Synthesis, characterization, anticancer and in silico studies of a pyrazole-tethered thiazolidine-2,4-dione derivative

Autor:	Ashanul Haque, Meher Rizvi, Khalaf M. Alenezi, Raoudha Soury, Md. Mushtque, Musherah M. Alshammari
Rok vydání:	2021
Předmět:	chemistry.chemical_compound Structural Biology Chemistry In silico Knoevenagel condensation General Medicine Pyrazole Cytotoxicity Molecular Biology Combinatorial chemistry Derivative (chemistry) Thiazolidine 2 4 dione Molecular hybridization
Zdroj:	Journal of Biomolecular Structure and Dynamics. 40:13075-13082
ISSN:	1538-0254 0739-1102
DOI:	10.1080/07391102.2021.1981451
Popis:	A new pyrazole-tethered thiazolidine-2,4-dione derivative (8) has been synthesized by the Knoevenagel condensation of 3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (4) and 3-(2,4-dioxothiazolidin-3-yl)propanenitrile (7). The structure of the final compound was confirmed by standard spectroscopic techniques including IR spectroscopy, 1H-NMR spectroscopy, and ESI-MS mass spectrometry. Molecular features including frontier molecular orbital (HOMO-LUMO) energies, reactivity descriptors and molecular electrostatic potential (ESP) of the title molecule were determined using density functional theory (DFT) calculation. The in vitro cytotoxicity of both the intermediate (4) and final (8) compounds were investigated against cancerous (SW-480 and MCF-7) and normal (HEK-293) cell lines by MTT assay. Compound (8) displayed higher activity than (4) with higher sensitivity against breast cancer cell line and lesser toxicity. The experimental data were further complemented by docking and absorption, distribution, metabolism, and excretion (ADME) studies. Communicated by Ramaswamy H. Sarma
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::355f9977f831d730d9fe2c721f232832 https://doi.org/10.1080/07391102.2021.1981451 Zobrazit plný text záznamu