Design, computational studies, synthesis and in vitro antimicrobial evaluation of benzimidazole based thio-oxadiazole and thio-thiadiazole analogues was written by Noureldin, Nada A.;Richards, Jennifer;Kothayer, Hend;Baraka, Mohammed M.;Eladl, Sobhy M.;Wootton, Mandy;Simons, Claire. And the article was included in BMC Chemistry in 2021.Reference of 14425-64-0 This article mentions the following:
Two series of benzimidazole based thio-oxadiazole and thio-thiadiazole analogs were designed and synthesized as novel antimicrobial drugs through inhibition of phenylalanyl-tRNA synthetase (PheRS), which is a promising antimicrobial target. Compounds were designed to mimic the structural features of phenylalanyl adenylate (Phe-AMP) the PheRS natural substrate. A 3D conformational alignment for the designed compounds and the PheRS natural substrate revealed a high level of conformational similarity, and a mol. docking study indicated the ability of the designed compounds to occupy both Phe-AMP binding pockets. A mol. dynamics (MD) simulation comparative study was performed to understand the binding interactions with PheRS from different bacterial microorganisms. The synthetic pathway of the designed compounds proceeded in five steps starting from benzimidazole. The fourteen synthesized compounds 5a-d, 6a-c, 8a-d and 9a-c were purified, fully characterised and obtained in high yield. In vitro antimicrobial evaluation against five bacterial strains showed a moderate activity of compound 8b with MIC value of 32 μg/mL against S. aureus, while all the synthesized compounds showed weak activity against both E. faecalis and P. aeruginosa (MIC 128 μg/mL). Compound 8b provides a lead compound for further structural development to obtain high affinity PheRS inhibitors. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Reference of 14425-64-0).
1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Reference of 14425-64-0
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary