[2-(purin-9-yl)ethylidene]bisphosphonic acid | 1075726-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: [2-(purin-9-yl)ethylidene]bisphosphonic acid
• 英文别名: [2-(Purin-9-yl)ethyl]-bisphosphonic acid；(1-phosphono-2-purin-9-ylethyl)phosphonic acid
• CAS: 1075726-48-5
• 化学式: C₇H₁₀N₄O₆P₂
• 分子量: 308.127
• InChiKey: JGHPTTVGCUEGGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,1-双(二乙氧基磷酰基)乙烯 、 嘌呤 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 [2-(purin-9-yl)ethylidene]bisphosphonic acid 、 [2-(purin-7-yl)ethylidene]bisphosphonic 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

文献信息

• [EN] GEMINAL BISPHOSPHONATES, THEIR PREPARATION AND THEIR USE IN THE FIELD OF ONCOLOGY<br/>[FR] BISPHOSPHONATES GÉMINAUX, LEUR PRÉPARATION ET LEUR UTILISATION DANS LE DOMAINE DE L'ONCOLOGIE
  申请人：TETRAPHARM S R L

  公开号：WO2009056952A1

  公开（公告）日：2009-05-07

  The object of the present invention are bisphosphonic geminal compounds, structurally relatable to zoledronic acid, a method for their preparation, their pharmaceutical composition and their use in oncology for the treatment of tumoral pathologies

  本发明的对象是双膦酸基化合物，结构上类似于左氧磷酸，以及它们的制备方法、药物组合物和它们在肿瘤学中用于治疗肿瘤病理的用途。
• 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.