A Study of Some New Chalcone Derivatives from Cholic Acid Based on Synthesis, Characterization, and Biological Activity

Abstract

Cholic acid, also known as 3\(\alpha\),7\(\alpha\),12\(\alpha\)-trihydroxy-5\(\beta\)-cholan-24-oic acid is a primary bile acid that is insoluble in water (soluble in alcohol and acetic acid), it is a white crystalline substance. Salts of cholic acid are called cholates. Cholic acid, along with chenodeoxycholic acid, is one of the two major bile acids produced by the liver, where it is synthesized from cholesterol. N-(4-acetylphenyl)-3',7',12'-trihydroxy-5'-cholan-24-amide was synthesized from reaction of cholic acid with 4-amino acetophenone by using DMAP as acatalyst and DCC as acoupling agent then the obtained product reacts with some substituted benzaldehyde derivatives by using NaOH as acatalyst to prepare chalcone derivatives(3,4,5,6,7). Finally, the products (3,6) were allowed to react with thiourea with presence alcoholic NaOH as a catalyst with a reflex to give thiazine derivatives (8,9). All the chalcone derivatives have weak to moderate activity against S. aureus, but all derivatives show moderate to strong activity against Candida albicans. The reactions were monitored by thin-layer chromatography (TLC) technique. All the new compounds were characterized by melting points, elemental analysis, FT-IR, 1H NMR, 13C NMR spectroscopies. Antimicrobial activity of the synthesized derivatives was also determined.