A simple stereoselective synthesis and biological evaluation of FR181157: Orally active prostacyclin mimetic

被引:9
作者
Hattori, K [1 ]
Tabuchi, S [1 ]
Okitsu, O [1 ]
Taniguchi, K [1 ]
机构
[1] Fujisawa Pharmaceut Co Ltd, Med Chem Res Labs, Yodogawa Ku, Osaka 532, Japan
关键词
D O I
10.1016/j.bmcl.2003.09.054
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Synthetic method of novel prostaglandin (PG) mimetic: FR181175 without PG skeleton are described. The key to success is creation of a chiral epoxide using Sharpless AD reaction with high ee yield. FR181157 shows high potency and agonist efficacy at the IP receptor and has good bioavailability. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4277 / 4279
页数:3
相关论文
共 19 条
[1]  
BOIE Y, 1994, J BIOL CHEM, V269, P12173
[2]   PROSTACYCLIN AND VASCULAR FUNCTION - IMPLICATIONS FOR HYPERTENSION AND ATHEROSCLEROSIS [J].
DUSTING, GJ ;
MACDONALD, PS .
PHARMACOLOGY & THERAPEUTICS, 1990, 48 (03) :323-344
[3]  
HAMANAKA N, 1995, BIOORG MED CHEM LETT, V5, P1077, DOI 10.1016/0960-894X(95)00169-T
[4]   MOLECULAR DESIGN OF NOVEL PGI(2) AGONISTS WITHOUT PG SKELETON .4. [J].
HAMANAKA, N ;
TAKAHASHI, K ;
NAGAO, Y ;
TORISU, K ;
TOKUMOTO, H ;
KONDO, K .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (10) :1083-1086
[5]  
HAMANAKA N, 1995, BIOORG MED CHEM LETT, V5, P1071, DOI 10.1016/0960-894X(95)00168-S
[6]  
HAMANAKA N, 1995, BIOORG MED CHEM LETT, V5, P1065, DOI 10.1016/0960-894X(95)00167-R
[7]   MECHANISM OF ELIMINATION REACTIONS .22. ANOMALOUS ELIMINATION FROM THE TRIMETHYLNEOMENTHYLAMMONIUM ION [J].
HUGHES, ED ;
WILBY, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (OCT) :4094-4101
[8]   CLONING AND EXPRESSION OF A CDNA FOR THE HUMAN PROSTACYCLIN RECEPTOR [J].
KATSUYAMA, M ;
SUGIMOTO, Y ;
NAMBA, T ;
IRIE, A ;
NEGISHI, M ;
NARUMIYA, S ;
ICHIKAWA, A .
FEBS LETTERS, 1994, 344 (01) :74-78
[9]   A SIMPLIFIED PROCEDURE FOR THE STEREOSPECIFIC TRANSFORMATION OF 1,2-DIOLS INTO EPOXIDES [J].
KOLB, HC ;
SHARPLESS, KB .
TETRAHEDRON, 1992, 48 (48) :10515-10530
[10]   RESEARCHES IN THE MENTHONE SERIES .17. CONFIGURATIONS OF MENTHOLS AND MENTHYLAMINES [J].
MCNIVEN, NL ;
READ, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (JAN) :153-158