Hydroxy-[1-hydroxy-1-phosphono-3-(thian-1-ium-1-yl)propyl]phosphinate | 950816-99-6

• 英文名称: Hydroxy-[1-hydroxy-1-phosphono-3-(thian-1-ium-1-yl)propyl]phosphinate
• CAS: 950816-99-6
• 化学式: C₈H₁₈O₇P₂S
• 分子量: 320.24
• InChiKey: UUOLPSVCVQFXEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(Thian-1-ium-1-yl)propanoic acid;chloride 在 磷酸 、 吡啶盐酸盐 、 三氯化磷 作用下， 反应 4.0h， 以560 mg的产率得到Hydroxy-[1-hydroxy-1-phosphono-3-(thian-1-ium-1-yl)propyl]phosphinate
  参考文献：
  名称：

  Activity of Sulfonium Bisphosphonates on Tumor Cell Lines

  摘要：

  We investigated three series of sulfonium bisphosphonates for their activity in inhibiting the growth of three human tumor cell lines. The first series consisted of 6 cyclic sulfonium bisphosphonates, the most active species having an (average) IC50 of 89,mu M. The second consisted of 10 phenylalkyl and phenylalkoxy bisphosphonates, the most active species having an IC50 of 18,mu M. The third series consisted of 17 n-alkyl sulfonium bisphosphonates, the most active species having an IC50 of similar to 240 nM. Three QSAR models showed that the experimental cell growth inhibition results could be well predicted. We also determined the structures of one sulfonium bisphosphonate bound to farnesyl diphosphate synthase, finding that it binds exclusively to the dimethylallyl diphosphate binding site. These results are of interest since they show that sulfonium bisphosphonates can have potent activity against a variety of tumor cell lines, the most active species having IC50 values much lower than conventional nitrogen-containing bisphosphonates.

  DOI：

  10.1021/jm700991k