1-丁基-5-氟嘧啶-2,4-二酮 | 69243-15-8

• 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: 1-丁基-5-氟嘧啶-2,4-二酮
• 英文名称: 1-Butan-1-sulfonyl-5-fluor-1H-pyrimidin-2,4-dion
• 英文别名: 1-Butyl-5-fluorouracil；1-butyl-5-fluoropyrimidine-2,4-dione
• CAS: 69243-15-8
• 化学式: C₈H₁₁FN₂O₂
• mdl: MFCD20544638
• 分子量: 186.186
• InChiKey: RCHKDVLSPJBSLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Carbonic acid benzyl ester 3-butyl-5-fluoro-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester 在 palladium carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到1-丁基-5-氟嘧啶-2,4-二酮
  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

• Studies on antitumor agents. V. Syntheses and antitumor activities of 5-fluorouracil derivatives.
  作者：JUNICHI YAMASHITA、ICHIRO YAMAWAKI、SHUICHI UEDA、MITSUGI YASUMOTO、NORIO UNEMI、SADAO HASHIMOTO

  DOI：10.1248/cpb.30.4258

  日期：——

  Six types of 5-fluorouracil (5-FU) derivatives were synthesized ; namely, 2, 4-di-O-substituted, 2-O-substituted, 4-O-substituted, 1, 3-disubstituted, 1-substituted and 3-substituted compounds. After oral administration of these compounds to rats, the blood levels of 5-FU were determined. Among O-substituted derivatives, a 4-O-substituted derivative was most easily activated to 5-FU and 2-O-substituted derivatives were next most easily activated. Among N-substituted derivatives, acyl and sulfonyl derivatives showed the highest 5-FU releasing abilities and 1-alkoxymethyl substituted derivatives showed low ability. N-Alkyl substituted derivatives were not activated to 5-FU. Several compounds which gave higher blood levels of 5-FU than that obtained with 1-(tetrahydro-2-furyl)-5-fluorouracil (Thf-FU), as well as same related compounds, were selected and their antitumor activities were examined. The 2-O-substituted derivatives, 2-butoxy-5-fluoro-4 (1H)-pyrimidone (11) and 2-benzyloxy-5-fluoro-4 (1H)-pyrimidone (19), were as effective as Thf-FU. The activities of 2, 4-di-O-substituted derivatives, 2, 4-dibutoxy-5-fluoropyrimidine (1) and 2, 4-dibenzyloxy-5-fluoropyrimidine (6), against Ehrlich carcinoma and against sarcoma 180, respectively, were the same as those of Thf-FU. The 1-substituted derivatives, 1-ethoxymethyl-5-fluorouracil (49) and 1-(1-ethoxy-1-phenylmethyl)-5-fluorouracil (50), were found to be as effective as Thf-FU.

  合成了六类氟尿嘧啶（5-FU）衍生物，即2,4-二-O-取代、2-O-取代、4-O-取代、1,3-二取代、1-取代和3-取代的化合物。在大鼠口服这些化合物后，测定了5-FU的血药浓度。在O-取代衍生物中，4-O-取代衍生物最容易被激活为5-FU，其次是2-O-取代衍生物。在N-取代衍生物中，酰基和磺酰基衍生物显示出最高的5-FU释放能力，1-烷氧甲基取代衍生物的释放能力较低。N-烷基取代衍生物未被激活为5-FU。选择了几种在血中5-FU水平高于1-(四氢-2-呋喃基)-5-氟尿嘧啶（Thf-FU）的化合物，以及一些相关化合物，并对其抗肿瘤活性进行了检测。2-O-取代衍生物，2-丁氧基-5-氟-4(1H)-嘧啶酮（11）和2-苄氧基-5-氟-4(1H)-嘧啶酮（19），与Thf-FU一样有效。2,4-二-O-取代衍生物，2,4-二丁氧基-5-氟嘧啶（1）和2,4-二苄氧基-5-氟嘧啶（6），对艾氏癌和肉瘤180的活性与Thf-FU相同。1-取代衍生物，1-乙氧甲基-5-氟尿嘧啶（49）和1-(1-乙氧基-1-苯甲基)-5-氟尿嘧啶（50），发现与Thf-FU一样有效。
• Amino sulfonyl compounds
  申请人：CV6 Therapeutics (NI) Limited

  公开号：US11168059B2

  公开（公告）日：2021-11-09

  Provided herein are dUTPase inhibitors, compositions comprising such compounds and methods of using such compounds and compositions.

  本文提供了 dUTP 酶抑制剂、包含此类化合物的组合物以及使用此类化合物和组合物的方法。
• YAMASHITA, JUN-ICHI;YAMAWAKI, ICHIRO;UEDA, SHUICHI;YASUMOTO, MITSUGI;UNEM+, CHEM. AND PHARM. BULL., 1982, 30, N 12, 4258-4267
  作者：YAMASHITA, JUN-ICHI、YAMAWAKI, ICHIRO、UEDA, SHUICHI、YASUMOTO, MITSUGI、UNEM+

  DOI：——

  日期：——
• 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：——
• 5-Fluoro-uracil immunoassay
  申请人：Salamone J. Salvatore

  公开号：US20070154972A1

  公开（公告）日：2007-07-05

  Novel conjugates of 5-fluoro-uracil and novel 5-fluoro-uracil immunogens and monoclonal antibodies generated by these immunogens which are useful in immunoassays for the quantification and monitoring of 5-fluoro-uracil in biological fluids.