ethyl 8-nitro-4-oxo-4H-chromene-2-carboxylate | 110683-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl 8-nitro-4-oxo-4H-chromene-2-carboxylate
• 英文别名: ethyl 8-nitro-4-oxo-4H-benzopyran-2-carboxylate；ethyl 8-nitro-4-oxochromene-2-carboxylate
• CAS: 110683-75-5
• 化学式: C₁₂H₉NO₆
• 分子量: 263.207
• InChiKey: GECOLABOBGRIGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  ethyl 8-nitro-4-oxo-4H-chromene-2-carboxylate 在 potassium carbonate 、 盐酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 以96%的产率得到8-nitro-4-oxo-4H-chromene-2-carboxylic acid
  参考文献：
  名称：

  8-Benzamidochromen-4-one-2-carboxylic Acids: Potent and Selective Agonists for the Orphan G Protein-Coupled Receptor GPR35

  摘要：

  8-Amido-chromen-4-one-2-carboxylic acid derivatives were identified as novel agonists at the G protein-coupled orphan receptor GPR35. They were characterized by a beta-arrestin recruitment assay and optimized to obtain agonists with nanomolar potency for the human GPR35. The compounds were found to exhibit high selectivity versus the related GPR55. The most potent agonists were 6-bromo-8-(4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (85, EC50 12.1 nM) and 6-bromo-8-(2-chloro-4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (90, EC50 11.1 nM), both of which were >1700 fold selective versus GPR55. Most compounds were considerably less potent at rat and mouse than at human GPR35. 6-Bromo-8-(2-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (87) was the only derivative that activated GPR35 of all three species at similar, low micromolar concentration. Compounds 85 and 90 are the most potent agonists at the human GPR35 known to date and might thus serve as powerful pharmacological tools to further elucidate the receptor's (patho)physiological role and its potential as a future drug target.

  DOI：

  10.1021/jm400587g
• 作为产物：
  描述：

  硫酸二乙酯 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 60.0~70.0 ℃ 、101.33 kPa 条件下， 反应 23.0h， 以96%的产率得到ethyl 8-nitro-4-oxo-4H-chromene-2-carboxylate
  参考文献：
  名称：

  EP1479667

  摘要：

  公开号：

文献信息

• Malonic acid receptors with decarboxylative activity
  作者：César Raposo、Alicia Luengo、Marta Almaraz、Mercedes Martín、MaLuisa Mussons、MaCCruz Caballero、Joaquín R. Morán

  DOI：10.1016/0040-4020(96)00719-3

  日期：1996.9

  The geometry and electronic properties of several malonic acids receptors are studied with a view to optimizing their decarboxylative activity.

  为了优化它们的脱羧活性，研究了几种丙二酸受体的几何形状和电子性质。
• New potent antagonists of leukotrienes C4 and D4. 1. Synthesis and structure-activity relationships
  作者：Hisao Nakai、Mitoshi Konno、Shunji Kosuge、Shigeru Sakuyama、Masaaki Toda、Yoshinobu Arai、Takaaki Obata、Nobuo Katsube、Tsumoru Miyamoto

  DOI：10.1021/jm00396a013

  日期：1988.1

  (p-Amylcinnamoyl)anthranilic acid (3a) had moderate antagonist activities against LTD4-induced smooth muscle contraction on guinea pig ileum and LTC4-induced bronchoconstriction in anesthetized guinea pigs. Modifications were made in the hydrophobic part (cinnamoyl moiety) and the hydrophilic part (anthranilate moiety) of 3a. A series of 8-(benzoylamino)-2-tetrazol-5-yl-1,4-benzodioxans and 8-(ben

  （p-戊基肉桂酰基）邻氨基苯甲酸（3a）对LTD4-诱导的豚鼠回肠平滑肌收缩和LTC4诱导的豚鼠支气管收缩具有中等程度的拮抗活性。对3a的疏水部分（肉桂酰基部分）和亲水部分（邻氨基苯甲酸酯部分）进行了修饰。揭示了一系列的8-（苯甲酰基氨基）-2-四唑-5-基-1，4-苯并二恶烷和8-（苯甲酰基氨基）-2-四唑-5-基-4-氧代-4H-1-苯并吡喃。白三烯C4和D4的有效拮抗剂。在这两个系列中，ONO-RS-347（18k）和ONO-RS-411（19h）分别是最有效和口服活性的拮抗剂。讨论了构效关系。
• Benzopyran derivatives having leukotriene-antagonistic action
  申请人：Laboratorios Menarini S.A.

  公开号：US05990142A1

  公开（公告）日：1999-11-23

  The present invention relates to novel 4-oxo-4H-1-benzopyran compounds containing benzyloxymethyl, 3-phenylpropyl, or other araliphatic substituents in their 8-position. These compounds show a leukotriene-antagonistic activity. The compounds are characterized by good oral adsorption. The compounds of the present invention may be used as anti-inflammatory and antiallergic medicaments, and in the treatment of cardiovascular diseases.

  本发明涉及具有苄氧甲基、3-苯基丙基或其他芳基取代基的新型4-氧代-4H-1-苯并吡喁化合物，其位于它们的8位。这些化合物显示出白三烯拮抗活性。这些化合物具有良好的口服吸收特性。本发明的化合物可用作抗炎和抗过敏药物，并用于心血管疾病的治疗。
• Quinolinyl-chromone derivatives and use for treatment of hypersensitive
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04977162A1

  公开（公告）日：1990-12-11

  This invention relates to certain quinolinyl-chromone compounds and their use as valuable pharmaceutical agents, particularly as lipoxygenase inhibitors and/or leukotriene antagonists possessing anti-inflammatory and anti-allergic properties.

  这项发明涉及某些喹啉基-香豆素化合物及其作为有价值的药用剂的用途，特别是作为脂氧酶抑制剂和/或白三烯拮抗剂，具有抗炎和抗过敏性能。
• Quinolinyl-benzopyran derivatives as antagonists of leukotriene D4
  申请人：——

  公开号：US05082849A1

  公开（公告）日：1992-01-21

  This invention relates to certain quinolinyl-benzopyran compounds and their use as valuable pharmaceutical agents, particularly as lipoxygenase inhibitors and/or leukotriene antagonists and/or mediator release inhibitors possessing anti-inflammatory and anti-allergic properties.

  这项发明涉及某些喹啉基-苯并吡喁化合物及其作为有价值的药物代理的用途，特别是作为脂氧合酶抑制剂和/或白三烯拮抗剂和/或介质释放抑制剂，具有抗炎和抗过敏特性。