5-nitro-N-phenethylfuran-2-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-nitro-N-phenethylfuran-2-carboxamide
• 英文别名: 5-nitro-furan-2-carboxylic acid phenethyl-amide；5-nitrofuran-2-carboxylic acid phenethyl-amide；5-nitro-N-phenethyl-furan-2-carboxamide；5-nitro-N-(2-phenylethyl)furan-2-carboxamide
• 化学式: C₁₃H₁₂N₂O₄
• mdl: MFCD01211960
• 分子量: 260.249
• InChiKey: SJKVNWXSVBJHHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  5-硝基-2-糠酸 、 2-苯乙胺 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 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以81%的产率得到5-nitro-N-phenethylfuran-2-carboxamide
  参考文献：
  名称：

  Synthesis and Evaluation of Nitrofuranylamides as Novel Antituberculosis Agents

  摘要：

  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.

  DOI：

  10.1021/jm049972y

文献信息

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

  公开号：US20050222408A1

  公开（公告）日：2005-10-06

  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, arylsulfanyl, arylsulfinyl, arylsulfonyl 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 by microorganisms, including Mycobacterium tuberculosis.

  具有一般结构的化合物：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分别独立地从CH、氮、硫和氧组成的群体中选择；R1从硝基、卤素、烷基酯、芳基硫醚、芳基亚砜、芳基砜基和磺酸中选择；t为1到3的整数；X为取代酰胺，并且使用这些新化合物治疗由微生物引起的感染的方法，包括结核分枝杆菌。
• Optimization of N-benzyl-5-nitrofuran-2-carboxamide as an antitubercular agent
  作者：Ricardo Gallardo-Macias、Pradeep Kumar、Mark Jaskowski、Todd Richmann、Riju Shrestha、Riccardo Russo、Eric Singleton、Matthew D. Zimmerman、Hsin Pin Ho、Véronique Dartois、Nancy Connell、David Alland、Joel S. Freundlich

  DOI：10.1016/j.bmcl.2018.12.053

  日期：2019.2

  The optimization campaign for a nitrofuran antitubercular hit (N-benzyl-5-nitrofuran-2-carboxamide; JSF-3449) led to the design, synthesis, and biological profiling of a family of analogs. These compounds exhibited potent in vitro antitubercular activity (MIC = 0.019-0.20 μM) against the Mycobacterium tuberculosis H37Rv strain and low in vitro cytotoxicity (CC50 = 40->120 μM) towards Vero cells. Significant

  硝基呋喃抗结核药物（N-benzyl-5-nitrofuran-2-carboxamide；JSF-3449）的优化活动促成了一系列类似物的设计、合成和生物学分析。这些化合物对结核分枝杆菌 H37Rv 菌株表现出有效的体外抗结核活性 (MIC = 0.019-0.20 μM)，对 Vero 细胞具有低体外细胞毒性 (CC50 = 40->120 μM)。通过引入 α, α-二甲基苄基部分实现了小鼠肝微粒体稳定性和小鼠药代动力学特征的显着改善。在这些化合物中，JSF-4088 因其体外抗结核效力 (MIC = 0.019 μM) 和 Vero 细胞毒性 (CC50 > 120 μM) 而备受瞩目。这些发现为这一有希望的抗结核小分子系列的持续进化提供了基本原理。
• Anti-infective compounds
  申请人：Brodin Priscille

  公开号：US20110178077A1

  公开（公告）日：2011-07-21

  The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.

  本发明涉及小分子化合物及其在治疗细菌感染，特别是结核病方面的用途。
• [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
• US8785452B2
  申请人：——

  公开号：US8785452B2

  公开（公告）日：2014-07-22