Pentanoic acid 6,6'-diisopropyl-8,8'-dimethyl-5,4',5'-tris-pentanoyloxy-[9,9']bi[naphtho[1,8-de][1,2]oxazinyl]-4-yl ester | 103068-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Pentanoic acid 6,6'-diisopropyl-8,8'-dimethyl-5,4',5'-tris-pentanoyloxy-[9,9']bi[naphtho[1,8-de][1,2]oxazinyl]-4-yl ester
• CAS: 103068-46-8
• 化学式: C₅₀H₆₀N₂O₁₀
• 分子量: 849.034
• InChiKey: BUNDVXRIHQABAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.36
• 重原子数：
  62.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  148.38
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Pentanoic acid 6,6'-diisopropyl-8,8'-dimethyl-5,4',5'-tris-pentanoyloxy-[9,9']bi[naphtho[1,8-de][1,2]oxazinyl]-4-yl ester 在 戊酸酐 、 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 gossylic nitrile 1,1'-dipentanoate
  参考文献：
  名称：

  Biologically active derivatives of gossypol: synthesis and antimalarial activities of peri-acylated gossylic nitriles

  摘要：

  A series of peri-acylated gossylic nitriles were synthesized from gossypol dioxime by treatment of the dioxime with the appropriate acid anhydride and its salt. The reaction pathway was elucidated by isolation and characterization of intermediates. Peri-acylated gossylic nitriles (acyl = acetyl, propionyl, butyryl, and valeryl) were compared with gossypol for activity against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum. The gossylic nitriles all retain activity, with activity increasing with the length of the peri-acyl group. Gossylic nitrile 1,1'-divalerate shows antimalarial activity comparable to gossypol itself. The peri-acylated gossylic nitriles are strong inhibitors of parasite lactate dehydrogenase.

  DOI：

  10.1021/jm00159a043
• 作为产物：
  描述：

  gossypol dioxime 在 戊酸酐 作用下， 反应 7.0h， 生成 Pentanoic acid 6,6'-diisopropyl-8,8'-dimethyl-5,4',5'-tris-pentanoyloxy-[9,9']bi[naphtho[1,8-de][1,2]oxazinyl]-4-yl ester
  参考文献：
  名称：

  Biologically active derivatives of gossypol: synthesis and antimalarial activities of peri-acylated gossylic nitriles

  摘要：

  A series of peri-acylated gossylic nitriles were synthesized from gossypol dioxime by treatment of the dioxime with the appropriate acid anhydride and its salt. The reaction pathway was elucidated by isolation and characterization of intermediates. Peri-acylated gossylic nitriles (acyl = acetyl, propionyl, butyryl, and valeryl) were compared with gossypol for activity against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum. The gossylic nitriles all retain activity, with activity increasing with the length of the peri-acyl group. Gossylic nitrile 1,1'-divalerate shows antimalarial activity comparable to gossypol itself. The peri-acylated gossylic nitriles are strong inhibitors of parasite lactate dehydrogenase.

  DOI：

  10.1021/jm00159a043