6-chloro-7-(ethoxycarbonylmethyl)-7H-purine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-chloro-7-(ethoxycarbonylmethyl)-7H-purine
• 英文别名: 6-Chloro-7-(carboxymethyl)purine Ethyl Ester；ethyl 2-(6-chloropurin-7-yl)acetate
• 化学式: C₉H₉ClN₄O₂
• 分子量: 240.649
• InChiKey: WWVCLWYHAWCOCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-7-(ethoxycarbonylmethyl)-7H-purine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  无金属、光介导、位点特异性、自由基 C6-H 嘌呤与醇的烷基化，草酸盐介入，无催化剂

  摘要：

  报告了一种温和实用的方案，用于在蓝色 LED 照射下草酸盐干预嘌呤与醇的高度区域选择性 C6-H 烷基化。这种转化不需要过渡金属催化剂，对水分不敏感，也不需要N 2保护。此外，该方法显示出广泛的功能组兼容性并且易于放大。

  DOI：

  10.1002/ejoc.202201491
• 作为产物：
  描述：

  氯乙酸乙酯 、 6-氯嘌呤 在 三乙胺 作用下， 以 水 为溶剂， 反应 0.13h， 以12%的产率得到6-chloro-7-(ethoxycarbonylmethyl)-7H-purine
  参考文献：
  名称：

  Anti-proliferative activity of 2,6-dichloro-9- or 7-(ethoxycarbonylmethyl)-9H- or 7H-purines against several human solid tumour cell lines

  摘要：

  As leads we took several benzo-fused seven- and six-membered scaffolds linked to the pyrimidine or purine moieties with notable anti-proliferative activity against human breast, colon and melanoma cancerous cell lines. We then decided to maintain the double-ringed nitrogenous bases and change the other components to the ethyl acetate moiety. This way six purine and two 5-fluorouracil derivatives were obtained and evaluated against the MCF-7, HCT-116, A-375 and G-361 cancer cell lines. Two QSARs are obtained between the anti-proliferative IC50 values for compounds 26-33 and the clog P against the melanoma cell lines A-375 and G-361. Our results show that two of the analogues [ethyl 2-(2,6-dichloro-9H- or 7H-purine-9- or 7-yl)acetates (30 and 33, respectively)] are potent cytotoxic agents against all the tumour cell lines assayed, showing single-digit micromolar IC50 values. This exemplifies the potential of our previously reported purine compounds to qualify as lead structures for medicinal chemistry campaigns, affording simplified analogues easy to synthesize and with a noteworthy bioactivity. The selective activity of 30 and 33 against the melanoma cell line A-375, via apoptosis, supposes a great advantage for a future therapeutic use. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.012

文献信息

• Regioselective N9 alkylation of purine rings assisted by β-cyclodextrin
  作者：Qian Zhang、Gang Cheng、Yong-Zhen Huang、Gui-Rong Qu、Hong-Ying Niu、Hai-Ming Guo

  DOI：10.1016/j.tet.2012.07.025

  日期：2012.9

  Under the assistance of beta-cyclodextrin, purine was effectively alkylated at N9 together with up to 99% conversion and good to excellent yield using water as the solvent. High regioselectivity-N9/N7 selectivity>99:1 was attributed to the beta-cyclodextrin cavity blocked the N7 of purines ring. (c) 2012 Elsevier Ltd. All rights reserved.
• 7-(Carboxymethyl)-6-chloropurine Ethyl Ester
  作者：G. Sood、C. H. Schwalbe、W. Fraser

  DOI：10.1107/s010827019800345x

  日期：1998.9.15

  Alkylation of 6-chloropurine using ethyl bromoacetate gives a mixture of regioisomers from which the title compound, C9H9ClN4O2, was isolated in crystalline form. The ethyl acetate fragment attached at N7 avoids steric hindrance by emerging from the ring almost orthogonally. Two ring C atoms donate weak intermolecular hydrogen bonds to the carbonyl O12 and ring N3 atoms.