Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents

Gomha, Sobhi M.; Edrees, Mastoura M.; Altalbawy, Farag M. A.

doi:10.3390/ijms17091499

Open AccessArticle

Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents

by

Sobhi M. Gomha

¹

,

Mastoura M. Edrees

^2,3

and

Farag M. A. Altalbawy

^4,*

¹

Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt

²

Department of Organic Chemistry, National Organization for Drug Control and Research (NODCAR), Giza 12311, Egypt

³

Faculty of Science, King Khalid University, Abha 61413, Saudi Arabia

⁴

Department of Measurements and Environmental Applications, National Institute of Laser Enhanced Sciences (NILES), Cairo University, Giza 12613, Egypt

^*

Author to whom correspondence should be addressed.

Int. J. Mol. Sci. 2016, 17(9), 1499; https://doi.org/10.3390/ijms17091499

Submission received: 2 April 2016 / Revised: 24 August 2016 / Accepted: 1 September 2016 / Published: 7 September 2016

(This article belongs to the Section Biochemistry)

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Abstract

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.

Keywords: bis-heterocycles; bis-chalcones; hydrazonoyl halides; anticancer agents

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MDPI and ACS Style

Gomha, S.M.; Edrees, M.M.; Altalbawy, F.M.A. Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents. Int. J. Mol. Sci. 2016, 17, 1499. https://doi.org/10.3390/ijms17091499

AMA Style

Gomha SM, Edrees MM, Altalbawy FMA. Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents. International Journal of Molecular Sciences. 2016; 17(9):1499. https://doi.org/10.3390/ijms17091499

Chicago/Turabian Style

Gomha, Sobhi M., Mastoura M. Edrees, and Farag M. A. Altalbawy. 2016. "Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents" International Journal of Molecular Sciences 17, no. 9: 1499. https://doi.org/10.3390/ijms17091499

APA Style

Gomha, S. M., Edrees, M. M., & Altalbawy, F. M. A. (2016). Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents. International Journal of Molecular Sciences, 17(9), 1499. https://doi.org/10.3390/ijms17091499

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

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Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents

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