(2S,3S)-1-(4-tert-butylphenyl)-3-[[3-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-4-oxoazetidine-2-carboxylic acid | 647003-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (2S,3S)-1-(4-tert-butylphenyl)-3-[[3-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-4-oxoazetidine-2-carboxylic acid
• CAS: 647003-13-2
• 化学式: C₃₃H₃₄N₂O₅
• 分子量: 538.643
• InChiKey: XRVNSFDHOMAYDC-YTMVLYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl (2S,3S)-1-(4-tert-butylphenyl)-3-[[3-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-4-oxoazetidine-2-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S,3S)-1-(4-tert-butylphenyl)-3-[[3-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-4-oxoazetidine-2-carboxylic acid
  参考文献：
  名称：

  Discovery of azetidinone acids as conformationally-constrained dual PPARα/γ agonists

  摘要：

  A novel class of azetidinone acid-derived dual PPAR alpha/gamma agonists has been synthesized for the treatment of diabetes and dyslipidemia. The preferred stereochemistry in this series for binding and functional agonist activity against both PPAR alpha and PPAR gamma receptors was shown to be 3S,4S. Synthesis, in vitro and in vivo activities of compounds in this series are described. A high-yielding method for N-arylation of azetidinone esters is also described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.126

文献信息

• SUBSTITUTED HETEROCYCLIC DERIVATIVES USEFUL AS ANTIDIABETIC AND ANTIOBESITY AGENTS AND METHOD
  申请人：Cheng T. W. Peter

  公开号：US20070287713A1

  公开（公告）日：2007-12-13

  wherein Z 1 is (CH 2 ) q or C═O; Z 2 is (CH 2 ) p or C═O; D is —CH═ or C═O or (CH 2 ) m where m is 0, 1, 2 or 3; n=0, 1 or 2; p=1 or 2; q=0, 1 or 2; Q is C or N; A is (CH 2 ) x where x is 1 to 5, or A is (CH 2 ) x 1 , where x 1 is 1 to 5 with an alkenyl bond or an alkynyl bond embedded anywhere in the chain, or A is —(CH 2 ) x 2 —O—(CH 2 ) x 3 — where x 2 is 0 to 5 and x 3 is 0 to 5, provided that at least one of x 2 and x 3 is other than 0; B is a bond or is (CH 2 ) x 4 where x 4 is 1 to 5; X is CH or N; X 2 is C, N, O or S; X 3 is C, N, O or S; X 4 is C, N, O or S; X 5 is C, N, O or S; X 6 is C, N, O or S; provided that at least one of X 2 , X 3 , X 4 X 5 and X 6 is N; and at least one of X 2 , X 3 , X 4 X 5 and X 6 is C. R 1 is H or alkyl; R 2 is H, alkyl, alkoxy, halogen, amino, substituted amino or cyano; R 2a , R 2b and R 2c may be the same or different and are selected from H, alkyl, alkoxy, halogen, amino, substituted amino or cyano; and R 3 , E, Z and Y are as defined herein.

  其中Z1为(CH2)q或C═O；Z2为(CH2)p或C═O；D为—CH═或C═O或(CH2)m，其中m为0、1、2或3；n=0、1或2；p=1或2；q=0、1或2；Q为C或N；A为(CH2)x，其中x为1到5，或A为(CH2)x1，其中x1为1到5，具有烯丙基键或炔基键嵌入链中的任何位置，或A为—(CH2)x2—O—(CH2)x3—，其中x2为0到5，x3为0到5，前提是x2和x3中至少有一个不为0；B为键或(CH2)x4，其中x4为1到5；X为CH或N；X2、X3、X4、X5和X6为C、N、O或S；前提是X2、X3、X4、X5和X6中至少有一个为N；并且X2、X3、X4、X5和X6中至少有一个为C。R1为H或烷基；R2为H、烷基、烷氧基、卤素、氨基、取代氨基或氰基；R2a、R2b和R2c可以相同也可以不同，选择自H、烷基、烷氧基、卤素、氨基、取代氨基或氰基；而R3、E、Z和Y的定义如前所述。
• US7279485B2
  申请人：——

  公开号：US7279485B2

  公开（公告）日：2007-10-09
• US7951793B2
  申请人：——

  公开号：US7951793B2

  公开（公告）日：2011-05-31
• Discovery of azetidinone acids as conformationally-constrained dual PPARα/γ agonists
  作者：Wei Wang、Pratik Devasthale、Dennis Farrelly、Liqun Gu、Thomas Harrity、Michael Cap、Cuixia Chu、Lori Kunselman、Nathan Morgan、Randy Ponticiello、Rachel Zebo、Litao Zhang、Kenneth Locke、Jonathan Lippy、Kevin O’Malley、Vinayak Hosagrahara、Lisa Zhang、Pathanjali Kadiyala、Chiehying Chang、Jodi Muckelbauer、Arthur M. Doweyko、Robert Zahler、Denis Ryono、Narayanan Hariharan、Peter T.W. Cheng

  DOI：10.1016/j.bmcl.2008.01.126

  日期：2008.3

  A novel class of azetidinone acid-derived dual PPAR alpha/gamma agonists has been synthesized for the treatment of diabetes and dyslipidemia. The preferred stereochemistry in this series for binding and functional agonist activity against both PPAR alpha and PPAR gamma receptors was shown to be 3S,4S. Synthesis, in vitro and in vivo activities of compounds in this series are described. A high-yielding method for N-arylation of azetidinone esters is also described. (C) 2008 Elsevier Ltd. All rights reserved.