Design, synthesis, and preliminary biological evaluation of novel ketone derivatives of shikimic acid

被引:7
作者
Jiang, Min [1 ,2 ]
Xiong, Bing [2 ]
Shen, Yu-mei [1 ]
Yang, Chunhao [2 ]
机构
[1] Shanghai Jiao Tong Univ, Minist Educ, Key Lab Syst Biomed, Shanghai Ctr Syst Biomed, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[2] Chinese Acad Sci, SIBS, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
来源
RSC ADVANCES | 2013年 / 3卷 / 43期
基金
中国国家自然科学基金;
关键词
II DEHYDROQUINASE; MYCOBACTERIUM-TUBERCULOSIS; STREPTOMYCES-COELICOLOR; APICOMPLEXAN PARASITES; COMPETITIVE INHIBITORS; ENOLATE INTERMEDIATE; ARYLBORONIC ACIDS; ACYL CHLORIDES; DRUG DESIGN; PATHWAY;
D O I
10.1039/c3ra43755h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We herein report the discovery of novel shikimic acid derivatives via Suzuki coupling and Liebeskind-Srogl reaction. Fourteen compounds were synthesized and evaluated against M. tuberculosis H(37)Rv (ATCC 95054). Most of these compounds displayed activities against M. tuberculosis with MIC ranging from 4 to 16 mu g mL(-1). These substances are promising antimycobacterial prototypes.
引用
收藏
页码:20599 / 20605
页数:7
相关论文
共 34 条
[1]   THE SHIKIMATE PATHWAY - A METABOLIC TREE WITH MANY BRANCHES [J].
BENTLEY, R .
CRITICAL REVIEWS IN BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1990, 25 (05) :307-384
[2]   Mycobacterium tuberculosis Shikimate Kinase Inhibitors: Design and Simulation Studies of the Catalytic Turnover [J].
Blanco, Beatriz ;
Prado, Veronica ;
Lence, Emilio ;
Otero, Jose M. ;
Garcia-Doval, Carmela ;
van Raaij, Mark J. ;
Llamas-Saiz, Antonio L. ;
Lamb, Heather ;
Hawkins, Alastair R. ;
Gonzalez-Bello, Concepcion .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (33) :12366-12376
[3]   Synthesis of 3-alkyl enol mimics inhibitors of type II dehydroquinase: factors influencing their inhibition potency [J].
Blanco, Beatriz ;
Sedes, Antia ;
Peon, Antonio ;
Lamb, Heather ;
Hawkins, Alastair R. ;
Castedo, Luis ;
Gonzalez-Bello, Concepcion .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (18) :3662-3676
[4]   Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes [J].
Bumagin, NA ;
Korolev, DN .
TETRAHEDRON LETTERS, 1999, 40 (15) :3057-3060
[5]   Structural investigation of inhibitor designs targeting 3-dehydroquinate dehydratase from the shikimate pathway of Mycobacterium tuberculosis [J].
Dias, Marcio V. B. ;
Snee, William C. ;
Bromfield, Karen M. ;
Payne, Richard J. ;
Palaninathan, Satheesh K. ;
Ciulli, Alessio ;
Howard, Nigel I. ;
Abell, Chris ;
Sacchettini, James C. ;
Blundell, Tom L. .
BIOCHEMICAL JOURNAL, 2011, 436 :729-739
[6]   Mycobacterial shikimate pathway enzymes as targets for drug design [J].
Ducati, R. G. ;
Basso, L. A. ;
Santos, D. S. .
CURRENT DRUG TARGETS, 2007, 8 (03) :423-435
[7]   Industrial synthesis of the key precursor in the synthesis of the anti-influenza drug oseltamivir phosphate (Ro 64-0796/002, GS-4104-02):: Ethyl (3R,4S,5S)-4,5-epoxy-3-(1-ethyl-propoxy)-cyclohex-1-ene-1-carboxylate [J].
Federspiel, M ;
Fischer, R ;
Hennig, M ;
Mair, HJ ;
Oberhauser, T ;
Rimmler, G ;
Albiez, T ;
Bruhin, J ;
Estermann, H ;
Gandert, C ;
Göckel, V ;
Götzö, S ;
Hoffmann, U ;
Huber, G ;
Janatsch, G ;
Lauper, S ;
Röckel-Stäbler, O ;
Trussardi, R ;
Zwahlen, AG .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (04) :266-274
[8]   (1R,4S,5R)-3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid:: the fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases [J].
Frederickson, M ;
Roszak, AW ;
Coggins, JR ;
Lapthorn, AJ ;
Abell, C .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (11) :1592-1596
[9]   Selective inhibition of type II dehydroquinases [J].
Frederickson, M ;
Parker, EJ ;
Hawkins, AR ;
Coggins, JR ;
Abell, C .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2612-2613
[10]   Challenges in tuberculosis drug research and development [J].
Ginsberg, Ann M. ;
Spigelman, Melvin .
NATURE MEDICINE, 2007, 13 (03) :290-294