Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones.

Autor: Mashayekhi, Vida; Haj Mohammad Ebrahim Tehrani, Kamaleddin; Azerang, Parisa; Sardari, Soroush; Kobarfard, Farzad

Publication year: 2021

Archives of pharmacal research

issn:1976-3786 0253-6269

doi: 10.1007/s12272-013-0242-z

Abstract:

Based on the structural elements of bioactive indole-based compounds, a series of novel 1-substituted indole-3-carboxaldehyde thiosemicarbazones were synthesized as potential antimycobacterial and anticancer agents. The derivatives were prepared via a two-step methodology including N-alkylation(benzylation) of indole-3-carboxaldehyde and conversion of the intermediate aldehydes to corresponding thiosemicarbazones. The derivatives were evaluated for their antimycobacterial activity and compounds 3d (R = propyl) and 3q (R = 4-nitrobenzyl) were among the most potent and selective derivatives with IC(50) values of 0.9 and 1.9 μg/mL respectively. The anticancer activity of the derivatives was also assessed against a panel of tumor cell lines. Compounds 3t, 3u, 3v and 3w efficiently inhibited the majority of the cancer cell lines with considerable selectivity.

Language: eng

Pmid: 24062081

Tags: Humans; Animals; Mice; 1-Substituted indole-3-carboxaldehydes; Anti-Bacterial Agents/chemical synthesis/chemistry/*pharmacology; Anticancer; Antimycobacterial activity; Antineoplastic Agents/chemical synthesis/chemistry/*pharmacology; Cell Line, Tumor; Indoles/chemical synthesis/chemistry/*pharmacology; Inhibitory Concentration 50; MTT assay; Mycobacterium bovis/drug effects; Neoplasms/drug therapy/pathology; Structure-Activity Relationship; Thiosemicarbazone; Thiosemicarbazones/chemical synthesis/chemistry/*pharmacology

Link: https://pubmed.ncbi.nlm.nih.gov/24062081/