Abstract
A series of pyrazolopyridine derivatives is synthesized from emyl-4-amino-6-memyl-1-(mphtha[1,2-d]-[1,3]tmazol-2-yl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (3), and the products are tested for their anti-proliferative activity. Treatment of compound 3 with sodium hydroxide and following reaction with acetic anhydride gives 2-amino-5-methyl-7-(naphtho[1,2-d]thiazol-2-yl)pyrazolo[4′,3′:5,6]pyrido[4,3-d][1,3]oxazin-4 (7H)-one (5). Compound 3 reacts with phenyl isothiocyanate to afford thiourea derivative 6, which upon treatment with KOH gives 3-phenyl-5-methyl -7-(naphtho[1,2-d][1,3]thiazol-2-yl)-2-thioxo-1,2,3,7-tetrahydro-4H-pyrazolo[4′,3′:5,6]pyrido[4,3-d]pyrimidin-4-one (7). Upon reaction of compound 3 with benzoyl isothiocyanate the benzoyl thiourea derivative 8 is formed. Its cyclization with an alkali leads to 5-methyl-7-(naphtha[1,2-d]thiazol-2-yl)-2-thioxo-1,2,3,7-tetrahydro-4H-pyrazolo-[4′,3′:5,6]pyrido[4,3-d]pyrimidin-4-one (9). Reaction of compound 3 with hydrazine gives 4-amino-6-methyl-1-(naphtho[1,2-d][1,3]thiazol-2-yl)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide (10), reaction of which with formaldehyde gives 3-amino-5-methyl-7-(naphtho[1,2-d][1,3]thiazol-2-yl)-1,2,3,7-tetrahydro-4H-pyrazolo[4′,3′:5,6]pyrido[4,3-d]pyrimidin-4-one (11). More reactions of compound 3 are presented. Some synthesized pyrazolopyridine derivatives are tested as anti-proliferative agents. The detailed synthesis, spectroscopic data, and anti-proliferative activity are reported.
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The authors acknowledge the President of Taibah University, Al- Madina AL-Munawara, Kingdom of Saudi Arabia for providing the ongoing support of scientific research. Also, the authors extend their appreciation to the Deanship of Scientific Research and Toxicological Research Center in Taibah University, Al-Madina AL-Munawara, Kingdom of Saudi Arabia for funding this work through the research group project no. 8014/1437.
The authors are grateful to the Deanship of Scientific Research, king Saud University for funding through Vice Deanship of Scientific Research Chairs.
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No conflict of interest was declared by the authors.
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Fayed, A.A., Bahashwan, S.A., Yousif, M.N.M. et al. Synthesis and Antiproliferative Activity of Some Newly Synthesized Pyrazolopyridine Derivatives. Russ J Gen Chem 89, 1209–1217 (2019). https://doi.org/10.1134/S1070363219060173
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DOI: https://doi.org/10.1134/S1070363219060173