Multicomponent Solvent-free Synthesis, Antibacterial Evaluation and QSAR Study of 2-(Bis(benzylthio)methylene)malononitriles

Acta Chimica Slovenica

Parviz Baranipour¹  Hojat Samareh Delarami¹  Reza Aryan¹  Mahmood Sanchooli¹  Pouya Karimi¹  Hamid Beyzaei¹ 

[1] University of Zabol;

关键词: Multicomponent reaction;    Solvent-free;    Thioether;    Antimicrobial activity;    QSAR;   

DOI  :  10.17344/acsi.2018.4621

来源: DOAJ

【 摘 要 】

Multicomponent reaction of malononitrile, carbon disulphide and various benzyl halides was developed as an efficient strategy for the synthesis of 2-(bis(benzylthio)methylene)malononitrile derivatives via two different procedures: (a) in the presence of K2CO3 as a base in acetonitrile and (b) under solvent-free conditions in the presence of triethylamine. Higher yields with shorter reaction times were obtained from the latter procedure. Inhibitory activity of all derivatives was evaluated against 22 pathogenic bacteria including both Gram-negative and Gram-positive strains. Thioether 4b showed broad-spectrum antibacterial activities according to the antibiogram tests. DFT calculations (B3LYP/6-311++G**) were performed to determine the type of drug–receptor interactions. It was found that reversible dipole–dipole forces play a key role in most interactions.

【 授权许可】

Unknown