(2R,3S)-dimethyl <2-hydroxy-4-phenyl-3-(tritylamino)butyl>phosphonate | 107591-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3S)-dimethyl <2-hydroxy-4-phenyl-3-(tritylamino)butyl>phosphonate
• 英文别名: (2R,3S)-1-dimethoxyphosphoryl-4-phenyl-3-(tritylamino)butan-2-ol
• CAS: 107591-62-8
• 化学式: C₃₁H₃₄NO₄P
• 分子量: 515.589
• InChiKey: HPLUHZFXNRLUOU-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-dimethyl <2-hydroxy-4-phenyl-3-(tritylamino)butyl>phosphonate 、 溶剂黄146 、 三乙胺 生成 (4S,5R)-5-<(dimethylphosphinyl)methyl>-4-(phenylmethyl)oxazolidin-2-one
  参考文献：
  名称：

  DELLARIA, J. F. ,, JR.;MAKI, R. G., TETRAHEDRON LETT., 1986, 27, N 21, 2337-2340

  摘要：

  DOI：
• 作为产物：
  描述：

  三苯基氯甲烷 在 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 (2R,3S)-dimethyl <2-hydroxy-4-phenyl-3-(tritylamino)butyl>phosphonate
  参考文献：
  名称：

  New inhibitors of renin that contain novel phosphostatine Leu-Val replacements

  摘要：

  A novel series of renin inhibitors based on the Phe8-His9-Leu10-Val11 substructure of renin's natural substrate, angiotensinogen, is reported. These inhibitors retain the Phe8-His9 portion of the native substructure and employ novel phosphostatine Leu10-Val11 replacements (LVRs). The phosphostatine LVRs were prepared by condensing a dialkyl phosphonate ester stabilized anion with either N-t-Boc-amino aldehydes or N-tritylamino aldehydes (derived from the corresponding amino acid). Structure-activity relationships at the Leu10 side chain revealed that the LVR derived from L-cyclohexylalanine provided a 130-fold boost in potency over the LVR derived from L-leucine. The dialkyl ester moiety was varied and a loss in potency was incurred when the alkyl ester was chain extended or alpha-branched; dimethyl esters provided optimum potency. The phosphonate moiety was replaced by a half-acid half-ester phosphonate and dimethylphosphinate; both replacements lead to a loss in potency. The more potent inhibitors (IC50 = 20-50 nM) were found to be selective inhibitors for renin over porcine pepsin and bovine cathepsin D (little or no inhibition was observed at 10(-5) M).

  DOI：

  10.1021/jm00164a011