Synthesis, antibacterial and antifungal activities of 3-(1,2,4-triazol-3-yl)-4-thiazolidinones

A new series of 3-(1,2,4-triazol-3-yl)-4-thiazolidinone derivatives has been synthesized by the reaction of Schiff bases of 3-amino-1,2,4-triazoles with mercaptoacetic acid and 2-mercaptopropionic acid. Their antibacterial and antifungal activities were evaluated against S. aureus, S. epidermidis, C. albicans and C. glabrata

5-Chloro-N-{4-oxo-2-[4-(trifluoromethyl)-phenyl]-1,3-thiazolidin-3-yl}-3-phenyl-1H- indole-2-carboxamide

In the title compound, C25H17ClF3N3O2S, the five-membered 1,3-thiazolidine ring adopts a twist conformation. The three F atoms of the CF3 group are disordered over two sets of sites with refined occupancies of 0.542 (18) and 0.458 (18). In the nine-membered 1H-indoline ring system, the 1H-pyrrole ring forms a dihedral angle of 4.7 (2)degrees with the benzene ring, while it is twisted at an angle of 46.5 (2)degrees with respect to the attached phenyl ring. The dihedral angle between the phenyl and trifluoromethyl-substituted benzene rings is 56.0 (2)degrees. In the crystal, N-H center dot center dot center dot O hydrogen bonds connect the molecules into a three-dimensional network. In addition, weak C-H center dot center dot center dot O hydrogen bonds and weak C-H center dot center dot center dot pi interactions are observed

Synthesis and biological evaluation of indole-2-carbohydrazides and thiazolidinyl-indole-2-carboxamides as potent tubulin polymerization inhibitors

A new series of N'-(substituted phenyl)-5-chloro/iodo-3-phenyl-1H-indole-2-carbohydrazide (5, 6) and N-[2-(substituted phenyl)-4-oxo-1,3-thiazolidin-3-yl]-5-iodo/chloro-3-phenyl-1H-indole-2-carboxamide (7, 8) derivatives were synthesized and evaluated for their anticancer properties. Compounds 5a and 6b, selected as prototypes by the National Cancer Institute for screening against the full panel of 60 human tumor cell lines at a minimum of five concentrations at 10-fold dilutions, demonstrated remarkable antiproliferative activity against leukemia, non-small cell lung cancer, colon cancer, central nervous system (CNS) cancer, melanoma, ovarian cancer, renal cancer, and breast cancer (MCF-7) cell lines with GI(50) values < 0.4 mu M. A subset of the compounds was then tested for their potential to inhibit tubulin polymerization. Compounds 6f and 6g showed significant cytotoxicity at the nM level on MCF-7 cells and exhibited significant inhibitory activity on tubulin assembly and colchicine binding at about the same level as combretastatin A-4. Finally, docking calculations were performed to identify the binding mode of these compounds. Group 5 and 6 compounds interacted with the colchicine binding site through hydrophobic interactions similar to those of colchicine. These compounds with antiproliferative activity at high nanomolar concentration can serve as scaffolds for the design of novel microtubule targeting agents