Three-dimensional QSAR analysis and design of new 1,2,4-oxadiazole antibacterials

被引：43

作者：

Leemans, Erika ^{[1
]}

Mahasenan, Kiran V. ^{[1
]}

Kumarasiri, Malika ^{[1
]}

Spink, Edward ^{[1
]}

Ding, Derong ^{[1
]}

O'Daniel, Peter I. ^{[1
]}

Boudreau, Marc A. ^{[1
]}

Lastochkin, Elena ^{[1
]}

Testero, Sebastian A. ^{[1
]}

Yamaguchi, Takao ^{[1
]}

Lee, Mijoon ^{[1
]}

Hesek, Dusan ^{[1
]}

Fisher, Jed F. ^{[1
]}

Chang, Mayland ^{[1
]}

Mobashery, Shahriar ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2016年 / 26卷 / 03期

基金：

美国国家卫生研究院;

关键词：

1,2,4-Oxadiazole; Antibiotic; 3D-QSAR; CoMFA; STAPHYLOCOCCUS-AUREUS; ANTIBIOTIC-RESISTANCE; COMFA MODELS; DRUG DESIGN; 3D QSAR; PREDICTION; DISCOVERY; SELECTION; PROTEINS; BINDING;

D O I：

10.1016/j.bmcl.2015.12.041

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The oxadiazole antibacterials, a class of newly discovered compounds that are active against Gram-positive bacteria, target bacterial cell-wall biosynthesis by inhibition of a family of essential enzymes, the penicillin-binding proteins. Ligand-based 3D-QSAR analyses by comparative molecular field analysis (CoMFA), comparative molecular shape indices analysis (CoMSIA) and Field-Based 3D-QSAR evaluated a series of 102 members of this class. This series included inactive compounds as well as compounds that were moderately to strongly antibacterial against Staphylococcus aureus. Multiple models were constructed using different types of energy minimization and charge calculations. CoMFA derived contour maps successfully defined favored and disfavored regions of the molecules in terms of steric and electrostatic properties for substitution. (C) 2016 Published by Elsevier Ltd.

引用

页码：1011 / 1015

页数：5

共 34 条

[1] Improving known classes of antibiotics: an optimistic approach for the future [J].

Bush, Karen .

CURRENT OPINION IN PHARMACOLOGY, 2012, 12 (05) :527-534

[2] Tackling antibiotic resistance [J].

Bush, Karen ;

Courvalin, Patrice ;

Dantas, Gautam ;

Davies, Julian ;

Eisenstein, Barry ;

Huovinen, Pentti ;

Jacoby, George A. ;

Kishony, Roy ;

Kreiswirth, Barry N. ;

Kutter, Elizabeth ;

Lerner, Stephen A. ;

Levy, Stuart ;

Lewis, Kim ;

Lomovskaya, Olga ;

Miller, Jeffrey H. ;

Mobashery, Shahriar ;

Piddock, Laura J. V. ;

Projan, Steven ;

Thomas, Christopher M. ;

Tomasz, Alexander ;

Tulkens, Paul M. ;

Walsh, Timothy R. ;

Watson, James D. ;

Witkowski, Jan ;

Witte, Wolfgang ;

Wright, Gerry ;

Yeh, Pamela ;

Zgurskaya, Helen I. .

NATURE REVIEWS MICROBIOLOGY, 2011, 9 (12) :894-896

[3] APPLICATION OF RESP CHARGES TO CALCULATE CONFORMATIONAL ENERGIES, HYDROGEN-BOND ENERGIES, AND FREE-ENERGIES OF SOLVATION [J].

CORNELL, WD ;

CIEPLAK, P ;

BAYLY, CI ;

KOLLMAN, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9620-9631

[4] COMPARATIVE MOLECULAR-FIELD ANALYSIS (COMFA) .1. EFFECT OF SHAPE ON BINDING OF STEROIDS TO CARRIER PROTEINS [J].

CRAMER, RD ;

PATTERSON, DE ;

BUNCE, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :5959-5967

[5] Pushing the boundaries of 3D-QSAR [J].

Cramer, Richard D. ;

Wendt, Bernd .

JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 2007, 21 (1-3) :23-32

[6] The inevitable QSAR renaissance [J].

Cramer, Richard D. .

JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 2012, 26 (01) :35-38

[7] The evolution of Staphylococcus aureus [J].

Deurenberg, Ruud H. ;

Stobberingh, Ellen E. .

INFECTION GENETICS AND EVOLUTION, 2008, 8 (06) :747-763

[8] Exploration of the structure-activity relationship of 1,2,4-oxadiazole antibiotics [J].

Ding, Derong ;

Boudreau, Marc A. ;

Leemans, Erika ;

Spink, Edward ;

Yamaguchi, Takao ;

Testero, Sebastian A. ;

O'Daniel, Peter I. ;

Lastochkin, Elena ;

Chang, Mayland ;

Mobashery, Shahriar .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (21) :4854-4857

[9] PHASE: a new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results [J].

Dixon, Steven L. ;

Smondyrev, Alexander M. ;

Knoll, Eric H. ;

Rao, Shashidhar N. ;

Shaw, David E. ;

Friesner, Richard A. .

JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 2006, 20 (10-11) :647-671

[10] Pandrug-resistant Gram-negative bacteria: the dawn of the post-antibiotic era? [J].

Falagas, Matthew E. ;

Bliziotis, Ioannis A. .

INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, 2007, 29 (06) :630-636

← 1 2 3 4 →