6-氯-9-环戊基嘌呤 | 5444-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 6-氯-9-环戊基嘌呤
• 英文名称: 6-chloro-9-cyclopentyl-9H-purine
• 英文别名: 6-chloro-9-cyclopentylpurine
• CAS: 5444-81-5
• 化学式: C₁₀H₁₁ClN₄
• 分子量: 222.677
• InChiKey: UHTKSLVKLNJYII-UHFFFAOYSA-N

物化性质

• 熔点：
  97 °C
• 沸点：
  392.6±45.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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-氯-9-环戊基嘌呤 在 乙醇 、 氨 作用下， 生成 9-环戊基腺嘌呤
  参考文献：
  名称：

  Synthesis of Potential Anticancer Agents. XII. 9-Alkyl-6-substituted-purines²

  摘要：

  DOI：

  10.1021/ja01535a041
• 作为产物：
  描述：

  溴代环戊烷 、 6-氯嘌呤 在 四丁基氢氧化铵 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以90%的产率得到6-氯-9-环戊基嘌呤
  参考文献：
  名称：

  微波辐照下嘌呤的区域选择性烷基化反应

  摘要：

  通常在阴离子形成后通过用碱和烷基卤处理进行的嘌呤烷基化是复杂的，并且在最好的情况下，获得了N-烷基化化合物的混合物。嘌呤衍生物可以从N -7 和N -9 的烷基化中获得。在这项工作中，对反应条件进行了优化，以区域选择性地获得N -9 的烷基化产物。已经尝试了不同的碱，氢氧化四丁基铵产生了最好的结果。反应取决于所使用的碱和溶剂的类型，并且在使用微波辐照的帮助下显着改善，这也通过减少副产物的形成而显着减少了反应时间。

  DOI：

  10.1002/jhet.4407

文献信息

• Nickel catalyzed alkylation of N-aromatic heterocycles with Grignard reagents through direct C–H bond functionalization
  作者：Peng-Yang Xin、Hong-Ying Niu、Gui-Rong Qu、Rui-Fang Ding、Hai-Ming Guo

  DOI：10.1039/c2cc32396f

  日期：——

  A novel protocol for nickel-catalyzed direct sp2 C–H bond alkylation of N-aromatic heterocycles has been developed. This new reaction proceeded efficiently at room temperature using a Grignard reagent as the coupling partner. This approach provides new access to a variety of alkylated N-aromatic heterocycles which are potentially of great importance in medicinal chemistry.

  一种新的协议已被开发用于镍催化的N-芳香族杂环直接sp² C–H键烷基化反应。该反应在室温下以格里尼亚试剂作为耦合伙伴高效进行。这种方法为获取各种烷基化的N-芳香族杂环提供了新的途径，这些化合物在药物化学中可能具有重要价值。
• Regioselective alkylation reaction of purines under microwave irradiation
  作者：Arturo Vinuesa、Miquel Viñas、Daniel Jahani、Jaume Ginard、Nuria Mur、Maria Dolors Pujol

  DOI：10.1002/jhet.4407

  日期：2022.3

  The alkylation of purines which is generally carried out after anion formation by treatment with a base and alkyl halide is complicated and in the best cases, mixtures of N-alkylated compounds are obtained. Purine derivatives can be acquired from alkylation at N-7 and N-9. In this work, the reaction conditions have been optimized to obtain the alkylation products of N-9 regioselectively. Different

  通常在阴离子形成后通过用碱和烷基卤处理进行的嘌呤烷基化是复杂的，并且在最好的情况下，获得了N-烷基化化合物的混合物。嘌呤衍生物可以从N -7 和N -9 的烷基化中获得。在这项工作中，对反应条件进行了优化，以区域选择性地获得N -9 的烷基化产物。已经尝试了不同的碱，氢氧化四丁基铵产生了最好的结果。反应取决于所使用的碱和溶剂的类型，并且在使用微波辐照的帮助下显着改善，这也通过减少副产物的形成而显着减少了反应时间。
• Discovery of 3-(((9H-purin-6-yl)amino)methyl)-4,6-dimethylpyridin-2(1H)-one derivatives as novel tubulin polymerization inhibitors for treatment of cancer
  作者：Qiangsheng Zhang、Xi Hu、Guoquan Wan、Jia Wang、Lu Li、Xiuli Wu、Zhihao Liu、Luoting Yu

  DOI：10.1016/j.ejmech.2019.111728

  日期：2019.12

  A new series of 3-(((9H-purin-6-yl)amino)methyl)-4,6-dimethylpyridin-2(1H)-one derivatives were designed, synthesized and demonstrated to act as tubulin polymerization inhibitors. These new derivatives showed significant antitumor activities, among which SKLB0533 demonstrated to be the most potent compound, with IC50 values ranging from 44.5 to 135.5 nM against seven colorectal carcinoma (CRC) cell

  设计，合成并证明了新的3-（（（9H-嘌呤-6-基）氨基）甲基）-4,6-二甲基吡啶-2（1H）-one衍生物可作为微管蛋白聚合抑制剂。这些新的衍生物显示出显着的抗肿瘤活性，其中SKLB0533被证明是最有效的化合物，针对7种结直肠癌（CRC）细胞系的IC50值为44.5至135.5 nM。值得注意的是，SKLB0533没有表现出对其他潜在靶标的活性，例如420种激酶和EZH2。此外，SKLB0533抑制微管蛋白聚合，使细胞周期停在G2 / M期并诱导CRC细胞凋亡。此外，SKLB0533抑制了HCT116异种移植模型中的肿瘤生长，而没有引起明显的主要器官相关毒性，
• Visible-Light-Mediated Monoselective Ortho C–H Arylation of 6-Arylpurine Nucleosides with Diazonium Salts
  作者：Lei Liang、Ming-Sheng Xie、Hai-Xia Wang、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/acs.joc.7b00659

  日期：2017.6.2

  A combined palladium- and photoredox-catalyzed monoselective arylation of 6-arylpurine nucleosides has been developed by employing purine as a directing group via the photoredox reaction, and many functional groups are well tolerated in this direct C-H arylation condition. Various of functionalized purines (nucleosides) which are potentially of great importance in medicinal chemistry could be obtained under visible light irradiation at room temperature within 4 h.
• Synthesis and antimicrobial evaluation of some new substituted purine derivatives
  作者：Meral Tunçbilek、Zeynep Ateş-Alagöz、Nurten Altanlar、Arzu Karayel、Süheyla Özbey

  DOI：10.1016/j.bmc.2008.12.050

  日期：2009.2

  A series of 8,9-disubstituted adenines (4, 5, 8), 6-substituted aminopurines (10-13) and 9-(p-fluorobenzyl/cyclopentyl)-6-substituted aminopurines (16, 17, 19-30) have been prepared and the antimicrobial activities of these compounds against Staphylococcus aureus, methicillin-resistant S. aureus (MRSA, standard and clinical isolate), Bacillus subtilis, Escherichia coli and Candida albicans were evaluated. 6[(N-phenylaminoethyl)amino]-9H-purine (12) which has no substitution at N-9 position and 9-cyclopentyl-6-[(4-fluorobenzyl) amino]-9H-purine (24) exhibited excellent activity against C. albicans with MIC 3.12 mu g/mL. These compounds displayed better antifungal activity than that of standard oxiconazole. Furthermore, compound 22 carrying 4-chlorobenzylamino group at the 6-position of the purine moiety exhibited comparable antibacterial activity with that of the standard ciprofloxacin against both of the drug-resistant bacteria (MRSA, standard and clinical isolate). (C) 2008 Elsevier Ltd. All rights reserved.