(Z)-3-[2-(1-N-Boc-D-leucyl)-4-methylphenyl]-2-propenoic acid | 690630-06-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-3-[2-(1-N-Boc-D-leucyl)-4-methylphenyl]-2-propenoic acid
• CAS: 690630-06-9
• 化学式: C₂₁H₂₉NO₆
• 分子量: 391.464
• InChiKey: XUMSTVWSGBHOQK-SIJIIQCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-[2-(1-N-Boc-D-leucyl)-4-methylphenyl]-2-propenoic acid 在 4-二甲氨基吡啶 、 N,N'-bis[2-oxo-3-oxazolidinyl]-phosphorodiamidic chloride 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (4R,7S,13R,16S,19Z)-7-benzyl-16-[(4-hydroxyphenyl)methyl]-13,23-dimethyl-4-(2-methylpropyl)-2-oxa-5,8,11,14,17-pentazabicyclo[19.4.0]pentacosa-1(21),19,22,24-tetraene-3,6,9,12,15,18-hexone
  参考文献：
  名称：

  The effect of substitution patterns on the release rates of opioid peptides DADLE and [Leu5]-enkephalin from coumarin prodrug moieties

  摘要：

  A coumarin-based prodrug system has been developed in our laboratory for the preparation of esterase-sensitive prodrugs of amines, peptides, and peptidomimetics. The drug release rates from this prodrug system were found to be dependent on the structural features of the drug moiety. The effect of the phenyl ring substitutions on the release kinetics of such prodrugs of model amines was examined recently and it was found that appropriately positioned alkyl substituents on the phenyl ring could help to facilitate the release. Aimed at further understanding the structure-release rate relationship of the coumarin-based cyclic prodrugs, we synthesized and examined a series of substituted coumarinic acid derivatives of opioid peptides, DADLE, and [Leu(5)]-enkephalin. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2003.12.002
• 作为产物：
  描述：

  2-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-4-methylphenol 在 4-二甲氨基吡啶 、 manganese(IV) oxide 、 sodium chlorite 、 phosphate buffer 、 双氧水 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (Z)-3-[2-(1-N-Boc-D-leucyl)-4-methylphenyl]-2-propenoic acid
  参考文献：
  名称：

  The effect of substitution patterns on the release rates of opioid peptides DADLE and [Leu5]-enkephalin from coumarin prodrug moieties

  摘要：

  A coumarin-based prodrug system has been developed in our laboratory for the preparation of esterase-sensitive prodrugs of amines, peptides, and peptidomimetics. The drug release rates from this prodrug system were found to be dependent on the structural features of the drug moiety. The effect of the phenyl ring substitutions on the release kinetics of such prodrugs of model amines was examined recently and it was found that appropriately positioned alkyl substituents on the phenyl ring could help to facilitate the release. Aimed at further understanding the structure-release rate relationship of the coumarin-based cyclic prodrugs, we synthesized and examined a series of substituted coumarinic acid derivatives of opioid peptides, DADLE, and [Leu(5)]-enkephalin. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2003.12.002