(E)-2-{[3-(4-methoxy-3-propargyloxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-{[3-(4-methoxy-3-propargyloxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid
• 英文别名: 2-[[(E)-3-(4-methoxy-3-prop-2-ynoxyphenyl)prop-2-enoyl]amino]benzoic acid
• 化学式: C₂₀H₁₇NO₅
• 分子量: 351.359
• InChiKey: AZNDZKQTYKZVSR-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2-{[3-(4-methoxy-3-propargyloxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid 、 2-叠氮-N-苯基乙酰胺 在 copper(II) sulfate L-ascorbic acid sodium salt 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 以80%的产率得到(E)-2-[[3-(4-methoxy-3-((1-(2-oxo-2-(phenylamino)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid
  参考文献：
  名称：

  WO2008/3141

  摘要：

  公开号：
• 作为产物：
  描述：

  2-(羧基乙酰氨基)苯甲酸 、 4-甲氧基-3-丙-2-炔氧基苯甲醛 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以64%的产率得到(E)-2-{[3-(4-methoxy-3-propargyloxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid
  参考文献：
  名称：

  Evaluation and optimization of antifibrotic activity of cinnamoyl anthranilates

  摘要：

  Tranilast is an anti-inflammatory drug in use for asthma and atopic dermatitis. In studies over the last decade it has been revealed that tranilast can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. We report a structure-activity study aimed at optimizing the antifibrotic activity of tranilast. A series of cinnamoyl anthranilates were prepared and assessed for their ability to prevent TGF-beta-stimulated production of collagen in cultured renal mesangial cells. We reveal derivatives with improved potency and reduced cellular toxicity relative to tranilast. 3-Methoxy-4-propargyloxycinnamoyl anthranilate reduces albuminuria in a rat model of progressive diabetes, and thus has potential as an innovative treatment for diabetic nephropathy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.120

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。
• METHODS OF TREATING EYE DISEASES ASSOCIATED WITH INFLAMMATION AND VASCULAR PROLIFERATION
  申请人：OccuRx Pty Ltd

  公开号：EP3485883A1

  公开（公告）日：2019-05-22

  Methods for treating eye diseases associated with inflammation and / or vascular proliferation in subjects are disclosed. The methods include administering therapeutically effective amounts of a tranilast compound, in particular (E)-2-[[3-(3-Methoxy-4-propargyloxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid or (E)-2-[[3,4-Bis(difluoromethoxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid or pharmaceutically acceptable salts or solvates thereof.

  本发明公开了治疗与受试者炎症和/或血管增生相关的眼部疾病的方法。这些方法包括给药治疗有效量的氨替司特化合物，特别是(E)-2-[[3-(3-甲氧基-4-丙炔氧基)苯基)-1-氧代-2-丙烯基]氨基]苯甲酸或(E)-2-[[3,4-双(二氟甲氧基)苯基)-1-氧代-2-丙烯基]氨基]苯甲酸或其药学上可接受的盐或溶液。
• Methods of treating eye diseases associated with inflammation and vascular proliferation
  申请人：Occurx Pty Ltd

  公开号：US10695353B2

  公开（公告）日：2020-06-30

  Methods for treating eye diseases associated with inflammation and/or vascular proliferation in subjects are disclosed. The methods include administering therapeutically effective amounts of a tranilast compound, in particular (E)-2-[[3-(3-Methoxy-4-propargyloxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid or (E)-2-[[3,4-Bis(difluoromethoxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid or pharmaceutically acceptable salts or solvates thereof.

  本发明公开了治疗与受试者炎症和/或血管增生相关的眼部疾病的方法。这些方法包括给药治疗有效量的氨替司特化合物，特别是(E)-2-[[3-(3-甲氧基-4-丙炔氧基)苯基)-1-氧代-2-丙烯基]氨基]苯甲酸或(E)-2-[[3,4-双(二氟甲氧基)苯基)-1-氧代-2-丙烯基]氨基]苯甲酸或其药学上可接受的盐或溶液。
• Therapeutic compounds
  申请人：Fibrotech Therapeutics PTY LTD

  公开号：EP2799427B1

  公开（公告）日：2018-07-04