N-(prop-2-yn-1-yl)thieno[3,2-d]pyrimidin-4-amine

• 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: N-(prop-2-yn-1-yl)thieno[3,2-d]pyrimidin-4-amine
• 英文别名: N-prop-2-ynylthieno[3,2-d]pyrimidin-4-amine
• 化学式: C₉H₇N₃S
• mdl: MFCD16661765
• 分子量: 189.241
• InChiKey: BJYHHZZXKZGYOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(5-azido-2-hydroxybenzamido)benzoate 、 N-(prop-2-yn-1-yl)thieno[3,2-d]pyrimidin-4-amine 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以62%的产率得到methyl 3-[2-hydroxy-5-(4-(thieno[3,2-d]pyrimidin-4-ylamino)methyl-1H-1,2,3-triazol-1-yl)benzamido]benzoate
  参考文献：
  名称：

  신규한 트리아졸 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 오로라 키나제 관련 약학적 조성물

  摘要：

  本发明涉及一种新的三唑衍生物，其制备方法及其作为有效成分包含在含有Aurora激酶相关药物的制剂中，根据本发明的新三唑衍生物，其光学异构体或其药学上可接受的盐，通过Aurora激酶表现出优异的纳摩尔单位的抑制活性，并且作为含有该化合物的药学制剂在治疗各种癌症或肿瘤方面具有有益效果。

  公开号：

  KR101723881B1
• 作为产物：
  描述：

  4-氯噻吩并[3,2-d]嘧啶 、 炔丙胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以59%的产率得到N-(prop-2-yn-1-yl)thieno[3,2-d]pyrimidin-4-amine
  参考文献：
  名称：

  Design, synthesis, and evaluation of hinge-binder tethered 1,2,3-triazolylsalicylamide derivatives as Aurora kinase inhibitors

  摘要：

  A series of hinge-binder tethered 1,2,3-triazolylsalicylamide derivatives were designed, synthesized, and evaluated for the Aurora kinase inhibitory activities. The novel hinge-binder tethered 1,2,3-triazolylsalicylamide scaffold was effectively assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC). A variety of alkynes with hinge binders were used to search proper structures-binding relationship to the hinge region. The synthesized 1,2,3-triazolylsalicylamide derivatives showed significant Aurora kinase inhibitory activity. In particular, 8a inhibited Aurora A kinase with an IC50 value of 0.284 mu M, whereas 8m inhibited Aurora B kinase with an IC50 value of 0.364 mu M. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.042

文献信息

• 신규한 트리아졸 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 오로라 키나제 관련 약학적 조성물
  申请人：Ewha University - Industry Collaboration Foundation 이화여자대학교 산학협력단(220040083301) BRN ▼110-82-10456

  公开号：KR101723881B1

  公开（公告）日：2017-04-07

  본 발명은 신규한 트리아졸 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 오로라 키나제 관련 약학적 조성물에 관한 것으로, 본 발명에 따른 신규한 트리아졸 유도체, 이의 광학 이성질체, 또는 이의 약학적으로 허용 가능한 염은, 오로라 키나제로써 나노몰 단위의 우수한 저해활성을 나타내며, 이를 함유하는 약학적 조성물로써 다양한 암 또는 종양의 치료에 유용한 효과가 있다.

  本发明涉及一种新的三唑衍生物，其制备方法及其作为有效成分包含在含有Aurora激酶相关药物的制剂中，根据本发明的新三唑衍生物，其光学异构体或其药学上可接受的盐，通过Aurora激酶表现出优异的纳摩尔单位的抑制活性，并且作为含有该化合物的药学制剂在治疗各种癌症或肿瘤方面具有有益效果。
• Design, synthesis, and evaluation of hinge-binder tethered 1,2,3-triazolylsalicylamide derivatives as Aurora kinase inhibitors
  作者：Yunkyung Jeong、Jooyeon Lee、Jae-Sang Ryu

  DOI：10.1016/j.bmc.2016.03.042

  日期：2016.5

  A series of hinge-binder tethered 1,2,3-triazolylsalicylamide derivatives were designed, synthesized, and evaluated for the Aurora kinase inhibitory activities. The novel hinge-binder tethered 1,2,3-triazolylsalicylamide scaffold was effectively assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC). A variety of alkynes with hinge binders were used to search proper structures-binding relationship to the hinge region. The synthesized 1,2,3-triazolylsalicylamide derivatives showed significant Aurora kinase inhibitory activity. In particular, 8a inhibited Aurora A kinase with an IC50 value of 0.284 mu M, whereas 8m inhibited Aurora B kinase with an IC50 value of 0.364 mu M. (C) 2016 Elsevier Ltd. All rights reserved.