2-(N-octyl-imidazolium-1-yl)ethylidene-1,1-bisphosphonic acid | 1426824-34-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-(N-octyl-imidazolium-1-yl)ethylidene-1,1-bisphosphonic acid
• 英文别名: 2-(N-octylimidazolium-1-yl)ethylidene-1,1-bisphosphonic acid；hydrogen (2-(1-octyl-1H-imidazol-3-ium-3-yl)-1-phosphonoethyl)phosphonate；Hydron;[2-(3-octylimidazol-1-ium-1-yl)-1-phosphonatoethyl]phosphonic acid；hydron;[2-(3-octylimidazol-1-ium-1-yl)-1-phosphonatoethyl]phosphonic acid
• CAS: 1426824-34-1
• 化学式: C₁₃H₂₆N₂O₆P₂
• 分子量: 368.307
• InChiKey: APSZDONPODFPJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-溴辛烷 在 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 生成 2-(N-octyl-imidazolium-1-yl)ethylidene-1,1-bisphosphonic acid
  参考文献：
  名称：

  Chemo-Immunotherapeutic Antimalarials Targeting Isoprenoid Biosynthesis

  摘要：

  We synthesized 30 lipophilic bisphosphonates and tested them in malaria parasite killing (targeting parasite geranylgeranyl diphosphate synthase, GGPPS) and human gamma delta T cell activation (targeting human farnesyl diphosphate synthase, FPPS). Similar patterns of activity were seen in inhibiting human FPPS and Plasmodium GGPPS, with short to medium chain-length species having most activity. In cells, shorter chain-length species had low activity, due to poor membrane permeability, and longer chain length species were poor enzyme inhibitors. Optimal activity was thus seen with similar to C-10 side-chains, which have the best combination of enzyme inhibition and cell penetration. We also solved the crystal structure of one potent inhibitor, bound to FPPS. The results are of interest since they suggest the possibility of a combined chemo/immuno-therapeutic approach to antimalarial development in which both direct parasite killing and gamma delta T cell activation can be achieved with a single compound.

  DOI：

  10.1021/ml4000436

文献信息

• [EN] LIPOPHILIC BISPHOSPHONATES AND METHODS OF USE<br/>[FR] BISPHOSPHONATES LIPOPHILES ET PROCÉDÉS D'UTILISATION
  申请人：SALK INST FOR BIOLOGICAL STUDI

  公开号：WO2016081281A1

  公开（公告）日：2016-05-26

  Disclosed herein are lipophilic bisphosphonate compounds and embodiments of a method for making the same. The compounds may inhibit FPPS and/or GGPPS enzymes. The compounds are useful for treating a disease, such as cancer, such as those with a KRAS mutation. In some embodiments, the compounds are used to prevent or treat a cancer, such as a lung cancer that has a KRAS mutation.

  本文披露了疏水性双膦酸盐化合物及其制备方法的实施例。这些化合物可以抑制FPPS和/或GGPPS酶。这些化合物可用于治疗疾病，如癌症，尤其是具有KRAS突变的癌症。在某些实施例中，这些化合物被用于预防或治疗癌症，如具有KRAS突变的肺癌。