octamethyl 1,6-dihydroxyhexan-1,1,6,6-tetrakisphosphonate | 123746-93-0

• 英文名称: octamethyl 1,6-dihydroxyhexan-1,1,6,6-tetrakisphosphonate
• 英文别名: 1,1,6,6-tetrakis(dimethoxyphosphoryl)hexane-1,6-diol
• CAS: 123746-93-0
• 化学式: C₁₄H₃₄O₁₄P₄
• 分子量: 550.311
• InChiKey: KOLXAYSYPKJGMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  32.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  182.58
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  octamethyl 1,6-dihydroxyhexan-1,1,6,6-tetrakisphosphonate 在 盐酸 作用下， 反应 75.0h， 以50%的产率得到1,6-bishydroxyhexylidene-1,1,6,6-tetraphosphonic acid
  参考文献：
  名称：

  SYNTHÈSE ET ÉTUDE STRUCTURALE D′ACIDES DIHYDROXYTÉTRAPHOSPHONIQUES ET DE SELS DE CES ACIDES. 1: SEL DE CUIVRE DE L′ACIDE 1,6-DIHYDROXYHEXYLIDENE-1,1,6,6-TÉTRAPHOSPHONIQUE (DHHTP)

  摘要：

  The synthesis of 1,6-bishydroxyhexylidene-1,1,6,6-tetraphosphonic acid (DHHTP, 5) and its copper complex is described. The structure of the copper complex has been determined by X-ray analysis.

  DOI：

  10.1080/10426509608046423
• 作为产物：
  描述：

  亚磷酸氢二甲酯 、 Tetramethyl adipoylbisphosphonate 生成 octamethyl 1,6-dihydroxyhexan-1,1,6,6-tetrakisphosphonate
  参考文献：
  名称：

  SYNTHÈSE ET ÉTUDE STRUCTURALE D′ACIDES DIHYDROXYTÉTRAPHOSPHONIQUES ET DE SELS DE CES ACIDES. 1: SEL DE CUIVRE DE L′ACIDE 1,6-DIHYDROXYHEXYLIDENE-1,1,6,6-TÉTRAPHOSPHONIQUE (DHHTP)

  摘要：

  The synthesis of 1,6-bishydroxyhexylidene-1,1,6,6-tetraphosphonic acid (DHHTP, 5) and its copper complex is described. The structure of the copper complex has been determined by X-ray analysis.

  DOI：

  10.1080/10426509608046423

文献信息

• Kanaan, Marwan; Burgada, Ramon, Phosphorus and Sulfur and the Related Elements, 1988, vol. 37, p. 217 - 230
  作者：Kanaan, Marwan、Burgada, Ramon

  DOI：——

  日期：——
• In Vitro and In Vivo Effects of Tetrakisphosphonates on Bone Resorption, Tumor Osteolysis, Ectopic Calcification, and Macrophages
  作者：Joel M. Van Gelder、Eli Breuer、Ada Schlossman、Asher Ornoy、Jukka Mönkkönen、Johanna Similä、Thomas Klenner、Heidi Stadler、Burkhard Krempien、N. Patlas、Gershon Golomb

  DOI：10.1021/js960429h

  日期：1997.3

  The biological effects of bisphosphonates in calcium-related disorders are attributed to the incorporation of the bisphosphonates in bone, enabling direct interaction with osteoclasts and/or osteoblasts. The high accumulation of bisphosphonates in bone, due to their high affinity to hydroxyapatite (HAP), is essential for mediating in vitro and in vivo activity. In this study we examined the activity of tetrakisphosphonates, molecules containing two P-C-P type bisphosphonate moieties connected by a carbon chain. The novel compounds were examined in a battery of in vitro and in vivo models including HAP formation and dissolution, ectopic calcification, bone resorption, tumor osteolysis, and of macrophage-like cells (anti- or pro-inflammatory properties). The inhibition of ectopic calcification was ranked as follows: geminal bisphosphonates > bisacylphosphonates > tetrakisphosphonates. Pamidronate, but not the tetrakisphosphonates, was an effective antiosteolytic agent. Neither DNTP (tetrasodium 1,9-dihydroxynonane,1,1,9,9-tetrakisphosphonate) nor the bisacylphosphonate, PiBP (pimeloylbisphosphonate) seem to possess strong macrophage suppressive or inductive effects and can be considered to be relatively inactive in terms of anti- or pro-inflammatory action. A significant anticalcification effect was caused by various phosphonates, such as the tetrakisphosphonates, but DNTP, a tetrakisphosphonate, was found toxic as it impeded somatic growth and bone development.