共 20 条
Synthesis and biological activity of diaryl ether inhibitors of malarial enoyl acyl carrier protein reductase.: Part 2:: 2′-substituted triclosan derivatives
被引:57
作者:

Freundlich, JS
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Yu, M
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Lucumi, E
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Kuo, M
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Tsai, HC
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Valderramos, JC
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Karagyozov, L
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Jacobs, WR
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Schiehser, GA
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Fidock, DA
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Jacobus, DP
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Sacchettini, JC
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA
机构:
[1] Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA
[2] Yeshiva Univ Albert Einstein Coll Med, Dept Microbiol & Immunol, Bronx, NY 10461 USA
[3] Yeshiva Univ Albert Einstein Coll Med, Howard Hughes Med Inst, Bronx, NY 10461 USA
[4] Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA
关键词:
antimalarial;
diaryl ether;
phenol;
D O I:
10.1016/j.bmcl.2006.01.051
中图分类号:
R914 [药物化学];
学科分类号:
100701 ;
摘要:
2'-substituted analogs of triclosan have been synthesized to target inhibition of the key malarial enzyme Plasmodium falciparum enoyl acyl carrier protein reductase (PfENR). Many of these compounds exhibit good potency (EC50<500 nM) against in vitro cultures of drug-resistant and drug-sensitive strains of the P. falciparum parasite and modest (I-50=1-20 mu M) potency against purified PfENR enzyme. Compared to triclosan, this survey of 2'-substituted derivatives has afforded gains in excess of 20- and 30-fold versus the 3D7 and Dd2 strains of parasite, respectively. (C) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2163 / 2169
页数:7
相关论文
共 20 条
[1]
Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
[J].
AbdelMagid, AF
;
Carson, KG
;
Harris, BD
;
Maryanoff, CA
;
Shah, RD
.
JOURNAL OF ORGANIC CHEMISTRY,
1996, 61 (11)
:3849-3862

AbdelMagid, AF
论文数: 0 引用数: 0
h-index: 0
机构: R. W. Johnson Pharmaceutical Res. I., Department of Chemical Development, Spring House

Carson, KG
论文数: 0 引用数: 0
h-index: 0
机构: R. W. Johnson Pharmaceutical Res. I., Department of Chemical Development, Spring House

Harris, BD
论文数: 0 引用数: 0
h-index: 0
机构: R. W. Johnson Pharmaceutical Res. I., Department of Chemical Development, Spring House

Maryanoff, CA
论文数: 0 引用数: 0
h-index: 0
机构: R. W. Johnson Pharmaceutical Res. I., Department of Chemical Development, Spring House

Shah, RD
论文数: 0 引用数: 0
h-index: 0
机构: R. W. Johnson Pharmaceutical Res. I., Department of Chemical Development, Spring House
[2]
Titanium(IV) isopropoxide mediated solution phase reductive amination on an automated platform: Application in the generation of urea and amide libraries
[J].
Bhattacharyya, S
;
Fan, L
;
Vo, L
;
Labadie, J
.
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING,
2000, 3 (02)
:117-124

Bhattacharyya, S
论文数: 0 引用数: 0
h-index: 0
机构:
Argonaut Technol, San Carlos, CA 94070 USA Argonaut Technol, San Carlos, CA 94070 USA

Fan, L
论文数: 0 引用数: 0
h-index: 0
机构:
Argonaut Technol, San Carlos, CA 94070 USA Argonaut Technol, San Carlos, CA 94070 USA

Vo, L
论文数: 0 引用数: 0
h-index: 0
机构:
Argonaut Technol, San Carlos, CA 94070 USA Argonaut Technol, San Carlos, CA 94070 USA

Labadie, J
论文数: 0 引用数: 0
h-index: 0
机构:
Argonaut Technol, San Carlos, CA 94070 USA Argonaut Technol, San Carlos, CA 94070 USA
[3]
TITANIUM(IV) ISOPROPOXIDE AND SODIUM-BOROHYDRIDE - A REAGENT OF CHOICE FOR REDUCTIVE AMINATION
[J].
BHATTACHARYYA, S
.
TETRAHEDRON LETTERS,
1994, 35 (15)
:2401-2404

BHATTACHARYYA, S
论文数: 0 引用数: 0
h-index: 0
机构: Vijoygarth College, Department of Chemistry, Calcutta
[4]
TERTIARY CARBINAMINES BY ADDITION OF ORGANOCERIUM REAGENTS TO NITRILES AND KETIMINES
[J].
CIGANEK, E
.
JOURNAL OF ORGANIC CHEMISTRY,
1992, 57 (16)
:4521-4527

CIGANEK, E
论文数: 0 引用数: 0
h-index: 0
机构: The Du Pont Merck Pharmaceutical Co., Inc., Wilmington
[5]
Antimalarial drug discovery: Efficacy models for compound screening
[J].
Fidock, DA
;
Rosenthal, PJ
;
Croft, SL
;
Brun, R
;
Nwaka, S
.
NATURE REVIEWS DRUG DISCOVERY,
2004, 3 (06)
:509-520

Fidock, DA
论文数: 0 引用数: 0
h-index: 0
机构: Albert Einstein Coll Med, Dept Microbiol & Immunol, Bronx, NY 10461 USA

Rosenthal, PJ
论文数: 0 引用数: 0
h-index: 0
机构: Albert Einstein Coll Med, Dept Microbiol & Immunol, Bronx, NY 10461 USA

Croft, SL
论文数: 0 引用数: 0
h-index: 0
机构: Albert Einstein Coll Med, Dept Microbiol & Immunol, Bronx, NY 10461 USA

