Open AccessDesign, Synthesis and Antimicrobial Evaluation of Novel 2-Thiobenzimidazole Derivatives: in silico and in vitro Approach
Author(s) -
Chilamakuru Naresh Babu,
Singirisetty Triveni,
M Jyothi,
B. Yamuna,
A. Yamini
Publication year - 2020
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2020.22821
Subject(s) - chemistry , benzimidazole , dna gyrase , adme , lanosterol , antimicrobial , stereochemistry , lipinski's rule of five , imidazole , combinatorial chemistry , antibacterial activity , docking (animal) , in vitro , in silico , biochemistry , escherichia coli , organic chemistry , bacteria , medicine , genetics , sterol , nursing , cholesterol , biology , gene
The development of potent antimicrobial agents is more essential due to resistance developed inmicroorganisms towards the existing drugs. The diversity in the biological retort profile of benzimidazolemore attracted the attention to develop novel compounds to its various potential against microorganisms.In present work, designed molecular structures docked against DNA gyrase subunit B and lanosterol14α-demethylase (LAD) proteins. Interestingly, most of the compounds revealed excellent dockingscores and interactions compared with the co-crystal ligands KKK, 1YN of LAD proteins 3LD6,5V5Z than DNA gyrase subunit B proteins 5L3J and 4P8O. Then, the molecular properties werepredicted by the Swiss ADME tool, the compounds showed no violation in Lipinski’s rule and goodsynthetic accessibility. These compounds synthesized by stirring of 2-mercapto benzimidazole (1),epichlorohydrin (2) in the presence of sodium hydroxide gives 1-(1H-benzo[d]imidazole-2-ylthio)-3-chloropropan-2-ol (3), which upon refluxing with different substituted aliphatic and aromatic aminesin methanol produces novel benzimidazole derivatives (4a-l). These compounds were characterizedby their melting point, FT-IR, 1H NMR and Mass spectral data. The synthesized molecules screenedfor antibacterial and antifungal activity. The compound 4l exhibited excellent activity at MIC 0.4μg/mL against C. albicans. Compounds 4c and 4e showed MIC at 3.12 μg/mL against E. coli and thecompounds 4l and 4J exhibited MIC at 3.12 μg/mL against S. aureus. Docking studies and activityresult reveals the novel benzimidazole compound 4l has excellent antifungal and antibacterial effect.