(+/-)-cis-9-[2-(hydroxymethyl)cyclopentyl]hypoxanthine

• 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: (+/-)-cis-9-[2-(hydroxymethyl)cyclopentyl]hypoxanthine
• 英文别名: 9-[(1R,2S)-2-(hydroxymethyl)cyclopentyl]-1H-purin-6-one
• 化学式: C₁₁H₁₄N₄O₂
• 分子量: 234.258
• InChiKey: MURBYUURYLXTDD-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  79.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  顺式-(2-氨基-环戊基)-甲醇 在 盐酸 、 sodium hydroxide 、 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 41.0h， 生成 (+/-)-cis-9-[2-(hydroxymethyl)cyclopentyl]hypoxanthine
  参考文献：
  名称：

  A Novel Approach for the Virtual Screening and Rational Design of Anticancer Compounds

  摘要：

  A topological substructural approach to molecular design (TOSS-MODE) has been introduced for the selection and design of anticancer compounds. A quantitative model that discriminates anticancer compounds from the inactive ones in a training series was obtained. This model permits the correct classification of 91.43% of compounds in an external prediction set with only 1.43% of false actives and 7.14% of false inactives. The model developed is then used in a simulation of a virtual search for Ras FTase inhibitors; 87% of the Ras FTase inhibitors used in this simulated search were correctly classified, thus indicating the ability of the TOSS-MODE model of finding lead compounds with novel structures and mechanism of action. Finally, a series of carbonucleosides was designed, and the compounds were classified as active/inactive anticancer compounds by using the model developed here. From the compounds so-designed, 20 were synthesized and evaluated experimentally for their antitumor effects on the proliferation of murine leukemia cells (L1210/0) and human T-lymphocyte cells (Molt4/C8 and CEM/0); 80% of these compounds were well-classified, as active or inactive, and only two pairs of isomeric compounds were false actives. The chloropurine derivatives were the most active compounds, especially compounds 6c,d.

  DOI：

  10.1021/jm991172d