2-(6-Chloro-purin-9-yl)-1-phenyl-ethanone | 344340-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(6-Chloro-purin-9-yl)-1-phenyl-ethanone
• 英文别名: 2-(6-Chloro-9H-purin-9-yl)-1-phenylethanone；2-(6-chloropurin-9-yl)-1-phenylethanone
• CAS: 344340-40-5
• 化学式: C₁₃H₉ClN₄O
• 分子量: 272.694
• InChiKey: GXSZSEDUUQZLEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  60.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-(6-Chloro-purin-9-yl)-1-phenyl-ethanone 在 氨 作用下， 以 水 为溶剂， 以63.6%的产率得到2-(6-amino-9H-purin-9-yl)-1-phenylethanone
  参考文献：
  名称：

  Design, synthesis and characterization of N9/N7-substituted 6-aminopurines as VEGF-R and EGF-R inhibitors

  摘要：

  In this study we report on the design, synthesis and biological characterization of novel N-9 or N-7 arylethanone-substituted 6-aminopurines and 6-methoxypurines, respectively, as EGF-R and VEGF-R. inhibitors. The compounds were initially profiled in a panel of 24 cancer-relevant protein kinases. Dependent on the regio-substitution of the purine core we found inhibition activity for EGF-R. and VEGF-R with IC50 values in the mu M range. The two novel N-9/N-7 2-(6-amino-purine)-1-(1H-indole-3-yl)ethanone derivatives were characterized in an enhanced panel of 78 kinases showing the N-9 derivative to also inhibit MNK1 and IRR while the N-7 isomer was found to be specific for VEGF-R2. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.012
• 作为产物：
  描述：

  2-溴苯乙酮 、 6-氯嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(6-Chloro-purin-9-yl)-1-phenyl-ethanone
  参考文献：
  名称：

  Design, synthesis and characterization of N9/N7-substituted 6-aminopurines as VEGF-R and EGF-R inhibitors

  摘要：

  In this study we report on the design, synthesis and biological characterization of novel N-9 or N-7 arylethanone-substituted 6-aminopurines and 6-methoxypurines, respectively, as EGF-R and VEGF-R. inhibitors. The compounds were initially profiled in a panel of 24 cancer-relevant protein kinases. Dependent on the regio-substitution of the purine core we found inhibition activity for EGF-R. and VEGF-R with IC50 values in the mu M range. The two novel N-9/N-7 2-(6-amino-purine)-1-(1H-indole-3-yl)ethanone derivatives were characterized in an enhanced panel of 78 kinases showing the N-9 derivative to also inhibit MNK1 and IRR while the N-7 isomer was found to be specific for VEGF-R2. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.012

文献信息

• Asymmetric Synthesis of 3-Amine-tetrahydrothiophenes with a Quaternary Stereocenter via Nickel(II)/Trisoxazoline-Catalyzed Sulfa-Michael/Aldol Cascade Reaction: Divergent Access to Chiral Thionucleosides
  作者：Ke-Xin Huang、Ming-Sheng Xie、Ji-Wei Sang、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/acs.orglett.0c03747

  日期：2021.1.1

  Ni(II)/trisoxazoline-catalyzed asymmetric sulfa-Michael/Aldol cascade reaction is introduced to access chiral 3-amine-tetrahydrothiophene derivatives containing a quaternary stereocenter (32 examples, up to 93% yield, > 20:1 dr and 92% ee). Moreover, the novel strategy offers an efficient and convenient approach to construct chiral thionucleoside analogues.

  引入通常有用的Ni（II）/三恶唑啉催化的不对称磺胺-Michael / Aldol级联反应以访问含有季立体中心的手性3-胺-四氢噻吩衍生物（32个实例，最高收率93％，> 20：1 dr和92％ee）。此外，该新颖策略提供了构建手性硫代核苷类似物的有效且方便的方法。
• Dalby, Christine; Bleasdale, Christine; Clegg, William, Angewandte Chemie, 1993, vol. 105, # 12, p. 1822 - 1823
  作者：Dalby, Christine、Bleasdale, Christine、Clegg, William、Elsegood, Mark R. J.、Golding, Bernard T.、Griffin, Roger J.

  DOI：——

  日期：——
• Rasmussen, Malcolm; Hope, Janet M., Australian Journal of Chemistry, 1982, vol. 35, # 3, p. 525 - 534
  作者：Rasmussen, Malcolm、Hope, Janet M.

  DOI：——

  日期：——
• RASMUSSEN, M.;HOPE, J., AUSTRAL. J. CHEM., 1982, 35, N 3, 525-534
  作者：RASMUSSEN, M.、HOPE, J.

  DOI：——

  日期：——