Side chain methyl analogues of Delta(8)-THC

被引：22

作者：

Huffman, JW ^{[1
]}

Lainton, JAH ^{[1
]}

Banner, WK ^{[1
]}

Duncan, SG ^{[1
]}

Jordan, RD ^{[1
]}

Yu, S ^{[1
]}

Dai, D ^{[1
]}

Martin, BR ^{[1
]}

Wiley, JL ^{[1
]}

Compton, DR ^{[1
]}

机构：

[1] VIRGINIA COMMONWEALTH UNIV,MED COLL VIRGINIA,DEPT PHARMACOL & TOXICOL,RICHMOND,VA 23298

来源：

TETRAHEDRON | 1997年 / 53卷 / 05期

关键词：

D O I：

10.1016/S0040-4020(96)01134-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of both side chain epimers of 1'- (4), 2'- (5), 3'-methyl- (6) and 4'-methyl-Delta(8)- tetrahydrocannabinol (7) has been carried out. The synthetic approach entailed the acid catalyzed condensation of the appropriate substituted resorcinol with menthadienol to provide the Delta(8)-THC analogue. Both isomers of 1'- (4) and 2'-Delta(8)-THC (5) were more potent than Delta(8)-THC, both in vitro and in vivo. The 3'-methyl isomers (6) were approximately equal in potency to Delta(8)-THC, and 4'-methyl-Delta(8)-THC was less potent. There was relatively little difference in potency between the epimers of 4, 5, and 6. (C) 1997, Elsevier Science Ltd.

引用

页码：1557 / 1576

页数：20

共 33 条

[31] RAPID PROCEDURE FOR HYDROLYSIS OF AMIDES TO ACIDS [J].

VAUGHN, HL ;

ROBBINS, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (08) :1187-1189

[32] CLEAVAGE OF HINDERED ALPHA-METHYLBENZYLAMIDES, INTERMEDIATES IN THE RESOLUTION OF CARBOXYLIC-ACIDS [J].

WEBSTER, FX ;

MILLAR, JG ;

SILVERSTEIN, RM .

TETRAHEDRON LETTERS, 1986, 27 (41) :4941-4944

[33] Phenethylamines. IV. Dimethoxy and dihydroxyphenyl-n-propylamines (ss-methyl-ss-phenethylamines) [J].

Woodruff, EH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :2859-2862

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