Article detail · 2023
Semicarbazides Carrying Indole Core: Synthesis, Cytotoxicity Evaluation against Human Breast Cancer Cell Lines, and Molecular Modeling Studies
Journal
Chemistry &BiodiversityISSN 1612-1872
The ISSN points to another catalog journal; the name is from the YÖKSİS record.
- Year
- 2023
- Type
- article
Data source split
- YÖKSİS YÖKSİS article record
- YÖKSİS venue Chemistry &Biodiversity
- Catalog match (ISSN) Chemistry and Biodiversity
- OpenAlex OpenAlex enrichment (abstract, citations, topics)
Abstract
English (OpenAlex)
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 1H‐NMR, 13C‐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.
Topics
- Synthesis and biological activity
- Synthesis and Characterization of Heterocyclic Compounds
- Synthesis and Biological Evaluation
Primary topic Synthesis and biological activity