Tetraethyl 2-(pyrazol-1-yl)ethane-1,1-diphosphonate | 118054-60-7

• 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-(pyrazol-1-yl)ethane-1,1-diphosphonate
• 英文别名: 1-[2,2-bis(diethoxyphosphoryl)ethyl]pyrazole
• CAS: 118054-60-7
• 化学式: C₁₃H₂₆N₂O₆P₂
• 分子量: 368.307
• InChiKey: XMXDUMYXXYJAFS-UHFFFAOYSA-N

物化性质

• 沸点：
  475.4±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  88.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Tetraethyl 2-(pyrazol-1-yl)ethane-1,1-diphosphonate 在 盐酸 、 水 作用下， 反应 3.0h， 生成 2-(pyrazol-1-yl)ethane-1,1-diphosphonic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Novel Aminobisphosphonates Possessing an in Vivo Antitumor Activity Through a γδ-T Lymphocytes-Mediated Activation Mechanism

  摘要：

  A small series of aminobisphosphonates (N-BPs) structurally related to zoledronic acid was synthesized with the aim of improving activity toward activation of human gamma delta T cells and in turn their in vivo antitumor activity. The absence of the 1-OH moiety, together with the position and the different basicity of the nitrogen, appears crucial for antitumor activity. In comparison to zoledronic acid, compound 6a shows a greater ability to activate gamma delta T cells expression (100 times more) and a proapoptotic effect that is better than zoledronic acid. The potent activation of gamma delta T cells, in addition to evidence of the in vivo antitumor activity of 6a, suggests it may be a new potential drug candidate for cancer treatment.

  DOI：

  10.1021/jm801003y
• 作为产物：
  描述：

  吡唑 、 1,1-双(二乙氧基磷酰基)乙烯 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 Tetraethyl 2-(pyrazol-1-yl)ethane-1,1-diphosphonate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Novel Aminobisphosphonates Possessing an in Vivo Antitumor Activity Through a γδ-T Lymphocytes-Mediated Activation Mechanism

  摘要：

  A small series of aminobisphosphonates (N-BPs) structurally related to zoledronic acid was synthesized with the aim of improving activity toward activation of human gamma delta T cells and in turn their in vivo antitumor activity. The absence of the 1-OH moiety, together with the position and the different basicity of the nitrogen, appears crucial for antitumor activity. In comparison to zoledronic acid, compound 6a shows a greater ability to activate gamma delta T cells expression (100 times more) and a proapoptotic effect that is better than zoledronic acid. The potent activation of gamma delta T cells, in addition to evidence of the in vivo antitumor activity of 6a, suggests it may be a new potential drug candidate for cancer treatment.

  DOI：

  10.1021/jm801003y

文献信息

• Substituted alkanediphosphonic acids and pharmaceutical use
  申请人：Ciba-Geigy Corporation

  公开号：US04939130A1

  公开（公告）日：1990-07-03

  Alkanediphosphonic acids, in particular heteroarylalkanediphosphonic acids of formula ##STR1## wherein R.sub.1 is a 5-membered heteroaryl radical which may be fused with benzene or cyclohexene nuclei and which contains, as hetero atoms, 2 to 4 N-atoms or 1 or 2 N-atoms as well as 1 O- or S-atom, and which is unsubstituted or C-substituted by lower alkyl, phenyl or phenyl which is substituted by lower alkyl, lower alkoxy and/or halogen, or by lower alkoxy, hydroxy, di-lower alkylamino, lower alkylthio and/or halogen, and/or is N-substituted at a N-atom which is capable of substitution by lower alkyl, lower alkoxy and/or halogen, and R.sub.2 is hydrogen, hydroxy, amino, lower alkylthio or halogen, and salts thereof, have regulatory action on calcium metabolism and can be used as medicaments for the treatment of diseases associated with impairment of calcium metabolism. The compounds are obtained for example by converting, in a compound of formula ##STR2## wherein X.sub.1 is a functionally modified phosphono group and X.sub.2 is a free or functionally modified phosphono group, X.sub.1 and, if appropriate X.sub.2, into the free phosphono group.

  烷基二膦酸，特别是公式##STR1##中的杂环烷基二膦酸，其中R.sub.1是一个五元杂环基团，可以与苯或环己烯核融合，并且包含作为杂原子的2至4个N原子或1或2个N原子以及1个O或S原子，其未被取代或被低碳基，苯基或被低碳基，低烷氧基和/或卤素取代的苯基取代，或被低烷氧基，羟基，二低烷基氨基，低烷基硫基和/或卤素取代，和/或在可被低碳基，低烷氧基和/或卤素取代的N原子处被N取代，R.sub.2是氢，羟基，氨基，低烷基硫基或卤素，以及其盐，对钙代谢具有调节作用，可用作治疗与钙代谢障碍相关疾病的药物。例如，通过将公式##STR2##化合物中的X.sub.1为功能修饰的膦酸基团，将X.sub.1和如适当的X.sub.2转化为自由膦酸基团来获得化合物。
• US4939130A
  申请人：——

  公开号：US4939130A

  公开（公告）日：1990-07-03
• Design, Synthesis, and Biological Evaluation of Novel Aminobisphosphonates Possessing an in Vivo Antitumor Activity Through a γδ-T Lymphocytes-Mediated Activation Mechanism
  作者：Daniele Simoni、Nicola Gebbia、Francesco Paolo Invidiata、Marco Eleopra、Paolo Marchetti、Riccardo Rondanin、Riccardo Baruchello、Stefano Provera、Carla Marchioro、Manlio Tolomeo、Luciana Marinelli、Vittorio Limongelli、Ettore Novellino、Aaron Kwaasi、James Dunford、Simona Buccheri、Nadia Caccamo、Francesco Dieli

  DOI：10.1021/jm801003y

  日期：2008.11.13

  A small series of aminobisphosphonates (N-BPs) structurally related to zoledronic acid was synthesized with the aim of improving activity toward activation of human gamma delta T cells and in turn their in vivo antitumor activity. The absence of the 1-OH moiety, together with the position and the different basicity of the nitrogen, appears crucial for antitumor activity. In comparison to zoledronic acid, compound 6a shows a greater ability to activate gamma delta T cells expression (100 times more) and a proapoptotic effect that is better than zoledronic acid. The potent activation of gamma delta T cells, in addition to evidence of the in vivo antitumor activity of 6a, suggests it may be a new potential drug candidate for cancer treatment.