4-(5-(4-(2,2-dimethylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)benzaldehyde | 635702-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-(4-(2,2-dimethylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)benzaldehyde
• 英文别名: 4-[5-[4-(2,2-Dimethylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]benzaldehyde
• CAS: 635702-01-1
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: KDEKJNYCFLQWDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-(4-(2,2-dimethylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)benzaldehyde 、 3-吖丁啶羧酸 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 1-(4-{5-[4-(2,2-Dimethyl-propyl)-phenyl]-[1,2,4]oxadiazol-3-yl}-benzyl)-azetidine-3-carboxylic acid
  参考文献：
  名称：

  Discovery of Potent 3,5-Diphenyl-1,2,4-oxadiazole Sphingosine-1-phosphate-1 (S1P₁) Receptor Agonists with Exceptional Selectivity against S1P₂ and S1P₃

  摘要：

  A class of 3,5-diphenyl-1,2,4-oxadiazole based compounds have been identified as potent sphingosine-1-phosphate-1 (S1P(1)) receptor agonists with minimal affinity for the S1P(2) and S1P3 receptor subtypes. Analogue 26 (S1P(1) IC50 = 0.6 nM) has an excellent pharmacokinetics profile in the rat and dog and is efficacious in a rat skin transplant model, indicating that S1P(3) receptor agonism is not a component of inummosuppressive efficacy.

  DOI：

  10.1021/jm0503244
• 作为产物：
  描述：

  4-(羟甲基)苯甲腈 在 草酰氯 、 盐酸羟胺 、 碳酸氢钠 、 二甲基亚砜 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4-(5-(4-(2,2-dimethylpropyl)phenyl)-1,2,4-oxadiazol-3-yl)benzaldehyde
  参考文献：
  名称：

  Discovery of Potent 3,5-Diphenyl-1,2,4-oxadiazole Sphingosine-1-phosphate-1 (S1P₁) Receptor Agonists with Exceptional Selectivity against S1P₂ and S1P₃

  摘要：

  A class of 3,5-diphenyl-1,2,4-oxadiazole based compounds have been identified as potent sphingosine-1-phosphate-1 (S1P(1)) receptor agonists with minimal affinity for the S1P(2) and S1P3 receptor subtypes. Analogue 26 (S1P(1) IC50 = 0.6 nM) has an excellent pharmacokinetics profile in the rat and dog and is efficacious in a rat skin transplant model, indicating that S1P(3) receptor agonism is not a component of inummosuppressive efficacy.

  DOI：

  10.1021/jm0503244

文献信息

• [EN] PROCESS FOR MAKING AZETIDINE-3-CARBOXYLIC ACID<br/>[FR] PROCEDE DE FABRICATION DE L'ACIDE AZETIDINE-3-CARBOXYLIQUE
  申请人：MERCK & CO INC

  公开号：WO2004035538A1

  公开（公告）日：2004-04-29

  The present invention is directed to an improved process for synthesizing azetidine-3-carboxylic acid, comprising triflating diethylbis(hydroxymethyl)malonate followed by azetidine ring-formation by intramolecular cyclization using an amine, decarboxylation to give the mono acid azetidine and hydrogenation to give the title compound. Azetidine-3-carboxylic acid is useful as an intermediate for making certain S1P?1#191/Edg1 receptor agonists, which are immunosupressive agents.

  本发明涉及一种改进的合成氮杂环丙氨酸的方法，包括对二乙基双(羟甲基)丙二酸酯进行三氟甲基化处理，然后通过内环化反应使用胺进行氮杂环丙烷环的形成，再进行脱羧反应得到单羧基氮杂环丙烷，最后进行氢化反应得到目标化合物。氮杂环丙氨酸可作为制备某些S1P?1#191/Edg1受体激动剂的中间体，这些激动剂是免疫抑制剂。
• 1-((5-aryl-1,2,4-oxadiazol-3-yl) benzyl)azetidine-3-carboxylates and 1-((5-aryl-1,2,4-oxadiazol-3-yl)benzyl) pyrrolidine-3-carboxylates as edg receptor agonists
  申请人：Chen Weirong

  公开号：US20050245575A1

  公开（公告）日：2005-11-03

  The present invention encompasses compounds of Formula I: as well as the pharmaceutically acceptable salts and hydrates thereof. The compounds are useful for treating immune mediated diseases and conditions, such as bone marrow, organ and tissue transplant rejection. Pharmaceutical compositions and methods of use are included.

  本发明涵盖公式I的化合物，以及其药学上可接受的盐和水合物。这些化合物可用于治疗免疫介导的疾病和病况，例如骨髓、器官和组织移植排斥反应。还包括药物组合物和使用方法。
• US7199142B2
  申请人：——

  公开号：US7199142B2

  公开（公告）日：2007-04-03
• Discovery of Potent 3,5-Diphenyl-1,2,4-oxadiazole Sphingosine-1-phosphate-1 (S1P₁) Receptor Agonists with Exceptional Selectivity against S1P₂ and S1P₃
  作者：Zhen Li、Weirong Chen、Jeffrey J. Hale、Christopher L. Lynch、Sander G. Mills、Richard Hajdu、Carol Ann Keohane、Mark J. Rosenbach、James A. Milligan、Gan-Ju Shei、Gary Chrebet、Stephen A. Parent、James Bergstrom、Deborah Card、Michael Forrest、Elizabeth J. Quackenbush、L. Alexandra Wickham、Hugo Vargas、Rose M. Evans、Hugh Rosen、Suzanne Mandala

  DOI：10.1021/jm0503244

  日期：2005.10.1

  A class of 3,5-diphenyl-1,2,4-oxadiazole based compounds have been identified as potent sphingosine-1-phosphate-1 (S1P(1)) receptor agonists with minimal affinity for the S1P(2) and S1P3 receptor subtypes. Analogue 26 (S1P(1) IC50 = 0.6 nM) has an excellent pharmacokinetics profile in the rat and dog and is efficacious in a rat skin transplant model, indicating that S1P(3) receptor agonism is not a component of inummosuppressive efficacy.