SYNTHESIS OF 7-FLUORO-2,4-METHYLENE-17,20-DIMETHYLPROSTACYCLINS - NOVEL STABLE PROSTACYCLIN ANALOGS AS POTENT ANTIANGINAL AGENTS

被引:22
作者
MATSUMURA, Y
SHIMADA, T
NAKAYAMA, T
URUSHIHARA, M
ASAI, T
MORIZAWA, Y
YASUDA, A
机构
[1] Research Center, Asahi Glass Co., Ltd., Kanagawa-ku, Yokohama, 221
关键词
D O I
10.1016/0040-4020(95)00468-N
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of new stable fluoroprostacyclins, 7-fluoro-2,4-methylene-17,20-dimethylprostacyclins (1, 2) with potent and long-lasting anti-anginal activities has been achieved. The cyclobutylene prostaglandin skeleton 10 was constructed efficiently according to three-component coupling reaction. Stereospecific fluorination of silyl ether 11 and subsequent cyclization of the fluoride 12 successfully provided the desired 7-fluoro-2,4-methylene-17,20-dimethylprostacyclin.
引用
收藏
页码:8771 / 8782
页数:12
相关论文
共 55 条
[1]  
[Anonymous], 1993, ORGANOFLUORINE COMPO
[2]   SYNTHESIS OF NEW STABLE FLUOROPROSTACYCLIN ANALOGS WITH POTENT ANTIANGINAL ACTIVITY [J].
ASAI, T ;
MORIZAWA, Y ;
SHIMADA, T ;
NAKAYAMA, T ;
URUSHIHARA, M ;
MATSUMURA, Y ;
YASUDA, A .
TETRAHEDRON LETTERS, 1995, 36 (02) :273-276
[3]   PROSTAGLANDIN CHEMISTRY .20. SYNTHESIS OF CHEMICALLY STABLE PROSTACYCLIN ANALOGS [J].
BANNAI, K ;
TORU, T ;
OBA, T ;
TANAKA, T ;
OKAMURA, N ;
WATANABE, K ;
HAZATO, A ;
KUROZUMI, S .
TETRAHEDRON, 1983, 39 (22) :3807-3819
[4]  
BEZUGLOV VV, 1984, DOKL AKAD NAUK SSSR+, V277, P1400
[5]  
BOIE Y, 1994, J BIOL CHEM, V269, P12173
[6]   SYNTHESIS OF THERAPEUTICALLY USEFUL PROSTAGLANDIN AND PROSTACYCLIN ANALOGS [J].
COLLINS, PW ;
DJURIC, SW .
CHEMICAL REVIEWS, 1993, 93 (04) :1533-1564
[7]   SYNTHESIS OF A STABLE ANALOG OF THROMBOXANE-A2 WITH METHYLENE REPLACING THE 9,11-BRIDGING OXYGEN [J].
COREY, EJ ;
PONDER, JW ;
ULRICH, P .
TETRAHEDRON LETTERS, 1980, 21 (02) :137-140
[8]   SYNTHESIS OF VANES PROSTAGLANDIN X,6,9ALPHA-OXIDO-9ALPHA,15ALPHA-DIHYDROXYPROSTA-(Z)5,(E)13-DIENOIC ACID [J].
COREY, EJ ;
KECK, GE ;
SZEKELY, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) :2006-2008
[9]   SYNTHESIS OF 5-FLUOROPROSTACYCLIN [J].
DJURIC, SW ;
GARLAND, RB ;
NYSTED, LN ;
PAPPO, R ;
PLUME, G ;
SWENTON, L .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :978-990
[10]  
Filler R., 1982, BIOMEDICAL ASPECTS F