Abstract
The preparation of 3α,7β-dihydroxy-22,23-methylene-5β-cholan-24-oic acid (2-sulfoethyl)amide (5) by the one-step EEDQ-induced conjugation between ursodeoxycholic acid "cyclopropylog" (4) and taurine is described. The presence of a cyclopropyl ring adjacent to the amide bond is shown to make it resistant to degradation by intestinal bacteria. This new cyclopropylog is neither deconjugated at the C-24 amide bond nor 7-dehydroxylated when incubated with human stools in anaerobic conditions.
| Original language | English |
|---|---|
| Pages (from-to) | 239-242 |
| Number of pages | 4 |
| Journal | Journal of Medicinal Chemistry |
| Volume | 28 |
| Issue number | 2 |
| Publication status | Published - 1985 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Bile acids with cyclopropane-containing side chain. 2. Synthesis and properties of 3α,7β-dihydroxy-22,23-methylene-5β-cholan-24-oic acid (2-sulfoethyl)amide. / Pellicciari, Roberto; Cecchetti, Sergio; Natalini, Benedetto; Roda, Aldo; Grigolo, Brunella; Fini, Adamo.
In: Journal of Medicinal Chemistry, Vol. 28, No. 2, 1985, p. 239-242.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Bile acids with cyclopropane-containing side chain. 2. Synthesis and properties of 3α,7β-dihydroxy-22,23-methylene-5β-cholan-24-oic acid (2-sulfoethyl)amide
AU - Pellicciari, Roberto
AU - Cecchetti, Sergio
AU - Natalini, Benedetto
AU - Roda, Aldo
AU - Grigolo, Brunella
AU - Fini, Adamo
PY - 1985
Y1 - 1985
N2 - The preparation of 3α,7β-dihydroxy-22,23-methylene-5β-cholan-24-oic acid (2-sulfoethyl)amide (5) by the one-step EEDQ-induced conjugation between ursodeoxycholic acid "cyclopropylog" (4) and taurine is described. The presence of a cyclopropyl ring adjacent to the amide bond is shown to make it resistant to degradation by intestinal bacteria. This new cyclopropylog is neither deconjugated at the C-24 amide bond nor 7-dehydroxylated when incubated with human stools in anaerobic conditions.
AB - The preparation of 3α,7β-dihydroxy-22,23-methylene-5β-cholan-24-oic acid (2-sulfoethyl)amide (5) by the one-step EEDQ-induced conjugation between ursodeoxycholic acid "cyclopropylog" (4) and taurine is described. The presence of a cyclopropyl ring adjacent to the amide bond is shown to make it resistant to degradation by intestinal bacteria. This new cyclopropylog is neither deconjugated at the C-24 amide bond nor 7-dehydroxylated when incubated with human stools in anaerobic conditions.
UR - http://www.scopus.com/inward/record.url?scp=0021961366&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0021961366&partnerID=8YFLogxK
M3 - Article
C2 - 3968688
AN - SCOPUS:0021961366
VL - 28
SP - 239
EP - 242
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
SN - 0022-2623
IS - 2
ER -