A 4-(o-chlorophenyl)-2-aminothiazole: microwave assisted synthesis, spectral, thermal, XRD and biological studies

Spectrochim Acta A Mol Biomol Spectrosc. 2013 Nov:115:393-8. doi: 10.1016/j.saa.2013.06.058. Epub 2013 Jun 27.

Abstract

A 4-(o-chlorophenyl)-2-aminothiazole (CPAT) has been synthesized by reacting o-chloroacetophenone, iodine and thiourea under microwave irradiation as a green chemistry approach. The reactions proceed selectively and within a couple of minutes giving high yields of the products. The compound was characterized by elemental, spectral (UV-visible, IR, NMR and GC-MS), XRD and thermal analyses. The TG curve of the compound was analyzed to calculate various kinetic parameters (n, E, Z, ΔS and ΔG) by using Coats-Redfern (C.R.), MacCallum-Tanner (M.T.) and Horowitz-Metzger (H.M.) method. The compound was tested for the evaluation of antibacterial activity against B. subtilis and E. coli and antifungal activity against A. niger and C. albicans. The compound was evaluated for their in vitro nematicidal activity on plant parasitic nematode Meloidogyne javanica and molluscicidal activity on fresh water helminthiasis vector snail Lymnea auricularia. The compound is biologically active in very low concentration. X-ray diffraction study suggests a triclinic crystal system for the compound.

Keywords: Aminothiazole; Green chemistry; Microwave mediated synthesis; Molluscicidal activities; Nematicidal.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthelmintics / pharmacology
  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Escherichia coli / drug effects
  • Fungi / drug effects
  • Kinetics
  • Lymnaea / drug effects
  • Lymnaea / parasitology
  • Microbial Sensitivity Tests
  • Microwaves*
  • Mollusca / drug effects
  • Plant Roots / drug effects
  • Plant Roots / parasitology
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Temperature
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry*
  • Thiazoles / pharmacology*
  • Tylenchoidea / drug effects
  • X-Ray Diffraction*

Substances

  • 4-(o-chlorophenyl)-2-aminothiazole
  • Anthelmintics
  • Anti-Infective Agents
  • Thiazoles
  • 2-aminothiazole