1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-6-methyluracil | 36807-62-2

• 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: 1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-6-methyluracil
• 英文别名: 2',3',5'-tri-O-acetyl-6-methyluridine；2',3',5'-Tri-O-acetyl-6-methyluridin；O^2'_,O3'_,O5'-triacetyl-6-methyl-uridine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 36807-62-2
• 化学式: C₁₆H₂₀N₂O₉
• 分子量: 384.343
• InChiKey: MTCIDHNSOWEWMQ-NMFUWQPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  142.99
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-6-methyluracil 在 selenium(IV) oxide 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 O^2'_,O3'_,O5'-triacetyl-6-formyl-uridine
  参考文献：
  名称：

  尿苷的6-取代和5,6-二取代衍生物：立体选择性合成，与尿苷磷酸化酶的相互作用以及体外抗肿瘤活性。

  摘要：

  描述了通过路易斯酸催化的（a）三甲基硅烷化的6-烷基-4-烷基硫尿嘧啶与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-的缩合反应合成6-烷基尿苷的立体选择程序。 D-核呋喃糖（ABR）和（b）三甲基甲硅烷基化的6-烷基-3-苄基尿嘧啶与ABR。随后通过使用配合物BBr3-THF的新的改性方法，使用1N三氟乙酸除去4-甲硫基，并除去3-苄基。此外，通过依次用SeO 2氧化并用四丁基硼氢化铵还原6-甲基尿苷（5）获得6-（羟甲基）尿苷（39）和5-氟-6-（羟甲基）尿苷（40）。分别通过39和40的DAST处理，获得了5-氟-6-甲基尿苷和3-氟-6-甲基尿苷（35），以及它们相应的6-氟甲基同源物41和42。对于前述关于糖基键的固定顺式构象的所有核苷，1 H NMR光谱进一步证实戊糖环主要存在于构象N（3'-内）。大多数核苷是大肠杆菌嘧啶核苷磷酸化酶的弱底物。其中两个39和41具有6-C

  DOI：

  10.1021/jm950675q
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 在 甲醇 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 24.5h， 生成 1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-6-methyluracil
  参考文献：
  名称：

  尿苷的6-取代和5,6-二取代衍生物：立体选择性合成，与尿苷磷酸化酶的相互作用以及体外抗肿瘤活性。

  摘要：

  描述了通过路易斯酸催化的（a）三甲基硅烷化的6-烷基-4-烷基硫尿嘧啶与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-的缩合反应合成6-烷基尿苷的立体选择程序。 D-核呋喃糖（ABR）和（b）三甲基甲硅烷基化的6-烷基-3-苄基尿嘧啶与ABR。随后通过使用配合物BBr3-THF的新的改性方法，使用1N三氟乙酸除去4-甲硫基，并除去3-苄基。此外，通过依次用SeO 2氧化并用四丁基硼氢化铵还原6-甲基尿苷（5）获得6-（羟甲基）尿苷（39）和5-氟-6-（羟甲基）尿苷（40）。分别通过39和40的DAST处理，获得了5-氟-6-甲基尿苷和3-氟-6-甲基尿苷（35），以及它们相应的6-氟甲基同源物41和42。对于前述关于糖基键的固定顺式构象的所有核苷，1 H NMR光谱进一步证实戊糖环主要存在于构象N（3'-内）。大多数核苷是大肠杆菌嘧啶核苷磷酸化酶的弱底物。其中两个39和41具有6-C

  DOI：

  10.1021/jm950675q

文献信息

• NMR-based conformational analysis of 2′,6-disubstituted uridines and antiviral evaluation of new phosphoramidate prodrugs
  作者：Fábio da Paixão Soares、Elisabetta Groaz、Eveline Lescrinier、Johan Neyts、Pieter Leyssen、Piet Herdewijn

  DOI：10.1016/j.bmc.2015.07.003

  日期：2015.9

  Six novel phosphoramidate prodrugs of uridine analogues, with structural modifications introduced at the 6- and 2',6-positions, have been prepared and evaluated for selective antiviral activity against hepatitis C virus, as well as other positive-stranded RNA viruses. An analysis of the conformational properties of the parent nucleosides was carried out using two-dimensional NMR spectroscopy based experiments, highlighting a 3'-endo (North) sugar puckering preference and syn orientation. (C) 2015 Elsevier Ltd. All rights reserved.
• FELCZAK, K.;KULIKOWSKI, T.;VILPO, J. A.;GIZIEWICZ, J.;SHUGAR, D., NUCLEOSIDES AND NUCLEOTIDES, 6,(1987) N 1-2, 257-260
  作者：FELCZAK, K.、KULIKOWSKI, T.、VILPO, J. A.、GIZIEWICZ, J.、SHUGAR, D.

  DOI：——

  日期：——
• New Biocides Based on N4-Alkylcytidines: Effects on Microorganisms and Application for the Protection of Cultural Heritage Objects of Painting
  作者：Liudmila A. Alexandrova、Ivan A. Oskolsky、Dmitry A. Makarov、Maxim V. Jasko、Inna L. Karpenko、Olga V. Efremenkova、Byazilya F. Vasilyeva、Darya A. Avdanina、Anna A. Ermolyuk、Elizaveta E. Benko、Stanislav G. Kalinin、Tat’yana V. Kolganova、Maria Ya. Berzina、Irina D. Konstantinova、Alexander O. Chizhov、Sergey N. Kochetkov、Alexander A. Zhgun

  DOI：10.3390/ijms25053053

  日期：——

  The rapid increase in the antibiotic resistance of microorganisms, capable of causing diseases in humans as destroying cultural heritage sites, is a great challenge for modern science. In this regard, it is necessary to develop fundamentally novel and highly active compounds. In this study, a series of N4-alkylcytidines, including 5- and 6-methylcytidine derivatives, with extended alkyl substituents, were obtained in order to develop a new generation of antibacterial and antifungal biocides based on nucleoside derivatives. It has been shown that N4-alkyl 5- or 6-methylcytidines effectively inhibit the growth of molds, isolated from the paintings in the halls of the Ancient Russian Paintings of the State Tretyakov Gallery, Russia, Moscow. The novel compounds showed activity similar to antiseptics commonly used to protect works of art, such as benzalkonium chloride, to which a number of microorganisms have acquired resistance. It was also shown that the activity of N4-alkylcytidines is comparable to that of some antibiotics used in medicine to fight Gram-positive bacteria, including resistant strains of Staphylococcus aureus and Mycobacterium smegmatis. N4-dodecyl-5- and 6-methylcytidines turned out to be the best. This compound seems promising for expanding the palette of antiseptics used in painting, since quite often the destruction of painting materials is caused by joint fungi and bacteria infection.