6-ethyl-9-β-D-ribofuranosylpurine | 16006-62-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-ethyl-9-β-D-ribofuranosylpurine
• 英文别名: Ribofuranosyl-6-aethylpurin；1-(6-ethyl-purin-9-yl)-β-D-1-deoxy-ribofuranose；(2R,3R,4S,5R)-2-(6-ethylpurin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2R,3R,4S,5R)-2-(6-ethylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 16006-62-5
• 化学式: C₁₂H₁₆N₄O₄
• 分子量: 280.283
• InChiKey: AGKGZTUSZIPPRS-UGKPPGOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,3,5-三-O-乙酰基-6-氯嘌呤-9-β-D-呋喃核糖苷 在 甲醇 、 氨 、 zinc dibromide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 6-ethyl-9-β-D-ribofuranosylpurine
  参考文献：
  名称：

  Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: Palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides

  摘要：

  A series of C-6 alkyl, cycloalkyl, and aryl-9-(beta-D-ribofuranosyl)purines were synthesized and their substrate activities with Escherichia colt purine nucleoside phosphorylase (E. coli PNP) were evaluated. (Ph3P)(4)Pd-mediated cross-coupling reactions of 6-chloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-purine (6) with primary alkyl (Me, Et, n-Pr, n-Bu, isoBu) zinc halides followed by treatment with NH3/MeOH gave the corresponding 6-alkyl-9-(beta-D-ribofuranosyl)purine derivatives 7-11, respectively, in good yields. Reactions of 6 with cycloalkyl(propyl, butyl, pentyl)zinc halides and aryl (phenyl, 2-thienyl)zinc halides gave under similar conditions the corresponding 6-cyclopropyl, cyclobutyl, cyclopentyl, phenyl, and thienyl -9-(beta-D-ribofuranosyl)purine derivatives 12-16, respectively in high yields. E. colt PNP showed a high tolerance to the steric and hydrophobic environment at the 6-position of the synthesized purine ribonucleosides. Significant cytotoxic activity was observed for 8, 12, 15, and 16. Evaluation of 12 and 16 against human tumor xenografts in mice did not demonstrate any selective antitumor activity. In addition, 6-methyl-9-(beta-D-arabinofuranosyl)purine (18) was prepared and evaluated. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.039

文献信息

• [EN] PROCESS FOR FORMING A CARBON-CARBON BOND<br/>[FR] PROCÉDÉ DE FORMATION D'UNE LIAISON CARBONE-CARBONE
  申请人：UNIV MANCHESTER

  公开号：WO2019215426A1

  公开（公告）日：2019-11-14

  A process for forming a carbon-carbon bond to couple an aryl or heteroaryl group of a first compound with an aryl or heteroaryl group of a second compound, the process comprising reacting the first compound with the second compound in the presence of a catalytically effective amount of a neutral or cationic ruthenium(II) catalyst of formula (I):

  一种形成碳-碳键的工艺，用于将第一化合物中的芳基或杂芳基团与第二化合物中的芳基或杂芳基团偶联，该工艺包括在存在公式(I)的中性或阳离子钌(II)催化剂的催化有效量下，使第一化合物与第二化合物反应：
• Synthesis of 6-alkyl and 6-aryl substituted 9-β--ribofuranosyl purines via the nickel catalyzed coupling of grignard reagents to 2′,3′,5′-tris-0-(t-butyldimethylsilysl)-9-β--ribofuranosyl-6-chloropurine
  作者：Donald E. Bergstrom、P.Anantha Reddy

  DOI：10.1016/s0040-4039(00)88701-8

  日期：1982.1

  A series of 6-substituted purine nucleosides have been synthesized in moderate yield by the nickel catalyzed cross coupling reaction between alkyl- and aryl- Grignard reagents and 2′,3′,5′-tris-0-(t-butyldimethylsilyl)-9-β-D-ribofuranosyl-6-chloropurine.

  通过烷基和芳基-格氏试剂与2'，3'，5'-tris-0-（叔丁基二甲基甲硅烷基）-9之间的镍催化交叉偶联反应，以中等收率合成了一系列6-取代的嘌呤核苷。 -β-D-呋喃呋喃糖基-6-氯嘌呤。
• Yamane, Akira; Matsuda, Akira; Ueda, Tohru, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 150 - 156
  作者：Yamane, Akira、Matsuda, Akira、Ueda, Tohru

  DOI：——

  日期：——
• Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: Palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides
  作者：Abdalla E.A. Hassan、Reham A.I. Abou-Elkhair、James M. Riordan、Paula W. Allan、William B. Parker、Rashmi Khare、William R. Waud、John A. Montgomery、John A. Secrist

  DOI：10.1016/j.ejmech.2011.10.039

  日期：2012.1

  A series of C-6 alkyl, cycloalkyl, and aryl-9-(beta-D-ribofuranosyl)purines were synthesized and their substrate activities with Escherichia colt purine nucleoside phosphorylase (E. coli PNP) were evaluated. (Ph3P)(4)Pd-mediated cross-coupling reactions of 6-chloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-purine (6) with primary alkyl (Me, Et, n-Pr, n-Bu, isoBu) zinc halides followed by treatment with NH3/MeOH gave the corresponding 6-alkyl-9-(beta-D-ribofuranosyl)purine derivatives 7-11, respectively, in good yields. Reactions of 6 with cycloalkyl(propyl, butyl, pentyl)zinc halides and aryl (phenyl, 2-thienyl)zinc halides gave under similar conditions the corresponding 6-cyclopropyl, cyclobutyl, cyclopentyl, phenyl, and thienyl -9-(beta-D-ribofuranosyl)purine derivatives 12-16, respectively in high yields. E. colt PNP showed a high tolerance to the steric and hydrophobic environment at the 6-position of the synthesized purine ribonucleosides. Significant cytotoxic activity was observed for 8, 12, 15, and 16. Evaluation of 12 and 16 against human tumor xenografts in mice did not demonstrate any selective antitumor activity. In addition, 6-methyl-9-(beta-D-arabinofuranosyl)purine (18) was prepared and evaluated. (C) 2011 Elsevier Masson SAS. All rights reserved.