A Short and Efficient Synthesis of the Selective H4 Receptor Agonist 4-Methylhistamine

被引：0

作者：

Rivara, Mirko ^{[1
]}

Zuliani, Valentina ^{[1
]}

Plazzi, Pier V. ^{[1
]}

Bordi, Fabrizio ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Farmaceut, I-43100 Parma, Italy

来源：

LETTERS IN ORGANIC CHEMISTRY | 2009年 / 6卷 / 01期

关键词：

4-methylhistamine; histamine; H-4-receptor; n-butyllithium; H-4-agonist; yield; EOSINOPHIL CHEMOTAXIS; MEDIATES CHEMOTAXIS; HISTAMINE; IDENTIFICATION; DERIVATIVES; CELLS;

D O I：

10.2174/157017809787003223

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of the selective H-4 receptor agonist 4-methylhistamine is described. This approach can be used to prepare, without purification steps and in high yield, significant quantities of the product, useful as pharmacological tool to investigate the physiological roles of the histamine H-4 receptor.

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页码：88 / 89

页数：2

相关论文

共 17 条

[1] 2,5-DILITHIATION OF N-PROTECTED IMIDAZOLES - SYNTHESES OF 2,5-DISUBSTITUTED DERIVATIVES OF 1-METHOXYMETHYL-IMIDAZOLE, 1-TRIPHENYLMETHYL-IMIDAZOLE, AND 1-(N,N-DIMETHYLSULPHONAMIDO)-IMIDAZOLE [J].

CHADWICK, DJ ;

NGOCHINDO, RI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03) :481-486

[2] CONVENIENT SYNTHESIS OF 4-METHYLHISTAMINE AND RACEMIC ALPHA,4-DIMETHYLHISTAMINE AND ALPHA,4-DIMETHYLHISTIDINE [J].

DAVEY, DD ;

LUMMA, WC .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3211-3213

[3] POTENTIAL HISTAMINE H2-RECEPTOR ANTAGONISTS .3. METHYLHISTAMINES [J].

DURANT, GJ ;

EMMETT, JC ;

GANELLIN, CR ;

ROE, AM ;

SLATER, RA .

JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (07) :923-928

[4] AN ALTERNATIVE SYNTHESIS OF HOMOHISTAMINE AND STRUCTURALLY RELATED (IMIDAZOLE-4-YL)ALKYLAMINES [J].

ELZ, S ;

SCHUNACK, W .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1987, 42 (02) :238-242

[5] Compared pharmacology of human histamine H3 and H4 receptors:: structure-activity relationships of histamine derivatives [J].

Gbahou, F ;

Vincent, L ;

Humbert-Claude, M ;

Tardivel-Lacombe, J ;

Chabret, C ;

Arrang, JM .

BRITISH JOURNAL OF PHARMACOLOGY, 2006, 147 (07) :744-754

[6] Histamine H4 receptor stimulation suppresses IL-12p70 production and mediates chemotaxis in human monocyte-derived dendritic cells [J].

Gutzmer, R ;

Diestel, C ;

Mommert, S ;

Köther, B ;

Stark, H ;

Wittmann, M ;

Werfel, T .

JOURNAL OF IMMUNOLOGY, 2005, 174 (09) :5224-5232

[7] Histamine H4 receptor mediates chemotaxis and calcium mobilization of mast cells [J].

Hofstra, CL ;

Desai, PJ ;

Thurmond, RL ;

Fung-Leung, WP .

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2003, 305 (03) :1212-1221

[8] Genomics meets histamine receptors: New subtypes, new receptors [J].

Hough, LB .

MOLECULAR PHARMACOLOGY, 2001, 59 (03) :415-419

[9]

LENNARTZ HG, 1978, EUR J MED CHEM, V13, P229

[10] Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor:: Identification of 4-methylhistamine as the first potent and selective H4 receptor agonist [J].

Lim, HD ;

van Rijn, RM ;

Ling, P ;

Bakker, RA ;

Thurmond, RL ;

Leurs, R .

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2005, 314 (03) :1310-1321