ISOSTERISM AND BIOISOSTERISM CASE-STUDIES WITH MUSCARINIC AGONISTS

被引：0

作者：

FLOERSHEIM, P ^{[1
]}

POMBOVILLAR, E ^{[1
]}

SHAPIRO, G ^{[1
]}

机构：

[1] SANDOZ PHARMA LTD,PRECLIN RES,CH-4002 BASEL,SWITZERLAND

来源：

CHIMIA | 1992年 / 46卷 / 7-8期

关键词：

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis and activity of enantiomerically pure analogues of pilocarpine and muscarinic agonists with the azabicyclo[2.2.1]heptane skeleton is described. Structure-activity relationships support a flexible model in which a coulombic interaction as well as two H-bonding interactions with the receptor are necessary for potent muscarinic agonist activity. In this context, a critical appraisal of the concepts of isosterism and bioisosterism is put forward, isosterism is redefined, and bioisosterism is discarded in favor of the new concept of bioanalogy.

引用

页码：323 / 334

页数：12

共 73 条

[1] HYDROGEN-BONDING .9. SOLUTE PROTON DONOR AND PROTON ACCEPTOR SCALES FOR USE IN DRUG DESIGN [J].

ABRAHAM, MH ;

DUCE, PP ;

PRIOR, DV ;

BARRATT, DG ;

MORRIS, JJ ;

TAYLOR, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (10) :1355-1375

[2] STRUCTURE OF 7A-HYDROXY-4-PHENYL-1,2,4,4A,5,6,7,7A-OCTAHYDRO-CYCLOPENTA[D][1,3]THIAZINE-2-THIONE [J].

ARGAY, G ;

KALMAN, A ;

PERJESI, P ;

SZABO, D .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1987, 43 :324-326

[3]

BIRDSALL NJM, 1989, TRENDS PHARM SCI S, V10, pR7

[4]

BODDEKE HWGM, 1992, N-S ARCH PHARMACOL, V345, P257

[5] ABSOLUTE-CONFIGURATION OF 3-SUBSTITUTED 1-AZABICYCLO[2.2.1]HEPTANES [J].

BOELSTERLI, J ;

EGGNAUER, U ;

POMBOVILLAR, E ;

WEBER, HP ;

WALKINSHAW, M ;

GOULD, RO .

HELVETICA CHIMICA ACTA, 1992, 75 (02) :507-512

[6] THE MOLECULAR-BASIS OF MUSCARINIC RECEPTOR DIVERSITY [J].

BONNER, TI .

TRENDS IN NEUROSCIENCES, 1989, 12 (04) :148-151

[7] EFFECTS OF SULFUR SUBSTITUENTS ON STRUCTURAL-PROPERTIES OF PURINES - CRYSTAL-STRUCTURES OF GUANINE PICRATE MONOHYDRATE AND 6-THIOGUANINE PICRATE MONOHYDRATE [J].

BUGG, CE ;

THEWALT, U .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1975, 31 (JAN15) :121-127

[8]

BURGER A, 1991, FORTSCHR ARZNEIM FOR, V31, P287

[9] BINDING-STUDIES WITH [H-3] CIS-METHYLDIOXOLANE IN DIFFERENT TISSUES - UNDER CERTAIN CONDITIONS [H-3] CIS-METHYLDIOXOLANE LABELS PREFERENTIALLY BUT NOT EXCLUSIVELY AGONIST HIGH-AFFINITY STATES OF MUSCARINIC M2-RECEPTORS [J].

CLOSSE, A ;

BITTIGER, H ;

LANGENEGGER, D ;

WANNER, A .

NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 1987, 335 (04) :372-377

[10]

CLOUGH SC, 1982, J HETEROCYCLIC CHEM, V22, P1489

← 1 2 3 4 5 6 7 8 →