tetraethyl [2-(phenylsulfanyl)ethane-1,1-diyl]bis(phosphonate)

• 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: tetraethyl [2-(phenylsulfanyl)ethane-1,1-diyl]bis(phosphonate)
• 英文别名: tetraethyl C-(thiophenyl)methyl methylenebisphosphonate；2,2-Bis(diethoxyphosphoryl)ethylsulfanylbenzene
• 化学式: C₁₆H₂₈O₆P₂S
• 分子量: 410.408
• InChiKey: PNPTZZLHNYXGNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tetraethyl [2-(phenylsulfanyl)ethane-1,1-diyl]bis(phosphonate) 在 水 作用下， 反应 22.0h， 生成 [2-(phenylsulfanyl)ethane-1,1-diyl]bis(phosphonic acid)
  参考文献：
  名称：

  Low toxicity and unprecedented anti-osteoclast activity of a simple sulfur-containing gem-bisphosphonate: A comparative study

  摘要：

  Bisphosphonates (BPs) are key drugs for the treatment of bone resorption diseases like osteoporosis, Paget's disease and some forms of tumors. Recent findings underlined the importance of lipophilic N-containing BPs to ensure high biological activity. Herein we present some unprecedented results concerning the low toxicity and good anti-osteoclast activity of low molecular weight hydrophilic S-containing BPs. A series of S and N-containing BPs bearing aromatic and aliphatic substitution were prepared through Michael addition reaction between vinylidenebisphosphonate tetraethyl ester and the proper nucleophile under basic catalysis. S-containing BPs showed a generally low toxicity, determined with the neutral-red assay using the L929 cell line, and, in particular for an aliphatic one, a good biological activity assessed on primary cultures of human osteoclasts. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.032
• 作为产物：
  描述：

  1,1-双(二乙氧基磷酰基)乙烯 、 苯硫酚 以 氯仿 为溶剂， 反应 24.0h， 以90%的产率得到tetraethyl [2-(phenylsulfanyl)ethane-1,1-diyl]bis(phosphonate)
  参考文献：
  名称：

  Michael addition reactions of ethenylidenebisphosphonates

  摘要：

  DOI：

  10.1016/0022-328x(88)80134-7

文献信息

• Michael addition reactions of ethenylidenebisphosphonates
  作者：David W. Hutchinson、David M. Thornton

  DOI：10.1016/0022-328x(88)80134-7

  日期：1988.6
• HUTCHINSON, DAVID W.;THORNTON, DAVID M., J. ORGANOMET. CHEM., 346,(1988) N 3, 341-348
  作者：HUTCHINSON, DAVID W.、THORNTON, DAVID M.

  DOI：——

  日期：——
• Low toxicity and unprecedented anti-osteoclast activity of a simple sulfur-containing gem-bisphosphonate: A comparative study
  作者：Donatella Granchi、Alessandro Scarso、Giulio Bianchini、Andrea Chiminazzo、Alberto Minto、Paolo Sgarbossa、Rino A. Michelin、Gemma Di Pompo、Sofia Avnet、Giorgio Strukul

  DOI：10.1016/j.ejmech.2013.04.032

  日期：2013.7

  Bisphosphonates (BPs) are key drugs for the treatment of bone resorption diseases like osteoporosis, Paget's disease and some forms of tumors. Recent findings underlined the importance of lipophilic N-containing BPs to ensure high biological activity. Herein we present some unprecedented results concerning the low toxicity and good anti-osteoclast activity of low molecular weight hydrophilic S-containing BPs. A series of S and N-containing BPs bearing aromatic and aliphatic substitution were prepared through Michael addition reaction between vinylidenebisphosphonate tetraethyl ester and the proper nucleophile under basic catalysis. S-containing BPs showed a generally low toxicity, determined with the neutral-red assay using the L929 cell line, and, in particular for an aliphatic one, a good biological activity assessed on primary cultures of human osteoclasts. (C) 2013 Elsevier Masson SAS. All rights reserved.