1-(2-hydroxymethylcyclopentyl)uracil

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(2-hydroxymethylcyclopentyl)uracil
• 英文别名: cis-1<(2-hydroxymethyl)cyclopentyl>uridine；(+/-)-cis-1-[2-(hydroxymethyl)cyclopentyl]uracil；1-[(1R,2S)-2-(hydroxymethyl)cyclopentyl]pyrimidine-2,4-dione
• 化学式: C₁₀H₁₄N₂O₃
• 分子量: 210.233
• InChiKey: KTKFZSBHUWABAO-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxymethylcyclopentyl)uracil 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以76%的产率得到(+/-)-cis-5-Bromo-1-[2-(hydroxymethyl)cyclopentyl]-5-uracil
  参考文献：
  名称：

  嘧啶和嘌呤核苷的 1,2-二取代碳环类似物的合成

  摘要：

  嘧啶和嘌呤核苷的 1,2-二取代碳环类似物 Lour e Santana,a Marta Teijeira,a Carmen Terán,b Eugenio Uriarte,*a Dolores Viñaa a Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, 西班牙传真 [phone]；电子邮件：[e-mail] b Departamento de Química Orgánica, Universidad de Vigo, Vigo, Spain 2001 年 1 月 22 日收到；2001 年 4 月 12 日修订

  DOI：

  10.1055/s-2001-16075
• 作为产物：
  描述：

  顺式-(2-氨基-环戊基)-甲醇 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 15.0h， 生成 1-(2-hydroxymethylcyclopentyl)uracil
  参考文献：
  名称：

  Synthesis ofCis-1-[(2-Hydroxymethyl) Cyclopentyl]Uridine and Determination of its Conformation by X-Ray Crystallography and Ami Theoretical Calculations

  摘要：

  The title compound 1 was prepared from racemic cis-2-hydroxymethylcyclo pentylamine, constructing the heterocyclic base in a two-step procedure (64 % yield). The crystal structure of the compound was determined and its conformation was studied using AM1 theoretical calculations. The calculated low-energy conformations were similar to those reported for several other nucleoside analogues, and one of them closely corresponded to the X-ray structure.

  DOI：

  10.1080/07328319608007386

文献信息

• A Novel Approach for the Virtual Screening and Rational Design of Anticancer Compounds
  作者：Ernesto Estrada、Eugenio Uriarte、Alina Montero、Marta Teijeira、Lourdes Santana、Erik De Clercq

  DOI：10.1021/jm991172d

  日期：2000.5.1

  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.
• Synthesis and Antiviral Activity of 1,2-Carbonucleosides
  作者：L. Santana、M. Teijeira、E. Uriarte、J. Balzarini、E. De Clercq

  DOI：10.1080/15257779508012417

  日期：1995.5.1

  Members of a new class of carbonucleoside analogues (OTC, one two substituted carbonucleosides) were synthesized and evaluated against HIV.
• Synthesis of 1,2-Disubstituted Carbocyclic Analogs of Pyrimidine and Purine Nucleosides
  作者：Eugenio Uriarte、Lourdes Santana、Marta Teijeira、Carmen Terán、Dolores Viña

  DOI：10.1055/s-2001-16075

  日期：——

  1,2-Disubstituted Carbocyclic Analogues of Pyrimidine and Purine Nucleosides Lour e Santana,a Marta Teijeira,a Carmen Terán,b Eugenio Uriarte,*a Dolores Viñaa a Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain Fax [phone]; E-mail: [e-mail] b Departamento de Química Orgánica, Universidad de Vigo, Vigo, Spain

  嘧啶和嘌呤核苷的 1,2-二取代碳环类似物 Lour e Santana,a Marta Teijeira,a Carmen Terán,b Eugenio Uriarte,*a Dolores Viñaa a Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, 西班牙传真 [phone]；电子邮件：[e-mail] b Departamento de Química Orgánica, Universidad de Vigo, Vigo, Spain 2001 年 1 月 22 日收到；2001 年 4 月 12 日修订
• Synthesis of<i>Cis</i>-1-[(2-Hydroxymethyl) Cyclopentyl]Uridine and Determination of its Conformation by X-Ray Crystallography and Ami Theoretical Calculations
  作者：Lourdes Santana、Marta Teijeira、Eugenio Uriarte、Carmen Teran、Umberto Casellato、Rodolfo Graziani

  DOI：10.1080/07328319608007386

  日期：1996.6

  The title compound 1 was prepared from racemic cis-2-hydroxymethylcyclo pentylamine, constructing the heterocyclic base in a two-step procedure (64 % yield). The crystal structure of the compound was determined and its conformation was studied using AM1 theoretical calculations. The calculated low-energy conformations were similar to those reported for several other nucleoside analogues, and one of them closely corresponded to the X-ray structure.