N-(3,4-dihydroxycinnamoyl)anthranilic acid | 53902-31-1

• 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: N-(3,4-dihydroxycinnamoyl)anthranilic acid
• 英文别名: avenanthramide 1c；2-{[3-(3,4-Dihydroxyphenyl)acryloyl]amino}benzoic acid；2-[3-(3,4-dihydroxyphenyl)prop-2-enoylamino]benzoic acid
• CAS: 53902-31-1
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: LLPIRWBXMYKFQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-[3,4-二(乙酰氧基)苯基]丙烯酸 在 吡啶 、 光气 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.0h， 生成 N-(3,4-dihydroxycinnamoyl)anthranilic acid
  参考文献：
  名称：

  N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites

  摘要：

  The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators has not been fully elucidated. N-Cinnamoylanthranilic acid derivatives (CADs) contain structural elements from the TRPA1 modulators cinnamaldehyde and flufenamic acid, so it was hypothesized that specific modulators could be found amongst them and more could be learnt about modulation of TRPA1 with these compounds. A series of CADs was therefore screened for agonism and antagonism in HEK293 cells stably transfected with WT-human (h)TRPA1, or C621A, F909A or F944A mutant hTRPA1. Derivatives with electron-withdrawing and/or electron-donating substituents were found to possess different activities. CADs with inductive electron-withdrawing groups were agonists with desensitising effects, and CADs with electron-donating groups were either partial agonists or antagonists. Site-directed mutagenesis revealed that the CADs do not undergo conjugate addition reaction with TRPA1, and that F944 is a key residue involved in the non covalent modulation of TRPA1 by CADs, as well as many other structurally distinct non-reactive TRPA1 ligands already reported. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.074

文献信息

• Therapeutic Compounds
  申请人：Williams Spencer John

  公开号：US20100130497A1

  公开（公告）日：2010-05-27

  Substituted cinnamoyl anthranilate compounds exhibiting anti-fibrotic activity; or derivatives thereof, analogues thereof, pharmaceutically acceptable salts thereof, and metabolites thereof; with the proviso that the compound is not Tranilast.

  具有抗纤维化活性的替代肉桂酰基蒽醇衍生物；或其衍生物、类似物、药学上可接受的盐和代谢物；但前提是该化合物不是曲安奈德。
• THERAPEUTIC COMPOUNDS
  申请人：Fibrotech Therapeutics Pty Ltd

  公开号：US20140357628A1

  公开（公告）日：2014-12-04

  Substituted cinnamoyl anthranilate compounds exhibiting anti-fibrotic activity; or derivatives thereof, analogues thereof, pharmaceutically acceptable salts thereof, and metabolites thereof, with the proviso that the compound is no Tranilast.

  具有抗纤维化活性的替代肉桂酰基蒽酸酯化合物；或其衍生物、类似物、药学上可接受的盐以及代谢物，但前提是该化合物不是曲安奈德。
• A method for the production of nuclear substituted cinnamoylanthranilic acid derivatives and intermediates thereof
  申请人：Kissei Pharmaceutical Co Ltd

  公开号：EP0074725A1

  公开（公告）日：1983-03-23

  The present invention provides an improved method for producing a nuclear substituted cinnamoyl-anthranilic acid compound. Illustrative of the process is the reaction of 3,4-dimethoxybenzaldehyde with 2-carboxymalonanilic acid in an inert solvent medium in the presence of piperidine to provide an intermediate salt precipitate, and the salt is treated with an acidic reagent to yield N-(3,4-dimethoxycinnamoyl)anthranilic acid product.

  本发明提供了一种生产核取代肉桂酰-氨基苯甲酸化合物的改进方法。 该工艺的示例是：在哌啶存在下，3,4-二甲氧基苯甲醛与 2-羧基丙二酸在惰性溶剂介质中反应，生成中间盐沉淀，该盐经酸性试剂处理后生成 N-(3,4-二甲氧基肉桂酰基)蒽酸产物。
• Host cells and methods for producing cinnamoyl anthranilate and analogs thereof
  申请人：Loque Dominique

  公开号：US10280441B2

  公开（公告）日：2019-05-07

  The present invention provides for a method of producing a cinnamoyl anthranilate, or analog thereof, in a genetically modified host cell.

  本发明提供了一种在转基因宿主细胞中生产肉桂酰蒽酸酯或其类似物的方法。
• Therapeutic compounds
  申请人：Fibrotech Therapeutics PTY LTD

  公开号：EP2799427B1

  公开（公告）日：2018-07-04