(S)-4-biphenyl-4-ylcarboxamido-4-(5-(4-hydroxyphenethyl)-1,3,4-oxadiazol-2-yl)butanoic acid | 1321975-94-3

• 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: (S)-4-biphenyl-4-ylcarboxamido-4-(5-(4-hydroxyphenethyl)-1,3,4-oxadiazol-2-yl)butanoic acid
• 英文别名: (4S)-4-[5-[2-(4-hydroxyphenyl)ethyl]-1,3,4-oxadiazol-2-yl]-4-[(4-phenylbenzoyl)amino]butanoic acid
• CAS: 1321975-94-3
• 化学式: C₂₇H₂₅N₃O₅
• 分子量: 471.513
• InChiKey: FVIFNRCNIPENOZ-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  cyclohexyl (S)-4-amino-4-(5-(4-hydroxyphenethyl)-1,3,4-oxadiazol-2-yl)butanoate 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-4-biphenyl-4-ylcarboxamido-4-(5-(4-hydroxyphenethyl)-1,3,4-oxadiazol-2-yl)butanoic acid
  参考文献：
  名称：

  Structure–activity study on a series of α-glutamic acid scaffold based compounds as new ADAMTS inhibitors

  摘要：

  A series of alpha-glutamic acid scaffold based 4-(benzamido)-4-(1,3,4-oxadiazol-2-yl) butanoic acids were designed and synthesized as new ADAMTS inhibitors. The compounds dose-dependently inhibited the enzymatic activities of ADAMTS-4 and ADAMTS-5. One of the most active compound 2h potently inhibited ADAMTS-4 and ADAMTS-5 with IC(50) values of 1.2 and 0.8 mu M, respectively. These inhibitors may serve as new lead compounds for further development of therapeutics to treat osteoarthritis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.009

文献信息

• Structure–activity study on a series of α-glutamic acid scaffold based compounds as new ADAMTS inhibitors
  作者：Lijie Peng、Lei Duan、Xiaofeng Liu、Mengjie Shen、Yingjun Li、Jiajie Yan、Honglin Li、Ke Ding

  DOI：10.1016/j.bmcl.2011.06.009

  日期：2011.8

  A series of alpha-glutamic acid scaffold based 4-(benzamido)-4-(1,3,4-oxadiazol-2-yl) butanoic acids were designed and synthesized as new ADAMTS inhibitors. The compounds dose-dependently inhibited the enzymatic activities of ADAMTS-4 and ADAMTS-5. One of the most active compound 2h potently inhibited ADAMTS-4 and ADAMTS-5 with IC(50) values of 1.2 and 0.8 mu M, respectively. These inhibitors may serve as new lead compounds for further development of therapeutics to treat osteoarthritis. (C) 2011 Elsevier Ltd. All rights reserved.