6-Chloro-9-cyclopropylmethyl-9H-purine | 195252-65-4

• 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: 6-Chloro-9-cyclopropylmethyl-9H-purine
• 英文别名: 6-chloro-9-(cyclopropylmethyl)purine
• CAS: 195252-65-4
• 化学式: C₉H₉ClN₄
• 分子量: 208.65
• InChiKey: KSWLMJXEYRAGCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  6-Chloro-9-cyclopropylmethyl-9H-purine 在 氨 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以68%的产率得到9-(Cyclopropylmethyl)purin-6-amine
  参考文献：
  名称：

  6-(Alkylamino)-9-alkylpurines. A New Class of Potential Antipsychotic Agents

  摘要：

  A series of 6-(alkylamino)-9-alkylpurines was synthesized and evaluated for the property of antagonizing the behavioral effects in animals of the dopamine agonist apomorphine. This model for identifying potential antipsychotic agents is based on the hypothesis that agents that antagonize apomorphine-induced aggressive behavior in rats and apomorphine-induced climbing in mice, but that do not block stereotyped behavior, could have an antipsychotic effect in humans without producing extrapyramidal side effects. The antiaggressive-behavior activity of lead compound 1 (6-(dimethylamino)-9-(3-phenylalaninamidobenzyl)-9H-purine) was improved 48-fold with 6-(cyclopropylamino)-9-(cyclopropylmethyl)-2-(trifluoromethyl)-9H-purine (80) (po ED50 of 2 mg/kg), which was obtained through an iterative sequence of structure-activity relationship studies that encompassed evaluation of the effects of structure variations at the purine 9-, 6-, and 2-positions. Potency was enhanced with a 9-cyclopropyl group, the duration of action was improved with the 6-(cyclopropylamino) substituent, potency was further enhanced with an N-formyl prodrug, and an agent with reduced cardiovascular effect emerged with the 2-trifluoromethyl purine 80. This potential antipsychotic agent was not developed further due to undesirable effects on the stomach.

  DOI：

  10.1021/jm960662s
• 作为产物：
  描述：

  以 甲醇 为溶剂， 反应 0.5h， 生成 6-Chloro-9-cyclopropylmethyl-9H-purine
  参考文献：
  名称：

  环丁烷核苷类似物的合成3：氧杂环丁菌素碳环衍生物的制备。

  摘要：

  描述了环丁烯核苷类似物的合成，其中核碱基被亚甲基束缚。6-氯嘌呤与3-羟甲基-环丁酮的偶合通过其三氟甲磺酸酯进行，得到N-7和N-9区域异构体，其相对产率对应于所计算的6-氯嘌呤基阴离子的电荷分布。N-烷基化的酮的立体选择性还原在每种情况下定量地产生一种立体异构体。结构分配基于光谱数据和单晶X射线衍射。尝试光激发N-7和N-9没有促进环扩环的酮。初步证据表明发生了光脱羰基化为环丙烷。

  DOI：

  10.1080/15257770.2018.1500697

文献信息

• 一种含SCF
  申请人：中国海洋大学

  公开号：CN111333651B

  公开（公告）日：2022-05-10

  本发明公开了一种含SCF3或SeCF3的杂环化合物及其制备方法，氯代杂环化合物1溶于EtOH溶液后，加入1.0‑2.0倍当量的硫脲或硒脲，然后在50‑120℃条件下搅拌1‑8小时，反应得到化合物2；将化合物2溶于Acetone或EA溶液后，加入2.0‑4.0倍当量的CF3SO2Na，0.2‑0.4倍当量Cu盐，然后逐滴加入2.0‑4.0倍当量的tBuOOH溶液，在25‑40℃条件下反应1.0‑2.0小时，得到化合物3，即所需的含SCF3或SeCF3的杂环化合物。本发明合成的化合物在治疗疾病方面存在巨大的潜力，本发明的合成路线每一个步骤都可以实现放大，收率可以达到85％，本发明提供的合成路线为具有生物活性的化合物的合成带来一条更为简洁有效的途径，收率高，可大规模制备，具有很广阔的应用前景。
• 一种硫代或硒代酰胺类化合物及其制备方法
  申请人：中国海洋大学

