Synthesis of novel benzimidazole functionalized chiral thioureas and evaluation of their antibacterial and anticancer activities

  • Bioorg Med Chem Lett. 2014 Oct 15;24(20):4822-5. doi: 10.1016/j.bmcl.2014.08.064.
Sridhar Madabhushi  1 ,  Kishore Kumar Reddy Mallu  2 ,  Venkata Sairam Vangipuram  2 ,  Srinivas Kurva  2 ,  Y Poornachandra  3 ,  C Ganesh Kumar  3
Affiliations
  • 1. Fluoroorganics Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500 007, India. Electronic address: [email protected].
  • 2. Fluoroorganics Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500 007, India.
  • 3. Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500 007, India.
PMID: 25241926 DOI: 10.1016/j.bmcl.2014.08.064
Abstract

A small library of benzimidazole functionalized chiral thioureas was prepared starting from natural Amino acids (S)-alanine, (S)-phenylalanine, (S)-valine and (S)-leucine and also their (R)-isomers and studied their antimicrobial activity against a various Gram-positive and Gram-negative Bacterial strains. In this study, compounds 5g and 5j were found to exhibit good Antibacterial activity against both Gram-positive and Gram-negative Bacterial strains such as Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus, Klebsiella planticola, Escherichia coli and Pseudomonas aeruginosa. In the cytotoxicity study, thioureas derived from non-natural Amino acids 5a-l showed good activity against human Cancer cell lines A549, MCF7, DU145, HeLa, and no cytotoxicity was observed with their antipodes 6a-l.

Keywords
Amino acids; Antibacterial activity; Anticancer activity; Chiral thioureas.