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
    BENTLEY, R
    [J]. 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
    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
    [J]. 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
    Blanco, Beatriz
    Sedes, Antia
    Peon, Antonio
    Lamb, Heather
    Hawkins, Alastair R.
    Castedo, Luis
    Gonzalez-Bello, Concepcion
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (18) : 3662 - 3676
  • [4] Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes
    Bumagin, NA
    Korolev, DN
    [J]. TETRAHEDRON LETTERS, 1999, 40 (15) : 3057 - 3060
  • [5] Structural investigation of inhibitor designs targeting 3-dehydroquinate dehydratase from the shikimate pathway of Mycobacterium tuberculosis
    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.
    [J]. BIOCHEMICAL JOURNAL, 2011, 436 : 729 - 739
  • [6] Mycobacterial shikimate pathway enzymes as targets for drug design
    Ducati, R. G.
    Basso, L. A.
    Santos, D. S.
    [J]. 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
    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
    [J]. 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
    Frederickson, M
    Roszak, AW
    Coggins, JR
    Lapthorn, AJ
    Abell, C
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (11) : 1592 - 1596
  • [9] Selective inhibition of type II dehydroquinases
    Frederickson, M
    Parker, EJ
    Hawkins, AR
    Coggins, JR
    Abell, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) : 2612 - 2613
  • [10] Challenges in tuberculosis drug research and development
    Ginsberg, Ann M.
    Spigelman, Melvin
    [J]. NATURE MEDICINE, 2007, 13 (03) : 290 - 294