3-(hex-3-ynyloxy)-4-methoxybenzaldehyde | 1001289-70-8

• 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: 3-(hex-3-ynyloxy)-4-methoxybenzaldehyde
• 英文别名: 3-hex-3-ynoxy-4-methoxybenzaldehyde
• CAS: 1001289-70-8
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: HARITRMKNKKLGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(hex-3-ynyloxy)-4-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-(3-(hex-3-ynyloxy)-4-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
• 作为产物：
  描述：

  异香兰素 、 hex-3-ynyl 4-methylbenzenesulfonate 在 crude product 、 EtOAc petrol 作用下， 以to provide 3-(hex-3-ynyloxy)-4-methoxybenzaldehyde (0.58 g, 50%) as a colourless crystalline solid的产率得到3-(hex-3-ynyloxy)-4-methoxybenzaldehyde
  参考文献：
  名称：

  Therapeutic compounds

  摘要：

  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、药学上可接受的盐和代谢产物；但前提是该化合物不是曲安奈德。

  公开号：

  US08765812B2

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：Willams Spencer John

  公开号：US08765812B2

  公开（公告）日：2014-07-01

  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酸酯化合物；或其衍生物、类似物、药学上可接受的盐和代谢产物；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。
• US8765812B2
  申请人：——

  公开号：US8765812B2

  公开（公告）日：2014-07-01
• US9561201B2
  申请人：——

  公开号：US9561201B2

  公开（公告）日：2017-02-07