5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid (biphenyl-4-ylmethyl)-amide | 870102-18-4

• 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: 5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid (biphenyl-4-ylmethyl)-amide
• 英文别名: 5-hydroxy-4-oxo-N-[(4-phenylphenyl)methyl]pyran-2-carboxamide
• CAS: 870102-18-4
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: OUGLYRIZWKQCPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid (biphenyl-4-ylmethyl)-amide 在 tetraphosphorus decasulfide 、 六甲基二硅氧烷 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.0h， 以68%的产率得到5-hydroxy-4-thioxo-4H-pyran-2-carboxylic acid (biphenyl-4-ylmethyl)-amide
  参考文献：
  名称：

  Synthesis of hydroxypyrone- and hydroxythiopyrone-based matrix metalloproteinase inhibitors: Developing a structure–activity relationship

  摘要：

  The zinc(II)-dependent matrix metalloproteinases (MMPs) are associated with a variety of diseases. Development of inhibitors to modulate MMP activity has been an active area of investigation for therapeutic development. Hydroxypyrones and hydroxythiopyrones are alternative zinc-binding groups (ZBGs) that, when combined with peptidomimetic backbones, comprise a novel class of MMP inhibitors (MMPi). In this report, a series of hydroxypyrone- and hydroxythiopyrone-based MMPi with aryl backbones at the 2-, 5-, and 6- positions of the hydroxypyrone ring have been synthesized. Synthetic routes for developing inhibitors with substituents at two of these positions (so-called double-handed inhibitors) are also explored. The MMP inhibition profiles and structure-activity relationship of synthesized hydroxypyrones and hydroxythiopyrones have been analyzed. The results here show that the ZBG, the position of the backbone on the ZBG, and the nature of the linker between the ZBG and backbone are critical for MMPi activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.044
• 作为产物：
  描述：

  5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid (biphenyl-4-ylmethyl)-amide 在 盐酸 、 三氟乙酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 5.0h， 以80%的产率得到5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid (biphenyl-4-ylmethyl)-amide
  参考文献：
  名称：

  Synthesis of hydroxypyrone- and hydroxythiopyrone-based matrix metalloproteinase inhibitors: Developing a structure–activity relationship

  摘要：

  The zinc(II)-dependent matrix metalloproteinases (MMPs) are associated with a variety of diseases. Development of inhibitors to modulate MMP activity has been an active area of investigation for therapeutic development. Hydroxypyrones and hydroxythiopyrones are alternative zinc-binding groups (ZBGs) that, when combined with peptidomimetic backbones, comprise a novel class of MMP inhibitors (MMPi). In this report, a series of hydroxypyrone- and hydroxythiopyrone-based MMPi with aryl backbones at the 2-, 5-, and 6- positions of the hydroxypyrone ring have been synthesized. Synthetic routes for developing inhibitors with substituents at two of these positions (so-called double-handed inhibitors) are also explored. The MMP inhibition profiles and structure-activity relationship of synthesized hydroxypyrones and hydroxythiopyrones have been analyzed. The results here show that the ZBG, the position of the backbone on the ZBG, and the nature of the linker between the ZBG and backbone are critical for MMPi activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.044

文献信息

• METALLOPROTEIN INHIBITORS
  申请人：Puerta T. David

  公开号：US20070117848A1

  公开（公告）日：2007-05-24

  The present invention relates to metalloprotein inhibitors comprising: a. an organic substituent and at least one zinc binding group (ZBG) covalently attached thereto; or b. a ZBG substituted by a side chain wherein the ZBG is of formula (I): wherein X is O or S and each R 1 , R 2 , R 3 , and R 4 is individually hydrogen or an organic radical. The metalloprotein inhibitors are useful for preventing or treating a pathological disease, condition, or symptom that is associated with pathological metalloprotein activity and/or that is alleviated by inhibition of said activity.

  本发明涉及金属蛋白酶抑制剂，包括：a. 有机取代基和至少一个锌结合基团（ZBG）共价连接在一起；或者b. 通过侧链取代的ZBG，其中ZBG的公式为（I）：其中X为O或S，每个R1、R2、R3和R4分别为氢或有机基团。这些金属蛋白酶抑制剂可用于预防或治疗与病理性金属蛋白酶活性相关的病理性疾病、状况或症状，或者通过抑制该活性缓解的病理性疾病、状况或症状。
• Metalloprotein Inhibitors
  申请人：Puerta David T.

  公开号：US20080161362A1

  公开（公告）日：2008-07-03

  The present invention relates to metalloprotein inhibitors comprising: a. an organic substituent and at least one zinc binding group (ZBG) covalently attached thereto; or b. a ZBG substituted by a side chain wherein the ZBG is of formula (I): wherein X is O or S and each R 1 , R 2 , R 3 , and R 4 is individually hydrogen or an organic radical. The metalloprotein inhibitors are useful for preventing or treating a pathological disease, condition, or symptom that is associated with pathological metalloprotein activity and/or that is alleviated by inhibition of said activity.
• USE OF MATRIX METALLOPROTEINASE INHIBITORS IN SKIN CARE
  申请人：Yu Betty

  公开号：US20090068255A1

  公开（公告）日：2009-03-12

  The application of matrix metalloproteinase (MMP) inhibitors to the skin inhibits the degradation of proteins found in the skin including collagen, elastin, and other basement membrane and extracellular matrix protein. MMP inhibitors may be used in both cosmetic compositions and pharmaceutical compositions for application to skin. MMP inhibitors are formulated with a cosmetically suitable vehicle or pharmaceutically acceptable excipient for application to the skin as creams, lotions, ointments, solutions, face masks, etc. As cosmetics, the inventive MMP inhibitor compositions are applied to the skin to prevent or reduce the appearance of wrinkles, pigmentation changes, loss of elasticity, or other effects associated with aging or sun damage. As pharmaceuticals, the inventive MMP inhibitor compositions may also be applied to the skin to treat or prevent a skin disease (e.g., proliferative disease, inflammatory disease).
• US7579486B2
  申请人：——

  公开号：US7579486B2

  公开（公告）日：2009-08-25
• US7705164B2
  申请人：——

  公开号：US7705164B2

  公开（公告）日：2010-04-27