  公开号：CN111377927A

  公开（公告）日：2020-07-07

  本发明公开了一种硫代或硒代酰胺类化合物及其制备方法，氯代芳香杂环化合物1溶于EtOH溶液后，加入1.0‑2.0倍当量的硫脲或硒脲，然后在50‑120℃条件下搅拌1‑8小时，反应得到化合物2，即所需的硫代或硒代酰胺类化合物。本发明的合成路线每一个步骤都可以实现放大，收率可以达到85％，本发明合成的化合物为合成含SCF3或SeCF3的嘌呤衍生物提供了医药中间体，本发明提供的合成路线为具有生物活性的化合物的合成带来一条更为简洁有效的途径，收率高，可大规模制备，具有很广阔的应用前景。
• Design, synthesis, and anti–tobacco mosaic virus activity evaluation of quinazolinone derivatives containing purine moieties
  作者：Yi Deng、Minghua Chen、Junming Yi、Yuguo Zheng

  DOI：10.1016/j.phytol.2023.11.003

  日期：2024.2

  In this study, a series of quinazolinone derivatives containing purine molecules were designed and synthesized, and their structures were characterized by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, and HRMS (High Resolution Mass Spectrometer). Antiviral bioassays against plant viruses indicated that some target compounds exhibited higher in vivo antiviral activity against tobacco

  本研究设计合成了一系列含有嘌呤分子的喹唑啉酮衍生物，并通过1 H 核磁共振、13 C 核磁共振和 HRMS（高分辨率质谱仪）对其结构进行了表征。针对植物病毒的抗病毒生物测定表明，一些目标化合物对烟草花叶病毒（TMV）表现出比商业药物利巴韦林更高的体内抗病毒活性。在500 mg/L浓度下，化合物A2表现出良好的抗TMV活性，治疗活性值和保护活性值分别为65.2%和60.2%，这些值优于利巴韦林（分别为50.1%和57.2%） 。其中，A2在体内表现出显着的针对TMV的治疗生物活性，其EC 50（半最大有效浓度）值为162.3 mg/L，优于利巴韦林（314.4 mg/L）。总之，含有嘌呤分子的喹唑啉酮衍生物可能为抗病毒药物的进一步研究提供基础。
• Chemoselective Perfluoromethylation of Thio- and Selenoamides
  作者：Xianhong Xu、Jianyu Zhang、Tao Xu

  DOI：10.1021/acs.orglett.0c03241

  日期：2020.11.6

  A chemo- and regioselective perfluoromethylation using thioamides/selenoamides (prepared one step from corresponding lactams) as starting materials has been discovered. The reaction demonstrated complementary chemoselectivity to the C-H trifluoromethylation of (hetero)arenes as well as remarkable functional group compatibility especially toward radical sensitive olefin-, alkyne-, and arylhalide-bearing substrates. The examples of perfluorothio-/selenolated drug molecules indicated application potential of this strategy in drug modification and drug-analogue preparation.
• 6-(Alkylamino)-9-alkylpurines. A New Class of Potential Antipsychotic Agents
  作者：James L. Kelley、R. Morris Bullock、Mark P. Krochmal、Ed W. McLean、James A. Linn、Micheal J. Durcan、Barrett R. Cooper

  DOI：10.1021/jm960662s

  日期：1997.9.1

  A series of 6-(alkylamino)-9-alkylpurines was synthesized and evaluated for the property of antagonizing the behavioral effects in animals of the dopamine agonist apomorphine. This model for identifying potential antipsychotic agents is based on the hypothesis that agents that antagonize apomorphine-induced aggressive behavior in rats and apomorphine-induced climbing in mice, but that do not block stereotyped behavior, could have an antipsychotic effect in humans without producing extrapyramidal side effects. The antiaggressive-behavior activity of lead compound 1 (6-(dimethylamino)-9-(3-phenylalaninamidobenzyl)-9H-purine) was improved 48-fold with 6-(cyclopropylamino)-9-(cyclopropylmethyl)-2-(trifluoromethyl)-9H-purine (80) (po ED50 of 2 mg/kg), which was obtained through an iterative sequence of structure-activity relationship studies that encompassed evaluation of the effects of structure variations at the purine 9-, 6-, and 2-positions. Potency was enhanced with a 9-cyclopropyl group, the duration of action was improved with the 6-(cyclopropylamino) substituent, potency was further enhanced with an N-formyl prodrug, and an agent with reduced cardiovascular effect emerged with the 2-trifluoromethyl purine 80. This potential antipsychotic agent was not developed further due to undesirable effects on the stomach.