Ethyl 2-[[1-adamantyloxy-[1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-benzylsulfanylpropanoate | 237394-36-4

• 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: Ethyl 2-[[1-adamantyloxy-[1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-benzylsulfanylpropanoate
• CAS: 237394-36-4
• 化学式: C₃₃H₄₄NO₆PS
• 分子量: 613.755
• InChiKey: ZTYLTMGIOBMQKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[[1-adamantyloxy-[1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-benzylsulfanylpropanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以92%的产率得到2-[[1-Adamantyloxy-[1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-benzylsulfanylpropanoic acid
  参考文献：
  名称：

  Phosphinic Pseudo-Tripeptides as Potent Inhibitors of Matrix Metalloproteinases:  A Structure−Activity Study

  摘要：

  Several phosphinic pseudo-tripeptides of general formula R-Xaa Psi (PO2-CH2)Xaa'-Yaa'-NH2 were synthesized and evaluated for their in vitro activities to inhibit stromelysin-3, gelatinases A and B, membrane type-1 matrix metalloproteinase, collagenases 1 and 2, and matrilysin. With the exception of collagenase-1 and matrilysin, phosphinic pseudo-tripeptides behave as highly potent inhibitors of matrix metalloproteinases, provided they contain in P-1' position an unusual long aryl-alkyl substituent. Study of structure-activity relationships regarding the influence of the R and Xaa' substituents in this series may contribute to the design of inhibitors able to block only a few members of the matrix metalloproteinase family.

  DOI：

  10.1021/jm9900164
• 作为产物：
  描述：

  benzyloxycarbonyl-1-aminoethyl-1-phosphinate 在 六甲基二硅氮烷 、 silver(l) oxide 作用下， 以 氯仿 为溶剂， 反应 4.5h， 生成 Ethyl 2-[[1-adamantyloxy-[1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-benzylsulfanylpropanoate
  参考文献：
  名称：

  Phosphinic Pseudo-Tripeptides as Potent Inhibitors of Matrix Metalloproteinases:  A Structure−Activity Study

  摘要：

  Several phosphinic pseudo-tripeptides of general formula R-Xaa Psi (PO2-CH2)Xaa'-Yaa'-NH2 were synthesized and evaluated for their in vitro activities to inhibit stromelysin-3, gelatinases A and B, membrane type-1 matrix metalloproteinase, collagenases 1 and 2, and matrilysin. With the exception of collagenase-1 and matrilysin, phosphinic pseudo-tripeptides behave as highly potent inhibitors of matrix metalloproteinases, provided they contain in P-1' position an unusual long aryl-alkyl substituent. Study of structure-activity relationships regarding the influence of the R and Xaa' substituents in this series may contribute to the design of inhibitors able to block only a few members of the matrix metalloproteinase family.

  DOI：

  10.1021/jm9900164