4-(2-oxo-2H-chromene-3-carbonylamino)-benzoic acid ethyl ester | 111947-24-1

• 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: 4-(2-oxo-2H-chromene-3-carbonylamino)-benzoic acid ethyl ester
• 英文别名: 4-(2-Oxo-2H-chromen-3-carbonylamino)-benzoesaeure-aethylester；ethyl 4-(2-oxo-2H-chromene-3-carboxamido)benzoate；ethyl 4-[(2-oxochromene-3-carbonyl)amino]benzoate
• CAS: 111947-24-1
• 化学式: C₁₉H₁₅NO₅
• mdl: MFCD00249909
• 分子量: 337.332
• InChiKey: MISJYZJMFQOBPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-oxo-2H-chromene-3-carbonylamino)-benzoic acid ethyl ester 在 水 作用下， 生成 Coumarin-3-carbonsaeure-<4-carboxy-anilid>
  参考文献：
  名称：

  Synthesis, Molecular Modeling, and Selective Inhibitory Activity against Human Monoamine Oxidases of 3-Carboxamido-7-Substituted Coumarins

  摘要：

  A large series of 3-carboxamido-7-substituted cournarins have been synthesized and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Taking into account all the relevant structural information on MAOs reported in the literature, we made some changes in the coumarin nucleus and examined with particular attention the effect on activity and selectivity of substituting at position 3 with N-aryl or N-alkyl carboxamide and at position 7 with a benzyloxy or a 4'-F-benzyloxy group. Some of the assayed compounds proved to be potent, selective inhibitors of hMAO-B with IC50 values in the micromolar range. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAOs, molecular modeling studies were carried out on new, high resolution, hMAO-A and hMAO-B crystallographic structures.

  DOI：

  10.1021/jm801496u
• 作为产物：
  描述：

  4-(2-氰基-乙酰氨基)-苯甲酸乙酯 在 哌啶 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-(2-oxo-2H-chromene-3-carbonylamino)-benzoic acid ethyl ester
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of N-substituted 2-oxo-2H-1-benzopyran-3-carboxamides and their 2-iminoanalogues

  摘要：

  A series of N-arylsubstituted 2-imino-2H-1-benzopyran-3-carboxamides 3a and b and 2-oxo-2H-1-benzopyran-3-carboxamides 4a-h were synthesized and evaluated for their anti-inflammatory activity in carrageenan-induced rat paw oedema assays and in acetic acid-induced peritonitis tests in albino rats. The resulting products were found to be active anti-inflammatory agents and their effects were comparable to that of piroxicam as the reference compound. In the consideration of the efficacy of the compounds in these assays, 2-imino/oxo-2H-1-benzopyran-3-carboxamides 3a and b and 4a-h were further studied at graded doses for their acute toxicity (ALD(50)) in albino mice and were essentially non-toxic at the highest dose tested. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00119-1

文献信息

• Synthesis and antiallergic activity in a series of cinnamic acid
  作者：A. S. Saraf、A. V. Simonyan

  DOI：10.1007/bf00777140

  日期：1992.7

  cinnamic acid derivatives, with the goal of creating new polyfunctional drugs based on them [4, 9, i0]. The increased interest in this group of compounds is due to the varied aspects of their pharmacological activity, their ability to regulate the activity of a number of enzyme systems participating in cell activation processes. A whole series of drugs has been created on the basis of cinnamic acid which

  近年来，对肉桂酸衍生物进行了深入研究，目标是基于它们创造新的多功能药物 [4, 9, i0]。对这组化合物的兴趣增加是由于它们药理活性的不同方面，它们能够调节参与细胞活化过程的许多酶系统的活性。以肉桂酸为基础研制的全系列药物，具有明显的抗过敏活性（桂利嗪、肉桂色林、曲尼司特等），抑制过敏靶细胞（脂肪细胞、嗜碱性粒细胞）分泌介质，降低敏感性效应器官和组织对介质（组胺、血清素、缓效过敏剂）的影响 [5, 12, 17]。这类化合物甚至令人感兴趣，因为它的代表（咖啡酸、阿魏酸等）广泛存在于天然标本（植物、水果、蔬菜等）中，并与黄酮类化合物一起参与许多生化过程，调节生物合成和动植物体内的交换反应 [21]。肉桂酸是生物体内多酚化合物代谢的可能产物，因此许多黄酮类化合物的生物活性与它们有特定的联系[13]。咖啡酸和阿魏酸抑制 5 和 12-1 环氧合酶，降低组织中白三烯的水平，并有可能用于治疗支气管哮喘
• Bedair, A. H., Journal fur praktische Chemie (Leipzig 1954), 1987, vol. 329, # 2, p. 359 - 364
  作者：Bedair, A. H.

  DOI：——

  日期：——
• Ichibagase; Terada, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1952, vol. 72, p. 1043
  作者：Ichibagase、Terada

  DOI：——

  日期：——
• BEDAIR A. H., J. PRAKT. CHEM., 329,(1987) N 2, 359-364
  作者：BEDAIR A. H.

  DOI：——

  日期：——
• Synthesis, Molecular Modeling, and Selective Inhibitory Activity against Human Monoamine Oxidases of 3-Carboxamido-7-Substituted Coumarins
  作者：Franco Chimenti、Daniela Secci、Adriana Bolasco、Paola Chimenti、Bruna Bizzarri、Arianna Granese、Simone Carradori、Matilde Yáñez、Francisco Orallo、Francesco Ortuso、Stefano Alcaro

  DOI：10.1021/jm801496u

  日期：2009.4.9

  A large series of 3-carboxamido-7-substituted cournarins have been synthesized and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Taking into account all the relevant structural information on MAOs reported in the literature, we made some changes in the coumarin nucleus and examined with particular attention the effect on activity and selectivity of substituting at position 3 with N-aryl or N-alkyl carboxamide and at position 7 with a benzyloxy or a 4'-F-benzyloxy group. Some of the assayed compounds proved to be potent, selective inhibitors of hMAO-B with IC50 values in the micromolar range. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAOs, molecular modeling studies were carried out on new, high resolution, hMAO-A and hMAO-B crystallographic structures.