5-fluoro-3-(ethoxycarbonylmethyl)-1H-pyrimidine-2,4-dione | 118004-33-4

• 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: 5-fluoro-3-(ethoxycarbonylmethyl)-1H-pyrimidine-2,4-dione
• 英文别名: ethyl 2-(5-fluoro-2,4-dioxo-1H-pyrimidin-3-yl)acetate
• CAS: 118004-33-4
• 化学式: C₈H₉FN₂O₄
• 分子量: 216.169
• InChiKey: PNCDWQUNEKFBDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-[5-fluoro-2,6-dioxo-3-(phenylmethoxycarbonyloxymethyl)pyrimidin-1-yl]acetate 在 palladium carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以92%的产率得到5-fluoro-3-(ethoxycarbonylmethyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  苄氧羰基氧甲基部分在 5-氟尿嘧啶保护基上的应用。尿嘧啶环酰胺氮的选择性烷基化

  摘要：

  描述了使用苄氧羰基氧甲基部分作为尿嘧啶环的酰胺氮保护基团的 5-氟尿嘧啶的选择性烷基化。以高产率进行保护、烷基化和脱保护。

  DOI：

  10.1246/cl.1988.1381

文献信息

• Anti-proliferative activity of 2,6-dichloro-9- or 7-(ethoxycarbonylmethyl)-9H- or 7H-purines against several human solid tumour cell lines
  作者：Fátima Morales、Alberto Ramírez、Ana Conejo-García、Cynthia Morata、Juan A. Marchal、Joaquín M. Campos

  DOI：10.1016/j.ejmech.2014.02.012

  日期：2014.4

  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.
• NAGASE, TOSHIO;SEIKE, KANZO;SHIRAISHI, KAZUTO;YAMADA, YUTAKA;OZAKI, SHOIC+, CHEM. LETT.,(1988) N 8, C. 1381-1384
  作者：NAGASE, TOSHIO、SEIKE, KANZO、SHIRAISHI, KAZUTO、YAMADA, YUTAKA、OZAKI, SHOIC+

  DOI：——

  日期：——
• Application of the Benzyloxycarbonyloxymethyl Moiety to a Protective Group of 5-Fluorouracil. Selective Alkylation of Amide Nitrogen of the Uracil Ring
  作者：Toshio Nagase、Kanzo Seike、Kazuto Shiraishi、Yutaka Yamada、Shoichiro Ozaki

  DOI：10.1246/cl.1988.1381

  日期：1988.8.5

  Selective alkylation of 5-fluorouracil using the benzyloxycarbonyloxymethyl moiety as a protective group of amide nitrogen of the uracil ring is described. Protection, alkylation and deprotection were carried out in high yields.

  描述了使用苄氧羰基氧甲基部分作为尿嘧啶环的酰胺氮保护基团的 5-氟尿嘧啶的选择性烷基化。以高产率进行保护、烷基化和脱保护。