Chemical modifications of bile acids under high-intensity ultrasound or microwave irradiation

被引:15
作者
Cravotto, G
Boffa, L
Turello, M
Parenti, M
Barge, A
机构
[1] Univ Turin, Dipartimento Sci & Tecnol Farm, I-10125 Turin, Italy
[2] Prodotti Chim & Alimentali Spa, I-15060 Basaluzzo, AL, Italy
[3] Univ Turin, Dipartimento Chim, IFM, I-10125 Turin, Italy
关键词
high-intensity ultrasound; microwave; synthesis; cholic acid; glycocholic acid; taurocholic acid;
D O I
10.1016/j.steroids.2004.09.007
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
High-intensity ultrasound (HIU) and microwave (MW) irradiation, having emerged as effective promoters of organic reactions, were exploited for the synthesis of bile acids derivatives. Esterification, amidation, hydrolysis, oxidation, and reduction were investigated. Compared to conventional methods, both techniques proved much more efficient, increasing product yields and dramatically cutting down reaction times. Scaled-up studies are now under way. (C) 2004 Elsevier Inc. All rights reserved.
引用
收藏
页码:77 / 83
页数:7
相关论文
共 42 条
[1]
An improved sonochemical reactor [J].
Cravotto, G ;
Omiccioli, G ;
Stevanato, L .
ULTRASONICS SONOCHEMISTRY, 2005, 12 (03) :213-217
[2]
CRAVOTTO G, Patent No. 2003106397
[3]
MICROWAVE-INDUCED ORGANIC-REACTIONS OF BILE-ACIDS - ESTERIFICATION, DEFORMYLATION AND DEACETYLATION USING MILD REAGENTS [J].
DAYAL, B ;
RAO, K ;
SALEN, G .
STEROIDS, 1995, 60 (06) :453-457
[4]
Rapid hydrogenation of unsaturated sterols and bile alcohols using microwaves [J].
Dayal, B ;
Ertel, NH ;
Rapole, KR ;
Asgaonkar, A ;
Salen, G .
STEROIDS, 1997, 62 (05) :451-454
[5]
7 beta-hydroxy bile alcohols: Facile synthesis and 2D H-1 NMR studies of 5 beta-cholestane-3 alpha,7 beta,12 alpha,25-tetrol [J].
Dayal, B ;
Ertel, NH ;
Padia, J ;
Rapole, KR ;
Salen, G .
STEROIDS, 1997, 62 (05) :409-414
[6]
Rapid hydrolysis of bile acid conjugates using microwaves:: Retention of absolute stereochemistry in the hydrolysis of (25R) 3α,7α,12α-trihydroxy-5β-cholestan-26-oyltaurine [J].
Dayal, B ;
Ertel, NH .
LIPIDS, 1998, 33 (03) :333-338
[7]
Duan WM, 2002, CELL TRANSPLANT, V11, P195
[8]
SELECTIVE OXIDATION WITH N-BROMOSUCCINIMIDE .1. CHOLIC ACID [J].
FIESER, LF ;
RAJAGOPALAN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (12) :3935-3938
[9]
OXIDATION OF STEROIDS .3. SELECTIVE OXIDATIONS AND ACYLATIONS IN THE BILE ACID SERIES [J].
FIESER, LF ;
RAJAGOPALAN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (12) :5530-5536
[10]
QUANTITATIVE STRUCTURE ANTIMICROBIAL ACTIVITY RELATIONSHIP IN 5-BETA-CHOLANYL-24-BENZYLAMINE DERIVATIVES [J].
FINI, A ;
RODA, A ;
BELLINI, AM ;
MENCINI, E ;
GUARNERI, M .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1990, 79 (07) :603-605