Synthesis and acetylcholinesterase inhibitory activity of fluorinated analogues of huperzine A

被引：21

作者：

Kaneko, S ^{[1
]}

Nakajima, N ^{[1
]}

Shikano, M ^{[1
]}

Katoh, T ^{[1
]}

Terashima, S ^{[1
]}

机构：

[1] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1996年 / 6卷 / 16期

关键词：

D O I：

10.1016/0960-894X(96)00337-X

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Three novel fluorinated analogues of huperzine A ( 1 ), (+/-)-12, 12, 12-trifluorohuperzine A ( 2 ), (+/-)-14,14,14-trifluorohuperzine A ( 3 ), and (+/-)-12,12,12,14,14,14-hexafluorohuperzine A ( 4 ), have been synthesized by employing TMSCF(3) as a trifluoromethylating agent. These analogues were found to still retain anti-acetylcholinesterase activity. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：1927 / 1930

页数：4

相关论文

共 24 条

[1] ALKALOIDS OF LYCOPODIUM-SELAGO - ON THE IDENTITY OF SELAGINE WITH HUPERZINE-A AND THE STRUCTURE OF A RELATED ALKALOID [J].

AYER, WA ;

BROWNE, LM ;

ORSZANSKA, H ;

VALENTA, Z ;

LIU, JS .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (10) :1538-1540

[2] TRADITIONAL CHINESE MEDICINES AND NEW DRUG DEVELOPMENT [J].

BAI, DL .

PURE AND APPLIED CHEMISTRY, 1993, 65 (06) :1103-1112

[3] A PALLADIUM-CATALYZED ROUTE TO HUPERZINE-A AND ITS ANALOGS AND THEIR ANTICHOLINESTERASE ACTIVITY [J].

CAMPIANI, G ;

SUN, LQ ;

KOZIKOWSKI, AP ;

AAGAARD, P ;

MCKINNEY, M .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7660-7669

[4] STEREOSPECIFIC SYNTHESES OF OLEFINS FROM 1,2-THIONOCARBONATES AND 1,2-TRITHIOCARBONATES . TRANS-CYCLOHEPTENE [J].

COREY, EJ ;

CAREY, FA ;

WINTER, RAE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (04) :934-&

[5] A NEW, STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS [J].

COREY, EJ ;

WINTER, RAE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (17) :2677-&

[6] A NEW AND RAPID COLORIMETRIC DETERMINATION OF ACETYLCHOLINESTERASE ACTIVITY [J].

ELLMAN, GL ;

COURTNEY, KD ;

ANDRES, V ;

FEATHERSTONE, RM .

BIOCHEMICAL PHARMACOLOGY, 1961, 7 (02) :88-&

[7] PREPARATION OF 5-(1-AMINOCYCLOHEXYL)-2(1H)-PYRIDINONES VIA THE RITTER REACTION [J].

FINK, DM ;

EFFLAND, RC .

SYNTHETIC COMMUNICATIONS, 1994, 24 (19) :2793-2796

[8]

Kozikowski A. P., 1991, J MED CHEM, V34, P3402

[9] SYNTHETIC CHEMISTRY, NEUROTRANSMISSION AND SECOND MESSENGERS [J].

KOZIKOWSKI, AP .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (01) :97-105

[10] SYNTHESIS AND ACETYLCHOLINESTERASE INHIBITORY ACTIVITY OF SEVERAL PYRIMIDONE ANALOGS OF HUPERZINE-A [J].

KOZIKOWSKI, AP ;

CAMPIANI, G ;

SAXENA, A ;

DOCTOR, BP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) :283-285