(E)-3-Methoxyacetoxy-4-[(4'-methoxyphenyl)methylidene]cyclodeca-1,5-diyne | 426207-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3-Methoxyacetoxy-4-[(4'-methoxyphenyl)methylidene]cyclodeca-1,5-diyne
• 英文别名: [(10E)-10-[(4-methoxyphenyl)methylidene]cyclodeca-2,8-diyn-1-yl] 2-methoxyacetate
• CAS: 426207-05-8
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: JJOBVKCOVCAHTP-OBGWFSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-Methoxyacetoxy-4-[(4'-methoxyphenyl)methylidene]cyclodeca-1,5-diyne 在 silica gel 作用下， 以8.8 mg的产率得到3-[1'-hydroxy-1'-(4''-methoxyphenyl)methyl]cyclodeca-3-en-1,5-diyne
  参考文献：
  名称：

  DNA Cleavage Potency, Cytotoxicity, and Mechanism of Action of a Novel Class of Enediyne Prodrugs

  摘要：

  We have discovered a novel class of (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes which exhibit promising enediyne-like DNA cleavage and cytotoxic activities. LC-MS analysis of the incubation mixture (pH 8.5, 37 degreesC) confirmed formation of 10-membered ring enediyne presumably via an allylic cation and suggested that the 1,4-benzenoid diradical might be one of the active species for DNA damage and cytotoxicity.

  DOI：

  10.1021/jm015588e
• 作为产物：
  描述：

  (E)-10-Iodo-2-[(4'-methoxyphenyl)methylidene]deca-3,9-diynal 在 chromium dichloride 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 nickel dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (E)-3-Methoxyacetoxy-4-[(4'-methoxyphenyl)methylidene]cyclodeca-1,5-diyne
  参考文献：
  名称：

  DNA Cleavage Potency, Cytotoxicity, and Mechanism of Action of a Novel Class of Enediyne Prodrugs

  摘要：

  We have discovered a novel class of (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes which exhibit promising enediyne-like DNA cleavage and cytotoxic activities. LC-MS analysis of the incubation mixture (pH 8.5, 37 degreesC) confirmed formation of 10-membered ring enediyne presumably via an allylic cation and suggested that the 1,4-benzenoid diradical might be one of the active species for DNA damage and cytotoxicity.

  DOI：

  10.1021/jm015588e

文献信息

• US6391916B1
  申请人：——

  公开号：US6391916B1

  公开（公告）日：2002-05-21