(+)-trans-(5S,6S)-5,6-dihydroxy-5,6-dihydrothymidine | 38645-24-8

• 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: (+)-trans-(5S,6S)-5,6-dihydroxy-5,6-dihydrothymidine
• 英文别名: (-)-trans-(5S,6S)-5,6-dihydroxy-5,6-dihydrothymidine；trans-5'-carboxy-5,6-dihydroxy-5,6-dihydro thymidine；(-)trans(5S,6S)-5,6-dihydroxy-5,6-dihydrothymidine；trans-(5S,6S)-5,6-dihydroxy-5,6-dihydrothymidine；(5S,6S) 5,6-dihydroxy-5,6-dihydrothymidine；(5S,6S)-5,6-Dihydro-5,6-dihydroxythymidine；(5S,6S)-5,6-dihydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,3-diazinane-2,4-dione
• CAS: 38645-24-8
• 化学式: C₁₀H₁₆N₂O₇
• 分子量: 276.246
• InChiKey: RKEITGVZZHXKON-NLFXGDPDSA-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：

  (+)-trans-(5S,6S)-5,6-dihydroxy-5,6-dihydrothymidine 以 水 为溶剂， 反应 1.5h， 生成 cis(+) et cis(-) 5,6-dihydroxy-5,6-dihydrothymidine
  参考文献：
  名称：

  Boorstein, R. J.; Cadet, J.; Hilbert, T., Journal de Chimie Physique et de Physico-Chimie Biologique, 1993, vol. 90, # 4, p. 837 - 852

  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 potassium osmate(VI) 甲基磺酰胺 、 bis-dihydroquinone phthalazine ligand 、 四丁基氟化铵 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 为溶剂， 反应 90.0h， 生成 (+)-trans-(5S,6S)-5,6-dihydroxy-5,6-dihydrothymidine
  参考文献：
  名称：

  Diastereoselective synthesis of hydroxylated dihydrothymidines resulting from oxidative stress

  摘要：

  DOI：

  10.1021/jo00074a057

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。
• Shaw, Anthony A.; Voituriez, Lucienne; Cadet, Jean, Journal of the Chemical Society. Perkin transactions II, 1988, p. 1303 - 1308
  作者：Shaw, Anthony A.、Voituriez, Lucienne、Cadet, Jean、Gregoli, Silvano、Symons, Martyn C.

  DOI：——

  日期：——
• 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：——
• Conformational and Electronic Properties of the Two <i>Cis </i>(5<i>S</i>,6<i>R</i>) and (5<i>R</i>,6<i>S</i>) Diastereoisomers of 5,6-Dihydroxy-5,6-dihydrothymidine:  X-ray and Theoretical Studies
  作者：Franck Jolibois、Lucienne Voituriez、André Grand、Jean Cadet

  DOI：10.1021/tx9501344

  日期：1996.1.1

  The structure of(+)-cis-(5S,6R)-5,6-dihydroxy-5,6-dihydrothymidine was obtained using X-ray crystallography [space group P2(1) with a = 10.130(3) Angstrom, b = 6.434(9) Angstrom, c = 11.02(5) Angstrom, and beta = 112.646(2)degrees]. The comparison of the two cis diastereoisomers of thymidine glycol (I,II) showed several structural and conformational differences. The solid state structures appear to be in agreement with the results of H-1 NMR studies which were carried out in aqueous solution. Conformational and electronic properties of the ground state of the molecules I and II were obtained using ab initio LSD-DFT theory. Only slight differences between the crystal structure and the optimized geometry are observed for each of the two oxidized nucleosides. On the other hand, molecules I and II exhibit significant differences in their electronic properties. In particular, the dipole moment of (5S,6R)-thymidine glycol (I) is twice smaller than that of the (5R,6S) diastereoisomer (II). It is noteworthy that these differences in the electronic properties between the two compounds may be related to changes in the rotameric population around the C4'-C5' bond. The repartition of the electrostatic potential is different in the two compounds. These observations lead to a better understanding of the structural changes when the above lesions are induced within a DNA molecule.
• Diastereoselective synthesis of hydroxylated dihydrothymidines resulting from oxidative stress
  作者：Mark R. Barvian、Marc M. Greenberg

  DOI：10.1021/jo00074a057

  日期：1993.10