38423-40-4Relevant articles and documents
Two-step synthetic route to 10-substituted isoalloxazines
Chattopadhyay, Prosenjit,Rai, Roopali,Pandey, Pramod S.
, p. 1857 - 1861 (2006)
10-Substituted isoalloxazines were synthesized in two steps starting from 1,2-phenylenediamine. Monoalkylation of the diamine resulted in 2-amino-N-alkylanilines, which were subsequently condensed with alloxan in boric acid and acetic acid to give 10-subs
Synthesis of 1,2-disubstituted benzimidazoles through DDQ-oxidized intramolecular dehydrogenative coupling of N,N′-dialkyl o-phenylenediamines
Feng, Yangyang,Ma, Youcai,Xiong, Ruimei,Xiong, Yan,Zhang, Xiaohui
supporting information, (2020/09/02)
The synthetic methodology of 1,2-disubstituted benzimidazoles has been developed, which starts from N,N′-dialkyl o-phenylenediamines via intramolecular dehydrogenative coupling under the oxidation of DDQ with mild conditions. Through detailed optimization of reaction conditions, only DDQ was found essential without any additives to reach to the highest yield of 99%. In the cases of linear aliphatic substituents, the synthesis of 1-alkyl-2-phenylbenzimidazoles showed high selectivities and their structures were identified by 2D NMR COSY correlation analysis. A plausible mechanism was proposed to interpret the observed reactivities and selectivities.
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.