7-benzyl-2-methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one | 1392817-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 7-benzyl-2-methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one
• 英文别名: 7-benzyl-2-methyl-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
• CAS: 1392817-32-1
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: PDPGNUOKMIKYTF-UHFFFAOYSA-N

物化性质

• 沸点：
  451.2±47.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-benzyl-2-methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one 在 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 6.0h， 生成 7-benzyl-N-(4-methoxyphenyl)-N,2-dimethyl-5H-pyrrolo[3,2-d]pyrimidin-4-amine
  参考文献：
  名称：

  Discovery of Antitubulin Agents with Antiangiogenic Activity as Single Entities with Multitarget Chemotherapy Potential

  摘要：

  Antiangiogenic agents (AA) are cytostatic, and their utility in cancer chemotherapy lies in their combination with cytotoxic chemotherapeutic agents. Clinical combinations of vascular endothelial growth factor receptor-2 (VEGFR2) inhibitors with antitubulin agents have been particularly successful. We have discovered a novel, potentially important analogue, that combines potent VEGFR2 inhibitory activity (comparable to that of sunitinib) with potent antitubulin activity (comparable to that of combretastatin A-4 (CA)) in a single molecule, with GI(50) values of 10(-7) M across the entire NCI 60 tumor cell panel. It potently inhibited tubulin assembly and circumvented the most clinically relevant tumor resistance mechanisms (P-glycoprotein and beta-III tubulin expression) to antimicrotubule agents. The compound is freely water-soluble as its HCl salt and afforded excellent antitumor activity in vivo, superior to docetaxel, sunitinib, or Temozolomide, without any toxicity.

  DOI：

  10.1021/ml4004793
• 作为产物：
  描述：

  苯甲醛 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 25.5h， 生成 7-benzyl-2-methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one
  参考文献：
  名称：

  Substituted Bicyclic Pyrimidine Compounds with Tubulin and Multiple Receptor Inhibition

  摘要：

  这项发明提供了替代的双环嘧啶化合物及其药用盐、水合物和溶剂合物，每种化合物具有微管和多重受体抑制特性。公开了治疗诊断为癌症的患者的方法，包括向患者投予治疗有效量的替代的双环嘧啶化合物和其药用盐、水合物和溶剂合物，用于治疗癌症。

  公开号：

  US20150284398A1

文献信息

• Substituted bicyclic pyrimidine compounds with tubulin and multiple receptor inhibition
  申请人：Duquesne University of the Holy Spirit

  公开号：US10358450B2

  公开（公告）日：2019-07-23

  This invention provides substituted bicyclic pyrimidine compounds and pharmaceutically acceptable salts, hydrates, and solvates of the compounds, each having tubulin and multiple receptor inhibition properties. Methods of treating a patient diagnosed with cancer is disclosed comprising administering to the patient a therapeutically effective amount of the substituted bicyclic pyrimidine compounds and pharmaceutically acceptable salts, hydrates, and solvates of the compounds, for treating cancer.

  本发明提供了取代的双环嘧啶化合物和这些化合物的药学上可接受的盐、水合物和溶液，每种化合物都具有抑制小管蛋白和多种受体的特性。本发明公开了治疗被诊断患有癌症的患者的方法，包括向患者施用治疗有效量的取代双环嘧啶化合物和该化合物的药学上可接受的盐、水合物和溶液来治疗癌症。
• BICYCLIC AND TRICYCLIC PYRIMIDINE TYROSINE KINASE INHIBITORS WITH ANTITUBULIN ACTIVITY AND METHODS OF TREATING A PATIENT
  申请人：Duquesne University of The Holy Spirit

  公开号：EP2670244B1

  公开（公告）日：2018-04-11
• SUBSTITUTED BICYCLIC PYRIMIDINE COMPOUNDS WITH TUBULIN AND MULTIPLE RECEPTOR INHIBITION
  申请人：Duquesne University of the Holy Spirit

  公开号：EP3125899A1

  公开（公告）日：2017-02-08
• US9732090B2
  申请人：——

  公开号：US9732090B2

  公开（公告）日：2017-08-15
• [EN] SUBSTITUTED BICYCLIC PYRIMIDINE COMPOUNDS WITH TUBULIN AND MULTIPLE RECEPTOR INHIBITION<br/>[FR] COMPOSÉS DE PYRIMIDINE BICYCLIQUES SUBSTITUÉS PAR DE LA TUBULINE ET INHIBITION DE MULTIPLES RÉCEPTEURS
  申请人：UNIV HOLY GHOST DUQUESNE

  公开号：WO2015153955A1

  公开（公告）日：2015-10-08

  This invention provides substituted bicyclic pyrimidine compounds and pharmaceutically acceptable salts, hydrates, and solvates of the compounds, each having tubulin and multiple receptor inhibition properties. Methods of treating a patient diagnosed with cancer is disclosed comprising administering to the patient a therapeutically effective amount of the substituted bicyclic pyrimidine compounds and pharmaceutically acceptable salts, hydrates, and solvates of the compounds, for treating cancer.