Object-oriented synthetic approach toward angular and linear fused pyrazoloquinolines of biological importance with InCl3 catalyst

Thangaraj Arasakumar, Sadasivam Mathusalini, Krishnasamy Lakshmi, Palathurai Subramaniam Mohan*, Athar Ata, Chia Her Lin

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

A simple and short approach for the synthesis of pyrazolo[3,4-b]quinoline (3a-3p) and pyrazolo[4,3-c]quinoline (6a-6 h) using various Lewis acid catalysts was developed. InCl3 was found to be more effective in providing greater yield of products compared to Yb(OTf)3, Sc(OTf)3, SnCl4, AlCl3, TiCl4, ZnCl2, FeCl3, and BF3 · Et2O. Moreover, a comparison of conventional and microwave methods has revealed that the latter method is more efficient compared to former one. Structures were confirmed by Fourier transform infrared, mass spectrometry, 1H and 13C NMR, X-ray crystallography, and elemental analyses. All of the synthesized compounds were evaluated for α-glucosidase inhibitory activity. Compounds 3a, 3p, 3i, 3 h, 3k, 3o, and 3 g exhibited anti α-glucosidase inhibitory activity with IC50 values of 57.5, 60.3, 65.9, 71.9, 80.8, 123.7, and 126.4 μM, respectively, which is quite comparable to the standard drug acarbose (IC50 = 115.8 μM).

Original languageEnglish
Pages (from-to)232-241
Number of pages10
JournalSynthetic Communications
Volume46
Issue number3
DOIs
Publication statusPublished - 2016 Feb 1
Externally publishedYes

Keywords

  • Angular and linear pyrazoloquinolines
  • enolizable 3-acyl quinolin-2-one
  • InCl
  • microwave irradiation
  • α-glucosidase inhibitory

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Object-oriented synthetic approach toward angular and linear fused pyrazoloquinolines of biological importance with InCl<sub>3</sub> catalyst'. Together they form a unique fingerprint.

Cite this