2,6-dichloro-9-(3-methoxyphenylmethyl)-9H-purine | 115204-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2,6-dichloro-9-(3-methoxyphenylmethyl)-9H-purine
• 英文别名: 2,6-Dichloro-9-[(3-methoxyphenyl)methyl]purine
• CAS: 115204-85-8
• 化学式: C₁₃H₁₀Cl₂N₄O
• 分子量: 309.155
• InChiKey: KFNYXHAANWHLIP-UHFFFAOYSA-N

物化性质

• 熔点：
  119-121 °C
• 沸点：
  465.0±55.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(三丁基锡烷基)呋喃 、 2,6-dichloro-9-(3-methoxyphenylmethyl)-9H-purine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三(2-呋喃基)膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以94%的产率得到2-Chloro-6-(2-furyl)-9-(3-methoxyphenylmethyl)-9H-purine
  参考文献：
  名称：

  Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines

  摘要：

  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.

  DOI：

  10.1021/jm0408924
• 作为产物：
  描述：

  3-甲氧基溴苄 、 2,6-二氯嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以35 %的产率得到2,6-dichloro-9-(3-methoxyphenylmethyl)-9H-purine
  参考文献：
  名称：

  基于结构的有效选择性 YTHDC1 配体设计

  摘要：

  N 6 -腺苷甲基化 (m 6 A) 是一种常见的 mRNA 转录后修饰，YTHDC1 是负责识别细胞核中这种修饰的读取蛋白。在这里，我们提出了一种基于蛋白质结构的药物化学活动，产生了 YTHDC1 抑制剂40 ，其平衡解离常数 ( K d ) 为 49 nM。复合物的晶体结构（1.6 Å 分辨率）验证了设计。化合物40对细胞质 m 6 A-RNA 读取器 YTHDF1-3 和 YTHDC2 具有选择性，并对急性髓系白血病 (AML) 细胞系 THP-1、MOLM-13 和 NOMO-1 显示出抗增殖活性。对于最终形成配体40的一系列化合物，生化测定中的亲和力与 THP-1 细胞系中的抗增殖活性之间的良好相关性提供了细胞中 YTHDC1 靶标参与的证据。细胞热位移测定进一步支持与细胞中 YTHDC1 的结合。因此，配体40是研究 YTHDC1 在 AML 中的作用的工具化合物。

  DOI：

  10.1021/acs.jmedchem.4c00599

文献信息

• Purine compounds
  申请人：Gundersen Lise-Lotte

  公开号：US20070203159A1

  公开（公告）日：2007-08-30

  The invention provides an antimycobacterial 6-aryl-9-(m- or p-substituted-benzyl) purine and purine analog compounds.

  这项发明提供了一种抗分枝杆菌的6-芳基-9-(m-或p-取代苄基)嘌呤和嘌呤类似化合物。
• Synthesis of 8-Bromo-<i>N</i>-benzylpurines via 8-Lithiated Purines: Scope and Limitations
  作者：Thywill Gamadeku、Lise-Lotte Gundersen

  DOI：10.1080/00397910903318708

  日期：2010.8.16

  9-Benzylpurines have been lithiated in the 8-position and subsequently brominated when trapped with BrCCl2CCl2Br. The 8-bromopurines were isolated in excellent yields when the benzyl group carried an alkoxy or alkyl group in the ortho or para position. Without these substituents, the conversion was generally less, and formation of 8,8'-purinyl dimers was observed. There was also evidence of debenzylation in some instances. Bromination of 7-benzylpurines employing the same set of reaction conditions has also been achieved.
• 9-Benzyl-6-(dimethylamino)-9H-purines with antirhinovirus activity
  作者：James L. Kelley、James A. Linn、Mark P. Krochmal、J. W. T. Selway

  DOI：10.1021/jm00118a025

  日期：1988.10

  A series of 9-benzyl-6-(dimethylamino)-9H-purines and 9-benzyl-2-chloro-6-(dimethylamino)-9H-purines were synthesized and tested in cell culture for activity against rhinovirus type 1B. The 9-benzylpurines that were unsubstituted in the 2-position had weak activity. However, introduction of a 2-chloro substituent resulted in a substantial increase in antiviral activity. One of the most active compounds, 2-chloro-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purine (29), had an IC50 value of 0.08 microM against serotype 1B. Four compounds were tested against 18 other rhinovirus serotypes, but the majority tested were less sensitive than type 1B. The range of serotype sensitivity for 29 varied from 0.08 to 14 microM. These 9-benzyl-2-chloro-9H-purines represent a new class of antiviral agents with in vitro activity against rhinoviruses.
• KELLEY, JAMES L.;LINN, JAMES A.;KROCHMAL, MARK P.;SELWAY, J. W. T., J. MED. CHEM., 31,(1988) N 10, C. 2001-2004
  作者：KELLEY, JAMES L.、LINN, JAMES A.、KROCHMAL, MARK P.、SELWAY, J. W. T.

  DOI：——

  日期：——
• 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.