Novel promising linezolid analogues: Rational design, synthesis and biological evaluation

被引：27

作者：

De Rosa, Margherita ^{[1
]}

Zanfardino, Anna ^{[3
]}

Notomista, Eugenio ^{[3
]}

Wichelhaus, Thomas A. ^{[4
]}

Saturnino, Carmela ^{[2
]}

Varcamonti, Mario ^{[3
]}

Soriente, Annunziata ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim & Biol, I-84084 Fisciano, SA, Italy

[2] Univ Salerno, Dipartimento Farm, I-84084 Fisciano, SA, Italy

[3] Univ Naples Federico II, Dipartimento Biol, I-80126 Naples, Italy

[4] Hosp Goethe Univ, Inst Med Microbiol & Infect Control, D-60596 Frankfurt, Germany

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 69卷

关键词：

Linezolid; Oxazolidinone; Thiourea; Antibacterial; Structure-activity relationship; OXAZOLIDINONE ANTIBACTERIAL AGENTS; ACTIVITY RELATIONSHIP SAR; CONFORMATIONAL PREFERENCES; RESISTANCE; DERIVATIVES; GENE;

D O I：

10.1016/j.ejmech.2013.09.035

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new series of 5-substituted oxazolidinones derived from linezolid, having urea and thiourea moieties at the C-5 side chain of the oxazolidinone ring, were prepared and their in vitro antibacterial activity was evaluated. The compound 10f demonstrated high antimicrobial activity, comparable to that of linezolid against Staphylococcus aureus. (C) 2013 Elsevier Masson SAS. All rights reserved.

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收藏

页码：779 / 785

页数：7

相关论文

共 30 条

[1] Oxazolidinone structure-activity relationships leading to linezolid [J].

Barbachyn, MR ;

Ford, CW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (18) :2010-2023

[2] Linezolid resistance in Staphylococcus aureus:: Gene dosage effect, stability, fitness costs, and cross-resistances [J].

Besier, Silke ;

Ludwig, Albrecht ;

Zander, Johannes ;

Brade, Volker ;

Wichelhaus, Thomas A. .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2008, 52 (04) :1570-1572

[3] Oxazolidinones: activity, mode of action, and mechanism of resistance [J].

Bozdogan, B ;

Appelbaum, PC .

INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, 2004, 23 (02) :113-119

[4] Linezolid (ZYVOX), the first member of a completely new class of antibacterial agents for treatment of serious gram-positive infections [J].

Brickner, Steven J. ;

Barbachyn, Michael R. ;

Hutchinson, Douglas K. ;

Manninen, Peter R. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (07) :1981-1990

[5] Conformational preferences and internal rotation in alkyl- and phenyl-substituted thiourea derivatives [J].

Bryantsev, VS ;

Hay, BP .

JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (14) :4678-4688

[6] Oxazolidinone antibiotics [J].

Diekema, DJ ;

Jones, RN .

LANCET, 2001, 358 (9297) :1975-1982

[7] Conformational preferences in model antiviral compounds: A spectroscopic and computational study of phenylurea and 1,3-diphenylurea [J].

Emery, R ;

Macleod, NA ;

Snoek, LC ;

Simons, JP .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2004, 6 (10) :2816-2820

[8]

Ford C. W., 2001, Current Drug Targets - Infectious Disorders, V1, P181, DOI 10.2174/1568005014606099

[9] New linezolid-like 1,2,4-oxadiazoles active against Gram-positive multiresistant pathogens [J].

Fortuna, Cosimo G. ;

Bonaccorso, Carmela ;

Bulbarelli, Alessandra ;

Caltabiano, Gianluigi ;

Rizzi, Laura ;

Goracci, Laura ;

Musumarra, Giuseppe ;

Pace, Andrea ;

Piccionello, Antonio Palumbo ;

Guarcello, Annalisa ;

Pierro, Paola ;

Cocuzza, Clementina E. A. ;

Musumeci, Rosario .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 65 :533-545

[10]

Gravestock MB, 2005, CURR OPIN DRUG DISC, V8, P469