(D,L)-3-(4-chlorobenzyl)-5-(2-phenyl-1-tert-butyloxycarbonylaminoethyl)-1,2,4-oxadiazole

• 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: (D,L)-3-(4-chlorobenzyl)-5-(2-phenyl-1-tert-butyloxycarbonylaminoethyl)-1,2,4-oxadiazole
• 英文别名: tert-butyl N-[1-[3-[(4-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl]-2-phenylethyl]carbamate
• 化学式: C₂₂H₂₄ClN₃O₃
• 分子量: 413.904
• InChiKey: BKQJHPGNSRJLGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (D,L)-3-(4-chlorobenzyl)-5-(2-phenyl-1-tert-butyloxycarbonylaminoethyl)-1,2,4-oxadiazole 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到(D,L)-5-(1-amino-2-phenylethyl)-3-(4-chlorobenzyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  1,2,4-Oxadiazole derivatives of phenylalanine: potential inhibitors of substance P endopeptidase

  摘要：

  The synthesis and the biological activity of a series of benzyl or aryl substituted 1,2,4-oxadiazole derivatives of phenyl-alanine are described. A base-promoted intermolecular cyclization reaction was performed using racemic tert-butyloxycarbonyl-protected phenylalanine methyl ester and an amidoxime. After deprotection of the amino function the compounds were evaluated for their affinity to rat brain NK1-receptors and as inhibitors of a specific substance P cleaving enzyme, substance P endopeptidase (SPE), isolated from human cerebrospinal fluid. The results indicate that several compounds are weak inhibitors of SPE. However, all compounds lacked appreciable NK1-receptor affinity.

  DOI：

  10.1016/0223-5234(93)90115-u
• 作为产物：
  描述：

  对氯苯乙腈 在 正丁基锂 、 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 18.5h， 生成 (D,L)-3-(4-chlorobenzyl)-5-(2-phenyl-1-tert-butyloxycarbonylaminoethyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  1,2,4-Oxadiazole derivatives of phenylalanine: potential inhibitors of substance P endopeptidase

  摘要：

  The synthesis and the biological activity of a series of benzyl or aryl substituted 1,2,4-oxadiazole derivatives of phenyl-alanine are described. A base-promoted intermolecular cyclization reaction was performed using racemic tert-butyloxycarbonyl-protected phenylalanine methyl ester and an amidoxime. After deprotection of the amino function the compounds were evaluated for their affinity to rat brain NK1-receptors and as inhibitors of a specific substance P cleaving enzyme, substance P endopeptidase (SPE), isolated from human cerebrospinal fluid. The results indicate that several compounds are weak inhibitors of SPE. However, all compounds lacked appreciable NK1-receptor affinity.

  DOI：

  10.1016/0223-5234(93)90115-u

文献信息

• 1,2,4-Oxadiazole derivatives of phenylalanine: potential inhibitors of substance P endopeptidase
  作者：S Borg、K Luthman、F Nyberg、L Terenius、U Hacksell

  DOI：10.1016/0223-5234(93)90115-u

  日期：1993.1

  The synthesis and the biological activity of a series of benzyl or aryl substituted 1,2,4-oxadiazole derivatives of phenyl-alanine are described. A base-promoted intermolecular cyclization reaction was performed using racemic tert-butyloxycarbonyl-protected phenylalanine methyl ester and an amidoxime. After deprotection of the amino function the compounds were evaluated for their affinity to rat brain NK1-receptors and as inhibitors of a specific substance P cleaving enzyme, substance P endopeptidase (SPE), isolated from human cerebrospinal fluid. The results indicate that several compounds are weak inhibitors of SPE. However, all compounds lacked appreciable NK1-receptor affinity.