80948-49-8Relevant 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 (2018/03/21)
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.
Synthesis and antimicrobial activity of cholic acid hydrazone analogues
Rasras, Anas J.M.,Al-Tel, Taleb H.,Al-Aboudi, Amal F.,Al-Qawasmeh, Raed A.
experimental part, p. 2307 - 2313 (2010/06/19)
Synthesis and antimicrobial activity of cholic acid analogues 4a-t are reported. The synthesis of 4a-t was accomplished from ethylcholate 2. The hydrazone moiety was introduced via coupling of the cholic acide hydrazide (3) with appropriately functionalized aldehyde utilizing acetic acid as a catalyst. Quiet of interest in relation to the synthesized hydrazones is the formation of two rotamers s-cis.E and s-trans.E. Most compounds showed stronger antimicrobial activity against Gram-positive bacteria than Cefaclor and Cefixime. Compounds 4d, 4i and 4j indicated 15-fold stronger antimicrobial activities against Enterobacter faecalis compared to Cefaclor and Cefixime. Some of the synthesized compounds (e.g. 4a, 4c, 4d, 4i, and 4l) reflected twofolds less activity against Escherichia coli relative to Cefixime.
Fluorescent anion sensor derived from cholic acid: The use of flexible side chain
Fang, Lei,Chan, Wing-Hong,He, Yong-Bing,Kwong, Daniel W. J.,Lee, Albert W. M.
, p. 7640 - 7646 (2007/10/03)
The fluorescent photoinduced electron transfer (PET) chemosensors 1-3 were synthesized from cholic acid. 1 and 2 containing amidothiourea groups as anion receptive sites demonstrated much higher affinity toward anions than 3 containing traditional thioure
