Structure-affinity relationships of the affinity of 2-pyrazolyl adenosine analogues for the adenosine A2A receptor

被引：29

作者：

Palle, VP

Elzein, EO

Gothe, SA

Li, ZH

Gao, ZH

Meyer, S

Blackburn, B

Zablocki, JA

机构：

[1] CV Therapeut, Dept Bioorgan Chem, Palo Alto, CA 94304 USA

[2] CV Therapeut, Dept Pharmacol Sci, Palo Alto, CA 94304 USA

[3] Tripos Inc, San Francisco, CA USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 20期

关键词：

D O I：

10.1016/S0960-894X(02)00609-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The structure-affinity relationships of two novel 2-substituted adenosine series containing a substituted pyrazole attached at the N-1 or C-4 position for the adenosine (ADO) A(2A) receptor are described. Compounds in the 2-(N-1-pyrazolyl) adenosine series IV provided the highest affinity for the ADO A(2A) receptor as compared to the 2-(C-4-pyrazolyl) series V. The main structural differences between the two series point to the N-1 nitrogen of series IV imparting more favorable binding interactions with the receptor than those of series V. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：2935 / 2939

页数：5

相关论文

共 19 条

[1] NEW COPPER CHEMISTRY .3. NEW PREPARATIONS OF ETHYL 3,3-DIETHOXYPROPIONATE AND (ETHOXYCARBONYL)MALONDIALDEHYDE - CU(I)-CATALYZED ACETAL FORMATION FROM A CONJUGATED TRIPLE BOND [J].

BERTZ, SH ;

DABBAGH, G ;

COTTE, P .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2216-2217

[2]

Feoktistov I, 1997, PHARMACOL REV, V49, P381

[3] Effects of CGS 21680, a selective adenosine A2A receptor agonist, on allergic airways inflammation in the rat [J].

Fozard, JR ;

Ellis, KM ;

Dantas, MFV ;

Tigani, B ;

Mazzoni, L .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2002, 438 (03) :183-188

[4] HIGHLY SELECTIVE ADENOSINE-A2 RECEPTOR AGONISTS IN A SERIES OF N-ALKYLATED 2-AMINOADENOSINES [J].

FRANCIS, JE ;

WEBB, RL ;

GHAI, GR ;

HUTCHISON, AJ ;

MOSKAL, MA ;

DEJESUS, R ;

YOKOYAMA, R ;

ROVINSKI, SL ;

CONTARDO, N ;

DOTSON, R ;

BARCLAY, B ;

STONE, GA ;

JARVIS, MF .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2570-2579

[5]

Gao ZH, 2001, J PHARMACOL EXP THER, V298, P209

[6] Pharmacological stress thallium scintigraphy with 2-cyclohexylmethylidenehydrazinoadenosine (WRC-0470) - A novel, short-acting adenosine A(2A) receptor agonist [J].

Glover, DK ;

Ruiz, M ;

Yang, JY ;

Koplan, BA ;

Allen, TR ;

Smith, WH ;

Watson, DD ;

Barrett, RJ ;

Beller, GA .

CIRCULATION, 1996, 94 (07) :1726-1732

[7] LITHIATION-MEDIATED C-C SILYL AND STANNYL MIGRATIONS OBSERVED IN 6-CHLORO-9-(BETA-D-RIBOFURANOSYL)PURINE [J].

KATO, K ;

HAYAKAWA, H ;

TANAKA, H ;

KUMAMOTO, H ;

MIYASAKA, T .

TETRAHEDRON LETTERS, 1995, 36 (36) :6507-6510

[8] A physiological role of the adenosine A3 receptor:: Sustained cardioprotection [J].

Liang, BT ;

Jacobson, KA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (12) :6995-6999

[9] NUCLEOSIDES AND NUCLEOTIDES .103. 2-ALKYNYLADENOSINES - A NOVEL CLASS OF SELECTIVE ADENOSINE-A2 RECEPTOR AGONISTS WITH POTENT ANTIHYPERTENSIVE EFFECTS [J].

MATSUDA, A ;

SHINOZAKI, M ;

YAMAGUCHI, T ;

HOMMA, H ;

NOMOTO, R ;

MIYASAKA, T ;

WATANABE, Y ;

ABIRU, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (02) :241-252

[10]

MITCHELL TN, 1992, SYNTHESIS-STUTTGART, P803