5-(tert-butyldiphenylsilanyloxymethyl)pyrazin-2-ylamine | 874476-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(tert-butyldiphenylsilanyloxymethyl)pyrazin-2-ylamine
• 英文别名: 5-[[tert-butyl(diphenyl)silyl]oxymethyl]pyrazin-2-amine
• CAS: 874476-57-0
• 化学式: C₂₁H₂₅N₃OSi
• 分子量: 363.535
• InChiKey: XPBCJTJDFUNADU-UHFFFAOYSA-N

物化性质

• 沸点：
  473.4±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldiphenylsilanyloxymethyl)pyrazin-2-ylamine 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.5h， 生成 [5-[[Tert-butyl(diphenyl)silyl]oxymethyl]pyrazin-2-yl]thiourea
  参考文献：
  名称：

  Identification of potent 5-pyrimidinyl-2-aminothiazole CDK4, 6 inhibitors with significant selectivity over CDK1, 2, 5, 7, and 9

  摘要：

  5-Pyrimidinyl-2-aminothiazole 1 was identified as an inhibitor of cyclin-dependent kinases (CDKs) by a screening of the Merck sample repository. The introduction of a methyl group at the C-5 or C-6 position on the pyrimidine ring, directed toward the gate keeper residue of CDK4 (Phe93), led to significant enhancement of selectivity for CDK4 over other CDKs. Compound 3 exhibited more than 300-fold selectivity for CDK4 over CDK1, 2, 5, 7, and 9. Subsequent improvements in aqueous solubility afforded compound 4, which is available for further in vivo studies and this compound inhibited pRb phosphorylation and BrdU incorporation in tumor models. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.048
• 作为产物：
  描述：

  (5-溴乙基吡嗪-2-基)氨基甲酸叔丁酯 在 咪唑 、 sodium hydroxide 、 18-冠醚-6 、 三氟乙酸 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 30.0h， 生成 5-(tert-butyldiphenylsilanyloxymethyl)pyrazin-2-ylamine
  参考文献：
  名称：

  Identification of potent 5-pyrimidinyl-2-aminothiazole CDK4, 6 inhibitors with significant selectivity over CDK1, 2, 5, 7, and 9

  摘要：

  5-Pyrimidinyl-2-aminothiazole 1 was identified as an inhibitor of cyclin-dependent kinases (CDKs) by a screening of the Merck sample repository. The introduction of a methyl group at the C-5 or C-6 position on the pyrimidine ring, directed toward the gate keeper residue of CDK4 (Phe93), led to significant enhancement of selectivity for CDK4 over other CDKs. Compound 3 exhibited more than 300-fold selectivity for CDK4 over CDK1, 2, 5, 7, and 9. Subsequent improvements in aqueous solubility afforded compound 4, which is available for further in vivo studies and this compound inhibited pRb phosphorylation and BrdU incorporation in tumor models. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.048

文献信息

• WO2008/74752
  申请人：——

  公开号：——

  公开（公告）日：——
• EP1754706
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] HETEROCYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES À UTILISER DANS LE TRAITEMENT DU CANCER
  申请人：[en]ARTIOS PHARMA LIMITED

  公开号：WO2023067353A1

  公开（公告）日：2023-04-27

  The invention relates to heterocyclic derivatives and their use in the treatment and prophylaxis of cancer, and to compositions containing said derivatives and processes for their preparation.
• Identification of potent 5-pyrimidinyl-2-aminothiazole CDK4, 6 inhibitors with significant selectivity over CDK1, 2, 5, 7, and 9
  作者：Tadashi Shimamura、Jun Shibata、Hideki Kurihara、Takashi Mita、Sachie Otsuki、Takeshi Sagara、Hiroshi Hirai、Yoshikazu Iwasawa

  DOI：10.1016/j.bmcl.2006.04.048

  日期：2006.7

  5-Pyrimidinyl-2-aminothiazole 1 was identified as an inhibitor of cyclin-dependent kinases (CDKs) by a screening of the Merck sample repository. The introduction of a methyl group at the C-5 or C-6 position on the pyrimidine ring, directed toward the gate keeper residue of CDK4 (Phe93), led to significant enhancement of selectivity for CDK4 over other CDKs. Compound 3 exhibited more than 300-fold selectivity for CDK4 over CDK1, 2, 5, 7, and 9. Subsequent improvements in aqueous solubility afforded compound 4, which is available for further in vivo studies and this compound inhibited pRb phosphorylation and BrdU incorporation in tumor models. (c) 2006 Elsevier Ltd. All rights reserved.