3-benzyl-2-(1-bromopropyl)thieno[2,3-e]pyrimidin-4-one | 545379-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 3-benzyl-2-(1-bromopropyl)thieno[2,3-e]pyrimidin-4-one
• 英文别名: 3-Benzyl-2-(1-bromopropyl)thieno[3,2-d]pyrimidin-4(3H)-one；3-benzyl-2-(1-bromopropyl)thieno[3,2-d]pyrimidin-4-one
• CAS: 545379-50-8
• 化学式: C₁₆H₁₅BrN₂OS
• 分子量: 363.278
• InChiKey: BPISEDFZNPHCTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyl-2-(1-bromopropyl)thieno[2,3-e]pyrimidin-4-one 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 methyl 4-[1-(3-benzyl-4-oxothieno[3,2-d]pyrimidin-2-yl)propyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]carbamoyl]benzoate
  参考文献：
  名称：

  Discovery of (+)-N-(3-Aminopropyl)-N-[1-(5-benzyl-3-methyl-4-oxo-[1,2]thiazolo[5,4-d]pyrimidin-6-yl)-2-methylpropyl]-4-methylbenzamide (AZD4877), a Kinesin Spindle Protein Inhibitor and Potential Anticancer Agent

  摘要：

  Structure activity relationship analysis identified (+)-N-(3-aminopropyl)-N-[1-(5-benzyl-3-methyl-4-oxo-[1,2]thiazolo[5,4-d]pyrimidin-6-yl)-2-methylpropyl]-4-methylbenzamide (AZD4877), from a series of novel kinesin spindle protein (KSP) inhibitors, as exhibiting both excellent biochemical potency and pharmaceutical properties suitable for clinical development. The selected compound arrested cells in mitosis leading to the formation of the monopolar spindle phenotype characteristic of KSP inhibition and induction of cellular death. A favorable pharmacokinetic profile and notable in vivo efficacy supported the selection of this compound as a clinical candidate for the treatment of cancer.

  DOI：

  10.1021/jm200629m
• 作为产物：
  描述：

  methyl 3-butyramidothiophene-2-carboxylate 在 ammonium hydroxide 、 溴 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 3-benzyl-2-(1-bromopropyl)thieno[2,3-e]pyrimidin-4-one
  参考文献：
  名称：

  Discovery of (+)-N-(3-Aminopropyl)-N-[1-(5-benzyl-3-methyl-4-oxo-[1,2]thiazolo[5,4-d]pyrimidin-6-yl)-2-methylpropyl]-4-methylbenzamide (AZD4877), a Kinesin Spindle Protein Inhibitor and Potential Anticancer Agent

  摘要：

  Structure activity relationship analysis identified (+)-N-(3-aminopropyl)-N-[1-(5-benzyl-3-methyl-4-oxo-[1,2]thiazolo[5,4-d]pyrimidin-6-yl)-2-methylpropyl]-4-methylbenzamide (AZD4877), from a series of novel kinesin spindle protein (KSP) inhibitors, as exhibiting both excellent biochemical potency and pharmaceutical properties suitable for clinical development. The selected compound arrested cells in mitosis leading to the formation of the monopolar spindle phenotype characteristic of KSP inhibition and induction of cellular death. A favorable pharmacokinetic profile and notable in vivo efficacy supported the selection of this compound as a clinical candidate for the treatment of cancer.

  DOI：

  10.1021/jm200629m

文献信息

• Mitotic kinesin inhibitors
  申请人：Fraley E Mark

  公开号：US20050228003A1

  公开（公告）日：2005-10-13

  The present invention relates to thienopyrimidinone compounds that are useful for treating cellular proliferative diseases, for treating disorders associated with KSP kinesin activity, and for inhibiting KSP kinesin. The invention also related to compositions which comprise these compounds, and methods of using them to treat cancer in mammals.

  本发明涉及一种对细胞增殖性疾病有用的噻唑嘧啶酮化合物，用于治疗与KSP动力蛋白活性相关的疾病，并抑制KSP动力蛋白。本发明还涉及包含这些化合物的组合物以及使用它们治疗哺乳动物癌症的方法。
• Substituted thienopyrimidinones as a mitotic kinesin inhibitor
  申请人：Merck & Co., Inc.

  公开号：US07378411B2

  公开（公告）日：2008-05-27

  The present invention relates to thienopyrimidinone compounds that are useful for treating cellular proliferative diseases, for treating disorders associated with KSP kinesin activity, and for inhibiting KSP kinesin. The invention also related to compositions which comprise these compounds, and methods of using them to treat cancer in mammals.

  本发明涉及一种对细胞增殖性疾病有用的噻吩嘧啶酮化合物，用于治疗与KSP肌动蛋白活性相关的疾病，并用于抑制KSP肌动蛋白。该发明还涉及包含这些化合物的组合物，以及使用它们治疗哺乳动物癌症的方法。
• MITOTIC KINESIN INHIBITORS
  申请人：Merck & Co., Inc.

  公开号：EP1463733A2

  公开（公告）日：2004-10-06
• EP1463733A4
  申请人：——

  公开号：EP1463733A4

  公开（公告）日：2006-01-11
• US7378411B2
  申请人：——

  公开号：US7378411B2

  公开（公告）日：2008-05-27