Convenient synthesis, characterization, cytotoxicity and toxicity of pyrazole derivatives.

Publisher: Slovenian Chemical Society Country of Publication: Slovenia NLM ID: 101247110 Publication Model: Print Cited Medium: Print ISSN: 1318-0207 (Print) Linking ISSN: 13180207 NLM ISO Abbreviation: Acta Chim Slov Subsets: MEDLINE

Original Publication: Ljubljana : Slovenian Chemical Society,

Antineoplastic Agents/*chemical synthesis ; Antineoplastic Agents/*pharmacology ; Pyrazoles/*chemistry ; Pyrazoles/*toxicity; Antineoplastic Agents/chemistry ; Antineoplastic Agents/toxicity ; Cell Proliferation/drug effects ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Hep G2 Cells ; Humans ; MCF-7 Cells ; Molecular Structure ; Pyrazoles/chemical synthesis ; Structure-Activity Relationship ; Tumor Cells, Cultured

3-Methyl-1H-pyrazol-5(4H)-one (1) was used as a template to develop new anticancer compounds and investigate their SAR. The ring modification of compound 1 occurred through its reaction with aromatic aldehydes and different reagents to afford the corresponding 6-oxopyrano[2,3-c]pyrazoles4a-c and their amino analogues 6-aminopyrano[2,3-c]pyrazoles6a-c, 8; the pyrazolopyrano[2,3-b]pyridines 10a-c and the chromenopyrano[2,3-c]pyrzolones13, 14. The reaction of compound 1 with thiourea and appropriate aromatic aldehydes afforded the pyrazolo[3,4-d]pyrimidine derivatives 17a-c. On the other hand, the pyrazolo[3,4-d]thiazole derivatives 22a-d were obtained via the reaction of 1 with sulpher and aryl isothiocyanates in presence of triethylamine. The reaction of compound 1 with phenylisothiocyanate followed by treatment with the a-halocarbonyl compounds 24a-c afforded the thiazole derivatives 25a-c. The synthesized products were evaluated for their cytotoxicity against cancer and normal cell lines. Most compounds showed significant anticancer activity without affecting the normal fibroblast cells. The toxicity of the mostpontent cytotoxic compounds was measured using Brine-Shrimp Lethality Assay.

0 (Antineoplastic Agents)
0 (Pyrazoles)

Date Created: 20150402 Date Completed: 20150522 Latest Revision: 20191113

20221213

10.17344/acsi.2014.828

25830970