Synthesis of diversely substituted 5-methylpyrazolo[1,5-a]pyrimidines assisted by ultrasound in aqueous media: Molecular docking for potential antiviral, anticancer activities

Authors

  • Jai Narain Vishwakarma Assam Don Bosco University
  • Shunan Kaping Assam Don Bosco University, Tapesia Gardens, Sonapur, 782402, Assam India
  • Rene Barbie Browne Assam Don Bosco University, Tapesia Gardens, Sonapur, 782402, Assam, India

DOI:

https://doi.org/10.56042/ijc.v63i12.12723

Abstract

5-Methylpyrazolo[1,5-a]pyrimidine derivatives were synthesized with starting materials that were either commercially or easily available. This was achieved by the ultrasound irradiation of 3-amino-1H-pyrazoles (3-7) and enaminones (2) assisted by KHSO4 in aqueous medium. The structures were established by spectral and analytical techniques. An X-ray crystallographic study of compound N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-7-(4-methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide (8b) confirmed the structural orientation and eliminated any ambiguity pertaining to its regioselectivity. Its space group is P21/n with the following unit cell parameters: a = 17.5775 (8), b = 7.1707 (4), c = 18.113 (1) Å, β = 91.449 (2) and Z = 4. Crystal structure was solved to a final R value of 0.062 and to a GOOF value of 1.09. Molecular docking of the compounds was executed to identify the potential antiviral and anticancer agents. Moreover, Molecular dynamics simulation study of the ligand 9c in a complex with 3pp0, revealed the stability of the potential ligand candidate 9c.

Author Biographies

Shunan Kaping, Assam Don Bosco University, Tapesia Gardens, Sonapur, 782402, Assam India

Department of Chemistry,

Ph. D, Researcher

Assam Don Bosco University

Rene Barbie Browne, Assam Don Bosco University, Tapesia Gardens, Sonapur, 782402, Assam, India

Department of Bio-Sciences

Ph. D

Assam Don Bosco University

Published

2024-12-24