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Facile Synthesis and Anticancer Evaluation of Novel 1-(Thiazol-2-yl)-3-(thiazol-5-yl)-5-(thiophen-2-yl) Pyrazolines

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Abstract

Some novel pyrazoline derivatives bearing thiazole and thiophene moieties have been efficiently synthesized and characterized. The synthetic approach involves condensation of 5-acetylthiazole 1 with 2-formyl thiophene 2 followed by heterocyclization of the produced chalcone 3 with hydrazine and thiosemicarbazide under different conditions to give selectively 1-substituted-3-(thiazol-5-yl)-5-(thiophen-2-yl)pyrazolines 4–6 and 8 in high yields. Heterocyclization of 1-thicarbomylpyrazoline 8 with 3-chloro-2,4-pentanedione, phenacyl bromide and hydrazonoyl bromides in boiling ethanol and TEA results in the respective 1-(thiazol-2-yl)-3-(thiazol-5-yl)-5-(thiophen-2-yl)pyrazolines 11, 12, and 14a–14f. Anticancer activity of the novel 1,3,5-trisubstituted pyrazolines has been evaluated, against breast (MCF-7), liver (HepG2), and colon (HCT-116) cancer cell lines, as well as epithelial (REP1) normal cell line. Among the synthesized pyrazolines, compounds 8, 14a, and 14f demonstrate the highest anticancer activity with IC50 values of 1.83, 5.47, and 11.43 µM, respectively, and presenting no evidence of human toxicity.

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Funding

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through a research group project under grant no. RGP.1/32/42. The authors would like to express their gratitude to King Khalid University, Abha, Saudi Arabia for providing administrative and technical support.

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Authors and Affiliations

  1. Chemistry Department, College of Science, King Khalid University, 9004, Abha, Saudi Arabia

    Samir Bondock, Omeer Albormani & Ahmed M. Fouda

  2. Chemistry Department, Faculty of Science, Mansoura University, 35516, Mansoura, Egypt

    Samir Bondock

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  1. Samir Bondock
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  2. Omeer Albormani
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  3. Ahmed M. Fouda
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Correspondence to Samir Bondock.

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Bondock, S., Albormani, O. & Fouda, A.M. Facile Synthesis and Anticancer Evaluation of Novel 1-(Thiazol-2-yl)-3-(thiazol-5-yl)-5-(thiophen-2-yl) Pyrazolines. Russ J Gen Chem 92, 1098–1108 (2022). https://doi.org/10.1134/S1070363222060226

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