85121-72-8Relevant academic research and scientific papers
New cholic acid analogs: Synthesis and 17β-hydroxydehydrogenase (17β-HSD) inhibition activity
Al-Masoudi, Najim A.,Sami, Abbas,Abdul-Rida, Nabeel A.,Fortscher, Martin
, p. 211 - 233 (2018)
The 17β-hydroxysteroid dehydrogenase (17β-HSD) enzyme family is involved in the biosynthesis of active steroids and its inhibition constitutes an interesting approach for treating estrogen-, androgen-dependent cancers and osteoporosis. In this study, a new series of cholic acid analogs was designed with the goal of improving the biological activity as 17β-HSD1 and 17β-HSD2 inhibitors. To this end, 23-cholyl amides 4-7, 3-O-p-toluenesulfonyl-23-cholyl amides 10-12, 23-cholyl-carbohydrazide 14, carbothioamide analog 15, and 23-cholyl-acylhydrazone derivatives 18-22 were synthesized from cholic acid (3) via coupling, sulfonation and substitution reactions. Basic treatment of keto group of 5 with p-bromoaniline afforded 8, meanwhile acidic treatment of 3 with thiosemicarbazide furnished the 23-cholyl-thiadiazole derivative 16. The synthesized compounds were evaluated for their inhibition activity against 17β-HSD1 and 17β-HSD2, and were found inactive at 1.0 μm concentration (inhibition 10%). However, the steroids 12, 21 and 22 showed inhibition of 21.1, 23.9 and 21.3%, respectively, against 17β-HSD2 at the same concentration. Therefore, these steroidal analogs can be further structurally modified to optimize their inhibition activity against 17β-HSD2 for the development of potential therapeutics.
PREPARATION METHOD FOR 3BETA-ARACHIDYLAMIDO-7ALPHA, 12ALPHA, 5BETA-CHOLAN-24-CARBOXYLIC ACID
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Page/Page column 4, (2012/11/08)
A method for preparing 3β-arachidylamido-7α,12α,5β-cholan-24-carboxylic acid represented by the following formula V is disclosed, which includes the following steps: converting cholic acid to the compound of formula III by acylation reaction and azidation reaction, reducing the compound of formula III to the compound of formula IV and in the end acylating the compound of formula IV with arachidoyl chloride to get the compound of formula V. The method avoids the use of protection groups.
