Solvent-Free Synthesis of 2-Alkylbenzothiazoles and Bile Acid Derivatives Containing Benzothiazole Ring by Using Active Carbon/Silica Gel and Microwave

J Oleo Sci. 2018;67(10):1209-1217. doi: 10.5650/jos.ess18036.

Abstract

A highly efficient and simple method for the synthesis of 2-alkylbenzothiazoles through the condensation of 2-aminothiophenol and aliphatic aldehydes in the presence of active carbon/silica gel is described. The reaction proceeded under solvent-free and microwave irradiation to afford 2-alkylbenzothiazoles in high yields. This method was extended to the synthesis of bile acid derivatives containing a benzothiazole ring and obtained the desired products in high yields. The anti-inflammatory activity and cytotoxicity of the newly synthesized benzothiazole derivatives of bile acid were tested; the results showed that anti-inflammatory activities of all tested compounds tested were higher than that of standard drugs, such as indomethacin.

Keywords: 2-alkylbenzothiazole; active carbon/silica gel; bile acid; microwave; solvent-free.

MeSH terms

  • Aldehydes / chemistry*
  • Aniline Compounds / chemistry*
  • Animals
  • Anti-Inflammatory Agents
  • Bile Acids and Salts / chemical synthesis*
  • Bile Acids and Salts / chemistry
  • Bile Acids and Salts / pharmacology
  • Charcoal / chemistry*
  • Fatty Acids / chemistry*
  • Female
  • Mice, Inbred ICR
  • Microwaves*
  • Organic Chemistry Phenomena
  • Silica Gel / chemistry*
  • Solvents
  • Thiadiazoles / chemical synthesis*
  • Thiadiazoles / chemistry
  • Thiadiazoles / pharmacology

Substances

  • Aldehydes
  • Aniline Compounds
  • Anti-Inflammatory Agents
  • Bile Acids and Salts
  • Fatty Acids
  • Solvents
  • Thiadiazoles
  • 2-aminothiophenol
  • Charcoal
  • benzo-1,2,3-thiadiazole
  • Silica Gel