6-(5-nitro-1H-indol-1-yl)-1-hexyl acetate | 231944-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-(5-nitro-1H-indol-1-yl)-1-hexyl acetate
• 英文别名: 6-(5-Nitroindol-1-yl)hexyl acetate
• CAS: 231944-33-5
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: SJRJANZBMSNFJO-UHFFFAOYSA-N

物化性质

• 沸点：
  465.5±25.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(5-nitro-1H-indol-1-yl)-1-hexyl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以91%的产率得到6-(5-nitro-1H-indol-1-yl)-1-hexanol
  参考文献：
  名称：

  Tethered Dimers as NAD Synthetase Inhibitors with Antibacterial Activity

  摘要：

  The solution-phase parallel synthesis of tethered dimers was employed to identify lead inhibitors of bacterial NAD synthetase. Active dimers contained two aromatic end groups joined by a polymethylene linker, with one end group containing a permanent positive charge. Effective inhibitors of NAD synthetase also inhibited the growth of Gram-positive (but not Gram-negative) bacteria, including antibiotic-resistant strains. The desmethyl precursors of active inhibitors lacked a permanent positive charge and were inactive as either enzyme inhibitors or antibacterial agents. Similarly, a close structural analogue of the most active inhibitors contained two additional ether oxygens in the tether and was inactive in both assays. These results are consistent with the premise that NAD synthetase inhibition is responsible for the antibacterial actions and support further studies on NAD synthetase as a new target for antibacterial agents.

  DOI：

  10.1021/jm030003x
• 作为产物：
  描述：

  二烷基二硫代磷酸锌 、 5-硝基吲哚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到6-(5-nitro-1H-indol-1-yl)-1-hexyl acetate
  参考文献：
  名称：

  Tethered Dimers as NAD Synthetase Inhibitors with Antibacterial Activity

  摘要：

  The solution-phase parallel synthesis of tethered dimers was employed to identify lead inhibitors of bacterial NAD synthetase. Active dimers contained two aromatic end groups joined by a polymethylene linker, with one end group containing a permanent positive charge. Effective inhibitors of NAD synthetase also inhibited the growth of Gram-positive (but not Gram-negative) bacteria, including antibiotic-resistant strains. The desmethyl precursors of active inhibitors lacked a permanent positive charge and were inactive as either enzyme inhibitors or antibacterial agents. Similarly, a close structural analogue of the most active inhibitors contained two additional ether oxygens in the tether and was inactive in both assays. These results are consistent with the premise that NAD synthetase inhibition is responsible for the antibacterial actions and support further studies on NAD synthetase as a new target for antibacterial agents.

  DOI：

  10.1021/jm030003x

文献信息

• INHIBITORS OF BACTERIAL NAD SYNTHETASE
  申请人：——

  公开号：US20040063758A1

  公开（公告）日：2004-04-01

  The present invention provides methods of synthesizing and screening inhibitors of bacterial NAD synthetase enzyme, compounds thereof, and methods of treating bacterial and microbial infections with inhibitors of bacterial NAD synthetase enzyme.

  本发明提供了合成和筛选细菌NAD合酶酶抑制剂的方法，以及这些化合物和使用细菌NAD合酶酶抑制剂治疗细菌和微生物感染的方法。
• METHODS OF SYNTHESIZING AND SCREENING INHIBITORS OF BACTERIAL NAD SYNTHETASE ENZYME, COMPOUNDS THEREOF AND METHODS OF TREATING BACTERIAL AND MICROBIAL INFECTIONS WITH THESE INHIBITORS
  申请人：THE UAB RESEARCH FOUNDATION

  公开号：EP1047692B1

  公开（公告）日：2004-07-21
• US6500852B1
  申请人：——

  公开号：US6500852B1

  公开（公告）日：2002-12-31
• US6727237B2
  申请人：——

  公开号：US6727237B2

  公开（公告）日：2004-04-27
• [EN] METHODS OF SYNTHESIZING AND SCREENING INHIBITORS OF BACTERIAL NAD SYNTHETASE ENZYME, COMPOUNDS THEREOF, AND METHODS OF TREATING BACTERIAL AND MICROBIAL INFECTIONS WITH INHIBITORS OF BACTERIAL NAD SYNTHETASE ENZYME<br/>[FR] PROCEDE DE SYNTHESE ET DE CRIBLAGE D'INHIBITEURS D'ENZYME SYNTHETASE NAD BACTERIENNE, COMPOSES A BASE DE CETTE ENZYME ET PROCEDES DE TRAITEMENT DES INFECTIONS BACTERIENNES ET MICROBIENNES AU MOYEN D'INHIBITEURS DE LADITE ENZYME
  申请人：THE UAB RESEARCH FOUNDATION

  公开号：WO1999036422A1

  公开（公告）日：1999-07-22

  (EN) The present invention provides methods of synthesizing and screening inhibitors of bacterial NAD synthetase enzyme, compounds thereof, and methods of treating bacterial and microbial infections with inhibitors of bacterial NAD synthetase enzyme.(FR) L'invention concerne des procédés qui permettent d'assurer la synthèse et le criblage d'inhibiteurs de l'enzyme synthétase NAD. L'invention concerne également des composés à base de cette enzyme et des procédés de traitement des infections bactériennes et microbiennes au moyen d'inhibiteurs de ladite enzyme.