5-[1-[(4-tert-butylphenyl)methyl]triazol-4-yl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione | 1187734-44-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-[1-[(4-tert-butylphenyl)methyl]triazol-4-yl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1187734-44-6
• 化学式: C₂₂H₂₇N₅O₅
• 分子量: 441.487
• InChiKey: BHUBBVHJLHXVLA-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(2R,3S,5R)-3-acetyloxy-5-[5-[1-[(4-tert-butylphenyl)methyl]triazol-4-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate 在 水 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 5-[1-[(4-tert-butylphenyl)methyl]triazol-4-yl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  C5-Modified nucleosides exhibiting anticancer activity

  摘要：

  We describe (i) a simple method for the synthesis of C5-modified nucleosides from 5-iodo-2'deoxyuridine and (ii) their activity against six types of human cancer cell lines (HCT15, MM231, NCI-H23, NUGC-3, PC-3, ACHN). We generated nitrile oxides in situ from oximes using a commercial bleaching agent; their cycloadditions with 5-ethynyl-2'-deoxyuridine yielded isoxazole derivatives possessing activity against the cancer cell lines. We synthesized several azides from benzylic bromides and their click reactions with 5-ethynyl-2'-deoxyuridine provided triazole derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.072

文献信息

• C5-Modified nucleosides exhibiting anticancer activity
  作者：Yoon-Suk Lee、Sun Min Park、Hwan Mook Kim、Song-Kyu Park、Kiho Lee、Chang Woo Lee、Byeang Hyean Kim

  DOI：10.1016/j.bmcl.2009.06.072

  日期：2009.8

  We describe (i) a simple method for the synthesis of C5-modified nucleosides from 5-iodo-2'deoxyuridine and (ii) their activity against six types of human cancer cell lines (HCT15, MM231, NCI-H23, NUGC-3, PC-3, ACHN). We generated nitrile oxides in situ from oximes using a commercial bleaching agent; their cycloadditions with 5-ethynyl-2'-deoxyuridine yielded isoxazole derivatives possessing activity against the cancer cell lines. We synthesized several azides from benzylic bromides and their click reactions with 5-ethynyl-2'-deoxyuridine provided triazole derivatives. (C) 2009 Elsevier Ltd. All rights reserved.