Synthesis, anticancer activity and ADMET studies of N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-[(3-substituted)ureido/thioureido] benzenesulfonamide derivatives

KARAKUŞ S., TOK F., Tuerk S., ŞALVA E., Tatar G., Taskin-Tok T., ...More

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.193, no.8, pp.528-534, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 193 Issue: 8
  • Publication Date: 2018
  • Doi Number: 10.1080/10426507.2018.1452924
  • Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.528-534
  • Keywords: Urea, thiourea, anticancer activity, in silico ADMET, BIOLOGICAL EVALUATION, MOLECULAR DOCKING, AGENTS, SULFONAMIDES, INHIBITORS, DISCOVERY, THIOUREAS, CURCUMIN, UREA
  • Karadeniz Technical University Affiliated: No

Abstract

A series of novel 4-[(3-substituted)ureido]-N-(5-methyl-1,3,4-thiadiazol-2-yl) benzenesulfonamides and 4-[(3-substituted)thioureido]-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamides were prepared from 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide (sulfamethizole). The structures of the synthesized compounds were determined by IR, H-1-NMR, MS and elemental analysis. The anticancer activity of these compounds was evaluated against human colorectal carcinoma (HCT116) and human cervix carcinoma (HeLa) cell lines. Compound 4 (4-{[(2,4-dichlorophenyl)carbamoyl]amino}-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide) showed marked anticancer activity, being the most active compounds in this series with the IC50 value of 13.92 +/- 0.22 mu M and 37.91 +/- 0.10 mu M against HeLa and HCT116, respectively. In silico, ADMET was used to examine their pharmacokinetic properties. ADMET (absorption, distribution, metabolism, excretion, and toxicity) studies were applied to develop new anticancer compound(s) with high selectivity.