One pot multi-component synthesis of functionalized spiropyridine and pyrido[2,3-d]pyrimidine scaffolds and their potent in-vitro anti-inflammatory and anti-oxidant investigations

Chem Biol Drug Des. 2019 Apr;93(4):464-472. doi: 10.1111/cbdd.13434. Epub 2018 Nov 28.

Abstract

A new series of functionalized fused pyridines 4(a-i) and fused pyrido[2,3-d]pyrimidines 8(a-c) were designed and synthesized through a multi-component reaction where in pyridine ring formation step plays a key role. All the newly formed compounds were well characterized by spectral techniques such as FTIR, 1 HNMR, 13 CNMR, HRMS and XRD. The potential therapeutic activities such as anti-inflammatory activity by protein denaturation and RBC membrane stabilization methods, and anti-oxidant activity by DPPH scavenging method of the newly synthesized compounds were studied. Interestingly, in-vitro testing of these compounds reveals that the compounds 4d, 4g, 4i, 8a and 8b showed comparable anti-inflammatory activity with respect to the standard drug, diclofenac. Similarly, fused pyridine 4f showed excellent anti-oxidant activity when compared with the standard, ascorbic acid.

Keywords: anti-inflammatory activity; anti-oxidant activity; barbituric acid; cyclic ketones; malononitrile; pyrrolidine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / pharmacology
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry*
  • Cattle
  • Cell Membrane / drug effects
  • Cell Membrane / metabolism
  • Erythrocytes / cytology
  • Humans
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Pyridines / pharmacology
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry*
  • Pyrimidines / pharmacology
  • Serum Albumin, Bovine / chemistry
  • Serum Albumin, Bovine / metabolism
  • Spiro Compounds / chemistry

Substances

  • Anti-Inflammatory Agents
  • Antioxidants
  • Pyridines
  • Pyrimidines
  • Spiro Compounds
  • pyrido(2,3-d)pyrimidine
  • Serum Albumin, Bovine