5-dodecyloxymethyl-1-(β-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione | 1334716-15-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-dodecyloxymethyl-1-(β-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(dodecoxymethyl)pyrimidine-2,4-dione
• CAS: 1334716-15-2
• 化学式: C₂₂H₃₈N₂O₇
• 分子量: 442.553
• InChiKey: DCCGZDKKMVGHCR-ANTGDGSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-(氯甲基)尿嘧啶 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 176.0h， 生成 5-dodecyloxymethyl-1-(β-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione
  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

• 5‐Substituted Uridines with Activity against Gram‐Positive Bacteria
  作者：Dmitry A. Makarov、Sergey D. Negrya、Maxim V. Jasko、Inna L. Karpenko、Pavel N. Solyev、Vladimir O. Chekhov、Dmitry N. Kaluzhny、Olga V. Efremenkova、Byazilya F. Vasilyeva、Alexander O. Chizhov、Darya A. Avdanina、Alexander A. Zhgun、Sergey N. Kochetkov、Liudmila A. Alexandrova

  DOI：10.1002/cmdc.202300366

  日期：2023.11.2

  The emergence of drug‐resistant strains of pathogenic microorganisms necessitates the creation of new drugs. A series of uridine derivatives containing an extended substituent at the C‐5 position as well as C‐5 alkyloxymethyl, alkylthiomethyl, alkyltriazolylmethyl, alkylsulfinylmethyl and alkylsulfonylmethyl uridines were obtained in order to explore their antimicrobial properties and solubility. It has been shown that new ribonucleoside derivatives have an order of magnitude better solubility in water compared to their 2′‐deoxy analogues and effectively inhibit the growth of a number of Gram‐positive bacteria, including resistant strains of Mycobacterium smegmatis (MIC=15–200 μg/mL) and Staphylococcus aureus (MIC=25–100 μg/mL). Their activity is comparable to that of some antibiotics used in medicine.

  摘要 由于病原微生物耐药菌株的出现，有必要研制新的药物。为了探索尿苷的抗菌性和溶解性，研究人员获得了一系列在 C-5 位含有扩展取代基的尿苷衍生物以及 C-5 烷氧基甲基、烷硫基甲基、烷基三唑基甲基、烷基亚磺酰甲基和烷基亚磺酰甲基尿苷。研究表明，与 2′-脱氧类似物相比，新的核糖核苷衍生物在水中的溶解度要高出一个数量级，并能有效抑制多种革兰氏阳性细菌的生长，包括耐药的烟曲霉菌株（MIC=15-200 μg/mL）和金黄色葡萄球菌（MIC=25-100 μg/mL）。它们的活性与某些药物中使用的抗生素相当。
• Synthesis of various 5-alkoxymethyluracil analogues and structure–cytotoxic activity relationship study
  作者：Lucie Brulíková、Petr Džubák、Marián Hajdúch、Jan Hlaváč

  DOI：10.1016/j.carres.2011.07.026

  日期：2011.10

  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.