N-(2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide | 287194-37-0

• 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-(2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide
• 英文别名: 5,6-epoxy-2-salicyloylamino-2-cyclohexen-1,4-dione；5,6-epoxy-2-salicyloylamino-2cyclohexen-1,4-dione；5,6-epoxy-2-salicyloylamino-2cyclohexen-1,4dione
• CAS: 287194-37-0
• 化学式: C₁₃H₉NO₅
• 分子量: 259.218
• InChiKey: DJSICXICJKSEMB-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C (decomp)
• 沸点：
  579.4±50.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  96
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide 在 氢氟酸 、 三乙酰氧基硼氢化钠 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 2.17h， 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：

  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 、 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 5.0h， 生成 N-(2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)-2-hydroxybenzamide
  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

• [EN] OXABICYCLO [4.1.O]HEPT-B-EN-S-YLCARBAMOYL DERIVATIVES INHIBITING THE NUCLEAR FACTOR-KAPPA(B) - (NF-KB)<br/>[FR] DÉRIVÉS D'OXABICYCLO[4.1.0]HEPT-B-EN-S-YLCARBAMOYLE INHIBANT LE FACTEUR NUCLÉAIRE KAPPA(B)-(NF-?B)
  申请人：PROFECTUS BIOSCIENCES INC

  公开号：WO2010148042A1

  公开（公告）日：2010-12-23

  The invention relates to compounds of formula (I), formula (II), formula (III) and formula (IV),and pharmaceutically acceptable salts thereof for the treatment of cancer, inflammation, auto-immune diseases, diabetes and diabetic complications, infection, cardiovascular disease and ischemia-reperfusion injuries.

  该发明涉及式(I)、式(II)、式(III)和式(IV)的化合物，以及这些化合物的药用盐，用于治疗癌症、炎症、自身免疫疾病、糖尿病和糖尿病并发症、感染、心血管疾病和缺血再灌注损伤。
• 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。
• Synthesis and Evaluation of DHMEQ Derivatives with Tertiary Hydroxyl Group Instead of Secondary Hydroxyl Group
  作者：Yoshimasa Imanishi、Takuro Terasaki、Takuya Sano、Osamu Ohno、Eiko Yasui

  DOI：10.1248/cpb.c22-00905

  日期：2023.4.1

  (DHMEQ) derivatives 6–9, which contain a tertiary hydroxyl group instead of the original secondary hydroxyl group, showed improved solubility in alcohol while maintaining their inhibitory activity against nitric oxide (NO) production, which is used as an indicator of nuclear factor-kappa B (NF-κB) inhibitory activity. We also synthesized a derivative 5 having a cyclopropane ring and a tertiary hydroxyl

  新合成的脱羟甲基环氧喹霉素 (DHMEQ) 衍生物6 – 9含有叔羟基而不是原来的仲羟基，在酒精中的溶解度有所提高，同时保持了对用作指示剂的一氧化氮 (NO) 产生的抑制活性核因子-kappa B (NF-κB) 抑制活性。我们还合成了一个导数5具有环丙烷环和叔羟基，并检测其对 NO 产生的抑制活性。虽然它与烧瓶中的亲核试剂发生反应，但它不会抑制 NO 的产生。从仲羟基到叔羟基的变化有助于提高化合物的溶解度，同时保留 NO 抑制活性，但对提高环丙烷形式的活性没有影响。DHMEQ 的仲羟基被转化为叔羟基的化合物将是优秀的 NF-κB 抑制剂候选者，因为它们的溶解度得到改善而不降低 NO 抑制活性。 全尺寸图像
• 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。