20443-38-3Relevant academic research and scientific papers
Synthesis of Benzimidazole-Fused Medium-Sized N,S-Heterocycles via Palladium-Catalyzed Cyclizations
Lopes, Alexandra Basilio,Wagner, Patrick,Gulea, Mihaela
, p. 1361 - 1370 (2019)
The synthesis of unprecedented benzimidazole-fused thiazocines, thiazonines, and thiazecines having an exocyclic double bond is reported. The process proceeds through an 8-, 9-, or 10-exo-dig cyclocarbopalladation followed by reduction. The scope and limitations were established and showed the importance of the precursor structure for the success of the reaction. A competition between the exo-dig and the endo-dig cyclization was observed for two substrates bearing an N-homopropargyl chain, the endo-cyclization leading to rarely encountered 10- and 11-membered N,S-heterocycles with a trans-endocyclic double bond. X-ray structures of three products were obtained by co-crystallization with fumaric acid and show the twisted structures of these molecules.
Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus
Ganji, Lata R.,Gandhi, Lekha,Musturi, Venkataramana,Kanyalkar, Meena A.
, p. 285 - 301 (2020/11/19)
The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.
Synthesis and antinociceptive activity of meperidine-like benzimidazole derivatives
Ercanli, Taner,Bal, Nur Banu,?zdemir, Elif Derya,Dündar, Yasemin,Uluda?, M. Orhan,?akir, Bilge,?zden, Tuncel,?nkol, Tijen
, p. 15 - 22 (2016/07/15)
(Graph presented) A series of novel benzimidazole derivatives have been prepared and characterized by IR, 1H-NMR spectroscopic data and elemental analysis. All the final compounds were screened for their antinociceptive activities with tail flick test. Among the synthesized compounds 3a, 4a, 4c, 8a, 9a exhibited significant antinociceptive activity. Compound 9a was found to have the highest antinociceptive activity at both 60 minutes and 120 minutes. Additionally, compounds 3a, 4a, 8a and 9a showed naloxone-reversible antinociceptive activity.
Multicomponent cascade reaction: Dual role of copper in the synthesis of 1,2,3-triazole tethered benzimidazo[1,2-a]quinoline and their photophysical studies
Nagesh, Hunsur Nagendra,Suresh, Amaroju,Reddy, Muthyala Nagarjuna,Suresh, Narva,Subbalakshmi, Jayanty,Chandra Sekhar, Kondapalli Venkata Gowri
, p. 15884 - 15894 (2016/02/26)
One-pot synthesis of 1,2,3-triazole tethered benzimidazo[1,2-a]quinolines through a multi-component reaction is demonstrated. The domino/cascade reaction proceeds via click reaction, in which 1,2,3-triazole motif augment methylene group reactivity/N-C bond formation/Knoevenagel condensation in sequence. Overall one C-C bond and three C-N bonds are formed in a single step. In addition, photophysical properties of these new compounds were studied and compound 5u emerged as good fluorogenic substrate with quantum yield ～0.21.
Discovery of membrane active benzimidazole quinolones-based topoisomerase inhibitors as potential DNA-binding antimicrobial agents
Zhang, Ling,Addla, Dinesh,Ponmani, Jeyakkumar,Wang, Ao,Xie, Dan,Wang, Ya-Nan,Zhang, Shao-Lin,Geng, Rong-Xia,Cai, Gui-Xin,Zhou, Cheng-He,Li, Shuo
, p. 160 - 182 (2018/05/17)
A series of novel benzimidazole quinolones as potential antimicrobial agents were designed and synthesized. Most of the prepared compounds exhibited good or even stronger antimicrobial activities in comparison with reference drugs. The most potent compound 15m was membrane active and did not trigger the development of resistance in bacteria. It not only inhibited the formation of biofilms but also disrupted the established Staphylococcus aureus and Escherichia coli biofilms. It was able to inhibit the relaxation activity of E. coli topoisomerase IV at 10 μM concentration. Moreover, this compound also showed low toxicity against mammalian cells. Molecular modeling and experimental investigation of compound 15m with DNA suggested that this compound could effectively bind with DNA to form a steady 15m-DNA complex which might further block DNA replication to exert the powerful bioactivities.
