Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones

Ikhlass ABBAS, (Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt)
Mohamed ELNEAIRY, (Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt)
Mahmoud ELASSER, (Regional Center for Mycology and Biotechnology, Al-Azhar University, Cairo, Egypt)
Bazada MOBROUK (Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt)
Turkish Journal of Chemistry
1 0
Yıl: 2015 Cilt: 39 Sayı: 3 Sayfa Aralığı: 510 - 531 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones

Öz:
Abstract: The reaction of thione 3 or its 2-methylthio derivative 4 with hydrazonoyl halides 5a-l, in the presence of triethylamine, yielded the corresponding triazolo[4,3-a]pyrimidin-5(1H)-ones 8a-l. The structure of compounds 8a-l was further confirmed by the reaction of 3 with the appropriate active chloromethylenes 11a-c followed by coupling of the products with benzenediazonium chloride to afford the azo-coupling products 6b, f, and j, which were converted in situ to 8b, f, and j. 2-Hydrazinyl-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(3H)-one (13) was prepared and condensed with different aldehydes 14a-f to give the corresponding hydrazone derivatives 15a-f. Oxidative cyclization of the hydrazones 15a-f give the corresponding triazolo[4,3-a] pyrimidin-5(1H)-one derivatives 16a-f.The antimicrobial activity of the products was evaluated and the results revealed that compounds 8f and 15f showed strong activity against gram-positive bacteria while compound 15d showed the highest activity against gram-negative bacteria. Moreover, compounds 15b, 8d, 8e, 8c, 8l, and 8j exhibited significant antifungal activity. In addition, the antitumoral activity of the synthesized products against different cancer cell lines was determined and the results revealed that compound 12c was the most active against MCF-7, HepG-2, HCT-116, and HeLa with IC50 values of 0.51, 0.72, 0.95, and 0.95, respectively, as compared with doxorubicin as positive control.
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APA ABBAS I, ELNEAIRY M, ELASSER M, MOBROUK B (2015). Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones. , 510 - 531.
Chicago ABBAS Ikhlass,ELNEAIRY Mohamed,ELASSER Mahmoud,MOBROUK Bazada Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones. (2015): 510 - 531.
MLA ABBAS Ikhlass,ELNEAIRY Mohamed,ELASSER Mahmoud,MOBROUK Bazada Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones. , 2015, ss.510 - 531.
AMA ABBAS I,ELNEAIRY M,ELASSER M,MOBROUK B Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones. . 2015; 510 - 531.
Vancouver ABBAS I,ELNEAIRY M,ELASSER M,MOBROUK B Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones. . 2015; 510 - 531.
IEEE ABBAS I,ELNEAIRY M,ELASSER M,MOBROUK B "Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones." , ss.510 - 531, 2015.
ISNAD ABBAS, Ikhlass vd. "Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones". (2015), 510-531.
APA ABBAS I, ELNEAIRY M, ELASSER M, MOBROUK B (2015). Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones. Turkish Journal of Chemistry, 39(3), 510 - 531.
Chicago ABBAS Ikhlass,ELNEAIRY Mohamed,ELASSER Mahmoud,MOBROUK Bazada Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones. Turkish Journal of Chemistry 39, no.3 (2015): 510 - 531.
MLA ABBAS Ikhlass,ELNEAIRY Mohamed,ELASSER Mahmoud,MOBROUK Bazada Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones. Turkish Journal of Chemistry, vol.39, no.3, 2015, ss.510 - 531.
AMA ABBAS I,ELNEAIRY M,ELASSER M,MOBROUK B Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones. Turkish Journal of Chemistry. 2015; 39(3): 510 - 531.
Vancouver ABBAS I,ELNEAIRY M,ELASSER M,MOBROUK B Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones. Turkish Journal of Chemistry. 2015; 39(3): 510 - 531.
IEEE ABBAS I,ELNEAIRY M,ELASSER M,MOBROUK B "Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones." Turkish Journal of Chemistry, 39, ss.510 - 531, 2015.
ISNAD ABBAS, Ikhlass vd. "Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones". Turkish Journal of Chemistry 39/3 (2015), 510-531.
Sayfa Oluşturulma Tarihi
22-04-2024 21:3

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