6-氯-9-苯基嘌呤 | 5470-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 6-氯-9-苯基嘌呤
• 英文名称: 6-Chloro-9-phenyl-9H-purine
• 英文别名: 6-chloro-9-phenylpurine；6-chloro-9-phenyl-9H-purine；6-Chlor-9-phenyl-9H-purin
• CAS: 5470-24-6
• 化学式: C₁₁H₇ClN₄
• mdl: MFCD16619574
• 分子量: 230.656
• InChiKey: MNWAWPZGZXXLBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 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

安全信息

• 海关编码：
  2933990090
• 储存条件：
  温度：2-8°C，环境气体：惰性气体

反应信息

• 作为反应物：
  描述：

  6-氯-9-苯基嘌呤 在 ammonium hydroxide 作用下， 反应 16.0h， 以95%的产率得到9-phenyladenine
  参考文献：
  名称：

  Synthetic Strategies to 9-Substituted 8-Oxoadenines

  摘要：

  Three synthetic routes to 9-substituted 8-oxoadenines have been studied: bromination of adenine followed by N-9-alkylation/arylation and finally hydrolysis; bromination of adenine, hydrolysis, and N-functionalization as the last step; and N-9-alkylation of adenine, halogenation, and finally hydrolysis. As long as the N-9-functional group is compatible with conditions required for introduction of the halogen, the latter strategy was the most efficient. Also, a strategy starting from 5-amino-4,6-dichloropyrimidine was found to be a very good alternative for synthesis of 9-substituted 8-oxoadenines. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.642051
• 作为产物：
  描述：

  9-苯基-3H-嘌呤-6-酮 在 三氯氧磷 作用下， 反应 1.0h， 以79.7%的产率得到6-氯-9-苯基嘌呤
  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

• CuBr Catalyzed C–N cross coupling reaction of purines and diaryliodonium salts to 9-arylpurines
  作者：Hong-Ying Niu、Chao Xia、Gui-Rong Qu、Qian Zhang、Yi Jiang、Run-Ze Mao、De-Yang Li、Hai-Ming Guo

  DOI：10.1039/c1ob05333g

  日期：——

  CuBr was found to be an efficient catalyst for the C–N cross coupling reaction of purine and diaryliodonium salts. 9-Arylpurines were synthesized in excellent yields with short reaction times (2.5 h). The method represents an alternative to the synthesis of 9-arylpurines viaCu(II) catalyzed C–N coupling reaction with arylboronic acids as arylating agents.

  CuBr被发现是嘌呤盐和二芳基碘鎓盐的C–N交叉偶联反应的有效催化剂。9-芳基嘌呤以极短的反应时间（2.5h）以优异的产率合成。该方法是通过以芳基硼酸为芳基化剂的Cu（II）催化的C–N偶联反应合成9-芳基嘌呤的替代方法。
• Selective adenosine receptor agents
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05256650A1

  公开（公告）日：1993-10-26

  Adenosine analogues which act selectively at adenosine receptors and which act in general as adenosine antagonists are disclosed. From in vitro studies it is known that specific physiological effects can be distinguished as a result of this selectivity and that adenosine receptor activity in vitro correlates with adenosine receptor activity in vivo. Pharmaceutical preparations of the subject compounds can be prepared on the basis of the selective binding activity of the compounds disclosed herein which will enhance certain physiological effects while minimizing others, such as decreasing blood pressure without decreasing heart rate.

