methyl 3-[2-(3-benzyloxycarbonylaminopropoxy)-3,5-dichlorophenyl]-2-(4-methoxybenzyloxyimino)propanoate | 882687-33-4

• 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: methyl 3-[2-(3-benzyloxycarbonylaminopropoxy)-3,5-dichlorophenyl]-2-(4-methoxybenzyloxyimino)propanoate
• 英文别名: methyl 3-[3,5-dichloro-2-[3-(phenylmethoxycarbonylamino)propoxy]phenyl]-2-[(4-methoxyphenyl)methoxyimino]propanoate
• CAS: 882687-33-4
• 化学式: C₂₉H₃₀Cl₂N₂O₇
• 分子量: 589.472
• InChiKey: OFRKTVZMWNDYHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  104.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 3-[2-(3-benzyloxycarbonylaminopropoxy)-3,5-dichlorophenyl]-2-(4-methoxybenzyloxyimino)propanoate 在 4-二甲氨基吡啶 、 lithium hydroxide 、 三氯化铝 、 苯甲醚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 硝基甲烷 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 3-[2-(3-aminopropoxy)-3,5-dichlorophenyl]-N-[2-(4-chlorophenyl)ethyl]-2-hydroxyiminopropanamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Purealin and Analogues as Cytoplasmic Dynein Heavy Chain Inhibitors

  摘要：

  Cytoplasmic dynein plays important roles in membrane transport, mitosis, and other cellular processes. A few small-molecule inhibitors of cytoplasmic dynein have been identified. We report here the first synthesis of purealin, a natural product isolated from the sea sponge Psammaplysilla purea, which is known to inhibit axonemal dynein. Also described are the first syntheses, by modular amide coupling reactions, of the natural product purealidin A (a component of purealin) and a small library of analogues. The library was examined for inhibition of cytoplasmic dynein heavy chain and cell growth. The compounds showed effective antiproliferative activity against a mouse leukemia cell line but selective activities against human carcinoma cell lines. Purealin and some of the analogues inhibited the microtubule-stimulated ATPase activity of recombinant cytoplasmic dynein heavy chain motor domain. The inhibitory effect of purealin was concentration dependent and uncompetitive, supporting the hypothesis that it does not compete with the binding of ATP.

  DOI：

  10.1021/jm051030l
• 作为产物：
  描述：

  3,5-二氯水杨醛 在 barium dihydroxide 、 sodium acetate 、 乙酸酐 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.67h， 生成 methyl 3-[2-(3-benzyloxycarbonylaminopropoxy)-3,5-dichlorophenyl]-2-(4-methoxybenzyloxyimino)propanoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Purealin and Analogues as Cytoplasmic Dynein Heavy Chain Inhibitors

  摘要：

  Cytoplasmic dynein plays important roles in membrane transport, mitosis, and other cellular processes. A few small-molecule inhibitors of cytoplasmic dynein have been identified. We report here the first synthesis of purealin, a natural product isolated from the sea sponge Psammaplysilla purea, which is known to inhibit axonemal dynein. Also described are the first syntheses, by modular amide coupling reactions, of the natural product purealidin A (a component of purealin) and a small library of analogues. The library was examined for inhibition of cytoplasmic dynein heavy chain and cell growth. The compounds showed effective antiproliferative activity against a mouse leukemia cell line but selective activities against human carcinoma cell lines. Purealin and some of the analogues inhibited the microtubule-stimulated ATPase activity of recombinant cytoplasmic dynein heavy chain motor domain. The inhibitory effect of purealin was concentration dependent and uncompetitive, supporting the hypothesis that it does not compete with the binding of ATP.

  DOI：

  10.1021/jm051030l