Title:An Efficient Nonconventional Glycerol-Based Solid Acid Catalyzed Synthesis and Biological Evaluation of Phosphonate Conjugates of 1,2,4-triazole Thiones
VOLUME: 13 ISSUE: 9
Author(s):Madugula S. R. Murty, Mohana R. Katiki, Busam R. Rao, Sai S. Narayanan, Ruby J. Anto, Sudhreer K. Buddana, Reddy S. Prakasham, Bethala L. A. P. Devi and Rachapudi B. N. Prasad
Affiliation:Medicinal Chemistry & Pharmacology Division, Discovery Laboratory, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Keywords:5-Aryl-1H-1, 2, 4-triazole-3-thione, diethyl phosphonate, anticancer activity, antibacterial activity, antifungal
activity.
Abstract:A series of diethyl (3-((5-aryl-1H-1,2,4-triazol-3-yl)thio)propyl)phos-phonates (7a–t) has
been synthesized in excellent yields by coupling diethyl (3-bromopropyl)phosphonate and 5-aryl-1H-1,2,4-triazol-3-thiones employing an efficient, green and nonconventional heterogeneous SO3Hcarbon
catalyst derived from glycerol. In addition, a facile and green approach for the esterification
of carboxylic acids by utilizing glycerol-based solid acid catalyst has been reported. Structures of the
synthesized compounds were characterized by IR, NMR and HRMS studies. These triazole derivatives
were screened for their in vitro cytotoxicity using the standard MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetra-zolium bromide) assay against a panel of five different human cancer cell lines
(HeLa: Cervix, A549: Lung, A375: Skin, MDA-MB-231: Breast and T98G: Brain). The antimicrobial
activities of the synthesized compounds were investigated against four bacterial strains: Bacillus
subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and three fungal strains:
Aspergillus niger, Aspergillus terreus, Aspergillus fumigatus. Preliminary results indicate that the
compound 7f displayed maximum anticancer activity and the compounds 7d, 7e, 7f, 7m and 7q exhibited
moderate antibacterial activity. The compounds 7g, 7h, 7o and 7p showed good antifungal
activity with high inhibition zone diameter compared to the standard drug.
