Synthesis and Characterization of New Series of 1,3-5-Triazine Hydrazone Derivatives with Promising Antiproliferative Activity

H. Al Rasheed, Hessa H. Al; M. Malebari, Azizah M.; A. Dahlous, Kholood A.; El-Faham, Ayman

doi:10.3390/molecules25112708

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Synthesis and Characterization of New Series of 1,3-5-Triazine Hydrazone Derivatives with Promising Antiproliferative Activity

Hessa H. Al H. Al Rasheed

^1,*,

Azizah M. M. Malebari

²,

Kholood A. A. Dahlous

¹ and

Ayman El-Faham

^1,3,*

Department of Chemistry, College of Science, King Saud University P.O. Box 2455, Riyadh 11451, Saudi Arabia

Department of Pharmaceutical Chemistry, College of Pharmacy, King Abdulaziz University, P.O.Box: 80260, Jeddah 21589, Saudi Arabia

Chemistry Department, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 12321, Egypt

Authors to whom correspondence should be addressed.

Academic Editor: Margherita Brindisi

Molecules 2020, 25(11), 2708; https://doi.org/10.3390/molecules25112708

Received: 10 May 2020 / Revised: 30 May 2020 / Accepted: 5 June 2020 / Published: 11 June 2020

(This article belongs to the Special Issue Nitrogen-Containing Heterocycles as Significant Molecular Scaffolds for Medicinal and Other Applications)

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Abstract

A new series of s-triazine hydrazone derivatives was prepared based on the reaction of 6-hydrazino-2,4-disubstituted-s-triazine with p-substituted benzaldehyde derivatives using a straightforward synthetic pathway. The antiproliferative activity of all synthesized compounds was evaluated against two human cancer cell lines; breast cancer MCF-7 and colon carcinoma HCT-116 using MTT assay. Among all, 11 compounds have shown strong to moderate antiproliferative activity with IC₅₀ values in the range 1.01–18.20 µM in MCF-7 and 0.97–19.51 µM in HCT-116. The best results were obtained with 4,4’-(6-(2-(pyridin-2-ylmethylene)hydrazinyl)-1,3,5-triazine-2,4-diyl) dimorpholine 11 (IC₅₀ = 1.0 µM and 0.98 µM in MCF-7 and HCT-116 cell lines, respectively). The substituents on the s-triazine core as well as the substituent at the benzylidene moiety have a great effect on the antiproliferative activity. Whereas compounds containing dimorpholino-s-triazine derivatives 8a–e showed more potent antiproliferative in MCF-7 compared to their analogs 7a–f (compounds containing two-piperidine rings), compounds containing one piperidine and one morpholine ring 9a–f showed better IC₅₀values in the range 10.4–22.2 µM. On the other hand, compounds containing two-piperidine rings 7a–f showed more potent antiproliferative in HCT-116 (IC₅₀ values in the range 8.8–19.5 µM) than their analogs 8a–e and 9a–f. View Full-Text

Keywords: s-Triazine; hydrazone derivatives; antiproliferative activity; MCF-7; HCT-116

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MDPI and ACS Style

H. Al Rasheed, H.H.A.; M. Malebari, A.M.; A. Dahlous, K.A.; El-Faham, A. Synthesis and Characterization of New Series of 1,3-5-Triazine Hydrazone Derivatives with Promising Antiproliferative Activity. Molecules 2020, 25, 2708. https://doi.org/10.3390/molecules25112708

AMA Style

H. Al Rasheed HHA, M. Malebari AM, A. Dahlous KA, El-Faham A. Synthesis and Characterization of New Series of 1,3-5-Triazine Hydrazone Derivatives with Promising Antiproliferative Activity. Molecules. 2020; 25(11):2708. https://doi.org/10.3390/molecules25112708

Chicago/Turabian Style

H. Al Rasheed, Hessa H.A., Azizah M. M. Malebari, Kholood A. A. Dahlous, and Ayman El-Faham. 2020. "Synthesis and Characterization of New Series of 1,3-5-Triazine Hydrazone Derivatives with Promising Antiproliferative Activity" Molecules 25, no. 11: 2708. https://doi.org/10.3390/molecules25112708

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Synthesis and Characterization of New Series of 1,3-5-Triazine Hydrazone Derivatives with Promising Antiproliferative Activity

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