9H-嘌呤,6-氯-9-(4-氯苯基)- | 103566-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 9H-嘌呤,6-氯-9-(4-氯苯基)-
• 英文名称: 6-chloro-9-(4-chlorophenyl)-9H-purine
• 英文别名: 6-chloro-9-(p-chlorophenyl)-9H-purine；6-chloro-9-(p-chlorophenyl)purine；6-chloro-9-(4-chloro-phenyl)-9H-purine；6-Chlor-9-(4-chlor-phenyl)-9H-purin；6-chloro-9-(4-chlorophenyl)purine
• CAS: 103566-04-7
• 化学式: C₁₁H₆Cl₂N₄
• 分子量: 265.101
• InChiKey: ZZCVJLLDJCPYBG-UHFFFAOYSA-N

物化性质

• 熔点：
  221-223 °C
• 沸点：
  439.5±55.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9H-嘌呤,6-氯-9-(4-氯苯基)- 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 7-(p-chlorophenyl)-1,2,4-triazolo[3,4-i]purine
  参考文献：
  名称：

  Basyouni, W. M.; Hosni, Hanaa M., Egyptian Journal of Chemistry, 2001, vol. 44, # 4-6, p. 251 - 268

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(p-chlorophenyl)-5-aminoimidazole-4-carboxamide 在 三氯氧磷 作用下， 反应 3.0h， 生成 9H-嘌呤,6-氯-9-(4-氯苯基)-
  参考文献：
  名称：

  El-Bayouki, Khairy A. M.; El-Sayed, Ali S.; Basyouni, Whaid M., Gazzetta Chimica Italiana, 1989, vol. 119, # 3, p. 163 - 166

  摘要：

  DOI：

文献信息

• A One-Pot Synthesis of Highly Functionalized Purines
  作者：Renaud Zelli、Waël Zeinyeh、Romain Haudecoeur、Julien Alliot、Benjamin Boucherle、Isabelle Callebaut、Jean-Luc Décout

  DOI：10.1021/acs.orglett.7b03209

  日期：2017.12.1

  Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine

  使用适合Vilsmeier型试剂的Traube合成，通过一锅简单，无金属的可扩展方法，可以高产量合成高取代的嘌呤。由5-氨基-4-氯嘧啶，制备新的9-芳基取代的氯嘌呤和用于肽核酸合成的中间体。还报道了允许从5-ami基-6-氨基嘧啶快速合成核糖核苷和7-苄基嘌呤的各种方法，以说明这种多功能工具箱的巨大潜力。该途径在核酸领域中对于直接和快速地获得各种新的8-烷基嘌呤核苷似乎是特别令人感兴趣的。
• Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines
  作者：Anne Kristin Bakkestuen、Lise-Lotte Gundersen、Bibigul T. Utenova

  DOI：10.1021/jm0408924

  日期：2005.4.1

  9-Aryl-, 9-arylsulfonyl- and 9-benzyl-6-(2-furyl)purines were synthesized by N-alkylation or N-arylation of the purine followed by Stille coupling to introduce the faryl substituent in the 6-position and the compounds screened for activity against Mycobacterium tuberculosis. The 9-aryl- and 9-sulfonylarylpurines exhibited weak activity toward the bacteria, but 9-benzylpurines were good inhibitors especially those carrying electron-donating substituents on the phenyl ring. A chlorine atom in the purine 2-position further enhanced activity. The high antimycobacterial activity (MIC 0.39,mu g/mL against M. tuberculosis), low toxicity against mammalian cells and activity inside macrophages found for 2-chloro-6-(2-furyl)-9-(4-methoxyphenylmethyl)9H-purine makes this compound a highly interesting potential antituberculosis drug.
• Regioselective N-9 arylation of purines employing arylboronic acids in the presence of Cu(II)
  作者：Anne Kristin Bakkestuen、Lise-Lotte Gundersen

  DOI：10.1016/s0040-4039(03)00576-8

  日期：2003.4

  9-Arylpurines are efficiently formed with complete regioselectivity when purines are treated with arylboronic acids in the presence of copper(II) acetate. A variety of substituents on both coupling partners are well tolerated. (C) 2003 Elsevier Science Ltd. All rights reserved.
• EL-BAYOUKI, KHAIRY A. M.;EL-SAYED, ALI S.;BASYOUNI, WHAID M., GAZZ. CHIM. ITAL., 119,(1989) N, C. 163-165
  作者：EL-BAYOUKI, KHAIRY A. M.、EL-SAYED, ALI S.、BASYOUNI, WHAID M.

  DOI：——

  日期：——
• METHOD FOR SYNTHESIZING DIVERSELY SUBSTITUTED PURINES
  申请人：UNIVERSITE GRENOBLE ALPES

  公开号：US20210163484A1

  公开（公告）日：2021-06-03

  The present invention relates to a method for synthesizing diversely substituted purines starting from a pyrimidine. Formula (I). The method comprises the formation of an amidine group on the pyrimidine by implementing a Vilsmeier type reagent, the functionalization of the pyrimidine with an amine and the cyclization to form the purine nucleus. Optional steps can also be performed in order to further functionalize the molecule. The invention also relates to new purines and new intermediate product.