3,3-dimethoxy-4,5-epoxy-6-hydroxy-2-salicyloylamino-cyclohexene | 326499-50-7

• 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: 3,3-dimethoxy-4,5-epoxy-6-hydroxy-2-salicyloylamino-cyclohexene
• 英文别名: 2-hydroxy-N-(5-hydroxy-2,2-dimethoxy-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide
• CAS: 326499-50-7
• 化学式: C₁₅H₁₇NO₆
• 分子量: 307.303
• InChiKey: WPYHMVOHDYLEJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3-dimethoxy-4,5-epoxy-6-hydroxy-2-salicyloylamino-cyclohexene 在 对甲苯磺酸 作用下， 反应 1.0h， 生成 2-hydroxy-N-(5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide
  参考文献：
  名称：

  Synthesis of NF-κB activation inhibitors derived from epoxyquinomicin C

  摘要：

  In order to develop new inhibitors of NF-kappa B activation, we designed and synthesized dehydroxymethyl derivatives of epoxyquinomicin C, namely, DHM2EQ and its regioisomer DHM3EQ. These derivatives were synthesized from 2,5-dimethoxyaniline in 5 steps. Since DHM2EQ was more active and less toxic than DHM3EQ, its stereochemical configuration was determined by X-ray crystallographic analysis. Each enantiomer of the protected DHM2EQ was separated by a chiral column and deprotected. DHM2EQ inhibited TNF-alpha-induced activation of NF-kappa B in human T cell leukemia cells, and also inhibited collagen-induced arthritis in a rheumatoid model in mice. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00114-1
• 作为产物：
  描述：

  邻乙酰水杨酰氯 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 碘苯二乙酸 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 生成 3,3-dimethoxy-4,5-epoxy-6-hydroxy-2-salicyloylamino-cyclohexene
  参考文献：
  名称：

  Synthesis of NF-κB activation inhibitors derived from epoxyquinomicin C

  摘要：

  In order to develop new inhibitors of NF-kappa B activation, we designed and synthesized dehydroxymethyl derivatives of epoxyquinomicin C, namely, DHM2EQ and its regioisomer DHM3EQ. These derivatives were synthesized from 2,5-dimethoxyaniline in 5 steps. Since DHM2EQ was more active and less toxic than DHM3EQ, its stereochemical configuration was determined by X-ray crystallographic analysis. Each enantiomer of the protected DHM2EQ was separated by a chiral column and deprotected. DHM2EQ inhibited TNF-alpha-induced activation of NF-kappa B in human T cell leukemia cells, and also inhibited collagen-induced arthritis in a rheumatoid model in mice. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00114-1

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
• Synthesis of NF-κB activation inhibitors derived from epoxyquinomicin C
  作者：Naoki Matsumoto、Akiko Ariga、Sakino To-e、Hikaru Nakamura、Naoki Agata、Shin-ichi Hirano、Jun-ichiro Inoue、Kazuo Umezawa

  DOI：10.1016/s0960-894x(00)00114-1

  日期：2000.5

  In order to develop new inhibitors of NF-kappa B activation, we designed and synthesized dehydroxymethyl derivatives of epoxyquinomicin C, namely, DHM2EQ and its regioisomer DHM3EQ. These derivatives were synthesized from 2,5-dimethoxyaniline in 5 steps. Since DHM2EQ was more active and less toxic than DHM3EQ, its stereochemical configuration was determined by X-ray crystallographic analysis. Each enantiomer of the protected DHM2EQ was separated by a chiral column and deprotected. DHM2EQ inhibited TNF-alpha-induced activation of NF-kappa B in human T cell leukemia cells, and also inhibited collagen-induced arthritis in a rheumatoid model in mice. (C) 2000 Elsevier Science Ltd. All rights reserved.