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

[1] DIRECT NITROSATION OF AROMATIC-HYDROCARBONS AND ETHERS WITH THE ELECTROPHILIC NITROSONIUM CATION [J].

BOSCH, E ;

KOCHI, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5573-5586

[2]

BOSSHARD HR, 1973, HELV CHIM ACTA, V56, P717

[3] CHIRAL ECONOMIC SYNTHESIS OF (R)-MUSCONE AND (S)-MUSCONE USING CYCLOFRAGMENTATION OF EPOXYSULFONES [J].

BRANCA, Q ;

FISCHLI, A .

HELVETICA CHIMICA ACTA, 1977, 60 (03) :925-944

[4]

BRAUNS DH, 1937, J RES NBS, V18, P315

[5] HYDROGENOLYSES WITH CHLOROALUMINUM HYDRIDES .2. BENZYLIC ALCOHOLS [J].

BREWSTER, JH ;

BAYER, HO ;

OSMAN, SF .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (01) :110-&

[6] HYDROGENOLYSIS OF AROMATIC CARBONYL COMPOUNDS AND ALCOHOLS WITH ALUMINIUM CHLORIDE AND LITHIUM ALUMINIUM HYDRIDE [J].

BROWN, BR ;

WHITE, AMS .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (AUG) :3755-3757

[7] SYNTHESIS OF ISOCOUMARINS VIA INDANONES [J].

CARTER, RH ;

COLYER, RM ;

HILL, RA ;

STAUNTON, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (13) :1438-1441

[8]

COMPTON DR, 1993, J PHARMACOL EXP THER, V265, P218

[9]

DEVANE WA, 1988, MOL PHARMACOL, V34, P605

[10]

EDERY H, 1972, ARZNEIMITTELFORSCH, V22, P1995

← 1 2 3 4 →