Abstract
The structure of seven bromoacetic substituted derivatives of bile acids are characterized by 1H MMR, 13C NMR, 2D NMR, FT-IR and mass spectrometry (ESI-MS) as well as PM5 semiempirical and B3LYP ab initio methods. Estimation of the pharmacotherapeutic potential has been accomplished for the synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS).
Highlights
Steroids are beside carbohydrates, amino acids, peptides and nucleobases a large class of natural compounds
Bromoacetyl substituted derivatives of lithocholic, deoxycholic and cholic acid were obtained by reaction of methyl esters of bile acids with bromoacetic acid bromide in toluene with TEBA and sodium hydride to give compounds 4–10.33 The syntheses of compounds 4–10 are depicted in Scheme 1
Some data about compounds 4 and 5, which were synthesized with potassium carbonate in chloroform, are given by Chattopadhyay.[27]
Summary
Amino acids, peptides and nucleobases a large class of natural compounds. Compounds of this type display a very important role in plant and animal organisms. Steroids play important functions in the regulation of metabolism (e.g., bile acids and vitamin D).[1,2,3,4] Especially important compounds are bile acids (e.g., lithocholic, deoxycholic and cholic) and their derivatives. The bile acids are produced from cholesterol in the liver and are stored in the gallbladder.[5,6,7,8,9,10] gallbladder contraction with feeding releases bile acids into the intestine. The terminal carboxylic acid group in C(17) side chain may be conjugated with taurine or glycine
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