Fmoc-bis(pivaloylmethoxy)phoshoSer-Ψ[(Z)CH=C]-Pro-2-aminoethyl-(3-indole) | 876732-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-bis(pivaloylmethoxy)phoshoSer-Ψ[(Z)CH=C]-Pro-2-aminoethyl-(3-indole)
• 英文别名: [2,2-dimethylpropanoyloxymethoxy-[(2R,3Z)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2R)-2-[2-(1H-indol-3-yl)ethylcarbamoyl]cyclopentylidene]propoxy]phosphoryl]oxymethyl 2,2-dimethylpropanoate
• CAS: 876732-64-8
• 化学式: C₄₆H₅₆N₃O₁₁P
• 分子量: 857.938
• InChiKey: RUYAGGLZNPDKMA-BVPJQTGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  61
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  181
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  Fmoc-Ser-Ψ[(Z)CH=C]-Pro-2-aminoethyl-(3-indole) 、 bis[(pivaloyloxy)methyl] chlorophosphate 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 以20%的产率得到Fmoc-bis(pivaloylmethoxy)phoshoSer-Ψ[(Z)CH=C]-Pro-2-aminoethyl-(3-indole)
  参考文献：
  名称：

  A phosphorylated prodrug for the inhibition of Pin1

  摘要：

  Fmoc-pSer-psi[(Z)CH = C]-Pro-(2)-N-(3)-ethylaminoindole 1, showed moderate inhibition towards the mitotic regulator, Pin1 (IC50 = 28.3 mu M). To improve the cell permeability, the charged phosphate was masked as the bis-pivaloyloxymethyl (POM) phosphate in Fmoc-(bisPOM)-pSer-psi[(Z)CH = C]-Pro-(2)-N-(3)-ethylaminoindole 2. Antiproliferative activity towards A2780 ovarian cancer cells of 1 (IC50 = 46.2 mu M) was improved significantly in 2 (IC50 = 26.9 mu M), comparable to the IC50 of 1 towards Pin1 enzymatic activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.073

文献信息

• [EN] ALKENE MIMICS<br/>[FR] ANALOGUES D'ALCENES
  申请人：VIRGINIA TECH INTELL PROP

  公开号：WO2006020417A3

  公开（公告）日：2006-07-13
• A phosphorylated prodrug for the inhibition of Pin1
  作者：Song Zhao、Felicia A. Etzkorn

  DOI：10.1016/j.bmcl.2007.09.073

  日期：2007.12

  Fmoc-pSer-psi[(Z)CH = C]-Pro-(2)-N-(3)-ethylaminoindole 1, showed moderate inhibition towards the mitotic regulator, Pin1 (IC50 = 28.3 mu M). To improve the cell permeability, the charged phosphate was masked as the bis-pivaloyloxymethyl (POM) phosphate in Fmoc-(bisPOM)-pSer-psi[(Z)CH = C]-Pro-(2)-N-(3)-ethylaminoindole 2. Antiproliferative activity towards A2780 ovarian cancer cells of 1 (IC50 = 46.2 mu M) was improved significantly in 2 (IC50 = 26.9 mu M), comparable to the IC50 of 1 towards Pin1 enzymatic activity. (c) 2007 Elsevier Ltd. All rights reserved.