7192-00-9Relevant articles and documents
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.
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.
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.).
