Synthesis and Antiproliferative Activity of Some Newly Synthesized Pyrazolopyridine Derivatives

Synthesis and Antiproliferative Activity of Some Newly Synthesized Pyrazolopyridine Derivatives

A series of pyrazolopyridine derivatives is synthesized from emyl-4-amino-6-memyl-1-(mphtha[1,2- d ]-[1,3]tmazol-2-yl)-1 H -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 re...

Full description

Saved in:
Bibliographic Details
Published in:Russian journal of general chemistry Vol. 89; no. 6; pp. 1209 - 1217
Main Authors: Fayed, A. A., Bahashwan, S. A., Yousif, M. N. M., Shafey, H. M. El, Amr, A. E., Yousif, N. M., Shadid, K. A.
Format: Journal Article
Language:English
Published: Moscow Pleiades Publishing 01-06-2019
Springer
Springer Nature B.V
Subjects:
Amino acids
Anhydrides
Antiproliferatives
Care and treatment
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Formaldehyde
Hydrazines
Hydroxides
Lung cancer
Naphtha
Pyridine
Resveratrol
Sodium hydroxide
Thiourea derivatives
Thioureas
lung cancer
pyrazolopyridine
anti-proliferative activity
cytotoxic assay
naphtho
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A series of pyrazolopyridine derivatives is synthesized from emyl-4-amino-6-memyl-1-(mphtha[1,2- d ]-[1,3]tmazol-2-yl)-1 H -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 (7 H )-one ( 5 ). Compound 3 reacts with phenyl i sothiocyanate 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-4 H -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-4 H -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)-1 H -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-4 H -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.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363219060173