Multi-component One-Pot Synthesis and Antimicrobial Activities of 3-methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo[5,4-b]pyrimidino[5,4-e]pyridine-5-one and Related Derivatives

Molecules. 2012 Dec 6;17(12):14464-83. doi: 10.3390/molecules171214464.

Abstract

The synthesis of 3-methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydropyrazolo[5,4-b] pyrimidino[5,4-e]pyridine-5-one (6) was achieved by two different one-pot multi-component synthesis (one-pot three-component and one-pot four component synthesis). Mono and dialkylation of 6 under different conditions gave compounds 7-11. The hydrazine 12 produced from reaction of 9 with N₂H₄ was subjected to reactions with some aromatic aldehydes, ethyl acetoacetate, acetyl acetone, ethyl cyanoacetate and triethyl orthoformate to give 13-17, respectively. Compound 12 upon reaction with CS₂, nitrous acid, benzoin, chloroacetone and phenacyl bromide gave 18,20,21,22. Alkylation of 18 with ethyl iodide, ethyl chloroacetate and phenacyl bromide gave 19a-c. The antibacterial and antifungal activities of selected derivatives were evaluated.

MeSH terms

  • Alkylation
  • Anti-Infective Agents* / chemical synthesis
  • Anti-Infective Agents* / pharmacology
  • Antifungal Agents* / chemistry
  • Antifungal Agents* / pharmacology
  • Bacteria / drug effects
  • Fungi / drug effects
  • Molecular Structure
  • Pyrazoles / chemistry*
  • Pyridines* / chemical synthesis
  • Pyridines* / chemistry
  • Pyridines* / pharmacology
  • Pyridones / chemistry*
  • Pyrimidines / chemistry*

Substances

  • 3-methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo(5,4-b)pyrimidino(5,4-e)pyridine-5-one
  • Anti-Infective Agents
  • Antifungal Agents
  • Pyrazoles
  • Pyridines
  • Pyridones
  • Pyrimidines