  抗腺苷类似物在腺苷受体上具有选择性作用，并通常作为腺苷拮抗剂。从体外研究中已知，由于这种选择性，可以区分特定的生理效应，并且体外腺苷受体活性与体内腺苷受体活性相关。根据本公开的化合物的选择性结合活性可以制备该类化合物的药物制剂，这将增强某些生理效应，同时减少其他效应，例如降低血压而不降低心率。
• Pd^II -Catalyzed Purine-Directed Ortho Nitration of 6-Arylpurines by C(sp² )-H Activation: A Practical Approach to Synthesize 6-(2-Nitroaryl)-Purine Derivatives
  作者：Quan Gou、Wenxi Li、Qingsheng Zhao、Jia Xie、Ping Luo、Guang Cao、Suiyun Chen、Jun Qin

  DOI：10.1002/ejoc.201800567

  日期：2018.8.15

  6‐(2‐Nitroaryl)‐purine can be obtained through PdII‐catalyzed C(sp2)–H activation of 6‐arylpurines in the presence of tBuONO/O2. The purine substituent acts as an ortho directing group for the nitration.

  在t BuONO / O 2存在下，Pd II催化6-芳基嘌呤的C（sp 2）-H活化可制得6-（2-硝基芳基）-嘌呤。嘌呤取代基充当硝化的邻位导向基团。
• 6-Substituted Purines as Inhibitors of 15-Lipoxygenase; a Structure-Activity Study
  作者：Anders Bråthe、Lise-Lotte Gundersen、Karl E. Malterud、Frode Rise

  DOI：10.1002/ardp.200400951

  日期：2005.4

  have a drug potential. In this study, purines with a variety of substituents have been examined as inhibitors of 15‐lipoxygenase (15‐LO) from soybeans. Several 6‐substitued purines where the purine ring and a phenyl ring in the substituent were separated by a “spacer” were synthesized and their ability to inhibit the enzyme was explored. Sepa ration of the purine and the phenyl rings with none, one or

  15-脂氧合酶 (15-LO) 与低密度脂蛋白 (LDL) 的氧化有关，该过程被认为对动脉粥样硬化的发展以及其他致病条件很重要。15-LO 的强效和选择性抑制剂可能具有药物潜力。在这项研究中，已将具有多种替代品的嘌呤作为来自大豆的 15-脂肪氧化酶 (15-LO) 的抑制剂进行了检测。合成了几种6-取代的嘌呤，其中取代基中的嘌呤环和苯环被“间隔基”隔开，并探索了它们抑制酶的能力。将嘌呤和苯环与无、一个或两个 sp3-碳分离导致基本上无活性的化合物，反式-苯乙烯基嘌呤和苯乙炔基嘌呤，另一方面，它们表现出接近众所周知的 15-LO 抑制剂槲皮素的活性。当“间隔基”是反式环丙基环时，也发现了高活性。垫片的形状很重要；相应的顺式环丙基嘌呤对酶的亲和力要低得多。无论 N-取代基位于 N-9 还是 N-7 上，即使 N-取代基相对较大，也仅发现对 15-LO 的抑制活性存在微小差异。此外，2 位和 8
• 6-(Alkylamino)-9-benzyl-9H-purines. A new class of anticonvulsant agents
  作者：James L. Kelley、Mark P. Krochmal、James A. Linn、Ed W. McLean、Francis E. Soroko

  DOI：10.1021/jm00398a019

  日期：1988.3

  electroshock-induced seizures (MES) in rats. Most compounds were prepared in three steps from 5-amino-4,6-dichloropyrimidine or in two steps via alkylation of 6-chloropurine. Potent anticonvulsant activity against MES resided in compounds that contain a benzyl substituent at the 9-position of 6-(methylamino)- or 6-(dimethyl-amino)purine. Among commonly used agents for control of seizures, this type of structure represents

  合成了几种9-烷基-6-取代的嘌呤，并测试了其对大鼠最大电击诱发的癫痫发作（MES）的抗惊厥活性。大多数化合物是从3-氨基-4,6-二氯嘧啶分三步制备的，也可以通过6-氯嘌呤的烷基化分两步制备的。针对MES的有效的抗惊厥活性存在于在6-（甲基氨基）-或6-（二甲基-氨基）嘌呤的9位上含有苄基取代基的化合物中。在控制癫痫发作的常用药物中，这种类型的结构代表了一类新型的强效惊厥药物。