2-(6-chloro-7H-purin-7-yl)-1-phenylethanone | 154771-44-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(6-chloro-7H-purin-7-yl)-1-phenylethanone
• 英文别名: 6-chloro-7-phenacylpurine；2-(6-chloropurin-7-yl)-1-phenylethanone
• CAS: 154771-44-5
• 化学式: C₁₃H₉ClN₄O
• 分子量: 272.694
• InChiKey: SEWULUKKZUZHOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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

反应信息

• 作为反应物：
  描述：

  2-(6-chloro-7H-purin-7-yl)-1-phenylethanone 在 甲酸 、 乙醇 作用下， 反应 2.5h， 以94%的产率得到7-phenacylhypoxanthine
  参考文献：
  名称：

  N 7取代的腺嘌呤，鸟嘌呤和6-巯基尿烷的区域选择性和高效合成

  摘要：

  摘要描述了用于制备N 7取代的腺嘌呤，鸟嘌呤和6-巯基尿烷的简单有效的方案。关键步骤是7-取代的6-氯嘌呤的区域选择性制备，所述7-取代的6-氯嘌呤是通过已知方法多样化合成腺嘌呤，鸟嘌呤和6-巯基尿烷的基础。 图形概要

  DOI：

  10.1007/s00706-012-0899-x
• 作为产物：
  描述：

  2-溴苯乙酮 、 6-氯嘌呤 生成 2-(6-chloro-7H-purin-7-yl)-1-phenylethanone
  参考文献：
  名称：

  Dalby, Christine; Bleasdale, Christine; Clegg, William, Angewandte Chemie, 1993, vol. 105, # 12, p. 1822 - 1823

  摘要：

  DOI：

文献信息

• Direct, Regioselective <i>N</i>-Alkylation of 1,3-Azoles
  作者：Shuai Chen、Russell F. Graceffa、Alessandro A. Boezio

  DOI：10.1021/acs.orglett.5b02994

  日期：2016.1.4

  Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.
• Design, synthesis and characterization of N9/N7-substituted 6-aminopurines as VEGF-R and EGF-R inhibitors
  作者：Christian Peifer、Stefanie Bühler、Dominik Hauser、Katrin Kinkel、Frank Totzke、Christoph Schächtele、Stefan Laufer

  DOI：10.1016/j.ejmech.2008.04.012

  日期：2009.4

  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.
• 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：——