10112-15-9Relevant articles and documents
THE MECHANISM OF N-ALKYLATION OF WEAK N-H-ACIDS BY PHASE TRANSFER CATALYSIS
Dehmlow, Eckehard V.,Thieser, Rainer,Zahalka, Hayder Ali,Sasson, Yoel
, p. 297 - 300 (1985)
The alkylation of aromatic amines in the presence of inorganic bases is accelerated by a PT catalyst even if KHCO3 is the base.ArNR(1-) ions seem not to be involved.A novel type of mechanism for a PTC process is proposed.
Unusual reactivity of zinc borohydride - Reduction of amides to amines
Narasimhan,Madhavan,Balakumar,Swarnalakshmi
, p. 391 - 394 (1997)
Zinc borohydride reduces secondary amides to the corresponding N-ethyl amines in excellent yields. The reduction requires only stoichiometric quantities of hydride and does not require the addition of any Lewis acid. The amides are isolated by simple hydrolysis of the reaction mixture.
Synthesis of new 1,2,3-triazole linked benzimidazole molecules as anti-proliferative agents
Sahay, Ishani I.,Ghalsasi, Prasanna S.
, p. 825 - 834 (2017)
One pot click chemistry is used to link triazole and benzimidazole pharmacophore to get N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)aniline and its derivatives. Flexible linkages in the form of –CH2–R or –O–R/–N–R were designed during synthesis. All the newly synthesized compounds were characterized by FT-IR and NMR spectroscopy as well as high-resolution mass spectrometry. Selected compounds were screened for in vitro anti-proliferative activity using National Cancer Institute (NCI)-60 human tumor cell line screening program. The most potent structure N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-4-chloroaniline 7e showed 40% growth inhibition in renal cancer cell line (UO-31) at 10 μM concentration.
Synthesis and evaluation of some new (1,2,4) triazolo(4,3-a)quinoxalin- 4(5h)-one derivatives as AMPA receptor antagonists
Abul-Khair, Hamada,Elmeligie, Salwa,Bayoumi, Ashraf,Ghiaty, Adel,El-Morsy, Ahmed,Hassan, Memy H.
, p. 1202 - 1208 (2013)
This study involves the synthesis and anticonvulsant evaluation of 1-ethyl-3-hydrazinylquinoxaline-2-(1H)-one (8), its chemical confirmations 9 and 10 and certain (1,2,4) triazolo(4,3-a)quinoxalin-4(5H)-one compounds 11, 12, 13, 13a, 13b, 13c, 13d, 13e, 13f, 14, 15, 16. The structure of the synthesized compounds was confirmed chemically by elemental analyses and spectral data (IR, 1H NMR, 13C NMR, and Mass). Docking studies were preformed to all of the synthesized compounds to predict, in a qualitative way, the anticonvulsant activity of the proposed compounds. There is a promising correlation between the results of molecular modeling and the anticonvulsant activity of the synthesized compounds. The highest fitting value was noticed for compounds 9 and 10, which showed the highest anticonvulsant activity.
Synthesis and in vitro antifungal evaluation of benzoimidazolyl-piperazinyl-phenylmethanone derivatives
Kankate, Rani S.,Gide, Parag S.,Belsare, Deepak P.
, p. 1855 - 1863 (2014)
Benzimidazole and piperazines are the important pharmacophores in the structures of many antifungal compounds. Further, the phenylmethanone are also a unique class of compounds whose antifungal profile is not much exploited. So to exploit their antifungal potential we have selected these three combinations and framed the novel parent structure for our research work. In this study a novel series of benzimidazoles derivatives was synthesized by microwave irradiation and characterized by 1H NMR, 13C NMR, Infra Red (IR), and Mass Spectroscopy (MS), and by elemental analysis. The screening of compound for in vitro (turbidimetric method) antifungal activity against C.albicans revealed activity in many of the compounds as comparable to that of ketoconazole.
In vivo- and in silico-driven identification of novel synthetic quinoxalines as anticonvulsants and AMPA inhibitors
Abulkhair, Hamada S.,Elmeligie, Salwa,Ghiaty, Adel,El-Morsy, Ahmed,Bayoumi, Ashraf H.,Ahmed, Hany E. A.,El-Adl, Khaled,Zayed, Mohamed F.,Hassan, Memy H.,Akl, Eman N.,El-Zoghbi, Mona S.
