SYNTHESIS OF 6,7-BENZOMORPHAN AND RELATED NONQUATERNARY CARBON STRUCTURES WITH MARKED ANALGETIC ACTIVITY

被引:51
作者
KANEMATSU, K
TAKEDA, M
JACOBSON, AE
MAY, EL
机构
[1] Laboratory of Chemistry, National Institutes of Health, Bethesda
关键词
D O I
10.1021/jm00303a015
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
6,7-Benzomorphan (9) has been synthesized from pyridine or 4-phenylpyridine. This compound (9), without a quaternary carbon or tertiary nitrogen, is codeine-like in analgetic activity as determined in the mouse hot-plate method. 2-Methyl-6,7-benzomorphan (8) and its 2′-hydroxy analog (15) are as active as their 5-methyl (quaternary carbon containing) relatives. © 1969, American Chemical Society. All rights reserved.
引用
收藏
页码:405 / +
页数:1
相关论文
共 19 条
[1]   PENTAZOCINE . STRONG ANALGESICS + ANALGESIC ANTAGONISTS IN BENZOMORPHAN SERIES [J].
ARCHER, S ;
PIERSO, NAK ;
BIRD, JG ;
ALBERTSON, NF ;
HARRIS, LS .
JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (02) :123-&
[2]   THE PREPARATION OF SOME SUBSTITUTED 2,6-BIS-(2-PYRIDYL)-PYRIDINES [J].
CASE, FH ;
KASPER, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (22) :5842-5844
[3]  
DESTEVENS G, 1965, ANALGETICS ED
[4]  
EDDY NB, 1953, J PHARMACOL EXP THER, V107, P385
[5]  
EDDY NB, 1966, SYNTHETIC ANALGES 2B, P115
[6]   CYANATION OF AMINE OXIDE SALTS - A NEW SYNTHESIS OF CYANOPYRIDINES [J].
FEELY, WE ;
BEAVERS, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (15) :4004-4007
[7]   THE SYNTHESIS AND RESOLUTION OF 3-HYDROXY-N-METHYLISOMORPHINAN [J].
GATES, M ;
WEBB, WG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (05) :1186-1194
[8]   SYNTHESIS OF 6,7-BENZOMORPHAN FROM 4-PHENYLPYRIDINE [J].
KANEMATSU, K ;
PARFITT, RT ;
JACOBSON, AE ;
AGER, JH ;
MAY, EL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (04) :1064-+
[9]   STRUCTURES RELATED TO MORPHINE .12. (+/-)-2'-HYDROXY-5,9-DIMETHYL-2-PHENETHYL-6,7-BENZOMORPHAN (NIH-7519) AND ITS OPTICAL FORMS [J].
MAY, EL ;
EDDY, NB .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (10) :1435-1437
[10]   INTEREXTING PHARMACOLOGICAL PROPERTIES OF OPTICAL ISOMERS OF ALPHA-5,9-DIETHYL-2'-HYDROXY-2-METHYL-6,7-BENZOMORPHAN [J].
MAY, EL ;
EDDY, NB .
JOURNAL OF MEDICINAL CHEMISTRY, 1966, 9 (06) :851-&