(E)-2-{[3-(4-cycloheptyloxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid | 1204415-53-1

• 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-cycloheptyloxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid
• 英文别名: 2-[[(E)-3-(4-cycloheptyloxy-3-methoxyphenyl)prop-2-enoyl]amino]benzoic acid
• CAS: 1204415-53-1
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: XCOMUKHCRYSICS-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-cycloheptyloxy-3-methoxybenzaldehyde 、 2-(羧基乙酰氨基)苯甲酸 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以75%的产率得到(E)-2-{[3-(4-cycloheptyloxy-3-methoxyphenyl)-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

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

  公开号：EP2642989B1

  公开（公告）日：2019-01-02
• US9839640B2
  申请人：——

  公开号：US9839640B2

  公开（公告）日：2017-12-12
• Evaluation and optimization of antifibrotic activity of cinnamoyl anthranilates
  作者：Steven C. Zammit、Alison J. Cox、Renae M. Gow、Yuan Zhang、Richard E. Gilbert、Henry Krum、Darren J. Kelly、Spencer J. Williams

  DOI：10.1016/j.bmcl.2009.09.120

  日期：2009.12

  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.