N-(2,2-dimethoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide | 287194-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2,2-dimethoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide
• 英文别名: 5,6-epoxy-4,4-dimethoxy-3-salicyloylamino-2-cyclohexenone
• CAS: 287194-32-5
• 化学式: C₁₅H₁₅NO₆
• 分子量: 305.287
• InChiKey: QEWNFXQPRKSOEB-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C
• 沸点：
  556.9±50.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2,2-dimethoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide 在 Daicel Chiralpack AD 、 三氟化硼乙醚 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 (-)-2-hydroxy-N-(2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide
  参考文献：
  名称：

  Preparation and biological activities of optically active dehydroxymethylepoxyquinomicin, a novel NF-κB inhibitor

  摘要：

  NF-kappaB is a transcription factor that induces inflammatory cytokines and anti-apoptotic proteins. We have designed a new NF-kappaB inhibitor based on the structure of the antibiotic epoxyquinomicin C. The designed compound, dehydroxymethylepoxyquinomicin (DHMEQ) was synthesized as a racemic form from 2,5-dimethoxyaniline through 5 steps. Application of racemic DHMEQ onto the chiral column (Chiralpak AD) directly gave enantiomeric DHMEQ after purification. (-)-DHMEQ was more potent than its enantiomer. (-)-DHMEQ was found to inhibit NF-kappaB activity and macrophage differentiation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in human monocyte THP-1 cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.103
• 作为产物：
  描述：

  acetic acid 2-(6,6-dimethoxy-3-oxocyclohexa-1,4-dienylcarbamoyl)phenyl ester 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以80%的产率得到N-(2,2-dimethoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide
  参考文献：
  名称：

  Preparation and biological activities of optically active dehydroxymethylepoxyquinomicin, a novel NF-κB inhibitor

  摘要：

  NF-kappaB is a transcription factor that induces inflammatory cytokines and anti-apoptotic proteins. We have designed a new NF-kappaB inhibitor based on the structure of the antibiotic epoxyquinomicin C. The designed compound, dehydroxymethylepoxyquinomicin (DHMEQ) was synthesized as a racemic form from 2,5-dimethoxyaniline through 5 steps. Application of racemic DHMEQ onto the chiral column (Chiralpak AD) directly gave enantiomeric DHMEQ after purification. (-)-DHMEQ was more potent than its enantiomer. (-)-DHMEQ was found to inhibit NF-kappaB activity and macrophage differentiation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in human monocyte THP-1 cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.103

文献信息

• Salicylamide derivatives
  申请人：Mercian Corporation

  公开号：US06566394B1

  公开（公告）日：2003-05-20

  Salicylamide derivatives represented by formulae (1a) and (1b); intermediates in the production thereof; a process for producing the same; and drugs containing the same as the active ingredient. The salicylamide derivatives represented by formulae (1a) and (1b) are useful as anti-inflammatory agents and immunosuppressive agents which exert an effect of inhibiting the activation of NF-&kgr;B with little side effects.

  公式（1a）和（1b）所代表的水杨酰胺衍生物；其生产的中间体；生产该衍生物的过程；以及含有该衍生物作为活性成分的药物。公式（1a）和（1b）所代表的水杨酰胺衍生物可用作抗炎剂和免疫抑制剂，其具有抑制NF-κB激活的作用，副作用较小。
• SALICYLAMIDE DERIVATIVES
  申请人：MERCIAN CORPORATION

  公开号：EP1219596A1

  公开（公告）日：2002-07-03

  Salicylamide derivatives represented by formulae (1a) and (1b); intermediates in the production thereof; a process for producing the same; and drugs containing the same as the active ingredient. The salicylamide derivatives represented by formulae (1a) and (1b) are useful as anti-inflammatory agents and immunosuppressive agents which exert an effect of inhibiting the activation of NF-κB with little side effects.

  由式(1a)和(1b)代表的水杨酰胺衍生物；生产这些衍生物的中间体；生产这些衍生物的工艺；以及含有这些衍生物作为活性成分的药物。由式（1a）和（1b）代表的水杨酰胺衍生物可用作抗炎剂和免疫抑制剂，它们具有抑制 NF-κB 活化的作用，且副作用小。
• US6566394B1
  申请人：——

  公开号：US6566394B1

  公开（公告）日：2003-05-20
• Preparation and biological activities of optically active dehydroxymethylepoxyquinomicin, a novel NF-κB inhibitor
  作者：Yoshikazu Suzuki、Chie Sugiyama、Osamu Ohno、Kazuo Umezawa

  DOI：10.1016/j.tet.2004.01.103

  日期：2004.8

  NF-kappaB is a transcription factor that induces inflammatory cytokines and anti-apoptotic proteins. We have designed a new NF-kappaB inhibitor based on the structure of the antibiotic epoxyquinomicin C. The designed compound, dehydroxymethylepoxyquinomicin (DHMEQ) was synthesized as a racemic form from 2,5-dimethoxyaniline through 5 steps. Application of racemic DHMEQ onto the chiral column (Chiralpak AD) directly gave enantiomeric DHMEQ after purification. (-)-DHMEQ was more potent than its enantiomer. (-)-DHMEQ was found to inhibit NF-kappaB activity and macrophage differentiation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in human monocyte THP-1 cells. (C) 2004 Elsevier Ltd. All rights reserved.