2-hydroxy-N-(5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide

• 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: 2-hydroxy-N-(5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: RTMIXZGHZZAOSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  99.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 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 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.67h， 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

文献信息

• 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。
• DRUG COMPOSITION CONTAINING NF-KAPPA B INHIBITOR
  申请人：Signal Creation Inc.

  公开号：EP1541139A1

  公开（公告）日：2005-06-15

  Pharmaceutical compositions for improving at least one symptom resulting from tumor cells, which contains a compound represented by the following general formula (1) or a pharmacologically acceptable salt thereof as an active ingredient. wherein R1 represents a hydrogen atom or a C2-4 alkanoyl group and R2 represents a group represented by the following formulae (A), (B), (C), (D), (E), (F) or (G): wherein R3 represents a C1-4 alkyl group.

  用于改善由肿瘤细胞引起的至少一种症状的药物组合物，其活性成分含有由下式通式(1)代表的化合物或其药理学上可接受的盐。 其中 R1 代表氢原子或 C2-4 烷酰基，R2 代表下式（A）、（B）、（C）、（D）、（E）、 （F）或（G）所代表的基团： 其中 R3 代表 C1-4 烷基。
• MEDICINAL COMPOSITION
  申请人：Keio University

  公开号：EP1600445A1

  公开（公告）日：2005-11-30

  (-)-DHM2EQ, which is useful as an antitumor agent and an anti-inflammatory agent, can be directly obtained by optically resolving (±)-DHM2EQ using an optically active column packed with an optical resolving agent containing, for example, amylose tris(3,5-dimethylphenylcarbamate) as an active ingredient. The (-)-DHM2EQ obtained by optical resolution using the optically active column or pharmacologically acceptable salt thereof is useful as a pharmaceutical composition for improving various symptoms.

  (-)-DHM2EQ可用作抗肿瘤剂和消炎剂，它可以通过使用光学活性柱对(±)-DHM2EQ进行光学解析而直接获得，光学活性柱中装有作为活性成分的淀粉三(3,5-二甲基苯基氨基甲酸酯)等光学解析剂。使用光学活性柱进行光学解析得到的(-)-DHM2EQ 或其药理上可接受的盐可用作改善各种症状的药物组合物。
• MACROPHAGE ACTIVATION INHIBITOR
  申请人：Signal Creation Inc.

  公开号：EP1656936A1

  公开（公告）日：2006-05-17

  A compound represented by the following general formula (1) : wherein R1 represents a hydrogen atom or a C2 to C4 alkanoyl group and R2 represents a group represented by the following formula (A), (B), (C), (D), (E), (F), or (G): wherein R3 represents a C1 to C4 alkyl group can inhibit macrophage activation. Accordingly, a macrophage activation inhibitor containing a compound represented by the general formula (1) or its pharmacologically acceptable salt as an active ingredient is useful as an agent for preventing, improving, or treating a disease resulting from infection with pathogens such as a bacterium and a virus.

  由以下通式(1)代表的化合物： 其中 R1 代表氢原子或 C2 至 C4 烷酰基，R2 代表下式（A）、（B）、（C）、（D）、（E）、 （F）或（G）所代表的基团： 其中 R3 代表 C1 至 C4 烷基的基团可抑制巨噬细胞活化。因此，含有通式（1）所代表的化合物或其药理上可接受的盐作为活性成分的巨噬细胞活化抑制剂可作为预防、改善或治疗因感染病原体（如细菌和病毒）而导致的疾病的药物。
• Drug composition containing nf-kb inhibitor
  申请人：Umezawa Kazuo

  公开号：US20060183794A1

  公开（公告）日：2006-08-17

  Pharmaceutical compositions for improving at least one symptom resulting from tumor cells, which contains a compound represented by the following general formula (1) or a pharmacologically acceptable salt thereof as an active ingredient. wherein R 1 represents a hydrogen atom or a C2-4 alkanoyl group and R 2 represents a group represented by the following formulae (A), (B), (C), (D), (E), (F) or (G): wherein R 3 represents a C1-4 alkyl group.

  用于改善由肿瘤细胞引起的至少一种症状的药物组合物，其活性成分包含由下式（1）代表的化合物或其药理学上可接受的盐。 其中 R 1 代表氢原子或 C2-4 烷酰基，R 2 代表下式(A)、(B)、(C)、(D)、(E)、(F)或(G)所代表的基团： 其中 R 3 代表 C1-4 烷基。