Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents.
A new series of 1,4-bis(1-(5-(aryldiazenyl)thiazol-2-yl)-5-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)benzenes 3a-i were synthesized via reaction of 5,5'-(1,4-phenylene)bis(3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide) (1) with hydrazonoyl halides 2a-i. In addition, reaction of 1 with ethyl chloroacetate afforded bis-thiazolone derivative 8 as the end product. Reaction of compound 8 with methyl glyoxalate gave bis-thiazolone derivative 10. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences and their alternative syntheses. All the synthesized compounds were evaluated for their anti-tumor activities against hepatocellular carcinoma (HepG2) cell lines, and the results revealed promising activities of compounds 3g, 5e, 3e, 10, 5f, 3i, and 3f with IC50 equal 1.37 ± 0.15, 1.41 ± 0.17, 1.62 ± 0.20, 1.86 ± 0.20, 1.93 ± 0.08, 2.03 ± 0.25, and 2.09 ± 0.19 μM, respectively.
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt. s.m.gomha@gmail.com.
Sobhi M
SM
Gomha
Department of Organic Chemistry, National Organization for Drug Control and Research (NODCAR), Giza 12311, Egypt. mmohamededrees@yahoo.com.|Faculty of Science, King Khalid University, Abha 61413, Saudi Arabia. mmohamededrees@yahoo.com.
Mastoura M
MM
Edrees
Department of Measurements and Environmental Applications, National Institute of Laser Enhanced Sciences (NILES), Cairo University, Giza 12613, Egypt. f_altalbawy@yahoo.com.
Farag M A
FM
Altalbawy
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D066241:Carbon-13 Magnetic Resonance Spectroscopy / Q000379:methods; D002470:Cell Survival / Q000187:drug effects; D002626:Chemistry, Pharmaceutical / Q000379:methods; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D056945:Hep G2 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D066244:Proton Magnetic Resonance Spectroscopy / Q000379:methods; D011720:Pyrazoles / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry*
D000970:Antineoplastic Agents; D011720:Pyrazoles; D013844:Thiazoles; D013876:Thiophenes; C031280:pyrazole
anticancer agents; bis-chalcones; bis-heterocycles; hydrazonoyl halides