N-((2S,3S)-2-(benzo[d][1,3]dioxol-5-yl)-3-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methoxymethoxy)propyl)benzamide | 1226976-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-((2S,3S)-2-(benzo[d][1,3]dioxol-5-yl)-3-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methoxymethoxy)propyl)benzamide
• 英文别名: N-[(2S,3S)-2-(1,3-benzodioxol-5-yl)-3-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methoxymethoxy)propyl]benzamide
• CAS: 1226976-44-8
• 化学式: C₂₅H₃₁NO₈
• 分子量: 473.523
• InChiKey: CLZGVQMOEWULAZ-HGSOSGBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-((2S,3S)-2-(benzo[d][1,3]dioxol-5-yl)-3-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methoxymethoxy)propyl)benzamide 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以98%的产率得到C₃₂H₃₇NO₁₀S
  参考文献：
  名称：

  Potent and selective inhibition of human cytochrome P450 3A4 by seco-pancratistatin structural analogs

  摘要：

  seco-Derivatives of the anticancer agent pancratistatin bearing the 2S,3S,4S,5S configuration were accessed via a novel, highly diastereoselective anti-aldol reaction. Structure-activity relationships reveal important insights into the seco-pancratistatin pharmacophore as a potent and selective inhibitor of human cytochrome P450 3A4 (CYP3A4), and highlight features of concern in advancing a potent, selective anticancer agent in the pancratistatin series. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.157
• 作为产物：
  描述：

  [(2S,3S,4S,5S)-2-(3',4'-methylenedioxy)phenyl-3-methoxymethyleneoxy-4,5-isopropylidene-dioxy-6-tert-butyldimethylsilyloxy]-1-benzoylaminohexane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以97%的产率得到N-((2S,3S)-2-(benzo[d][1,3]dioxol-5-yl)-3-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(methoxymethoxy)propyl)benzamide
  参考文献：
  名称：

  Potent and selective inhibition of human cytochrome P450 3A4 by seco-pancratistatin structural analogs

  摘要：

  seco-Derivatives of the anticancer agent pancratistatin bearing the 2S,3S,4S,5S configuration were accessed via a novel, highly diastereoselective anti-aldol reaction. Structure-activity relationships reveal important insights into the seco-pancratistatin pharmacophore as a potent and selective inhibitor of human cytochrome P450 3A4 (CYP3A4), and highlight features of concern in advancing a potent, selective anticancer agent in the pancratistatin series. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.157