2-(3,7-dimethyl-2,6-octadien-1-oxy)-5-fluoropyrimidin-4-one | 63650-57-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(3,7-dimethyl-2,6-octadien-1-oxy)-5-fluoropyrimidin-4-one
• 英文别名: 2-(3,7-dimethylocta-2,6-dienoxy)-5-fluoro-1H-pyrimidin-6-one
• CAS: 63650-57-7
• 化学式: C₁₄H₁₉FN₂O₂
• 分子量: 266.315
• InChiKey: ZMQODYPWKVWKCI-UHFFFAOYSA-N

物化性质

• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  香叶醇 、 2-氯-4-羟基-5-氟嘧啶 以 水 、 甲苯 为溶剂， 以61%的产率得到2-(3,7-dimethyl-2,6-octadien-1-oxy)-5-fluoropyrimidin-4-one
  参考文献：
  名称：

  5-Fluoropyrimidin-4-one compositions

  摘要：

  由以下公式表示的5-氟嘧啶-4-酮衍生物，其中R是直链或支链烷基，碳原子数为4至18，直链或支链烯基，碳原子数为2至18，氧化烷基，碳原子数为3至10，芳基或芳基烷基；制备该衍生物的方法；包含该衍生物作为有效成分和辅料的抗肿瘤组合物。

  公开号：

  US04080455A1

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。
• Preparation of 5-fluoropyrimidin-4-one derivatives
  申请人：Taisho Pharmaceutical Company Limited

  公开号：US04092313A1

  公开（公告）日：1978-05-30

  A 5-fluoropyrimidin-4-one derivative represented by the formula ##STR1## wherein R is straight-chain or branched-chain alkyl having 4 to 18 carbon atoms, straight-chain or branched-chain alkenyl having 2 to 18 carbon atoms, alkylene oxido having 3 to 10 carbon atoms, aryl or aralkyl; Processes for preparing the derivative; An anti-tumor composition containing the derivative as an effective component and an excipient.

  一种由以下公式表示的5-氟嘧啶-4-酮衍生物：##STR1## 其中R为直链或支链烷基，具有4到18个碳原子，直链或支链烯基，具有2到18个碳原子，具有3到10个碳原子的烷基氧化物，芳基或芳基烷基；制备该衍生物的方法；一种抗肿瘤组合物，包含该衍生物作为有效成分和载体。
• 5-Fluoropyrimidin-4-one compositions
  申请人：Taisho Pharmaceutical Company Limited

  公开号：US04080455A1

  公开（公告）日：1978-03-21

  A 5-fluoropyrimidin-4-one derivative represented by the formula ##STR1## wherein R is straight-chain or branched-chain alkyl having 4 to 18 carbon atoms, straight-chain or branched-chain alkenyl having 2 to 18 carbon atoms, alkylene oxido having 3 to 10 carbon atoms, aryl or aralkyl; Processes for preparing the derivative; An anti-tumor composition containing the derivative as an effective component and an excipient.

  由以下公式表示的5-氟嘧啶-4-酮衍生物，其中R是直链或支链烷基，碳原子数为4至18，直链或支链烯基，碳原子数为2至18，氧化烷基，碳原子数为3至10，芳基或芳基烷基；制备该衍生物的方法；包含该衍生物作为有效成分和辅料的抗肿瘤组合物。