Towards non-peptide ANG II AT1 receptor antagonists based on urocanic acid: rational design, synthesis and biological evaluation

被引：13

作者：

Agelis, George ^{[1
]}

Resvani, Amalia ^{[1
]}

Matsoukas, Minos-Timotheos ^{[1
]}

Tselios, Theodore ^{[1
]}

Kelaidonis, Konstantinos ^{[1
]}

Kalavrizioti, Dimitra ^{[2
]}

Vlahakos, Demetrios ^{[3
]}

Matsoukas, John ^{[1
]}

机构：

[1] Univ Patras, Dept Chem, Patras 26500, Greece

[2] Univ Patras, Sch Med, Dept Pharmacol, Patras 26500, Greece

[3] ATTIKON Univ Hosp, Dept Internal Med, Athens, Greece

来源：

AMINO ACIDS | 2011年 / 40卷 / 02期

关键词：

AT1; receptor; Urocanic acid; Pharmacophore; Molecular modelling; SIMULATING ENVIRONMENTS; BINDING; POTENT; ANTIHYPERTENSIVES; DISCOVERY; DUP-753;

D O I：

10.1007/s00726-010-0651-y

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

A series of o-, m- and p-benzyl tetrazole derivatives 11a-c has been designed, synthesized and evaluated as potential Angiotensin II AT1 receptor antagonists, based on urocanic acid. Compound 11b with tetrazole moiety at the m-position showed moderate, however, higher activity compared to the o- and p-counterpart analogues. Molecular modelling techniques were performed in order to extract their putative bioactive conformations and explore their binding modes.

引用

页码：411 / 420

页数：10

共 25 条

[1]

Design and in vivo analysis of potent non-thiol inhibitors of farnesyl protein transferase [J].

Anthony, NJ ;

Gomez, RP ;

Schaber, MD ;

Mosser, SD ;

Hamilton, KA ;

O'Neil, TJ ;

Koblan, KS ;

Graham, SL ;

Hartman, GD ;

Shah, D ;

Rands, E ;

Kohl, NE ;

Gibbs, JB ;

Oliff, AI .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (17) :3356-3368

[2]

NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS - THE DISCOVERY OF A SERIES OF N-(BIPHENYLYLMETHYL)IMIDAZOLES AS POTENT, ORALLY ACTIVE ANTIHYPERTENSIVES [J].

CARINI, DJ ;

DUNCIA, JV ;

ALDRICH, PE ;

CHIU, AT ;

JOHNSON, AL ;

PIERCE, ME ;

PRICE, WA ;

SANTELLA, JB ;

WELLS, GJ ;

WEXLER, RR ;

WONG, PC ;

YOO, SE ;

TIMMERMANS, PBMWM .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2525-2547

[3]

High-resolution crystal structure of an engineered human β2-adrenergic G protein-coupled receptor [J].

Cherezov, Vadim ;

Rosenbaum, Daniel M. ;

Hanson, Michael A. ;

Rasmussen, Soren G. F. ;

Thian, Foon Sun ;

Kobilka, Tong Sun ;

Choi, Hee-Jung ;

Kuhn, Peter ;

Weis, William I. ;

Kobilka, Brian K. ;

Stevens, Raymond C. .

SCIENCE, 2007, 318 (5854) :1258-1265

[4]

Determining the environment of the ligand binding pocket of the human angiotensin II type I (hAT1) receptor using the methionine proximity assay [J].

Clément, M ;

Martin, SS ;

Beaulieu, ME ;

Chamberland, C ;

Lavigne, P ;

Leduc, R ;

Guillemette, G ;

Escher, E .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2005, 280 (29) :27121-27129

[5]

THE DISCOVERY OF POTENT NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS - A NEW CLASS OF POTENT ANTIHYPERTENSIVES [J].

DUNCIA, JV ;

CHIU, AT ;

CARINI, DJ ;

GREGORY, GB ;

JOHNSON, AL ;

PRICE, WA ;

WELLS, GJ ;

WONG, PC ;

CALABRESE, JC ;

TIMMERMANS, PBMWM .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1312-1329

[6]

DZAU VJ, 1994, J HYPERTENS, V12, pS1

[7]

NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS - SYNTHESIS AND BIOLOGICAL-ACTIVITY OF POTENTIAL PRODRUGS OF BENZIMIDAZOLE-7-CARBOXYLIC ACIDS [J].

KUBO, K ;

KOHARA, Y ;

YOSHIMURA, Y ;

INADA, Y ;

SHIBOUTA, Y ;

FURUKAWA, Y ;

KATO, T ;

NISHIKAWA, K ;

NAKA, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (16) :2343-2349

[8]

LAM S, 2007, DRUG HIGHLIGHT CARDI, V15, P316

[9]

LAUTHDEVIGUERIE N, 1994, HETEROCYCLES, V37, P1561

[10]

LUITJEN JG, 1963, J RECL TRAV CHIM PAY, V81, P202

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