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Chem Biodivers ; 20(8): e202300609, 2023 Aug.
Article in English | MEDLINE | ID: mdl-37423889

ABSTRACT

In this article, we report the synthesis and cytotoxicity evaluation of novel indole-carrying semicarbazide derivatives (IS1-IS15). The target molecules were obtained by the reaction of aryl/alkyl isocyanates with 1H-indole-2-carbohydrazide that was in-house synthesized from 1H-indole-2-carboxylic acid. Following structural characterization by 1 H-NMR, 13 C-NMR, and HR-MS, IS1-IS15 were investigated for their cytotoxic activity against human breast cancer cell lines, MCF-7 and MDA-MB-231. According to the data obtained from the MTT assay, phenyl ring with a lipophilic group at its para-position and alkyl moiety were preferential substituents on the indole-semicarbazide scaffold for antiproliferative activity. The effect of IS12 (N-(4-chloro-3-(trifluoromethyl)phenyl)-2-(1H-indole-2-carbonyl)hydrazine-1-carboxamide), the compound that demonstrated remarkable antiproliferative activity on both cell lines, was also evaluated on the apoptotic pathway. Moreover, the calculation of critical descriptors constituting drug-likeness confirmed the position of the selected compounds in the anticancer drug development process. Finally, molecular docking studies suggested the inhibition of tubulin polymerization as the potential activity mechanism of this class of molecules.


Subject(s)
Antineoplastic Agents , Breast Neoplasms , Humans , Female , Structure-Activity Relationship , Molecular Docking Simulation , Breast Neoplasms/drug therapy , Drug Screening Assays, Antitumor , Cell Proliferation , Antineoplastic Agents/chemistry , Cell Line , Indoles/chemistry , Semicarbazides/pharmacology , Molecular Structure , Cell Line, Tumor
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