100880-52-2Relevant articles and documents
N-Doped Cationic PAHs by Rh(III)-Catalyzed Double C-H Activation and Annulation of 2-Arylbenzimidazoles with Alkynes
Villar, José M.,Suárez, Jaime,Varela, Jesús A.,Saá, Carlos
, p. 1702 - 1705 (2017)
A novel class of N-doped cationic PAHs (polycyclic aromatic hydrocarbons) bearing the benzo[c,d]fluoranthene scaffold has been synthesized by the Rh(III)-catalyzed double-oxidative annulation of 2-arylbenzimidazoles with alkynes. The overall process involves a double C-N bond formation through a double C-H/N-H functionalization.The solid-state structures and electronic properties of the new N-doped PAHs were analyzed. These cationic azapolycycles were readily reduced in the presence of LiAlH4 or by the addition of PhLi to give interesting phenyl and diphenylmethanediamine derivatives.
Liquid-phase synthesis of 2-substituted benzimidazoles, benzoxazoles and benzothiazoles
Chen, Chinpiao,Chen, Yi-Jing
, p. 113 - 115 (2004)
A novel acid fluoride for use in the liquid-phase synthesis of substituted benzimidazoles, benzoxazoles and benzothiazoles was developed. Its synthetic utility is exemplified by a structurally diverse set of aromatic heterocycles. Final cleavage is achiev
Oxidative Radical Relay Functionalization for the Synthesis of Benzimidazo[2,1-a]iso-quinolin-6(5H)-ones
Sun, Kai,Li, Guofeng,Li, Yuyang,Yu, Jie,Zhao, Qing,Zhang, Zhiguo,Zhang, Guisheng
, p. 1947 - 1954 (2020)
Here, a mild and general oxidative radical relay carbocyclization reaction with 2-arylbenzoimidazoles and cyclic ethers is reported. This method provides an efficient access to a wide range of structurally diverse benzimidazo[2,1-a]isoquinoline-6(5H)-ones under metal-free conditions. The wide substrate scope, good functional group tolerance, and scale-up operation of this method are expected to promote its potential applications in biotechnology and pharmacy. (Figure presented.).
Synthesis, docking studies and biological activity of new benzimidazole- Triazolothiadiazine derivatives as aromatase inhibitor
?avu?o?lu, Betül Kaya,?evik, Ulviye Acar,?zkay, Yusuf,Ilg?n, Sinem,Kaplanc?kl?, Zafer As?m,Levent, Serkan,Osmaniye, Derya,Sa?l?k, Begüm Nurpelin
, (2020)
In the last step of estrogen biosynthesis, aromatase enzyme catalyzes the conversion of androgens to estrogens. Aromatase inhibition is an important way to control estrogen-related diseases and estrogen levels. In this study, sixteen of benzimidazole-triazolothiadiazine derivatives have been synthesized and studied as potent aromatase inhibitors. First, these compounds were tested for their anti-cancer properties against human breast cancer cell line (MCF-7). The most active compounds 5c, 5e, 5k, and 5m on MCF-7 cell line were subject to further in vitro aromatase enzyme inhibition assays to determine the possible mechanisms of action underlying their activity. Compound 5e showed slight less potent aromatase inhibitory activity than that of letrozole with IC50 = 0.032 ± 0.042 μM, compared to IC50 = 0.024 ± 0.001 μM for letrozole. Furthermore, compound 5e and reference drug letrozole were docked into human placental aromatase enzyme to predict their possible binding modes with the enzyme. Finally, ADME parameters (absorption, distribution, metabolism, and excretion) of synthesized compounds (5a–5p) were calculated by QikProp 4.8 software.
Water extract of onion catalyst: An economical green route for the synthesis of 2-substituted and 1,2-disubstituted benzimidazole derivatives with high selectivity
Kaliyan, Prabakaran,Selvaraj, Loganathan,Muthu, Seenivasa Perumal
, p. 340 - 349 (2021)
An efficient, environmental friendly and substrate controlled method of synthesis of 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 with high selectivity has been achieved from the reaction of o-phenylenediamine 1 and aldehydes 2 in the presence of water extract of onion and selecting suitable reaction medium. This method is widely applicable for variety of aldehydes such as aromatic/aliphatic/heterocyclic aldehydes and 1,2-diamines to afford 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 in good to excellent yields (up to 96%). The developed method of water extract of onion catalysis produced 2-substituted benzimidazoles 3 from aromatic aldehydes having electron-withdrawing groups, whereas aromatic aldehydes bearing electron donating groups selectively furnished 1,2-disubstituted benzimidazole 4 derivatives. The process described here has several advantages of cheap, low energy consumption, commercially available starting materials, operational simplicity and nontoxic catalyst. The use of water extract of onion makes this present methodology green and giving a useful contribution to the existing methods available for the preparation of benzimidazole derivatives. In addition, Hammett correlation of substituent constant (σ) vs percentage (%) yield has been established.
N-hydroxyphthalimide/cobalt acetate, a new catalytic oxidative system for the synthesis of benzimidazoles
Coppola, Gary M.
, p. 3500 - 3507 (2008)
Benzimidazoles are readily prepared from 1,2-phenylenediamine and an aldehyde using air and catalytic N-hydroxyphthalimide/Co(OAc)2 as the oxidant. Both electron-donating and electron-withdrawing groups are tolerated. Copyright Taylor & Francis Group, LLC.
