Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones.
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 IC50values 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.
Department of Pharmaceutical Biotechnology, School of Pharmacy, Zanjan University of Medical Sciences, Zanjan, Iran.
Vida
V
Mashayekhi
Department of Medicinal Chemistry, School of Pharmacy, Zanjan University of Medical Sciences, Zanjan, Iran.
Kamaleddin
K
Haj Mohammad Ebrahim Tehrani
Drug Design and Bioinformatics Unit, Department of Medical Biotechnology, Biotechnology Research Center, Pasteur Institute, 13164, Tehran, Iran.
Parisa
P
Azerang
Drug Design and Bioinformatics Unit, Department of Medical Biotechnology, Biotechnology Research Center, Pasteur Institute, 13164, Tehran, Iran.
Soroush
S
Sardari
Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Vali Asr Ave., Niayesh Junction, P.O. Box 14155-6153, Tehran, Iran. kobarfard@sbmu.ac.ir.|Phytochemistry Research Center, Shahid Beheshti University of Medical Sciences, Tehran, Iran. kobarfard@sbmu.ac.ir.
Farzad
F
Kobarfard
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D051379:Mice; D009163:Mycobacterium bovis / Q000187:drug effects; D009369:Neoplasms / Q000188:drug therapy / Q000473:pathology; D013329:Structure-Activity Relationship; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D007211:Indoles; D013882:Thiosemicarbazones
1-Substituted indole-3-carboxaldehydes; Anticancer; Antimycobacterial activity; MTT assay; Thiosemicarbazone