NOVEL BENZIMIDAZOLE BASED EGFR INHIBITORS
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Page/Page column 13 ; 14, (2016/06/15)
The present invention disclosed a novel EGFR inhibitor compound of formula (I), process for preparation thereof and methods of treating abnormal cell growth in mammals by administering the compounds of formula (I). Wherein, R= -H, 3-CH3, 4-NO2, 4-Cl, 2-CH3, 4-CH3, 4-Br, 4-F R1= -H, -4-OCH3, -4-NO2,-2-NO2, -4-Cl, -2,4,6-CH3, -4-CH3, -2-F,4-Br, -4-CF3, -4-S-CH3, -4-Cl,-3-CF3, -3-S-CH3, -3,5-CF3, -2-S-CH3, -3-CF3,-4-OCF3, -Si-(CH3)3, -Si-(C2H5)3, (CH3)2-Si- C2H5.
Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents
Alasmary, Fatmah A.S.,Snelling, Anna M.,Zain, Mohammed E.,Alafeefy, Ahmed M.,Awaad, Amani S.,Karodia, Nazira
supporting information, p. 15206 - 15223 (2015/09/21)
A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds have some common features; three possess 5-halo substituents; two are derivatives of (S)-2-ethanaminebenzimidazole; and the others are derivatives of one 2-(chloromethyl)-1Hbenzo[ d]imidazole and (1H-benzo[d]imidazol-2-yl)methanethiol. The results from the antifungal screening were also very interesting: 23 compounds exhibited potent fungicidal activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives could be considered promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications.
Condensation of Ortho-phenylenediamines and Phenylhydrazines with Ethyl 4-Chloro-3-oxobutanoate: A Facile Approach for the Synthesis of Substituted 1 H-Benzimidazoles, Pyrazolones, and Pyrazoles
Dayakar, Cherupally,Jyothi, Dondra,Suman, Pathi,Raju, Bhimapaka China
, p. 1642 - 1651 (2015/06/25)
Substituted 1H-benzimidazoles, pyrazolones, and pyrazoles have been synthesized by the condensation of ortho-phenylenediamines and phenylhydrazines, respectively, with ethyl 4-chloro-3-oxobutanoate in good yields. The present approach is novel, straightforward, and being reported for the first time with ethyl 4-chloro-3-oxobutanoate.
Synthesis and in vitro antifungal evaluation of benzoimidazolyl-piperazinyl-phenylmethanone derivatives
Kankate, Rani S.,Gide, Parag S.,Belsare, Deepak P.
, p. 1855 - 1863 (2015/04/22)
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.
Synthesis and biological evaluation of novel pyrimidine-benzimidazol hybrids as potential anticancer agents
Shao, Kun-Peng,Zhang, Xu-Yao,Chen, Peng-Ju,Xue, Deng-Qi,He, Peng,Ma, Li-Ying,Zheng, Jia-Xin,Zhang, Qiu-Rong,Liu, Hong-Min
, p. 3877 - 3881 (2014/09/03)
A series of pyrimidine-benzimidazol hybrids was synthesized and evaluated for anticancer activity on four human cancer cell lines including MCF-7, MGC-803, EC-9706 and SMMC-7721. Some of the synthesized compounds exhibited moderate to potent activity against MGC-803 and MCF-7. Among them, compounds 5a-b and 6a-b showed most effective activity. Compounds 5b and 6b were more cytotoxic than 5-fluorouracil against all tested four human cancer cell lines, with IC50 values ranging from 2.03 to 10.55 μM and 1.06 to 12.89 μM, respectively. Flow cytometry analysis demonstrated that treatment of MGC-803 with 6b led to cell cycle arrest at G2/M phase accompanied by an increase in apoptotic cell death.
