5′-O-(decanoyl)uridine | 145355-71-1

• 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′-O-(decanoyl)uridine
• 英文别名: [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl decanoate
• CAS: 145355-71-1
• 化学式: C₁₉H₃₀N₂O₇
• 分子量: 398.456
• InChiKey: WFGZGVFNINQBOW-BNEJOLLZSA-N

物化性质

• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5′-O-(decanoyl)uridine 、 棕榈酰氯 在 吡啶 作用下， 反应 18.0h， 以85.1%的产率得到5′-O-decanoyl-2′,3′-di-O-palmitoyluridine
  参考文献：
  名称：

  带有酰基部分的 5'-O-尿苷衍生物的合成、抗菌、SAR、PASS、分子对接、分子动力学和药代动力学研究：POM 研究和药效团位点的鉴定

  摘要：

  摘要 由于其卓越的抗菌和药代动力学能力，许多基于核苷的酯显示出抗微生物的潜力，可用作解决多药耐药性致病问题的药物。在这项研究中，插入了几个脂肪族和芳香族基团来合成各种 5'- O-癸酰尿苷 ( 2-5 ) 和 5'- O-月桂酰尿苷衍生物 ( 6-7 )，用于抗菌、计算机计算、药代动力学和 POM (Petra /奥西里斯/莫林斯皮恩斯）。通过物理化学、元素和光谱分析证实了合成的尿苷衍生物的化学结构。体外针对五种细菌和两种真菌的抗菌筛选以及物质活性谱（PASS）的预测表明，与抗菌活性相比，这些尿苷衍生物具有良好的抗真菌特性。密度泛函理论（DFT）用于计算热力学和物理化学性质。对羊毛甾醇 14a-去甲基化酶 CYP51A1 (3JUV) 和黄曲霉(1R4U) 进行分子对接，并揭示了与靶标的结合亲和力和非共价相互作用。然后，进行了 150 ns 的分子动力学模拟，以确认微生物蛋白质在 sili

  DOI：

  10.1080/15257770.2022.2096898
• 作为产物：
  描述：

  acetone oxime decanoate 、 尿嘧啶核苷 以 四氢呋喃 为溶剂， 反应 4.0h， 以96%的产率得到5′-O-(decanoyl)uridine
  参考文献：
  名称：

  A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction

  摘要：

  Lipase-mediated acylation of nucleosides with oxime esters in organic solvents has been achieved. Candida antarctica lipases (SP435 and SP435A) showed high regioselectivity toward the primary hydroxyl group of both deoxy- and ribonucleosides, whereas other lipases exhibited poor results for this goal. 2'-Deoxynucleosides, such as thymidine and 2'-deoxyadenosine, were acylated with oxime esters carrying saturated, unsaturated, aromatic, and functionalized chains, giving 5'-O-acylated compounds together with small quantities of the 3'-O-acylated regioisomer. Uridine, adenosine, and inosine, as representative ribonucleosides, were acylated exclusively at the 5'-OH by using the same methodology. Nucleosides bearing a cytosine ring were found to be unreactive with oxime esters under the same conditions. 2'-Deoxycytidine was acylated with acid anhydrides and C. antarctica lipase to give N,5'-O-diacylated compounds, whereas cytidine gave mixtures, reason for which it had to be previously chemically N-acylated and then subjected to the oxime esters and lipase, giving the same results as ribonucleosides.

  DOI：

  10.1021/jo00055a018

文献信息

• A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction
  作者：Francisco Moris、Vicente Gotor

  DOI：10.1021/jo00055a018

  日期：1993.1

  Lipase-mediated acylation of nucleosides with oxime esters in organic solvents has been achieved. Candida antarctica lipases (SP435 and SP435A) showed high regioselectivity toward the primary hydroxyl group of both deoxy- and ribonucleosides, whereas other lipases exhibited poor results for this goal. 2'-Deoxynucleosides, such as thymidine and 2'-deoxyadenosine, were acylated with oxime esters carrying saturated, unsaturated, aromatic, and functionalized chains, giving 5'-O-acylated compounds together with small quantities of the 3'-O-acylated regioisomer. Uridine, adenosine, and inosine, as representative ribonucleosides, were acylated exclusively at the 5'-OH by using the same methodology. Nucleosides bearing a cytosine ring were found to be unreactive with oxime esters under the same conditions. 2'-Deoxycytidine was acylated with acid anhydrides and C. antarctica lipase to give N,5'-O-diacylated compounds, whereas cytidine gave mixtures, reason for which it had to be previously chemically N-acylated and then subjected to the oxime esters and lipase, giving the same results as ribonucleosides.
• Synthesis, antimicrobial, SAR, PASS, molecular docking, molecular dynamics and pharmacokinetics studies of 5′-<i>O</i>-uridine derivatives bearing acyl moieties: POM study and identification of the pharmacophore sites
  作者：Nasrin S. Munia、Mohammed A. Hosen、Khaldun M. A. Azzam、Mohammed Al-Ghorbani、Mohammed Baashen、Mohammed K. Hossain、Ferdausi Ali、Shafi Mahmud、Mst. S. S. Shimu、Faisal A. Almalki、Taibi B. Hadda、Hamid Laaroussi、Souad Naimi、Sarkar M. A. Kawsar

  DOI：10.1080/15257770.2022.2096898

  日期：2022.10.3

  and POM (Petra/Osiris/Molinspiration). The chemical structures of the synthesized uridine derivatives were confirmed by physicochemical, elemental, and spectroscopic analyses. In vitro antimicrobial screening against five bacteria and two fungi, as well as the prediction of substance activity spectra (PASS), revealed that these uridine derivatives have promising antifungal properties when compared to

  摘要 由于其卓越的抗菌和药代动力学能力，许多基于核苷的酯显示出抗微生物的潜力，可用作解决多药耐药性致病问题的药物。在这项研究中，插入了几个脂肪族和芳香族基团来合成各种 5'- O-癸酰尿苷 ( 2-5 ) 和 5'- O-月桂酰尿苷衍生物 ( 6-7 )，用于抗菌、计算机计算、药代动力学和 POM (Petra /奥西里斯/莫林斯皮恩斯）。通过物理化学、元素和光谱分析证实了合成的尿苷衍生物的化学结构。体外针对五种细菌和两种真菌的抗菌筛选以及物质活性谱（PASS）的预测表明，与抗菌活性相比，这些尿苷衍生物具有良好的抗真菌特性。密度泛函理论（DFT）用于计算热力学和物理化学性质。对羊毛甾醇 14a-去甲基化酶 CYP51A1 (3JUV) 和黄曲霉(1R4U) 进行分子对接，并揭示了与靶标的结合亲和力和非共价相互作用。然后，进行了 150 ns 的分子动力学模拟，以确认微生物蛋白质在 sili