4-chloro-2-pivaloylaminothieno[2,3-d]pyrimidine | 1028332-10-6

• 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: 4-chloro-2-pivaloylaminothieno[2,3-d]pyrimidine
• 英文别名: 2,2-dimethylpropanoic acid (4-chlorothieno[2,3-d]pyrimidin-2-yl)amide；n-(4-Chlorothieno[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide；N-(4-chlorothieno[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide
• CAS: 1028332-10-6
• 化学式: C₁₁H₁₂ClN₃OS
• 分子量: 269.755
• InChiKey: ZRFQYAFIVQRZBG-UHFFFAOYSA-N

物化性质

• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基硼酸 、 4-chloro-2-pivaloylaminothieno[2,3-d]pyrimidine 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以42%的产率得到N-(4-methylthieno[2,3-d]pyrimidin-2-yl)pivalamide
  参考文献：
  名称：

  Discovery of new thienopyrimidine derivatives as potent and orally efficacious phosphoinositide 3-kinase inhibitors

  摘要：

  A series of new thienopyrimidine derivatives has been discovered as potent PI3K inhibitors. The systematic SAR studies for these analogues are described. Among them, 8a and 9a exhibit nanomolar enzymatic potencies and sub-micromolar cellular anti-proliferative activities. 8a displays favorable pharmacokinetic profiles, while 9a easily undergoes deacetylation to yield a major metabolite 8a. Furthermore, 8a and 9a potently inhibit tumor growth in a dose-dependent manner in the NCI-H460 xenograft model with an acceptable safety profile. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.12.025
• 作为产物：
  描述：

  2-aminothieno[2,3-d]pyrimidin-4(3H)-one 在 三乙胺 、 三氯氧磷 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 4-chloro-2-pivaloylaminothieno[2,3-d]pyrimidine
  参考文献：
  名称：

  A practical synthesis of 5-functionalized thieno[2,3-d]pyrimidines

  摘要：

  The synthesis of 5-hydroxymethyl-, 5-acetoxymethyl-, 5-formyl- and 5-cyanothieno[2,3-d]pyrimidines, the (methyl)-5-carboxylate, and the respective amide functionality was accomplished by building up the functionalized molecule starting from appropriately substituted thiophene precursors. A similar strategy starting from the pyrimidine precursor and subsequent direct functionalization (formylation and cyanation) of the thieno[2,3-d]pyrimidine parent compound in position 5 was found to be less feasible. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.104

文献信息

• WO2008/59368
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] 2-AMINO PYRIDINE COMPOUNDS<br/>[FR] COMPOSÉS DE 2-AMINO PYRIDINE
  申请人：PFIZER PROD INC

  公开号：WO2008059368A2

  公开（公告）日：2008-05-22

  [EN] The present invention is directed to 2-aminopyrimidine compounds and pharmaceutically acceptable salts thereof, their synthesis and their use as HSP-90 inhibitors.
  [FR] La présente invention porte sur des composés de 2-aminopyrimidine et sur des sels acceptables du point de vue pharmaceutique de celle-ci, sur leur synthèse et sur leur utilisation comme inhibiteurs de HSP-90.
• A practical synthesis of 5-functionalized thieno[2,3-d]pyrimidines
  作者：Birgit Wilding、Stefan Faschauner、Norbert Klempier

  DOI：10.1016/j.tetlet.2015.05.104

  日期：2015.7

  The synthesis of 5-hydroxymethyl-, 5-acetoxymethyl-, 5-formyl- and 5-cyanothieno[2,3-d]pyrimidines, the (methyl)-5-carboxylate, and the respective amide functionality was accomplished by building up the functionalized molecule starting from appropriately substituted thiophene precursors. A similar strategy starting from the pyrimidine precursor and subsequent direct functionalization (formylation and cyanation) of the thieno[2,3-d]pyrimidine parent compound in position 5 was found to be less feasible. (C) 2015 Elsevier Ltd. All rights reserved.
• Discovery of new thienopyrimidine derivatives as potent and orally efficacious phosphoinositide 3-kinase inhibitors
  作者：Songwen Lin、Chunyang Wang、Ming Ji、Deyu Wu、Yuanhao Lv、Li Sheng、Fangbin Han、Yi Dong、Kehui Zhang、Yakun Yang、Yan Li、Xiaoguang Chen、Heng Xu

  DOI：10.1016/j.bmc.2017.12.025

  日期：2018.2

  A series of new thienopyrimidine derivatives has been discovered as potent PI3K inhibitors. The systematic SAR studies for these analogues are described. Among them, 8a and 9a exhibit nanomolar enzymatic potencies and sub-micromolar cellular anti-proliferative activities. 8a displays favorable pharmacokinetic profiles, while 9a easily undergoes deacetylation to yield a major metabolite 8a. Furthermore, 8a and 9a potently inhibit tumor growth in a dose-dependent manner in the NCI-H460 xenograft model with an acceptable safety profile. (C) 2017 Elsevier Ltd. All rights reserved.