Total synthesis of cyclostellettamine C, a bispyridinium macrocyclic alkaloid having muscarinic acetylcholine receptor antagonistic activity

被引：28

作者：

Anan, H ^{[1
]}

Seki, N ^{[1
]}

Noshiro, O ^{[1
]}

Honda, K ^{[1
]}

Yasumuro, K ^{[1
]}

Ozasa, T ^{[1
]}

Fusetani, N ^{[1
]}

机构：

[1] UNIV TOKYO,GRAD SCH AGR LIFE SCI,LAB AQUAT NAT PROD CHEM,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 33期

关键词：

D O I：

10.1016/0040-4020(96)00628-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclostellettamine C (1), a bispyridinium macrocyclic compound having muscarinic acetylcholine receptor antagonistic activity, was synthesized by the stepwise ring closure method via 3-(13-hydroxytridecyl)-1-[13-(3-pyridyl)tridecyl]pyridinium trifluoromethanesulfonate (21). Through this study, the structure of naturally originating 1 was synthetically and biologically confirmed. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：10849 / 10860

页数：12

共 7 条

[1] NEW HALOGENATION REAGENT SYSTEMS USEFUL FOR THE MILD ONE-STEP CONVERSION OF ALCOHOLS INTO IODIDES OR BROMIDES [J].

CLASSON, B ;

LIU, ZC ;

SAMUELSSON, B .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6126-6130

[2] A NEW EGF-ACTIVE POLYMERIC PYRIDINIUM ALKALOID FROM THE SPONGE CALLYSPONGIA-FIBROSA [J].

DAVIESCOLEMAN, MT ;

FAULKNER, DJ ;

DUBOWCHIK, GM ;

ROTH, GP ;

POLSON, C ;

FAIRCHILD, C .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5925-5930

[3] BIOACTIVE MARINE METABOLITES .29. HALICLAMINE-A AND HALICLAMINE-B, CYTOTOXIC MACROCYCLIC ALKALOIDS FROM A SPONGE OF THE GENUS HALICLONA [J].

FUSETANI, N ;

YASUMURO, K ;

MATSUNAGA, S ;

HIROTA, H .

TETRAHEDRON LETTERS, 1989, 30 (49) :6891-6894

[4] QUANTITATIVE DEALKYLATION OF ALKYL ETHERS VIA TREATMENT WITH TRIMETHYLSILYL IODIDE - NEW METHOD FOR ETHER HYDROLYSIS [J].

JUNG, ME ;

LYSTER, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3761-3764

[5] MARINE NATURAL-PRODUCTS - HALITOXIN, TOXIC COMPLEX OF SEVERAL MARINE SPONGES OF GENUS HALICLONA [J].

SCHMITZ, FJ ;

HOLLENBEAK, KH ;

CAMPBELL, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) :3916-3922

[6] MOLECULAR-BASIS OF MUSCARINIC ACETYLCHOLINE-RECEPTOR FUNCTION [J].

WESS, J .

TRENDS IN PHARMACOLOGICAL SCIENCES, 1993, 14 (08) :308-313

[7] THE M3-MUSCARINIC CHOLINOCEPTOR SUBTYPE IN RAT PROSTATE AND ITS DOWN-REGULATION BY AGING [J].

YAZAWA, H ;

HONDA, K .

JAPANESE JOURNAL OF PHARMACOLOGY, 1993, 61 (04) :319-324

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