Multistep Synthesis of Phosphazene Derivative of Chenodeoxycholicacid (CDCA)

GRAPHICAL ABSTRACT

Abstract

A new and more effective compound was synthesized by combining bile acid (chenodeoxycholic acid) and phosphazene. The synthesis started with chenodeoxycholic acid (CDCA). In the first step CDCA was converted to the CDCA methyl ester (methyl-4-(hexadecahydro-3,7-dihydroxy-10,13-dimethyl-1H-cyclopenta[a]phenanthren-17-yl) pentanoate). The mesylate was prepared from the methyl ester of CDCA and converted to the azide ester of CDCA by an S_N2 reaction. The azide group at C-3 of chenodeoxycholic acid methyl ester was converted to an amino group (3-methyl-4-(3-amino-hexadecahydro-7-hydroxy-10,13-dimethyl-1H-cyclopenta[a]phenanthren-17-yl)pentanoate). Then, this compound was allowed to react with hexachlorocyclotriphosphazene in toluene under an argon atmosphere. The structures of the synthesized chenodeoxycholic acid derivatives and of the new phosphazene compound were confirmed by FTIR, ¹H, ¹³C, ³¹P, ¹³C-DEPT NMR, MALDI-TOF mass spectra and elemental analysis.

Keywords:

• Phosphazene
• bile acid
• chenodeoxycholic acid

ACKNOWLEDGMENT

The authors thank Professor Yakup BARAN for his help.

FUNDING

The authors thank the TUBAP Scientific Research Project of Trakya University (TUBAP-2011-59)

SUPPLEMENTAL MATERIAL

Supplementary data for this article can be accessed on the publisher's website, www.tandfonline.com/gpss