5-nitro-furan-2-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide | 37542-57-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-nitro-furan-2-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide
• 英文别名: 5-nitro-N-(1,2,3,4-tetrahydronaphthalen-1-yl)furan-2-carboxamide
• CAS: 37542-57-7
• 化学式: C₁₅H₁₄N₂O₄
• 分子量: 286.287
• InChiKey: ZWTGFUBKLAQFCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  496.2±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2,3,4-四氢-1-萘胺 、 5-硝基-2-糠酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 14.0h， 以71%的产率得到5-nitro-furan-2-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide
  参考文献：
  名称：

  [EN] HETEROCYCLIC AMIDES WITH ANTI-TUBERCULOSIS ACTIVITY
  [FR] AMIDES HETEROCYCLIQUES A ACTIVITE ANTI-TUBERCULINIQUE

  摘要：

  公开号：

  WO2005007625A3

文献信息

• Heterocyclic amides with anti-tuberculosis activity
  申请人：Lee E. Richard

  公开号：US20050026968A1

  公开（公告）日：2005-02-03

  Compounds having the general structure: wherein A is selected from the group consisting of oxygen, sulfur, and NR 15 , and R 15 is selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl; B,D, and E are each independently selected from the group consisting of CH, nitrogen, sulfur and oxygen; R 1 is selected from the group consisting of nitro, halo, alkyl ester, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl and sulfonic acid; t is an integer from 1 to 3; and X is a substituted amide and methods of using the novel compounds for treating infections caused microorganisms, including Mycobacterium tuberculosis.

  具有以下通式的化合物：其中A从氧、硫和NR15组成的群体中选择，R15从H、烷基、芳基、取代烷基和取代芳基组成的群体中选择；B、D和E各自独立地从CH、氮、硫和氧组成的群体中选择；R1从硝基、卤素、烷基酯、苯基硫基、苯基亚硫基、苯基磺酰基和磺酸中选择；t为1至3的整数；X为取代酰胺。本发明提供了使用这些新化合物治疗由微生物引起的感染，包括结核分枝杆菌的方法。
• [EN] HETEROCYCLIC AMIDES WITH ANTI-TUBERCULOSIS ACTIVITY<br/>[FR] AMIDES HETEROCYCLIQUES A ACTIVITE ANTI-TUBERCULINIQUE
  申请人：UNIV TENNESSEE RES FOUNDATION

  公开号：WO2005007625A3

  公开（公告）日：2005-12-29
• Synthesis and Evaluation of Nitrofuranylamides as Novel Antituberculosis Agents
  作者：Rajendra P. Tangallapally、Raghunandan Yendapally、Robin E. Lee、Kirk Hevener、Victoria C. Jones、Anne J. M. Lenaerts、Michael R. McNeil、Yuehong Wang、Scott Franzblau、Richard E. Lee

  DOI：10.1021/jm049972y

  日期：2004.10.1

  In an effort to develop new and more potent therapies to treat tuberculosis, a library of compounds was screened for M. tuberculosis UDP-Gal mutase inhibition. Nitrofuranylamide 1 was identified as a hit in this screen, possessing good antituberculosis activity. This paper describes the synthesis and evaluation of an expanded set of nitrofaranylamides. We have discovered a number of nitrofaranylamides with submicromolar M. tuberculosis MIC values and acceptable therapeutic indexes. The MIC activity did not correlate with UDP-Gal mutase inhibition, suggesting an alternative primary cellular target was responsible for the antituberculosis activity. The compounds were only active against mycobacteria of the tuberculosis complex. On the basis of these results, four compounds were selected for in vivo testing in a mouse model of tuberculosis infection, and of these compounds one showed significant antituberculosis activity.