N-CBZ-β-alanine 2,3-O-isopropylidene-D-ribono-1,4-lactone ester | 122410-24-6

• 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: N-CBZ-β-alanine 2,3-O-isopropylidene-D-ribono-1,4-lactone ester
• 英文别名: [(3aR,6R,6aR)-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-6-yl]methyl 3-(phenylmethoxycarbonylamino)propanoate
• CAS: 122410-24-6
• 化学式: C₁₉H₂₃NO₈
• 分子量: 393.394
• InChiKey: YNZVWEGYOZSUII-FVQBIDKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  109.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-CBZ-β-alanine 2,3-O-isopropylidene-D-ribono-1,4-lactone ester 、 (S,S)-2,4-dibenzylglutaric anhydride 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 以64%的产率得到N-<(S,S)-2,4-dibenzyl-4-carboxybutyryl>-β-alanine 2,3-O-isopropylidene-D-ribono-1,4-lactone ester
  参考文献：
  名称：

  Enkephalinase inhibitors. 1. 2,4-Dibenzylglutaric acid derivatives

  摘要：

  The synthesis of two new series of dicarboxylic acid dipeptides and two sulfhydryl-containing inhibitors are described. The in vitro enkephalinase inhibition data and some in vivo analgesic data are presented for these compounds. For the dibenzylglutaric acid series structure-activity relationships and in vivo analgesic activity are discussed. The reverse amides, i.e., 4-amino-2,4-dibenzylbutyric acid derivatives, are also discussed. Two sulfhydryl-containing inhibitors showed good in vivo potency in the mouse jump-latency hot-plate test after peripheral administration at moderate low doses.

  DOI：

  10.1021/jm00132a005
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 、 N-CBZ-beta-丙氨酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-CBZ-β-alanine 2,3-O-isopropylidene-D-ribono-1,4-lactone ester
  参考文献：
  名称：

  Enkephalinase inhibitors. 1. 2,4-Dibenzylglutaric acid derivatives

  摘要：

  The synthesis of two new series of dicarboxylic acid dipeptides and two sulfhydryl-containing inhibitors are described. The in vitro enkephalinase inhibition data and some in vivo analgesic data are presented for these compounds. For the dibenzylglutaric acid series structure-activity relationships and in vivo analgesic activity are discussed. The reverse amides, i.e., 4-amino-2,4-dibenzylbutyric acid derivatives, are also discussed. Two sulfhydryl-containing inhibitors showed good in vivo potency in the mouse jump-latency hot-plate test after peripheral administration at moderate low doses.

  DOI：

  10.1021/jm00132a005

文献信息

• KSANDER, GARY M.;DIEFENBACHER, CLIVE G.;YUAN, ANDREW M.;CLARK, F.;SAKANE,+, J. MED. CHEM., 32,(1989) N2, C. 2519-2526
  作者：KSANDER, GARY M.、DIEFENBACHER, CLIVE G.、YUAN, ANDREW M.、CLARK, F.、SAKANE,+

  DOI：——

  日期：——