, (2021)
The lack of effective therapies for epileptic patients and the potentially harmful consequences of untreated seizure incidents have made epileptic disorders in humans a major health concern. Therefore, new and more potent anticonvulsant drugs are continually sought after,?to combat epilepsy. On the basis of the pharmacophoric structural specifications of effective α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) antagonists with an efficient anticonvulsant activity, the present work reports the design and synthesis of two novel sets of quinoxaline derivatives. The anticonvulsant activity of the synthesized compounds was evaluated in vivo according to the pentylenetetrazol-induced seizure protocol, and the results were compared with those of perampanel as a reference drug. Among the synthesized compounds, 24, 28, 32, and 33 showed promising activities with ED50 values of 37.50, 23.02, 29.16, and 23.86 mg/kg, respectively. Docking studies of these compounds suggested that AMPA binding could be the mechanism of action of these derivatives. Overall, the pharmacophore-based structural optimization, in vivo?and in silico docking, and druglikeness studies indicated that the designed compounds could serve as promising candidates for the development of effective anticonvulsant agents with good pharmacokinetic profiles.
Tetraphenylethylene-based blue light material containing benzimidazole unit as well as preparation method and application
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Paragraph 0027; 0028; 0029; 0090; 0091; 0092, (2017/10/10)
The invention discloses a tetraphenylethylene-based blue light material containing a benzimidazole unit. The tetraphenylethylene-based blue light material is shown as a structural formula I or II, wherein R1 is H, tert-butyl, n-butyl or hydroxyl, and R2 is alkyl. A 2-nitro-N-tert-butylphenyl amine or 2-nitro-N-n-butylphenyl amine precursor and a 4-formyl tetraphenylethylene precursor is firstly prepared, and then cyclization reaction is carried out to prepare a compound shown as the formula I or II. A preparation method of the compound is easy to operate, the reaction is moderate and the yield is high; the compound has relatively high decomposition temperature and glass-transition temperature, and shows blue fluorescence; the compound has a relatively good single-color property, so that an OLED (Organic Light Emitting Diode) device prepared by taking the compound as a luminescent material emits blue light; the starting voltage is 3.3V and the maximum brightness efficiency is 1.48cd/A. (The formula I and the formula II are shown in the description).
The thermal instability of 2,4 and 2,6-N-alkylamino-disubstituted and 2-N-alkylamino-substituted nitrobenzenes in weakly alkaline solution: Sec-amino effect
Walczak, Christopher,Payne, Thomas J.,Wade, Colin B.,Yonkey, Matthew,Scheid, Melissa,Badour, Alec,Mohanty, Dilip K.
, p. 681 - 687 (2015/05/13)
We report herein the preparation of two families of secondary amines by the reactions of two equivalents of monoamines with either 2,4 or 2,6-difluoronitrobenzenes in N,N-dimethylacetamide in the presence of anhydrous potassium carbonate, as precursors of biologically important nitric oxide donating N-nitrosamines. In both instances, these compounds could be prepared in quantitative yield when the reaction temperature was held below 130°C. Above this reaction temperature, an unexpected cyclization reaction between the nitro and newly formed adjacent secondary amine group leads to the formation of benzimidazole or quinoxaline rings in low yields. Reasonable reaction mechanisms for the cyclization reaction are proposed.
Imidoyl dichlorides as new reagents for the rapid formation of 2-aminobenzimidazoles and related azoles
Pollock, Julie A.,Kim, Sung Hoon,Katzenellenbogen, John A.
, p. 6097 - 6099 (2015/10/28)
The development of a reagent for the efficient synthesis of five- and six-membered azoles at room temperature is proposed. A variety of substituted 2-aminobenzimidazoles are synthesized in good to excellent yields. The ability to incorporate various protecting groups makes the imidoyl dichloride reagent amenable to a large number of syntheses. The reagent is applied to the total synthesis of the 2-aminobenzimidazole containing carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), from 2-chloro-3-nitropyridine in >60% yield in 6 steps.
Indole RSK inhibitors. Part 2: Optimization of cell potency and kinase selectivity
Kirrane, Thomas M.,Boyer, Stephen J.,Burke, Jennifer,Guo, Xin,Snow, Roger J.,Soleymanzadeh, Lida,Swinamer, Alan,Zhang, Yunlong,Madwed, Jeffery B.,Kashem, Mohammed,Kugler, Stanley,O'Neill, Margaret M.
scheme or table, p. 738 - 742 (2012/03/11)
A series of inhibitors for the 90 kDa ribosomal S6 kinase (RSK) based on an 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide scaffold were optimized for cellular potency and kinase selectivity. This led to the identification of compound 24, BIX 02565, an attractive candidate for use in vitro and in vivo to explore the role of RSK as a target for the treatment heart failure.