One-pot synthesis of benzimidazoles in water in the presence of SiO 2-OPO3H
Mirjalili,Bamoniri,Rahimi Kazerouni
, p. 35 - 40 (2014)
Silica-bound phosphoric acid (SiO2-OPO3H), as an eco-friendly, reusable, and heterogeneous catalyst, was applied for synthesis of 2-substituted benzimidazoles in water at 70°C. Very short reaction times, clean work-up, and high yields are among the advantages of this protocol.
Synthesis of novel benzimidazole–oxadiazole derivatives as potent anticancer activity
?evik, Ulviye Acar,Osmaniye, Derya,?avu?o?lu, Betül Kaya,Sa?lik, Begüm Nurpelin,Levent, Serkan,Ilgin, Sinem,Can, Nafiz ?ncü,?zkay, Yusuf,Kaplancikli, Zafer As?m
, p. 2252 - 2261 (2019)
DNA topoisomerase I regulates DNA topological structure in many cellular metabolic processes and is a validated target for the development of antitumor agents. In this work, a series of novel 2-[(5-(4-(5(6)-substituted-1H-benzimidazol-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)thio]-1-(4-substitutedphenyl)ethan-1-ones (4a–4s) derivatives have been synthesized and evaluated for DNA Topo I inhibition and cytotoxicity. The structures of the compounds (4a–4s) were confirmed by IR, 1H-NMR, 13C-NMR, 2D NMR, and mass spectroscopy. Anticancer activity of these compounds was assessed against two different human cancer cell lines A549 (human lung adenocarcinoma) and HepG2 (human liver cancer cell line), as well as normal mouse embryonic fibroblast cells (NIH3T3). IC50 values of compounds 4a, 4c, and 4f were highest than those exhibited for the reference drug cisplatin. Then, the inhibitory effect of 4a, 4c, and 4f compounds on topoisomerase I enzyme with the relaxation assay was investigated on supercoiled DNA using agarose gel electrophoresis. The Annexin V-FITC assay demonstrated that these compounds induce cell death by apoptosis.
Significant facilitation of metal-free aerobic oxidative cyclization of imines with water in synthesis of benzimidazoles
Lee, Ye-Sol,Cho, Yeon-Ho,Lee, Seungjae,Bin, Jong-Kwan,Yang, Joonghwan,Chae, Geesung,Cheon, Cheol-Hong
, p. 532 - 538 (2015)
A simple, convenient, and environmentally benign protocol for the synthesis of benzimidazoles from ortho-phenylenediamines and aldehydes via aerobic oxidation was developed in wet organic solvents. Notably, water significantly accelerated this transformation, which allowed us to achieve this important transformation without the assistance of any metal catalysts and other co-oxidants. Mechanistic studies suggested that water acts as the nucleophilic catalyst for this transformation by the conversion of disfavored 5-endo-trig cyclization of imines to favored 5-exo-tet cyclization via tetrahedral intermediates and the subsequent aerobic oxidation of the resulting benzimidazolines affords benzimidazoles.
MAO enzymes inhibitory activity of new benzimidazole derivatives including hydrazone and propargyl side chains
Can, ?zgür Devrim,Osmaniye, Derya,Demir ?zkay, ümide,Sa?l?k, Begüm Nurpelin,Levent, Serkan,Ilg?n, Sinem,Baysal, Merve,?zkay, Yusuf,Kaplanc?kl?, Zafer As?m
, p. 92 - 106 (2017)
In the present work, 15 new N’-(arylidene)-4-(1-(prop-2-yn-1-yl)-1H-benzo[d]imidazol-2-yl)benzohydrazide (4a-4o) were designed and synthesized. The structures of the synthesized compounds were elucidated using FT-IR, 1H-NMR, 13C-NMR, and HRMS spectral data. The inhibitory activity of the compounds 4a-4o against hMAO-A and hMAO-B enzymes was evaluated by using in?vitro Amlex Red reagent based fluorometric method. Due to lots of high-cost kits including this assay, we determined the ingredients of the kits from the data sheets of several suppliers, and adjusted a protocol by working with various concentrations and volumes of these ingredients. As a result, a fast and sensitive assay was applied as in the commercially available MAO kits with lower costs and clearer ingredients than those of the kits. The enzyme inhibition assay revealed that synthesized compounds have selective inhibition potency against hMAO-B. The compound 4e and 4f displayed IC50 values of 0.075?μM and 0.136?μM against hMAO-B, respectively. The reference drugs selegiline (IC50?=?0.040?μM) and rasagiline (IC50?=?0.066?μM) also displayed a significant inhibition against hMAO-B. The enzyme kinetic study was performed in order to observe the effect of the most active compound 4e on substrate-enzyme relationship and non-competitive inhibition of hMAO-B was determined. Cytotoxicity and genotoxicity studies were carried out and the compound 4e was found as non-cytotoxic and non-genotixic. Theoretical calculation of ADME properties suggested that compound 4e may have a good pharmacokinetic profile. The docking study of compound 4e revealed that there is a strong interaction between the active sites of hMAO-B and analyzed compound.
