2-[(2-carboxy-1-oxopropyl)amino]benzoic acid | 59770-51-3

• 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: 2-[(2-carboxy-1-oxopropyl)amino]benzoic acid
• 英文别名: 2-(2-carboxypropanoylamino)benzoic acid
• CAS: 59770-51-3
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: ZWZGYKYWGHFYDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2-carboxy-1-oxopropyl)amino]benzoic acid 、 3,4-双(二氟甲氧基)苯甲醛 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以37%的产率得到(E)-2-[[3-(3,4-bis(difluoromethoxy)phenyl)-2-methyl-1-oxo-2-propenyl]amino]benzoic acid
  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：

  甲基丙二酸亚异丙酯 、 邻氨基苯甲酸 在 甲苯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以2-[(2-Carboxy-1-oxopropyl)amino]benzoic acid (1.46 g, 85%) was obtained as a colourless solid的产率得到2-[(2-carboxy-1-oxopropyl)amino]benzoic acid
  参考文献：
  名称：

  HALOGENATED ANALOGUES OF ANTI-FIBROTIC AGENTS

  摘要：

  本发明涉及式（I）的卤代化合物，其中取代基如规范中所述。该化合物可用作抗纤维化剂。本发明还涉及其制备方法。

  公开号：

  US20110021815A1

文献信息

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

  公开号：WO2009079692A1

  公开（公告）日：2009-07-02

  The present invention relates to halogenated compounds of formula (I) with the substituents as described within the specification. The compounds may be useful as anti-fibrqtic agents. The present invention also relates to methods for their preparation.

  本发明涉及具有规定的取代基的式(I)的卤代化合物。这些化合物可能作为抗纤维化剂有用。本发明还涉及它们的制备方法。
• HALOGENATED ANALOGUES OF ANTI-FIBROTIC AGENTS
  申请人：Kelly Darren James

  公开号：US20120059188A9

  公开（公告）日：2012-03-08

  The present invention relates to halogenated compounds of formula (I) with the substituents as described within the specification. The compounds may be useful as anti-fibrotic agents. The present invention also relates to methods for their preparation.

  本发明涉及式(I)的卤代化合物，所述化合物的取代基如规范中所述。该化合物可以用作抗纤维化剂。本发明还涉及其制备方法。
• Halogenated analogues of anti-fibrotic agents
  申请人：Kelly Darren James

  公开号：US08624056B2

  公开（公告）日：2014-01-07

  The present invention relates to halogenated compounds of formula (I) with the substituents as described within the specification. The compounds may be useful as anti-fibrotic agents. The present invention also relates to methods for their preparation.

  本发明涉及公式（I）的卤代化合物，其取代基在规范中描述。这些化合物可能有用作为抗纤维化剂。本发明还涉及其制备方法。
• US8624056B2
  申请人：——

  公开号：US8624056B2

  公开（公告）日：2014-01-07
• 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.