Brun, R
论文数: 0 引用数: 0
h-index: 0
机构: Albert Einstein Coll Med, Dept Microbiol & Immunol, Bronx, NY 10461 USA

Nwaka, S
论文数: 0 引用数: 0
h-index: 0
机构: Albert Einstein Coll Med, Dept Microbiol & Immunol, Bronx, NY 10461 USA
[6]
Synthesis, biological activity, and X-ray crystal structural analysis of diaryl ether inhibitors of malarial enoyl acyl carrier protein reductase.: Part 1: 4′-substituted triclosan derivatives
[J].
Freundlich, JS
;
Anderson, JW
;
Sarantakis, D
;
Shieh, HM
;
Yu, M
;
Valderramos, JC
;
Lucumi, E
;
Kuo, M
;
Jacobs, WR
;
Fidock, DA
;
Schiehser, GA
;
Jacobus, DP
;
Sacchettini, JC
.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
2005, 15 (23)
:5247-5252

Freundlich, JS
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Anderson, JW
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Sarantakis, D
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Shieh, HM
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Yu, M
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Valderramos, JC
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Lucumi, E
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Kuo, M
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Jacobs, WR
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Fidock, DA
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Schiehser, GA
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Jacobus, DP
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA

Sacchettini, JC
论文数: 0 引用数: 0
h-index: 0
机构: Jacobus Pharmaceut Co, Dept Med Chem, Princeton, NJ 08540 USA
[7]
Slow-tight-binding inhibition of enoyl-acyl carrier protein reductase from Plasmodium falciparum by triclosan
[J].
Kapoor, M
;
Reddy, CC
;
Krishnasastry, MV
;
Surolia, N
;
Surolia, A
.
BIOCHEMICAL JOURNAL,
2004, 381
:719-724

Kapoor, M
论文数: 0 引用数: 0
h-index: 0
机构: Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India

Reddy, CC
论文数: 0 引用数: 0
h-index: 0
机构: Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India

Krishnasastry, MV
论文数: 0 引用数: 0
h-index: 0
机构: Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India

Surolia, N
论文数: 0 引用数: 0
h-index: 0
机构: Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India

Surolia, A
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India
[8]
Kinetic and structural analysis of the increased affinity of enoyl-ACP (acyl-carrier protein) reductase for triclosan in the presence of NAD+
[J].
Kapoor, M
;
Mukhi, PLS
;
Surolia, N
;
Suguna, K
;
Surolia, A
.
BIOCHEMICAL JOURNAL,
2004, 381
:725-733

Kapoor, M
论文数: 0 引用数: 0
h-index: 0
机构: Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India

Mukhi, PLS
论文数: 0 引用数: 0
h-index: 0
机构: Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India

Surolia, N
论文数: 0 引用数: 0
h-index: 0
机构: Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India

Suguna, K
论文数: 0 引用数: 0
h-index: 0
机构: Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India

Surolia, A
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India Indian Inst Sci, Mol Biophys Unit, Bangalore 560012, Karnataka, India
[9]
Mutational analysis of the triclosan-binding region of enoyl-ACP (acyl-carrier protein) reductase from Plasmodium falciparum
[J].
Kapoor, M
;
Gopalakrishnapai, J
;
Surolia, N
;
Surolia, A
.
BIOCHEMICAL JOURNAL,
2004, 381
:735-741

Kapoor, M
论文数: 0 引用数: 0
h-index: 0
机构: Jawaharlal Nehru Ctr Adv Sci Res, Mol Biol & Genet Unit, Bangalore, Karnataka, India

Gopalakrishnapai, J
论文数: 0 引用数: 0
h-index: 0
机构: Jawaharlal Nehru Ctr Adv Sci Res, Mol Biol & Genet Unit, Bangalore, Karnataka, India

Surolia, N
论文数: 0 引用数: 0
h-index: 0
机构:
Jawaharlal Nehru Ctr Adv Sci Res, Mol Biol & Genet Unit, Bangalore, Karnataka, India Jawaharlal Nehru Ctr Adv Sci Res, Mol Biol & Genet Unit, Bangalore, Karnataka, India

Surolia, A
论文数: 0 引用数: 0
h-index: 0
机构: Jawaharlal Nehru Ctr Adv Sci Res, Mol Biol & Genet Unit, Bangalore, Karnataka, India
[10]
Targeting tuberculosis and malaria through inhibition of enoyl reductase
[J].
Kuo, MR
;
Morbidoni, HR
;
Alland, D
;
Sneddon, SF
;
Gourlie, BB
;
Staveski, MM
;
Leonard, M
;
Gregory, JS
;
Janjigian, AD
;
Yee, C
;
Musser, JM
;
Kreiswirth, B
;
Iwamoto, H
;
Perozzo, R
;
Jacobs, WR
;
Sacchettini, JC
;
Fidock, DA
.
JOURNAL OF BIOLOGICAL CHEMISTRY,
2003, 278 (23)
:20851-20859

Kuo, MR
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Morbidoni, HR
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Alland, D
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Sneddon, SF
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Gourlie, BB
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Staveski, MM
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Leonard, M
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Gregory, JS
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Janjigian, AD
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Yee, C
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Musser, JM
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Kreiswirth, B
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Iwamoto, H
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Perozzo, R
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Jacobs, WR
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Sacchettini, JC
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA

Fidock, DA
论文数: 0 引用数: 0
h-index: 0
机构: Texas A&M Univ, Dept Biochem & Biophys, College Stn, TX 77843 USA