A concise, total synthesis and antibacterial evaluation of 2-hydroxy-1-(1H-indol-3-yl)-4-methylpentan-3-one

被引：12
|
作者：
Nguyen, Son T. [1 ]
Butler, Michelle M. [1 ]
Varady, Laszlo [2 ]
Peet, Norton P. [1 ]
Bowlin, Terry L. [1 ]
机构：
[1] Microbiotix Inc, Worcester, MA 01605 USA
[2] Rilas Technol Inc, Newton, MA 02459 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 19期
关键词：
Antibiotic; Xenorhabdus; Nematode; Acyloin natural products; XENORHABDUS-NEMATOPHILUS; BACTERIA XENORHABDUS; SORANGIUM-CELLULOSUM; INDOLE; BIOSYNTHESIS; ANTIBIOTICS;
D O I：
10.1016/j.bmcl.2010.08.003
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Treatment of racemic 2-hydroxy-3-(1H-indol-3yl)propionic acid methyl ester (5) with isopropyl magnesium chloride provided the title compound 1 and its isomer, 3-hydroxy-1-(indol-3-yl)-4-methylpentan-2-one (9). Both enantiomers (>96% ee) of each component were obtained via semi-preparative chiral supercritical fluid chromatography (SFC). In contrast to previous reports, these compounds, as well as their acetate derivatives, were not active or very weakly active against 16 bacterial strains, including Escherichia coli, Bacillus subtilis and Staphylococcus aureus. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5739 / 5742
页数：4
相关论文
共 50 条
  • [31] 2-[2-(1H-indol-3-yl)ethyliminiomethyl]-4-nitrophenolate
    Ali, Hapipah M.
    Mustafa, M. I. Mohamed
    Rizal, M. Razali
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O913 - U2590
  • [32] (Z)-3-(1H-indol-3-yl)-2-(4-nitrophenyl)acrylonitrile
    Qian, Bao-Hua
    Liu, Wei-Wei
    Hu, Hong-Wen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3627 - U4615
  • [33] (E)-Methyl 3-(1H-indol-3-yl)acrylate
    Li, Dong-Feng
    Zhu, Xiao-Fei
    Guan, Shuang
    Hou, Rui-Bin
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3290 - U976
  • [34] (Z)-3-(1H-indol-3-yl)-2-(3-thienyl)acrylonitrile and (Z)-3-[1-(4-tert-butylbenzyl)-1H-indol-3-yl]2-(3-thienyl)acrylonitrile
    Sonar, VN
    Parkin, S
    Crooks, PA
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : O78 - O80
  • [35] 2′-[(5-bromo-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide ethyl acetate solvate
    Ali, Hapipah M.
    Shimar, Jamaludin Nazzatush
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O2731 - U1620
  • [36] CHEMISTRY OF 3-(1H-INDOL-3-YL)-3-OXOPROPANENITRILE
    Fadda, Ahmed A.
    El-Mekabaty, Ahmed
    Mousa, Ibrahim A.
    Elattar, Khaled M.
    SYNTHETIC COMMUNICATIONS, 2014, 44 (11) : 1579 - 1599
  • [37] 4,6-Dimethoxypyrimidin-2-amine-2-(1H-indol-3-yl)acetic acid(1/1)
    Ebenezer, Samuel
    Muthiah, Packianathan Thomas
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2634 - U1124
  • [38] (E)-1-Diphenylmethylidene-2-[(1H-indol-3-yl)methylidene]hydrazine
    Archana, R.
    Anbazhagan, R.
    Sankaran, K. R.
    Thiruvalluvar, A.
    Butcher, R. J.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1586 - U705
  • [39] Methyl (E)-2-cyano-3-(1H-indol-3-yl)acrylate
    Sonar, VN
    Parkin, S
    Crooks, PA
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O1077 - O1078
  • [40] L-PROLINE-CATALYZED KNOEVENAGEL CONDENSATION: A FACILE, GREEN SYNTHESIS OF (E)-ETHYL 2-CYANO-3-(1H-INDOL-3-YL)ACRYLATES AND (E)-3-(1H-INDOL-3-YL)ACRYLONITRILES
    Venkatanarayana, M.
    Dubey, P. K.
    SYNTHETIC COMMUNICATIONS, 2012, 42 (12) : 1746 - 1759
12345