1-(4-thio-β-D-ribofuranosyl)-N₄-benzoyl-cytosine | 159981-07-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-(4-thio-β-D-ribofuranosyl)-N₄-benzoyl-cytosine
• 英文别名: N⁴-benzoyl-1-(4-thio-β-D-ribo-pentofuranosyl)cytosine；Cytidine, N-benzoyl-4'-thio-；N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)thiolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 159981-07-4
• 化学式: C₁₆H₁₇N₃O₅S
• 分子量: 363.394
• InChiKey: JMGKANANWDPXRP-BPGGGUHBSA-N

物化性质

• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  148
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-thio-β-D-ribofuranosyl)-N₄-benzoyl-cytosine 在 甲醇 、 氨 作用下， 反应 24.0h， 以72%的产率得到4'-硫代胞苷
  参考文献：
  名称：

  A New Synthesis of Some 4′-Thio-D-ribonucleosides and Preliminary Enzymatic Evaluation

  摘要：

  A new synthesis of 4'-thioribonucleosides is presented together with the enzymatic evaluation of the adenosine analogues with respect to adenosine kinase. The 4-thio-D-ribofuranosyl carbohydrate precursor ($) under bar 7 was obtained in good yield from D-ribose and further reacted with adenine and cytosine to give the a and beta anomers of 4'-thioadenosine and 4'-thiocytidine, respectively. 4'-thio-beta-($) under bar D-adenosine, ($) under bar 12 beta, is a poor substrate for bovine liver adenosine kinase but does not show substrate inhibition of the enzyme.

  DOI：

  10.1080/15257779408013205
• 作为产物：
  描述：

  甲基 2,3,5-三-O-苄基-D-呋喃核糖苷 在 吡啶 、 苯磺酰胺 、 TMSTf 、 三氟化硼乙醚 、 mercury(II) diacetate 、 三溴化硼 、 四丁基碘化铵 、 potassium carbonate 、 甲基磺酰氯 、 三苯基膦 、 barium carbonate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 59.25h， 生成 1-(4-thio-β-D-ribofuranosyl)-N₄-benzoyl-cytosine
  参考文献：
  名称：

  A New Synthesis of Some 4′-Thio-D-ribonucleosides and Preliminary Enzymatic Evaluation

  摘要：

  A new synthesis of 4'-thioribonucleosides is presented together with the enzymatic evaluation of the adenosine analogues with respect to adenosine kinase. The 4-thio-D-ribofuranosyl carbohydrate precursor ($) under bar 7 was obtained in good yield from D-ribose and further reacted with adenine and cytosine to give the a and beta anomers of 4'-thioadenosine and 4'-thiocytidine, respectively. 4'-thio-beta-($) under bar D-adenosine, ($) under bar 12 beta, is a poor substrate for bovine liver adenosine kinase but does not show substrate inhibition of the enzyme.

  DOI：

  10.1080/15257779408013205

文献信息

• Synthesis and structural elucidation of 1-(3-C-ethynyl-4-thio-β-<scp>D</scp>-ribofuranosyl)cytosine (4′-thioECyd)
  作者：Noriaki Minakawa、Daisuke Kaga、Yuka Kato、Kanji Endo、Motohiro Tanaka、Takuma Sasaki、Akira Matsuda

  DOI：10.1039/b204993g

  日期：——

  A practical synthesis of 1,4-anhydro-4-thio-D-ribitol (5) via 1,4-dibromo-1,4-dideoxy-2,3,5-tri-O-benzyl-L-lyxitol (12) is described. This method reduced our previous eleven step procedure starting from D-ribose by three steps. The Pummerer reaction of 1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-sulfinyl-D-ribitol (6) in the presence of N4-benzoylcytosine afforded the 4′-thiocytidine derivative 7b on a large scale. Starting with the resulting 7b, 1-(3-C-ethynyl-4-thio-β-D-ribofuranosyl)cytosine (4; 4′-thioECyd), of which the 4′-oxo congener ECyd (3) is a new type of potent antineoplastic nucleoside developed in our group, was synthesized via elaborate protection and deprotection procedures, and successive reaction with cerium trimethylsilylacetylide. X-Ray crystal structures of 4′-thioECyd (4) and ECyd (3) are presented in this paper. Although striking differences in bond lengths and angles were observed in C1′–S4′ and C4′–S4′, and C4′–S4′–C1′, the overall structures of each compound, including the sugar puckering mode and the syn/anti conformation around the glycosyl bond, were similar.

