5-氟-二氢-嘧啶-2,4-二酮 | 696-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-氟-二氢-嘧啶-2,4-二酮
• 中文别名: 5-氟二氢嘧啶-2,4-二酮
• 英文名称: Dihydro-5-fluorouracil
• 英文别名: Fluorouracil；5,6-dihydro-5-fluorouracil；5-fluoro-5,6-dihydrouracil；5-fluorodihydrouracil；5-fluorouracil；5-FU；5-fluoro-1,3-diazinane-2,4-dione
• CAS: 696-06-0
• 化学式: C₄H₅FN₂O₂
• 分子量: 132.094
• InChiKey: RAIRJKWTBBDDAR-UHFFFAOYSA-N

物化性质

• 熔点：
  228-230°C
• 溶解度：
  可溶于乙腈（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  5-氟-二氢-嘧啶-2,4-二酮 、 6-溴-1H-吲哚-1-羧酸叔丁酯 在 Ephos 、 dicyclohexyl-[2-propan-2- yloxy-6-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphanium methanesulfonic acid salt methyl-(2- phenylphenyl)azanide palladium⁽²⁺⁾ 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以48%的产率得到tert-butyl 6-(5-fluoro-2,4-dioxotetrahydropyrimidin-1(2H)-yl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  [EN] COMPOUNDS AND THEIR USE IN TREATING CANCER
  [FR] COMPOSÉS ET LEUR UTILISATION DANS LE TRAITEMENT DU CANCER

  摘要：

  本规范一般涉及到公式（I）的化合物及其药学上可接受的盐，其中A、Z、Y、RA、连接剂和v具有本规范中定义的任何含义。本规范还涉及使用这些化合物及其药学上可接受的盐在治疗人或动物体内的方法中，例如在预防或治疗癌症方面的应用。本规范还涉及到准备这些化合物所涉及的过程和中间体化合物，以及含有它们的制药组合物。

  公开号：

  WO2022069520A1
• 作为产物：
  描述：

  1,3-bis(4-methoxybenzyl)-5,6-dihydro-5-fluorouracil 在 ammonium cerium(IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以31%的产率得到5-氟-二氢-嘧啶-2,4-二酮
  参考文献：
  名称：

  Improved Chemical Syntheses of 5,6-Dihydro-5-fluorouracil

  摘要：

  5,6-Dihydro-5-fluorouracil (5-DHFU) is a metabolite of the chemotherapy drug 5-fluorouracil (5-FU) of importance for biological studies. 5-DHFU has been prepared by enzymatic reduction of 5-FU and in very low yield by hydrogenation of 5-FU; however, a practical chemical synthesis is not available. Facile racemic syntheses of 5-DHFU from 5-FU or uracil, using p-methoxybenzyl protecting groups followed by L-Selectride reduction, are reported.

  DOI：

  10.1021/jo071255z

文献信息

• Method for prediction of sensitivity to 5-fluorouracil-type anticancer agent
  申请人：Kobunai Takashi

  公开号：US08440398B2

  公开（公告）日：2013-05-14

  A factor affecting sensitivities to anticancer agents is analyzed and the validity of the factor is demonstrated. The present invention provides a method for predicting sensitivities to 5-fluorouracil-based anticancer agents using the copy number of dihydropyrimidine dehydrogenase gene as an indicator. Also disclosed are a kit and primers for use in predicting sensitivities to 5-fluorouracil-based anticancer agents.

  分析影响抗癌药物敏感性的因素，并证明了该因素的有效性。本发明提供了一种利用脱氢尿嘧啶酶基因拷贝数作为指标预测对5-氟尿嘧啶类抗癌药物敏感性的方法。同时还揭示了用于预测5-氟尿嘧啶类抗癌药物敏感性的试剂盒和引物。
• METHOD FOR PREDICTION OF SENSITIVITY TO 5-FLUOROURACIL-TYPE ANTICANCER AGENT
  申请人：Kobunai Takashi

  公开号：US20090197264A1

  公开（公告）日：2009-08-06

  A factor affecting sensitivities to anticancer agents is analyzed and the validity of the factor is demonstrated. The present invention provides a method for predicting sensitivities to 5-fluorouracil-based anticancer agents using the copy number of dihydropyrimidine dehydrogenase gene as an indicator. Also disclosed are a kit and primers for use in predicting sensitivities to 5-fluorouracil-based anticancer agents.

  本文分析了影响抗癌药物敏感性的因素，并证明了该因素的有效性。本发明提供了一种利用脱氢尿嘧啶酶基因的拷贝数作为指标预测5-氟尿嘧啶类抗癌药物敏感性的方法。同时还公开了用于预测5-氟尿嘧啶类抗癌药物敏感性的试剂盒和引物。
• THE SYNTHESIS OF 5-FLUOROPYRIMIDINES
  作者：Robert Duschinsky、Edward Pleven、Charles Heidelberger

  DOI：10.1021/ja01573a087

  日期：1957.8
• Synthesis of tritium-labeled 5-fluorouracil and 5-fluorocytosine
  作者：G. V. Sidorov、N. F. Myasoedov

  DOI：10.1134/s1066362211060142

  日期：2011.12

  The effect of various catalysts and temperature on the solid-phase isotope exchange of 5-fluorouracil and 5-fluorocytosine with tritium was studied. The isotope exchange yielding the desired compounds is accompanied by dehalogenation and hydrogenation of the 5,6-double bond of the pyrimidine ring. Performing the reaction at a temperature below 160 degrees C. allowed the process to be carried out selectively, i.e., with the preservation of the functional groups and double bond in the starting compound. The yields of various products formed in the reactions of tritium with the above compounds were estimated. Synthesis conditions were found, and tritium-labeled 5-fluorouracil and 5-fluorocytosine were prepared with the molar radioactivity of 0.45 Ci mmol(-1) (16.7 TBq mol(-1)) and 4.4 Ci mmol(-1) (0.16 PBq mol(-1)), respectively, and with the purity exceeding 98%.
• KURONO, MASATSUNEH;UMINO, JOSIKADZU;KIMURA, XIROMOTO;KODZAVA, XIROSI;MITA+
  作者：KURONO, MASATSUNEH、UMINO, JOSIKADZU、KIMURA, XIROMOTO、KODZAVA, XIROSI、MITA+

  DOI：——

  日期：——