Synthesis and in vitro anticancer activity of some novel tetrahydroquinoline derivatives bearing pyrazol and hydrazide moiety

Abstract

A new series of tetrahydroquinoline derivatives having pyrazol and hydrazide moieties were synthesized for the purpose of anticancer cell line evaluation. Syntheses of these compounds were firstly achieved by one pot four reactions.The reaction of 3-amino-tetrahydro-1H-pyrazolo [3,4-b]quinolin with aldehydes, indoline-2,3-dione derivatives to give 9a-c, 11a-c, and 13a,b, respectively. In similar manner for biological comparison, the reactions of compound 5 with the same aldehydes and indoline-2,3-dione derivatives to give 19a-c and 20a-c. The newly synthesized compounds were examined in vitro for their cytotoxic activity against HepG-2 and A549 cancer cells. The compounds 11a-c and 20a-c showed promising activity as anticancer agents against HepG-2 and A549 cancer cells.

Facile synthesis and in vitro anticancer evaluation of a new series of tetrahydroquinoline

“…In this study, THQ, chloroquinoline, pyrazolo quinoline, and mercapto quinoline moiety were constructed early at the sequence ring, allowing for a quick, flexible substitution and replacement route. Consequently, and in continuation of our research [31,32]. The primary tetrahydroquinoline ring's substitution profile was designed to include various equivalents that would offer a different electronic, lipophilic, and steric environment, influencing the biological activities targeted.…”

Recent Advances in the Development of Pyrazole Derivatives as Anticancer Agents

“…In vitro anticancer assays showed compound 105 effectively inhibited MCF7 and HeLa cells with GI50 of 30. Fathy et al prepared new tetrahydroquinoline-pyrazole-hydrazide derivatives and assayed their in vitro anticancer activity against HepG2 and A549 cells [125]. The highest inhibitory activity against HepG2 and A549 was demonstrated by compound 108 (IC 50 = 1.1 and 1.37 µM).…”

Synthesis, Crystal Growth, and Computational Investigation of New Tetrahydroisoquinoline Derivatives Potent against Molecule Nitric Oxide Synthases

“…Density functional theory (DFT) calculations were performed in the gas phase approximation using the Gaussian 09 software [12] to investigate the electronic and optical properties of IVa and IVb. The DFT study used the hybrid B3LYP functional with the double zeta split valence basis set (6-31+G(d,p)) method for optimization and property calculations, as this method is considered suitable for calculating the electronic and nonlinear optical properties of molecules and clusters.…”

“…In addition to NO, nNOS creates H 2 O 2 under physiological conditions, which contributes to endothelial-dependent vascular relaxation [10]. Endothelial nNOS-derived H 2 O 2 production failure has been linked to atherosclerosis [11] and hypertension [12]. By incorporating NO-donors (e.g., ester nitrates, furoxans, benzofuroxans, NONOates, S-nitrosothiols, or metal complexes) into molecules that already have potential therapeutic value, hybrid compounds with an NO release advantage can be produced while keeping the activity of the native medicine.…”