(3R,4R,5R)-3-acetoxy-N-allyloxycarbonyl-2-[(E)-1-(1-pyrrolidinyl)carbonyl-1-(1-naphthoyl)amino]methylidene-4,5-epoxypiperidine | 1254755-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3R,4R,5R)-3-acetoxy-N-allyloxycarbonyl-2-[(E)-1-(1-pyrrolidinyl)carbonyl-1-(1-naphthoyl)amino]methylidene-4,5-epoxypiperidine
• 英文别名: prop-2-enyl (1R,4E,5R,6R)-5-acetyloxy-4-[1-(naphthalene-1-carbonylamino)-2-oxo-2-pyrrolidin-1-ylethylidene]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate
• CAS: 1254755-03-7
• 化学式: C₂₈H₂₉N₃O₇
• 分子量: 519.554
• InChiKey: HVIVNVZYQLJOPM-AFBKGTOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-3-acetoxy-N-allyloxycarbonyl-2-[(E)-1-(1-pyrrolidinyl)carbonyl-1-(1-naphthoyl)amino]methylidene-4,5-epoxypiperidine 在 四(三苯基膦)钯 、 甲酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以60 mg的产率得到(3R,4R,5R)-3-acetoxy-2-[1-methoxycarbonyl-1-(1-naphthoyl)amino]methylidene-4,5-epoxypiperidine
  参考文献：
  名称：

  Synthesis and DNA cleavage evaluation of epoxypiperidine derivatives bearing a dehydroamino acid unit

  摘要：

  Epoxypiperidine derivatives bearing a dehydroamino acid unit were designed and synthesized as novel DNA alkylating agents based on the structure of azinomycins. A relaxation assay of plasmid DNA revealed that the epoxypiperidine derivative 3 has a DNA cleavage activity. Based on the studies, it would appear that the electron density of the amino group of epoxypiperidines plays a critically important role in the DNA cleavage. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.027
• 作为产物：
  描述：

  (3R,4R,5R)-N-allyloxycarbonyl-3-hydroxy-2-[(E)-1-(1-pyrrolidinyl)carbonyl-1-(1-naphthoyl)amino]methylidene-4,5-epoxypiperidine 、 乙酸酐 在 四氢吡咯 作用下， 反应 2.0h， 以86 mg的产率得到(3R,4R,5R)-3-acetoxy-N-allyloxycarbonyl-2-[(E)-1-(1-pyrrolidinyl)carbonyl-1-(1-naphthoyl)amino]methylidene-4,5-epoxypiperidine
  参考文献：
  名称：

  Synthesis and DNA cleavage evaluation of epoxypiperidine derivatives bearing a dehydroamino acid unit

  摘要：

  Epoxypiperidine derivatives bearing a dehydroamino acid unit were designed and synthesized as novel DNA alkylating agents based on the structure of azinomycins. A relaxation assay of plasmid DNA revealed that the epoxypiperidine derivative 3 has a DNA cleavage activity. Based on the studies, it would appear that the electron density of the amino group of epoxypiperidines plays a critically important role in the DNA cleavage. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.027