6-methyl-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione | 23316-76-9

• 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: 6-methyl-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione
• 英文别名: 2′,3′,5′-tri-O-benzoyl-6-methyluridine；O^2'_,O3'_,O5'-tribenzoyl-6-methyl-uridine；1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-6-methyl-1,2,3,4-tetrahydropyrimidin-2,4-dion；2',3',5'-tri-O-Benzoyl-6-methyl uridine；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(6-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 23316-76-9
• 化学式: C₃₁H₂₆N₂O₉
• 分子量: 570.555
• InChiKey: SWGULPYQUHNYIF-MIRJVGOZSA-N

物化性质

• 熔点：
  125-128 °C
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-methyl-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione 在 sodium hydroxide 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 6-甲基尿苷
  参考文献：
  名称：

  6-氮杂-和6-甲基-嘧啶核糖核苷亚磷酰胺的合成及其在双head核酶中的掺入

  摘要：

  摘要描述了6-修饰的嘧啶核糖核苷的亚磷酰胺的合成及其在锤头状核酶中的掺入及其对核酸酶稳定性和催化活性的影响。

  DOI：

  10.1080/15257779508012497
• 作为产物：
  描述：

  6-methyl-3-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)(1H)pyrimidine-2,4-dione 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 、 xylene 为溶剂， 反应 20.5h， 生成 6-methyl-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Vorbrueggen, Helmut; Krolikiewicz, Konrad; Bennua, Baerbel, Chemische Berichte, 1981, vol. 114, # 4, p. 1234 - 1255

  摘要：

  DOI：

文献信息

• Synthesis of 6-Aza- & 6-Methyl-pyrimidine Ribonucleoside Phosphoramidites and Their Incorporation in Hammerhead Ribozymes
  作者：Leonid Beigelman、Alexander Karpeisky、Nassim Usman

  DOI：10.1080/15257779508012497

  日期：1995.5.1

  Abstract The synthesis of phosphoramidites of 6-modified pyrimidine ribonucleosides and their incorporation into hammerhead ribozymes and influence on nuclease stability and catalytic activity is described.

  摘要描述了6-修饰的嘧啶核糖核苷的亚磷酰胺的合成及其在锤头状核酶中的掺入及其对核酸酶稳定性和催化活性的影响。
• BASE-MODIFIED ENZYMATIC NUCLEIC ACID
  申请人：——

  公开号：US20010006801A1

  公开（公告）日：2001-07-05

  Method to produce a more active ribozyme by introducing a modified base into a substrate binding arm of the ribozyme or its catalytic core.

  通过在核酶的底物结合臂或其催化核心中引入修饰碱基的方法来产生更活跃的核酶。
• Preparation of analogues of cytosine and 2-pyrimidinone nucleosides and their effect on bacterial (Escherichia coli A 19) cytidine aminohydrolase
  作者：Antonín Holý、Anita Ludziša、Ivan Votruba、Kateřina Šedivá、Helmut Pischel

  DOI：10.1135/cccc19850393

  日期：——

  The set of compounds investigated as substrates and inhibitors of bacterial cytidine aminohydrolase (EC 3.5.4.5) consists of cytidine analogues modified in the heterocyclic base or the sugar moiety and analogues of the similar type derived from l-(β-D-ribofuranosyl)-2-pyrimidone (I) and its isomers. The latter group of compounds includes also open-chain derivatives of neutral and acidic character. These compounds were prepared by novel synthetic procedures. Minimum necessary conditions for the structure of an inhibitor of cytidine aminohydrolase from E. coli A 19 include: a heterocyclic system containing an Rf-N-CO-N(H) fragment of a basic character in which Rf denotes a β-D-aldopentafuranoside with a 3-hydroxy group of ribo-configuration; the 5-hydroxy group of the sugar moiety may bear a substituent, except a phosphomonoester function. The heterocyclic base may also bear substituents in positions other than α to the nucleoside bond which do not reduce substantially the basicity of the system and do not change the conformation of the nucleoside molecule.

  研究作为细菌胞嘧啶氨水解酶（EC 3.5.4.5）底物和抑制剂的化合物集合包括在杂环碱基或糖基部分上修改的胞嘧啶类似物以及来源于l-(β-D-核糖呋喃苷)-2-嘧啶酮（I）及其异构体的类似物。后一组化合物还包括中性和酸性特性的开链衍生物。这些化合物是通过新颖的合成方法制备的。从大肠杆菌A 19的胞嘧啶氨水解酶的抑制剂结构的最低必要条件包括：含有基本性质的Rf-N-CO-N(H)片段的杂环系统，其中Rf表示带有核糖-构型的3-羟基的β-D-醛基五糖；糖基的5-羟基可能带有取代基，但不能是磷酸单酯功能团。杂环碱基还可能在不影响系统碱性和核苷酸键的构象的情况下，在核苷酸键的α位置以外带有取代基。
• Base-modified enzymatic nucleic acid
  申请人：Ribozyme Pharmaceuticals, Inc.

  公开号：US20030166896A1

  公开（公告）日：2003-09-04

  Method to produce a more active ribozyme by introducing a modified base into a substrate binding arm of the ribozyme or its catalytic core.

  通过在核酶的底物结合臂或其催化核心中引入修饰碱基的方法来产生更活跃的核酶。
• Direct regioselective arylsulfenylation and arylselenenylation at 5-position of uracils mediated by silver reagents
  作者：Chun Ho Lee、Yong Hae Kim

  DOI：10.1016/s0040-4039(00)79934-5

  日期：1991.5

  Electrophilic additions of phenylsulfenyl chloride or phenylselenenyl chloride to a carbon-carbon double bond of C-5,6 region of uracils in the presence of silver reagents such as Ag2O, AgBF4, or AgOCOCF3 directly gave the corresponding 5-phenylsulfydryl- or 5-phenylselenenyl uracils in good yields.