  1,4-脱水-4-硫代-D-核糖醇的实用合成 (5) 描述了1,4-二溴-1,4-二脱氧-2,3,5-三-O-苄基-L-来木糖醇(12)。该方法将我们之前从 D-核糖开始的十一个步骤减少了三个步骤。 1,4-脱水-2-O-(2,4-二甲氧基苯甲酰基)-3,5-O-(1,1,3,3-四异丙基二硅氧烷-1,3-二基)-4-亚磺酰基-的Pummerer反应D-核糖醇 (6) 在 N4-苯甲酰胞嘧啶存在下大规模提供 4α-硫胞苷衍生物 7b。从所得的 7b 开始，1-(3-C-乙炔基-4-硫代-β-D-呋喃核糖基)胞嘧啶 (4; 4-thioECyd)，其中 4-oxo 同系物 ECyd (3) 是我们课题组开发的一种新型强效抗肿瘤核苷，是通过精心的保护和脱保护程序，以及与三甲基甲硅烷基乙酰化铈的连续反应合成的。本文介绍了 4-thioECyd (4) 和 ECyd (3) 的 X 射线晶体结构。尽管在 C1-2-S4-2 和 C4-2-S4-2 以及 C4-2-S4-S4-C1-2 中观察到键长和角度的显着差异，但每种化合物的整体结构，包括糖褶皱模式和糖基键周围的顺式/反式构象，都是相似的。
• 4'-Thio-β-D-oligoribonucleotides: Nuclease Resistance and Hydrogen Bonding Properties
  作者：C. Leydier、L. Bellon、J. -L. Barascut、J. -L. Imbach

  DOI：10.1080/15257779508012526

  日期：1995.5.1

  The syntheses and the study of nuclease resistance and hydrogen bonding of modified oligoribonucleotides, i.e. 4'-thio-beta-D-oligoribonucleotides (4'-S-RNA), are reported.
• 4′-Thio-RNA: Synthesis, Base Pairing Properties and Interaction with Dimerization Initiation Site of HIV-1
  作者：David Dukhan、Florence De Valette、Roland Marquet、Bernard Ehresmann、Chantal Ehresmann、François Morvan、Jean-Louis Barascut、Jean-Louis Imbach

  DOI：10.1080/07328319908044740

  日期：1999.6

  In the present paper, we describe the synthesis of a modified 9-mer oligonucleotide, 4'-S-r(UGUGCACCU) containing for the first time 4'-thio-guanosine units. This modified 9-mer was found to inhibit in vitro genomic RNA dimerization as well as the wild type RNA.
• A New Synthesis of Some 4′-Thio-D-ribonucleosides and Preliminary Enzymatic Evaluation
  作者：C. Leydier、L. Bellon、J.-L. Barascut、J. Deydier、G. Maury、H. Pelicano、M. A. El Alaoui、J.-L. Imbach

  DOI：10.1080/15257779408013205

  日期：1994.12

  A new synthesis of 4'-thioribonucleosides is presented together with the enzymatic evaluation of the adenosine analogues with respect to adenosine kinase. The 4-thio-D-ribofuranosyl carbohydrate precursor ($) under bar 7 was obtained in good yield from D-ribose and further reacted with adenine and cytosine to give the a and beta anomers of 4'-thioadenosine and 4'-thiocytidine, respectively. 4'-thio-beta-($) under bar D-adenosine, ($) under bar 12 beta, is a poor substrate for bovine liver adenosine kinase but does not show substrate inhibition of the enzyme.