(E)-ethyl 2-(3,4-bis(difluoromethoxy)phenyl)ethenesulfonate | 1259024-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-ethyl 2-(3,4-bis(difluoromethoxy)phenyl)ethenesulfonate
• 英文别名: ethyl (E)-2-[3,4-bis(difluoromethoxy)phenyl]ethenesulfonate
• CAS: 1259024-67-3
• 化学式: C₁₂H₁₂F₄O₅S
• 分子量: 344.284
• InChiKey: OIICAGHXLIYACA-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-(3,4-bis(difluoromethoxy)phenyl)ethenesulfonate 在 吡啶 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 36.0h， 生成 (E)-2-[3,4-bis(difluoromethoxy)phenyl]-N-phenylethenesulfonamide
  参考文献：
  名称：

  3′,4′-Bis-difluoromethoxycinnamoylanthranilate (FT061): An orally-active antifibrotic agent that reduces albuminuria in a rat model of progressive diabetic nephropathy

  摘要：

  Cinnamoylanthranilates including tranilast have been identified as promising antifibrotics that can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. Structure-activity relationships aimed at improving potency and metabolic stability have led to the discovery of FT061. This compound, which bears a bis-difluoromethoxy catechol, attenuates TGF-beta-stimulated production of collagen in cultured renal mesangial cells (approx 50% at 3 mu M). When dosed orally at 20 mg/kg to male Sprague Dawley rats, FT061 exhibited a high bioavailability (73%), C-max of 200 mu M and T-max of 150 min, and a half-life of 5.4 h. FT061 reduced albuminuria when orally dosed in rats at 200 mg kg/day in a late intervention study of a rat model of progressive diabetic nephropathy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.100
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.33h， 生成 (E)-ethyl 2-(3,4-bis(difluoromethoxy)phenyl)ethenesulfonate
  参考文献：
  名称：

  3′,4′-Bis-difluoromethoxycinnamoylanthranilate (FT061): An orally-active antifibrotic agent that reduces albuminuria in a rat model of progressive diabetic nephropathy

  摘要：

  Cinnamoylanthranilates including tranilast have been identified as promising antifibrotics that can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. Structure-activity relationships aimed at improving potency and metabolic stability have led to the discovery of FT061. This compound, which bears a bis-difluoromethoxy catechol, attenuates TGF-beta-stimulated production of collagen in cultured renal mesangial cells (approx 50% at 3 mu M). When dosed orally at 20 mg/kg to male Sprague Dawley rats, FT061 exhibited a high bioavailability (73%), C-max of 200 mu M and T-max of 150 min, and a half-life of 5.4 h. FT061 reduced albuminuria when orally dosed in rats at 200 mg kg/day in a late intervention study of a rat model of progressive diabetic nephropathy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.100

文献信息

• [EN] ANALOGUES OF ANTI-FIBROTIC AGENTS<br/>[FR] ANALOGUES D'AGENTS ANTIFIBROTIQUES
  申请人：FIBROTECH THERAPEUTICS PTY LTD

  公开号：WO2010144959A1

  公开（公告）日：2010-12-23

  The present invention relates to analogues of anti-fibrotic agents having the formula (I) with the substituents as described within the specification. The present invention also relates to methods for their preparation.

  本发明涉及具有如规范中所述的取代基的抗纤维化剂的类似物，其化学式为(I)。本发明还涉及它们的制备方法。
• 3′,4′-Bis-difluoromethoxycinnamoylanthranilate (FT061): An orally-active antifibrotic agent that reduces albuminuria in a rat model of progressive diabetic nephropathy
  作者：Spencer J. Williams、Steven C. Zammit、Alison J. Cox、David M. Shackleford、Julia Morizzi、Yuan Zhang、Andrew K. Powell、Richard E. Gilbert、Henry Krum、Darren J. Kelly

  DOI：10.1016/j.bmcl.2013.09.100

  日期：2013.12

  Cinnamoylanthranilates including tranilast have been identified as promising antifibrotics that can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. Structure-activity relationships aimed at improving potency and metabolic stability have led to the discovery of FT061. This compound, which bears a bis-difluoromethoxy catechol, attenuates TGF-beta-stimulated production of collagen in cultured renal mesangial cells (approx 50% at 3 mu M). When dosed orally at 20 mg/kg to male Sprague Dawley rats, FT061 exhibited a high bioavailability (73%), C-max of 200 mu M and T-max of 150 min, and a half-life of 5.4 h. FT061 reduced albuminuria when orally dosed in rats at 200 mg kg/day in a late intervention study of a rat model of progressive diabetic nephropathy. (C) 2013 Elsevier Ltd. All rights reserved.