bracher, Franz,Hildebrand, Dirk
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p. 837 - 840
(2007/10/02)
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- Selenium Dioxide Oxidations in the Indole Area. Synthesis of β-Carboline Alkaloids
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A number of different piperidoindole systems have been subjected to oxidation with selenium dioxide.The bonding between the indole and piperidine unit has been varied to provide different systems, the oxidation of which has led to formation of either 2-acyl- or 3-acylindoles or fully aromatic β-carbolines, depending on the substrate chosen.The pattern of reactivity observed was in complete agreement with the ene mechanism proposed for selenium dioxide oxidations, and this can be employed to predict the regiochemistry of the oxidation.Use of this technology has resulted in a two-step synthesis of the indole alkaloid canthin-6-one (30a).
- Cain, M.,Campos, O.,Guzman, F.,Cook, J.M.
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p. 907 - 913
(2007/10/02)
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- SELENIUM DIOXIDE OXIDATIONS IN THE β-CARBOLINE AREA
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The reaction of 1-ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 11 with selenium dioxide has resulted in the synthesis of the β-carboline alkaloids, 1-acetyl-3-methoxycarbonyl-β-carboline 14 and 1-acetyl-β-carboline 15.Application of this technol
- Campos, Olivia,DiPierro, Mike,Cain, Michael,Mantei, Robert,Gawish, Ali,Cook, James M.
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p. 975 - 984
(2007/10/02)
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