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Russian Journal of General Chemistry

, Volume 89, Issue 6, pp 1209–1217 | Cite as

Synthesis and Antiproliferative Activity of Some Newly Synthesized Pyrazolopyridine Derivatives

  • A. A. Fayed
  • S. A. Bahashwan
  • M. N. M. Yousif
  • H. M. El Shafey
  • A. E. AmrEmail author
  • N. M. Yousif
  • K. A. Shadid
Article
  • 6 Downloads

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.

Keywords

naphtho pyrazolopyridine anti-proliferative activity cytotoxic assay lung cancer 

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. A. Fayed
    • 1
    • 2
  • S. A. Bahashwan
    • 3
  • M. N. M. Yousif
    • 2
  • H. M. El Shafey
    • 1
    • 4
  • A. E. Amr
    • 2
    • 5
    Email author
  • N. M. Yousif
    • 2
  • K. A. Shadid
    • 6
  1. 1.Respiratory Therapy Department, College of Medical Rehabilitation SciencesTaibah UniversityMadinah MunawaraSaudi Arabia
  2. 2.National Research CenterCairo, DokkiEgypt
  3. 3.Pharmacology and Toxicology Department, College of PharmacyTaibah UniversityMadina MunawarahSaudi Arabia
  4. 4.National Center for Radiation Research and TechnologyNasr City, CairoEgypt
  5. 5.Pharmaceutical Chemistry Department, Drug Exploration and Development Chair (DEDC), College of PharmacyKing Saud UniversityRiyadhSaudi Arabia
  6. 6.Department of Chemistry, Faculty of ScienceIslamic University in MadinahAlmadinah AlmonawarahSaudi Arabia

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