Synthesis of Pyridotriazolopyrimidines as Antitumor Agents. (15th June 2016)

• Record Type: Journal Article
• Authors: Abdallah, Magda A.; Gomha, Sobhi M.; Morad, Mahmoud A.; Elaasser, Mahmoud M.
• Is Part Of: Journal of heterocyclic chemistry. Volume 54:Number 2(2017:Mar.)
• Page Start: 1242
• Page End: 1251
• Publication Date: 2016-06-15
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2699
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract : 2‐Hydrazino‐5, 7‐di‐ p ‐tolylpyrido[2, 3‐ d ]pyrimidin‐4(3 H )‐one (4 ) was prepared and condensed with different aldehydes5a, 5b, 5c, 5d, 5e, 5f, 5g to give the corresponding hydrazone derivatives6a, 6b, 6c, 6d, 6e, 6f, 6g .Oxidative cyclization of the latter compounds6a, 6b, 6c, 6d, 6e, 6f, 6g gave the corresponding pyrido[2, 3‐ d ][1, 2, 4]triazolo[4, 3‐ a ]pyrimidin‐5(1 H )‐ones7a, 7b, 7c, 7d, 7e, 7f, 7g . Furthermore, compound4 reacted with benzoyl chloride, triethyl orthoformate, acetyl chloride, ethyl chloroformate, and carbon disulphide in alcoholic KOH solution to afford the corresponding pyrido[2, 3‐ d ][1, 2, 4]triazolo[4, 3‐ a ]pyrimidinones (7a, 8, 9, 10, 11 ). The reaction of thione3 or its 2‐methylthio derivative16 with hydrazonoyl halides12a, 12b, 12c, 12d, 12e, 12f, 12g, 12h, 12i, 12j, 12k, 12l, 12m yielded the corresponding pyrido[2, 3‐ d ][1, 2, 4]triazolo[4, 3‐ a ]pyrimidinones15a, 15b, 15c, 15d, 15e, 15f, 15g, 15h, 15i, 15j, 15k, 15l, 15m . The structures of all the products were confirmed by elemental and spectral analyses ( 1 H NMR, 13 C NMR, IR, and MS). In addition, the anticancer activity of 20 pyridotriazolopyrimidinones against two cancer cell lines namely MCF‐7 and HepG2 was evaluated, and the results revealed that compounds7d and9 have promising activity, compared with doxorubicin, which used as standard reference drug. Abstract :