7192-00-9Relevant academic research and scientific papers
Synthesis, molecular docking, α-glucosidase inhibition, and antioxidant activity studies of novel benzimidazole derivatives
Singh, Gagandeep,Singh, Amanjot,Singh, Varinder,Verma, Raman K.,Tomar, Jyoti,Mall, Rajiv
, p. 1846 - 1866 (2020/08/03)
A novel series of N-methyl/benzyl-substituted benzimidazolyl-linked para-substituted benzyl-based compounds containing 2,4-thiazolidinediones, dimethyl malonate (DMM), and diethyl malonate (DEM) 17–27 were designed, docked, synthesized, and evaluated for their antidiabetic activity studies. Structures of all the synthesized compounds were confirmed through 1H NMR, 13C NMR, FTIR, and mass spectrometry. Four targeted compounds (17–18 and 22–23) showed good inhibitory potential in the range of 4.10 ± 0.01 to 9.12 ± 0.06 μM. Furthermore, synthesized compounds 17–27 were evaluated for their antioxidant potential and compared with standard ascorbic acid and results showed that compound 18 (EC50 = 0.176 ± 0.002 mM) being the most active. Compounds 17–18 and 22–23 exhibited prominent antidiabetic as well as antioxidant activity. Compound 18 was considered a promising candidate for this series. The designed molecules were docked into α-glucosidase protein (PDB Code. 3TOP) to develop a correlation with the α-glucosidase inhibition studies and were also additionally docked into PPARγ proteins (PDB ID: 2PRG) with rosiglitazone (standard drug) to study their PPARγ binding affinity in comparison with rosiglitazone and to classify these compounds for their PPARγ agonistic behavior.
High performance benzoimidazolyl-based aminophenolate zinc complexes for isoselective polymerization of: Rac -lactide
Gong, Yanmei,Ma, Haiyan
, p. 10112 - 10115 (2019/08/30)
Zinc complexes supported by achiral benzoimidazolyl-based aminophenolate ligands exhibit high catalytic activities and excellent isoselectivities toward the ring-opening polymerization of rac-lactide under mild conditions.
Novel purine benzimidazoles as antimicrobial agents by regulating ROS generation and targeting clinically resistant Staphylococcus aureus DNA groove
Wang, Ya-Nan,Bheemanaboina, Rammohan R. Yadav,Cai, Gui-Xin,Zhou, Cheng-He
supporting information, p. 1621 - 1628 (2018/03/29)
A novel series of purine benzimidazole hybrids were designed and synthesized for the first time with the aim to circumvent the increasing antibiotic resistance. Hexyl appended hybrid 3c gave potent activities against most of the tested bacteria and fungi especially against multidrug-resistant strains Staphylococcus aureus (MIC = 4 μg/mL). Structure-activity relationships revealed that the benzimidazole fragment at the 9-position of purine played an important role in exerting potentially antibacterial activity. Both cell toxicity and ROS generation assays indicated that the purine derivative 3c showed low cytotoxicity and could be used as a safe agent. Molecular modeling suggested that hybrid 3c could bind with the residues of Topo IA through hydrogen bonds and electrostatic interactions. Quantum chemical studies were also performed on the target compound 3c to understand the structural features essential for activity. The active molecule 3c could effectively interact with S. aureus DNA to form 3c–DNA complex through groove binding mode, which might block DNA replication to display their powerful antimicrobial activity.
Discovery of Benzimidazole–Quinolone Hybrids as New Cleaving Agents toward Drug-Resistant Pseudomonas aeruginosa DNA
Wang, Ya-Nan,Bheemanaboina, Rammohan R. Yadav,Gao, Wei-Wei,Kang, Jie,Cai, Gui-Xin,Zhou, Cheng-He
, p. 1004 - 1017 (2018/04/30)
A series of benzimidazole–quinolone hybrids as new potential antimicrobial agents were designed and synthesized. Bioactive assays indicated that some of the prepared compounds exhibited potent antibacterial and antifungal activities. Notably, 2-fluorobenzyl derivative 5 b (ethyl 7-chloro-6-fluoro-1-[[1-[(2-fluorophenyl)methyl]benzimidazol-2-yl]methyl]-4-oxo-quinoline-3-carboxylate) showed remarkable antimicrobial activity against resistant Pseudomonas aeruginosa and Candida tropicalis isolated from infected patients. Active molecule 5 b could not only rapidly kill the tested strains, but also exhibit low toxicity toward Hep-2 cells. It was more difficult to trigger the development of bacterial resistance of P. aeruginosa against 5 b than that against norfloxacin. Molecular docking demonstrated that 5 b could effectively bind with topoisomerase IV–DNA complexes, and quantum chemical studies theoretically elucidated the good antimicrobial activity of compound 5 b. Preliminary experimental reaction mechanism exploration suggested that derivative 5 b could not intercalate into DNA isolated from drug-resistant P. aeruginosa, but was able to cleave DNA effectively, which might further block DNA replication to exert powerful bioactivities. In addition, compound 5 b is a promising antibacterial agent with membrane disruption abilities.
Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N4 Ligands Derived from Rigid Chiral Diamines
Chen, Xiangning,Gao, Bao,Su, Yijin,Huang, Hanmin
supporting information, p. 2535 - 2541 (2017/08/16)
A series of tetradentate sp2N/sp3N hybrid chiral N4 ligands derived from rigid chiral diamines were synthesized, which enabled the first manganese-catalyzed enantioselective epoxidation of electron-deficient alkenes with hydrogen peroxide (H2O2) as an oxidant. The reaction furnishes enantiomerically pure epoxy amides, epoxy ketones as well as epoxy esters in good yields and excellent enantioselectivities (up to 99.9% ee) with lower catalyst loading. Preliminary studies on structure–activity relationship demonstrated that maintaining comparatively lower electron-donating ability of the sp3N and relatively higher electron-donating ability of sp2N of the N4 ligands is beneficial to getting higher activity and selectivity, thus providing us a new view to understand epoxidation with H2O2. (Figure presented.).
Synthesis of new benzimidazole and phenylhydrazinecarbothiomide hybrids and their anticonvulsant activity
Siddiqui, Nadeem,Alam, Md. Shamsher,Ali, Ruhi,Yar, M. Shahar,Alam, Ozair
, p. 1390 - 1402 (2016/07/06)
A series of new benzimidazole derivatives (4a–p) were synthesized and evaluated for anticonvulsant activity in albino mice against two most adopted models, i.e. maximal electroshock seizure (MES)- and subcutaneous pentylenetetrazole (scPTZ)-induced seizures. Synthesized compounds were also screened for possible neurotoxicity using rotarod test. Among the synthesized compounds, 4p showed the most promising activity in MES and scPTZ screens, which was further subjected for oral activity in rats. At a dose of 30?mg/kg, it showed tremendous activity in the scPTZ screen. The acute toxicity study (LD50) of compounds showed that only two tested compounds 4f and 4m did not produce any mortality at any of the dose level. Molecular properties and pharmacokinetic parameters of the titled compounds were also determined using Lipinski’s rule of five. The promising results encourage future investigation on the rational modification of this nucleus for development of better compounds.
Synthesis of 1-alkyl-2-chloromethylbenzimidazole under green conditions
Rao, S. Srinivas,Reddy, Ch. Venkata Ramana,Dubey
, p. 98 - 100 (2015/01/30)
A green approach for the synthesis of 1-alkyl-2-chloromethylbenzimidazoles (3) (R1 = CH3, C2H5, CH2Ph) under, different conditions has been developed from 2-chloromethylbenzimidazole (2) by reaction with an alkylating agent (i.e. DMS, DES, PhCH2Cl) by physical grinding or by using green solvent like PEG-600 or by using micro-wave irradiation technique.
BENZIMIDAZOLES FOR THE TREATMENT OF CANCER
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Page/Page column 111-112, (2014/03/22)
The present invention relates to novel substituted benzimidazoles and stereoisomeric forms, prodrugs, solvates, hydrates and/or pharmaceutically acceptable salts of these compounds as well as pharmaceutical compositions containing at least one of these substituted benzimidazoles together with pharmaceutically acceptable carrier, excipient and/or diluents. Said novel substituted benzimidazoles binding to the prenyl binding pocket of PDEδ have been identified as useful for the prophylaxis and treatment of cancer by the inhibition of the binding of PDEδ to K-Ras and of oncogenic Ras signalling in cells by altering its localization leading to cell death or inhibition of proliferation.
A facile solvent-free synthesis of 1-alkyl/aralkyl-2-(1-arylsulfonyl alkyl) benzimidazoles using "tBAB" as surface catalyst
Dubey,Prasada Reddy,Srinivas
experimental part, p. 1317 - 1322 (2010/12/29)
Reaction 2-(α-chloroalkyl)benzimidazoles 1 with aryl sulphinate sodium salt 2 under solvent-free conditions in the presence of tetrabutylammonium bromide as surface catalyst, by simple physical grinding using mortar and pestle, gives 1H-2-(α-arylsulfonylalkyl)benzimidazoles 3. The latter on treatment with alkylating agents under solvent-free conditions results in 1-alkyl/aralkyl-2-(α-arylsulfonylalkyl)benzimidazoles 4. Alternatively, 4 can also be prepared directly from 1-alkyl/aralkyl-2-(α- chloroalkyl)benzimidazoles 5 by reaction with 2, which in turn could be prepared by reaction of 1 with alkylating agents under solvent-free conditions and all these reactions are free from organic solvents including experimental procedures.
Synthesis of 1-alkyl/aralkyl-2-(1-arylsulfonylalkyl)benzimidazoles under PTC conditions
Dubey,Prasada Reddy,Srinivas
, p. 488 - 491 (2008/09/18)
2-(α-chloroalkyl)benzimidazoles 1 on reaction with arylsulphinate sodium salt 2, in CH3CN under PTC conditions, gives 3 which on alkylation yields 1-alky/aralkyl-2-(α-aryl sulfonylalkyl)benzimidazoles 4. Alternatively, 4 can also be prepared by the reaction of 2 with 1-alkyl/aralkyl-2-(α-chloroalkyl)benzimidazole 5 in CH3CN using triethylbenzylammonium chloride (TEBAC) as PTC. 5 are obtained from 1 in turn, by alkylation in CH3CN under PTC conditions.
