(-)-cis-(5R,6S)-5,6-dihydroxy-5,6-dihydrothymidine | 38645-22-6

• 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: (-)-cis-(5R,6S)-5,6-dihydroxy-5,6-dihydrothymidine
• 英文别名: (-)cis(5R,6S)-5,6-dihydroxy-5,6-dihydrothymidine；cis-(5R,6S)-5,6-dihydroxy-5,6-dihydrothymidine；(5R,6S) 5,6-dihydroxy-5,6-dihydrothymidine；(5R,6S)-5,6-Dihydro-5,6-dihydroxythymidine；cis-5,6-dihydroxy-5,6-dihydro thymidine；5,6-dihydroxy-5,6-dihydro-thymidine；Thymidine, 5,6-dihydro-5,6-dihydroxy-, cis-；(5R,6S)-5,6-dihydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,3-diazinane-2,4-dione
• CAS: 38645-22-6
• 化学式: C₁₀H₁₆N₂O₇
• 分子量: 276.246
• InChiKey: RKEITGVZZHXKON-LFOMBHIWSA-N

物化性质

• 密度：
  1.645±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  140
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-cis-(5R,6S)-5,6-dihydroxy-5,6-dihydrothymidine 、 cis(+) et cis(-) 5,6-dihydroxy-5,6-dihydrothymidine 生成 5,6-dihydroxy-5-methyl-dihydro-pyrimidine-2,4-dione
  参考文献：
  名称：

  POLVERELLI, MICHEL;BERGER, MAURICE;CADET, JEAN, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 563-564

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-双-o-(t-丁基二甲基甲硅烷基)胸腺嘧啶脱氧核苷 在 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基咔唑 、 水 、 溶剂黄146 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 乙腈 、 叔丁醇 为溶剂， 生成 (-)-cis-(5R,6S)-5,6-dihydroxy-5,6-dihydrothymidine
  参考文献：
  名称：

  Independent generation of the major adduct of hydroxyl radical and thymidine. Examination of intramolecular hydrogen atom transfer in competition with thiol trapping.

  摘要：

  5,6-Dihydro-5-hydroxythymid-6-yl (1) has been generated from 2 via photoinduced electron transfer from N-methylcarbazole. In agreement with prior reports, deuterium incorporation in conjunction with H-2 NMR analysis of 5,6-dihydro-5-hydroxythymidine (3) formed from 1 provides no evidence for intramolecular hydrogen atom abstraction.

  DOI：

  10.1016/s0040-4039(00)60005-9

文献信息

• Studies on the chemistry of pyrimidine derivatives with dimethyldioxirane: synthesis, cytotoxic effect and antiviral activity of new 5,6-oxiranyl-5,6-dihydro and 5-hydroxy-5,6-dihydro-6-substituted uracil derivatives and pyrimidine nucleosides
  作者：Raffaele Saladino、Roberta Bernini、Claudia Crestini、Enrico Mincione、Alberto Bergamini、Stefano Marini、Anna Teresa Palamara

  DOI：10.1016/0040-4020(95)00380-q

  日期：1995.7

  The oxidation of uracil derivatives and pyrimidine nucleosides performed in CH2Cl2 with dimethyldioxirane afforded new 5,6-oxiranyl-5,6-dihydro and cis-/trans-5,6-dihvdroxv-5,6-dihydro-derivatives. When the oxidations were performed in the presence of methanol as nucleophile cis- and trans- 5-hydroxy-6-methoxy-5,6-dihydro derivatives were obtained in acceptable yields. Cis- and trans-1,3- dimethyl

  用二甲基二环氧乙烷在CH 2 Cl 2中进行尿嘧啶衍生物和嘧啶核苷的氧化，得到新的5，6-环氧乙烷基-5，6-二氢和顺式/反式-5，6-二羟基己酮-5，6-二氢衍生物。当在甲醇的存在下以亲核试剂的形式进行氧化时，以可接受的产率获得了顺式和反式5-羟基-6-甲氧基-5,6-二氢衍生物。通过1,3-二甲基-5,6-环氧乙烷基-5,6-二氢的亲核开环获得顺式和反式1,3-二甲基-5-羟基-6-烷基氨基-5,6-二氢尿嘧啶纯化形式的尿嘧啶。有趣的是，一些新的标题产品显示出低的细胞毒性和针对DNA和RNA病毒的选择性抗病毒活性。特别是化合物17b显示出对仙台病毒的强而有选择性的抑制作用，对单纯疱疹1病毒的影响较小。化合物17b在高浓度时也能够轻微抑制HIV-1病毒，但是在这种情况下，观察到了细胞毒性作用。
• Independent generation of the major adduct of hydroxyl radical and thymidine. Examination of intramolecular hydrogen atom transfer in competition with thiol trapping.
  作者：Mark R. Barvian、Marc M. Greenberg

  DOI：10.1016/s0040-4039(00)60005-9

  日期：1992.10

  5,6-Dihydro-5-hydroxythymid-6-yl (1) has been generated from 2 via photoinduced electron transfer from N-methylcarbazole. In agreement with prior reports, deuterium incorporation in conjunction with H-2 NMR analysis of 5,6-dihydro-5-hydroxythymidine (3) formed from 1 provides no evidence for intramolecular hydrogen atom abstraction.
• Cadet, J.; Voituriez, L.; Berger, M., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 12, p. 1643 - 1651
  作者：Cadet, J.、Voituriez, L.、Berger, M.、Myers, L. S., (Jr.)

  DOI：——

  日期：——
• Synthesis and Kinetic Study of the Deamination of the <i>Cis</i> Diastereomers of 5,6-Dihydroxy-5,6-dihydro-5-methyl-2‘-deoxycytidine
  作者：Carine Bienvenu、Jean Cadet

  DOI：10.1021/jo951900e

  日期：1996.1.1

  The main objectives of the present work were the synthesis of the two cis diastereomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine and the kinetic study of their hydrolytic deamination. The preparation of the two glycols, two main (OH)-O-.-mediated oxidation products of 5-methyl-2'-deoxycytidine, was achieved in two steps. The first one involved the synthesis of the two trans-(5R,6S)- and (5S,6R)-5-bromo-6-hydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine. In a subsequent step, the bromohydrins were specifically converted into the cis-(5S,6S) and (5R,6R) diastereomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine, respectively, under slightly alkaline conditions. The resulting glycols were purified by reverse phase high performance liquid chromatography and characterized by extensive spectroscopy measurements including C-13- and H-1-NMR analyses. Exact mass determination was Inferred from high resolution fast atom bombardment mass spectrometry measurements. Circular dichroism spectroscopy confirmed the diastereomeric relationship existing between the pair of glycols. Kinetic study of the deamination of the above glycols was carried out in phosphate buffer solutions (pH 7) at two different temperatures (37 degrees C and 25 degrees C) in order to determine the thermodynamic and kinetic parameters of the reaction.
• Boorstein, R. J.; Cadet, J.; Hilbert, T., Journal de Chimie Physique et de Physico-Chimie Biologique, 1993, vol. 90, # 4, p. 837 - 852
  作者：Boorstein, R. J.、Cadet, J.、Hilbert, T.、Lustig, M.、O'Donnell, R.、et al.

  DOI：——

  日期：——