Synthesis and Biological Evaluation of Biphenyl Amides That Modulate the US28 Receptor

被引：25

作者：

Kralj, Ana ^{[1
]}

Kurt, Elif ^{[1
]}

Tschammer, Nuska ^{[1
]}

Heinrich, Markus R. ^{[1
]}

机构：

[1] Univ Erlangen Nurnberg, Dept Chem & Pharmazie Pharmazeut Chem, D-91052 Erlangen, Germany

来源：

CHEMMEDCHEM | 2014年 / 9卷 / 01期

关键词：

amides; biphenyls; human cytomegalovirus; inverse agonism; US28; receptor; HUMAN-CYTOMEGALOVIRUS; INVERSE AGONISTS; REDUCTIVE CARBODIAZENYLATION; RADICAL ARYLATION; CHEMOKINE; IDENTIFICATION; PRECURSORS; INHIBITORS; INFECTION; ANILINES;

D O I：

10.1002/cmdc.201300369

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

To prepare and biologically evaluate 38 new potential US28 allosteric modulators, we employed a straightforward synthetic route involving radical arylation. The study was based on a former lead structure but with the dihydroisoquinolinone moiety replaced by substituted biphenyls. The investigation of structure-activity relationships among the new biphenyl-derived ligands led to a preliminary pharmacophore model and the discovery of four promising candidates with full inverse agonist properties.

引用

页码：151 / 168

页数：18

共 61 条

[1] The internal barriers of rotation for the 209 polychlorinated biphenyls [J].

Andersson, PL ;

Haglund, P ;

Tysklind, M .

ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH, 1997, 4 (02) :75-81

[2]

[Anonymous], 2011, BRIGHT GLO LUC ASS S

[3]

[Anonymous], 2011, PATHDETECT IN VIV SI

[4] Benzimidazole-substituted (3-phenoxypropyl)amines as histamine H3 receptor ligands [J].

Aslanian, Robert ;

Zhu, Xiaohong ;

Vaccaro, Henry A. ;

Shih, Neng-Yang ;

Piwinski, John J. ;

Williams, Shirley M. ;

West, Robert E., Jr. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (18) :5032-5036

[5] Highly chemoselective addition of amines to epoxides in water [J].

Azizi, N ;

Saidi, MR .

ORGANIC LETTERS, 2005, 7 (17) :3649-3651

[6] Antiviral drugs for cytomegalovirus diseases [J].

Biron, Karen K. .

ANTIVIRAL RESEARCH, 2006, 71 (2-3) :154-163

[7] Radical carbodiazenylation - A convenient and effective method to achieve carboamination of non-activated olefins [J].

Blank, Olga ;

Wetzel, Alexander ;

Ullrich, Daniela ;

Heinrich, Markus R. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (18) :3179-3189

[8] Chemokine sequestration by viral chemoreceptors as a novel viral escape strategy: Withdrawal of chemokines from the environment of cytomegalovirus-infected cells [J].

Bodaghi, B ;

Jones, TR ;

Zipeto, D ;

Vita, C ;

Sun, L ;

Laurent, L ;

Arenzana-Seisdedos, F ;

Virelizier, JL ;

Michelson, S .

JOURNAL OF EXPERIMENTAL MEDICINE, 1998, 188 (05) :855-866

[9] HOMOLYTIC ARYLATION OF AROMATIC AND POLYFLUOROAROMATIC COMPOUNDS [J].

BOLTON, R ;

WILLIAMS, GH .

CHEMICAL SOCIETY REVIEWS, 1986, 15 (02) :261-289

[10] US28 actions in HCMV infection: lessons from a versatile hijacker [J].

Boomker, JM ;

van Luyn, MJA ;

The, TH ;

de Leij, LFMH ;

Harmsen, MC .

REVIEWS IN MEDICAL VIROLOGY, 2005, 15 (04) :269-282

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