N-(2-Methoxyphenyl)thieno[3,2-d]pyrimidin-4-amine | 935843-07-5

• 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-(2-Methoxyphenyl)thieno[3,2-d]pyrimidin-4-amine
• CAS: 935843-07-5
• 化学式: C₁₃H₁₁N₃OS
• 分子量: 257.316
• InChiKey: YGBVIUZGGNSJJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-Methoxyphenyl)thieno[3,2-d]pyrimidin-4-amine 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-methoxyphenyl)-N-methylthieno[3,2-d]pyrimidin-4-amine
  参考文献：
  名称：

  Discovery of 4-anilino-N-methylthieno[3,2-d]pyrimidines and 4-anilino-N-methylthieno[2,3-d]pyrimidines as potent apoptosis inducers

  摘要：

  We report the discovery of N-((benzo[d][1,3]dioxol-5-yl)methyl)-6-phenylthieno[3,2-d] pyrimidin-4-amine (2a) as an apoptosis inducer using our proprietary cell-and caspase-based ASAP HTS assay, and SAR study of HTS hit 2a which led to the discovery of 4-anilino-N-methylthieno[3,2-d] pyrimidines and 4-anilino-N-methylthieno[2,3-d] pyrimidines as potent apoptosis inducers. Compounds 5d and 5e were the most potent with EC50 values of 0.008 and 0.004 mu M in T47D human breast cancer cells, respectively. Compound 5d was found to be highly active in the MX-1 breast cancer model. Functionally, compounds 5d and 5e both induced apoptosis through inhibition of tubulin polymerization. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.145
• 作为产物：
  描述：

  邻甲氧基苯胺 、 4-氯噻吩并[3,2-d]嘧啶 在 盐酸 作用下， 以 异丙醇 为溶剂， 生成 N-(2-Methoxyphenyl)thieno[3,2-d]pyrimidin-4-amine
  参考文献：
  名称：

  Discovery of 4-anilino-N-methylthieno[3,2-d]pyrimidines and 4-anilino-N-methylthieno[2,3-d]pyrimidines as potent apoptosis inducers

  摘要：

  We report the discovery of N-((benzo[d][1,3]dioxol-5-yl)methyl)-6-phenylthieno[3,2-d] pyrimidin-4-amine (2a) as an apoptosis inducer using our proprietary cell-and caspase-based ASAP HTS assay, and SAR study of HTS hit 2a which led to the discovery of 4-anilino-N-methylthieno[3,2-d] pyrimidines and 4-anilino-N-methylthieno[2,3-d] pyrimidines as potent apoptosis inducers. Compounds 5d and 5e were the most potent with EC50 values of 0.008 and 0.004 mu M in T47D human breast cancer cells, respectively. Compound 5d was found to be highly active in the MX-1 breast cancer model. Functionally, compounds 5d and 5e both induced apoptosis through inhibition of tubulin polymerization. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.145

文献信息

• N-aryl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20070099877A1

  公开（公告）日：2007-05-03

  Disclosed are N-aryl-thienopyrimidin-4-amines and analogs thereof, represented by the Formulae I-II: wherein Ar and R 1 -R 4 are defined herein. The present invention relates to the discovery that compounds having Formulae I-II are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  揭示了N-芳基噻吩吡嘧啶-4-胺及其类似物，由以下的式子I-II表示：其中Ar和R1-R4在此有所定义。本发明涉及发现具有式子I-II的化合物是半胱氨酸蛋白酶的激活剂和凋亡诱导剂。因此，本发明的半胱氨酸蛋白酶激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生细胞死亡，这些病况中存在细胞不受控制的生长和异常细胞的扩散。
• N-alkyl-N-aryl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20070213305A1

  公开（公告）日：2007-09-13

  Disclosed are N-alkyl-N-aryl-thienopyrimidin-4-amines and analogs thereof, represented by the Formulae I-II: wherein Ar, R 1 -R 4 and R 10 are defined herein. The present invention relates to the discovery that compounds having Formulae I-II are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及公开的N-烷基-N-芳基噻唑嘧啶-4-胺及其类似物，其由式I-II表示：其中Ar、R1-R4和R10如本文所定义。本发明关于发现具有式I-II的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于在多种临床情况下诱导细胞死亡，其中发生异常细胞的不受控制的生长和扩散。
• THIENOPYRIMIDINES HAVING MNK1/MNK2 INHIBITING ACTIVITY FOR PHARMACEUTICAL COMPOSITIONS
  申请人：Aicher Babette

  公开号：US20100056548A1

  公开（公告）日：2010-03-04

  The present invention relates to novel pharmaceutical compositions comprising thienopyrimidine compounds. Moreover, the present invention relates to the use of the thienopyrimidine compounds of the invention for the production of pharmaceutical compositions for the prophylaxis and/or treatment of diseases which can be influenced by the inhibition of the kinase activity of Mnk1 and/or Mnk2 (Mnk2a or Mnk2b) and/or variants thereof.

  本发明涉及包含噻唑嘧啶化合物的新型药物组合物。此外，本发明涉及使用本发明的噻唑嘧啶化合物制备预防和/或治疗可以受到Mnk1和/或Mnk2（Mnk2a或Mnk2b）及/或其变体的激酶活性抑制影响的疾病的药物组合物。
• INITIATOR SYSTEMS FOR POLYMERISABLE COMPOSITIONS
  申请人：Huntsman Advanced Materials (Switzerland) GmbH

  公开号：EP1685165A1

  公开（公告）日：2006-08-02
• THIENOPYRIMIDINES HAVING MNK1 /MNK2 INHIBITING ACTIVITY FOR PHARMACEUTICAL COMPOSITIONS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2004656B1

  公开（公告）日：2013-07-10