Coumarin-3-carbonsaeure-<4-carboxy-anilid> | 1847-05-8

• 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: Coumarin-3-carbonsaeure-<4-carboxy-anilid>
• 英文别名: 4-{[(2-oxo-2H-chromen-3-yl)carbonyl]amino}benzoic acid；4-[(2-oxochromene-3-carbonyl)amino]benzoic acid
• CAS: 1847-05-8
• 化学式: C₁₇H₁₁NO₅
• 分子量: 309.278
• InChiKey: IMGLCZZPWOJMLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Coumarin-3-carbonsaeure-<4-carboxy-anilid> 在 氯化亚砜 作用下， 反应 3.0h， 生成 4-[(2-oxo-2H-chromene-3-carbonyl)-amino]-benzoyl chloride
  参考文献：
  名称：

  N-取代的-2-oxo-2H-1-苯并吡喃-3-羧酰胺的合成及体外选择性抗幽门螺杆菌活性

  摘要：

  为了开发新的抗幽门螺杆菌药物，制备了五种新的和三种已知的N-取代的-2-氧代-2H-1-苯并吡喃-3-羧酰胺（香豆素-3-羧酰胺），并对其抗菌活性进行了评估。所有合成的化合物对具有临床相关性的不同种类的革兰氏阳性细菌和革兰氏阴性细菌以及各种病原真菌菌株都几乎没有或没有活性。在制备的化合物中，具有4-酰基-苯基的化合物在0.25-1μg/ ml MIC范围内对幽门螺杆菌对甲硝唑耐药的菌株表现出最佳活性，表明酰基功能的存在是活性的重要特征。

  DOI：

  10.1016/j.ejmech.2005.11.001
• 作为产物：
  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

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
• Image making medium
  申请人：——

  公开号：US20030035917A1

  公开（公告）日：2003-02-20

  The invention relates to an image support medium for creation of an aesthetic image that is an work or object for display. This support medium includes a polymer in an amount sufficient to enable the image to have at least one aesthetic element. In different embodiments, the image support medium is an image support stabilizer, the polymer is a synthetic absorbent or conductive polymer, or the polymer is a transparent or synthetic translucent polymer and a property of this transparent or translucent polymer is enhanced to facilitate the creation or preservation of the image by at least one stabilizer. The invention also relates to a method for preparing this image support medium. The method includes forming a reaction mixture comprising a monomer in an amount sufficient to provide or enable the image to have an aesthetic element, and processing the reaction mixture into a 2- or 3-dimensional shape.

  本发明涉及一种图像支持介质，用于创建作为作品或展示对象的美学图像。这种支撑介质包括一种聚合物，其用量足以使图像具有至少一种审美元素。在不同的实施例中，图像支持介质是一种图像支持稳定剂，聚合物是一种合成的吸收性或导电性聚合物，或者聚合物是一种透明或合成的半透明聚合物，并且这种透明或半透明聚合物的特性被至少一种稳定剂增强，以促进图像的创建或保存。本发明还涉及一种制备这种图像支持介质的方法。该方法包括形成由单体组成的反应混合物，其用量足以提供或使图像具有美学元素，并将反应混合物加工成 2 维或 3 维形状。
• US7629400B2
  申请人：——

  公开号：US7629400B2

  公开（公告）日：2009-12-08
• 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.
• Synthesis and in vitro selective anti-Helicobacter pylori activity of N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides
  作者：Franco Chimenti、Bruna Bizzarri、Adriana Bolasco、Daniela Secci、Paola Chimenti、Simone Carradori、Arianna Granese、Daniela Rivanera、Daniela Lilli、M. Maddalena Scaltrito、M. Immacolata Brenciaglia

  DOI：10.1016/j.ejmech.2005.11.001

  日期：2006.2

  In order to develop new anti-Helicobacter pylori agents, five new and three already known N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides (coumarin-3-carboxamides) were prepared and evaluated for their antibacterial activity. All synthesized compounds showed little or no activity against different species of Gram-positive and Gram-negative bacteria of clinical relevance and against various strains

  为了开发新的抗幽门螺杆菌药物，制备了五种新的和三种已知的N-取代的-2-氧代-2H-1-苯并吡喃-3-羧酰胺（香豆素-3-羧酰胺），并对其抗菌活性进行了评估。所有合成的化合物对具有临床相关性的不同种类的革兰氏阳性细菌和革兰氏阴性细菌以及各种病原真菌菌株都几乎没有或没有活性。在制备的化合物中，具有4-酰基-苯基的化合物在0.25-1μg/ ml MIC范围内对幽门螺杆菌对甲硝唑耐药的菌株表现出最佳活性，表明酰基功能的存在是活性的重要特征。