(E,E)-diethyl 1-(diethyl phosphonomethoxy)-5,9,13-trimethyl-4,8,12-tetradecatrienylphosphonate | 221379-95-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E,E)-diethyl 1-(diethyl phosphonomethoxy)-5,9,13-trimethyl-4,8,12-tetradecatrienylphosphonate
• CAS: 221379-95-9
• 化学式: C₂₆H₅₀O₇P₂
• 分子量: 536.626
• InChiKey: VJYJFFMJQDZHQI-OQAQWEHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.02
• 重原子数：
  35.0
• 可旋转键数：
  21.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (E,E)-diethyl 1-(diethyl phosphonomethoxy)-5,9,13-trimethyl-4,8,12-tetradecatrienylphosphonate 在 吡啶 、 2,4,6-三甲基吡啶 、 甲醇 、 三正丁胺 、 三甲基溴硅烷 、 N,N'-二环己基碳二亚胺 作用下， 生成 cyclic (E,E)-1-(hydroxyphosphonylmethoxy)-5,9,13-trimethyl-4,8,12-tetradecatrienylphosphonic anhydride, dipotassium salt
  参考文献：
  名称：

  Inhibitors of Protein:Farnesyl Transferase and Protein:Geranylgeranyl Transferase I: Synthesis of Homologous Diphosphonate Analogs of Isoprenylated Pyrophosphate

  摘要：

  Novel diphosphonate homologs 7a-7c, and their cyclic counterparts 8a-8c, of the previously synthesized farnesyl pyrophosphate analogs 1 and 2 were prepared and tested for their inhibition potency and specificity of the enzymes PFT and PGGT-I. Compound 2 was shown to be the most potent inhibitor of PFT (IC50 = 0.58 +/- 0.45 mu M) in this series. The novel compound 7a, the one carbon homolog of 2, proved to be the most potent inhibitor of PGGT-I (IC50 = 0.98 +/- 0.01 mu M). The cyclic analogs 8a-8c are generally less biologically active. The compounds 2 and 7a are nonspecific toward inhibition of PFT and PGGT-I: and may inhibit both farnesylation and geranylgeranylation processing of oncogenic proteins. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1101
• 作为产物：
  描述：

  反,反-氯化法呢酯 在 正丁基锂 、 草酰氯 、 甲基氯化镁 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 24.58h， 生成 (E,E)-diethyl 1-(diethyl phosphonomethoxy)-5,9,13-trimethyl-4,8,12-tetradecatrienylphosphonate
  参考文献：
  名称：

  Inhibitors of Protein:Farnesyl Transferase and Protein:Geranylgeranyl Transferase I: Synthesis of Homologous Diphosphonate Analogs of Isoprenylated Pyrophosphate

  摘要：

  Novel diphosphonate homologs 7a-7c, and their cyclic counterparts 8a-8c, of the previously synthesized farnesyl pyrophosphate analogs 1 and 2 were prepared and tested for their inhibition potency and specificity of the enzymes PFT and PGGT-I. Compound 2 was shown to be the most potent inhibitor of PFT (IC50 = 0.58 +/- 0.45 mu M) in this series. The novel compound 7a, the one carbon homolog of 2, proved to be the most potent inhibitor of PGGT-I (IC50 = 0.98 +/- 0.01 mu M). The cyclic analogs 8a-8c are generally less biologically active. The compounds 2 and 7a are nonspecific toward inhibition of PFT and PGGT-I: and may inhibit both farnesylation and geranylgeranylation processing of oncogenic proteins. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1101