Syntheses of heterocyclic derivatives as potential cytotoxic compounds evaluated toward hepatocellular and cervical carcinoma cell lines

ABSTRACT. Through the present work the 3-oxo-N,3-diphenylpropamide derivatives 5a,b were used to synthesize pridine, pyrazole and thiophene derivatives. 3-Phenylisoxazol-5(4H)-one produced from the reaction of ethyl benzoylacetate was used as the key starting compound for different multi-component reactions. The synthesized compounds were evaluated toward Hepatocellular carcinoma HepG2 and cervical carcinoma HeLa cell lines. Compounds 3b, 5b, 7b, 7d, 9c, 9d, 15e, 15f, 16b, 18b, 18e, 18f, 19e and 19f were the most cytotoxic compounds against the tested cell lines. The results obtained in this work encourage further work in the future to produce new cytotoxic compounds.   KEY WORDS: Diphenylpropamide, 3-Phenylisoxazole, Pyran, Pyridine, Cytotoxicity Bull. Chem. Soc. Ethiop. 2023, 37(1), 141-158.                                                              DOI:https://dx.doi.org/10.4314/bcse.v37i1.1

Uses of chalcone acetophenone to synthesis heterocyclic compounds with cytotoxic and c-Met kinase activities

ABSTRACT. The aim of present study was the uses of a series of α,β-unsaturated carbonyl compounds (chalcones), in the synthesis of pyridine, pyran, thiophene, thiazole, together with their uses in heterocyclic synthesis. The work has resulted in the synthesis of a variety of 2,5-dihydropyridine, hydrazide-hydrazone, thiophene derivatives, coumarin, pyran and thiazolo[4,5-d]thiazole derivatives. The antitumor activities of the newly synthesized products were carried out against three cancer cell lines namely MCF-7, NCI-H460 and SF-268 and normal human cell line WI38.  In addition, the inhibitions of most of the synthesized compounds against             c-Met kinase were studied and results showed that many compounds were of high inhibitions, and these are considered as promising anticancer agents. The results obtained encouraged further work in the future.    KEY WORDS: Chalcones, Heterocyclic, Pyridine, Pyran, Thiophene, Thiazole, Antitumor Bull. Chem. Soc. Ethiop. 2022, 36(1), 149-172.                                                             DOI: https://dx.doi.org/10.4314/bcse.v36i1.13                                                      &nbsp

Synthesis and cytotoxicity evaluation of thiazole derivatives obtained from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile

Reactivity of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile towards thioglycolic acid resulted in thiazole derivative 1. The latter reacted with different chemical reagents to give thiazole, pyrano[2,3-d]thiazole and thiazolo[4,5-d]thiazole derivatives. Cytotoxicity effects of the newly synthesized products against six cancer cell lines, namely, human gastric cancer (NUGC), human colon cancer (DLD-1), human liver cancer (HA22T and HEPG-2), human breast cancer (MCF) and nasopharyngeal carcinoma (HONE-1) as well as against a normal fibroblast cell (WI-38) were evaluated. The study showed that the 4,5,6,7 tetrahydrobenzo[b]thiophene derivatives 6a, 7, 8a,b, 9b and 10b,c were the most active compounds. Their potencies were attributed to the presence of the electron withdrawing groups

Novel Synthesis of Hydrazide-Hydrazone Derivatives and Their Utilization in the Synthesis of Coumarin, Pyridine, Thiazole and Thiophene Derivatives with Antitumor Activity

The reaction of cyanoacetyl hydrazine (1) with 3-acetylpyridine (2) gave the hydrazide-hydrazone derivative 3. The latter compound undergoes a series of heterocyclization reactions to give new heterocyclic compounds. The antitumor evaluation of the newly synthesized products against three cancer cell lines, namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) was performed. Most of the synthesized compounds showed high inhibitory effects

Uses of 3-(2-Bromoacetyl)-2H-chromen-2-one in the Synthesis of Heterocyclic Compounds Incorporating Coumarin: Synthesis, Characterization and Cytotoxicity

In this work, 3-bromoacetylcoumarin was used as the key starting material for the synthesis of pyran, pyridine, thiophene, thiazole and pyrazole derivatives through its reaction with different reagents. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data and elemental analyses. All of the synthesized compounds were screened for their in vitro anticancer activity against six human cancer cell lines, namely: human gastric cancer (NUGC), human colon cancer (DLD1), human liver cancer (HA22T and HEPG2), nasopharyngeal carcinoma (HONE1), human breast cancer (MCF) and normal fibroblast cells (WI38). The IC50 values (the sample concentration that produces 50% reduction in cell growth) in nanomolars (nM)) showed most of the compounds exhibited significant cytotoxic effect. Among these derivatives, compound 6d showed almost equipotent cytotoxic activity against NUGC (IC50 = 29 nM) compared to the standard CHS 828 (IC50 = 25 nM)

The reaction of cyanoacetylhydrazine with ω-bromo-(4methyl)acetophenone: Synthesis of heterocyclic derivatives with antitumor activity

molecule