2-[[1-Adamantyloxy-[1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-benzylsulfanylpropanoic acid | 237394-49-9

• 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: 2-[[1-Adamantyloxy-[1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-benzylsulfanylpropanoic acid
• CAS: 237394-49-9
• 化学式: C₃₁H₄₀NO₆PS
• 分子量: 585.701
• InChiKey: SCFOXSHNZAVFHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  、 2-[[1-Adamantyloxy-[1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]methyl]-3-benzylsulfanylpropanoic acid 生成 (1-Benzyloxycarbonylamino-ethyl)-{3-benzylsulfanyl-2-[(S)-1-carbamoyl-2-(1H-indol-3-yl)-ethylcarbamoyl]-propyl}-phosphinic 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：

  1-溴金刚烷 在 sodium hydroxide 、 silver(l) oxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 18.5h， 生成 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