(2R,3R)-2-((E)-2-[1,3]Dioxolan-2-yl-1-hydroxymethyl-vinyl)-3-hydroxy-pyrrolidine-1-carboxylic acid 4,5-dimethoxy-2-nitro-benzyl ester | 385369-16-4

• 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: (2R,3R)-2-((E)-2-[1,3]Dioxolan-2-yl-1-hydroxymethyl-vinyl)-3-hydroxy-pyrrolidine-1-carboxylic acid 4,5-dimethoxy-2-nitro-benzyl ester
• 英文别名: (4,5-dimethoxy-2-nitrophenyl)methyl (2R,3R)-2-[(E)-1-(1,3-dioxolan-2-yl)-3-hydroxyprop-1-en-2-yl]-3-hydroxypyrrolidine-1-carboxylate
• CAS: 385369-16-4
• 化学式: C₂₀H₂₆N₂O₁₀
• 分子量: 454.434
• InChiKey: OBONHYOIVUXKDS-AWIPFPIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  150.06
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-((E)-2-[1,3]Dioxolan-2-yl-1-hydroxymethyl-vinyl)-3-hydroxy-pyrrolidine-1-carboxylic acid 4,5-dimethoxy-2-nitro-benzyl ester 在 aluminum oxide 作用下， 生成 (2R,3R)-3-Carbamoyloxy-2-((E)-1-carbamoyloxymethyl-2-[1,3]dioxolan-2-yl-vinyl)-pyrrolidine-1-carboxylic acid 4,5-dimethoxy-2-nitro-benzyl ester
  参考文献：
  名称：

  DNA cross-linking by a phototriggered pyrrolic progenitor developed from monocrotaline

  摘要：

  A wide variety of pyrrolizidine alkaloids, such as monocrotaline, exert their cytotoxicity through the formation of DNA-DNA interstrand cross-links and DNA-protein cross-links. These pyrrolizidine alkaloids are oxidatively activated in vivo forming a highly reactive pyrrolic-type intermediate, which is responsible for the DNA cross-Linking reaction. The oxidative pathway of activation leads to undesired toxicity. Based on a previously reported photochemically triggered progenitor of monocrotaline, we describe here the semi-synthesis and DNA cross-linking of a dicarbamate analogue of the original phototriggered progenitor. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01341-7
• 作为产物：
  描述：

  (3aR,6R,7S,8R,12aR)-12-[1-[1,3]Dioxolan-2-yl-meth-(E)-ylidene]-7,8-dihydroxy-6,7,8-trimethyl-octahydro-4,10-dioxa-1-aza-cyclopentacycloundecene-5,9-dione 在 potassium cyanide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (2R,3R)-2-((E)-2-[1,3]Dioxolan-2-yl-1-hydroxymethyl-vinyl)-3-hydroxy-pyrrolidine-1-carboxylic acid 4,5-dimethoxy-2-nitro-benzyl ester
  参考文献：
  名称：

  DNA cross-linking by a phototriggered pyrrolic progenitor developed from monocrotaline

  摘要：

  A wide variety of pyrrolizidine alkaloids, such as monocrotaline, exert their cytotoxicity through the formation of DNA-DNA interstrand cross-links and DNA-protein cross-links. These pyrrolizidine alkaloids are oxidatively activated in vivo forming a highly reactive pyrrolic-type intermediate, which is responsible for the DNA cross-Linking reaction. The oxidative pathway of activation leads to undesired toxicity. Based on a previously reported photochemically triggered progenitor of monocrotaline, we describe here the semi-synthesis and DNA cross-linking of a dicarbamate analogue of the original phototriggered progenitor. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01341-7