5-isopropoxymethyluracil | 143424-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-isopropoxymethyluracil
• 英文别名: 5-(propan-2-yloxymethyl)-1H-pyrimidine-2,4-dione
• CAS: 143424-32-2
• 化学式: C₈H₁₂N₂O₃
• mdl: MFCD02175198
• 分子量: 184.195
• InChiKey: ZSQDBOLEBSEJQQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 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：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-isopropoxymethyluracil 在 硫酸氢铵 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 1-<(2-hydroxyethoxy)methyl>-5-isopropoxymethyluracil
  参考文献：
  名称：

  Abdel-Megied, Ahmed El-Sayed, Journal of Chemical Research, Miniprint, 1998, # 12, p. 3192 - 3197

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(氯甲基)尿嘧啶 、 异丙醇 生成 5-isopropoxymethyluracil
  参考文献：
  名称：

  Synthesis of various 5-alkoxymethyluracil analogues and structure–cytotoxic activity relationship study

  摘要：

  A number of 5-alkoxymethyluracil analogues were synthesized to evaluate their cytotoxic activity. 5-Alkoxymethyluracil derivatives 1 were prepared via known nucleophilic substitution of 5-chloromethyluracil 5 and subsequently transformed to their corresponding nucleosides 2. All prepared compounds were submitted to cytotoxic activity testing against drug sensitive and drug resistant leukaemia cells and solid tumour derived cell lines. In addition, the cytotoxic activity of 5-alkoxymethyluracil analogues 1 and 2 was compared with the previously published 5-[alkoxy(4-nitrophenyl)methyl]uracil analogues 3 and 4. Extensive structure-cytotoxic activity relationship studies are reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.026

文献信息

• Synthesis and antiviral properties of anomeric 5-isopropoxymethyl and 5-(3-hydroxypropoxynethyl)-2′-desoxyurudines
  作者：A. A. Bakhmedova、M. V. Kochetkova、I. V. Yartseva、é. V. Chekunova、S. Ya. Mel'nik

  DOI：10.1007/bf00772942

  日期：1992.3

  The preparation of 5-(3-hydroxypropoxymethyl)uracil (II) from 5-hydroxymethyluracil (I) and 1,3-propanediol was previously described in [3]. 5-Isopropoxymethyluracil (III) was synthesized by the reaction of I with isopropanol in the presence of hydrochloric acid. The 5-substituted uracils II and III were converted into the corresponding 2,4-bis(O-trimethylsilyl) derivatives which were glycosylated

  由 5-羟甲基尿嘧啶 (I) 和 1,3- 丙二醇制备 5-(3-羟丙氧基甲基) 尿嘧啶 (II) 之前在 [3] 中有所描述。5-异丙氧基甲基尿嘧啶 (III) 由 I 与异丙醇在盐酸存在下反应合成。5-取代的尿嘧啶 II 和 III 被转化为相应的 2,4-双（O-三甲基甲硅烷基）衍生物，这些衍生物通过 2-脱氧-3,5-二（Op-toluyl）-~-D-呋喃核糖基氯进行糖基化（ IV) 在无催化剂的二氯乙烷或乙腈中，在 SnCl 4 存在下。由此形成的 1-[2-脱氧-3,5-二(Op-toluyl)-~-D-呋喃核糖基]-5-(3 -羟丙氧基甲基)尿嘧啶(V)通过柱色谱分离为端基异构体a:~ = i:i的混合物。尝试通过结晶将混合物分离成单独的异头物，并且通过柱或制备型 TLC 也不成功。用甲醇钠在甲醇中对化合物 V 进行脱酰，得到异头异构体 L-（2-脱氧-D-呋喃核糖基）-5-（3-羟基丙氧基甲基）尿嘧啶
• NOVEL NANOCARRIER DELIVERED CANCER CHEMOTHERAPEUTIC AGENTS
  申请人：UNIVERSITY OF CINCINNATI

  公开号：US20160101188A1

  公开（公告）日：2016-04-14

  Compositions and methods for treating cancer in a subject are described herein. The composition includes modified nucleobases and nucleosides that are converted in the cell to nucleotides that are incorporated into growing DNA and result in termination of DNA elongation. The nucleobases and nucleotides are incorporated with a drug delivery system (DDS). The DDS includes β-cyclodextrin. The nucleobases and nucleotides are conjugated to the β-cyclodextrin by an acid labile linker that releases the nucleobases and nucleotides in the acidic environment of cancer cells. The DDS may also include a targeting ligand that targets the DDS/nucleobase or nucleotide conjugate to cancer cells. The DDS/nucleobase or nucleotide conjugate may self form into nanoparticles and may be administered to a subject with cancer in an amount effective to treat said cancer.

  本文描述了用于治疗患者癌症的组合物和方法。该组合物包括经过修饰的核碱基和核苷，这些核碱基和核苷在细胞中转化为核苷酸，并被合并到正在生长的DNA中，导致DNA延伸终止。这些核碱基和核苷与药物输送系统（DDS）一起使用。DDS包括β-环糊精。核碱基和核苷通过酸敏链连接到β-环糊精上，该链在癌细胞的酸性环境中释放核碱基和核苷。DDS还可以包括靶向配体，将DDS/核碱基或核苷共轭物靶向癌细胞。DDS/核碱基或核苷共轭物可以自行形成纳米粒子，并可以以有效治疗癌症的剂量给患者服用。