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

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

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

Molecules. 2020 Jun 11;25(11):E2708.

PMID: 32545272

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 IC50 values 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP287476179	2-Chloro-4-ethylamino-15N-6-isopropylamino-1,3,5-triazine		287476-17-9	Price

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