6-羟基-5,6-二氢胸腺嘧啶 | 13514-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-羟基-5,6-二氢胸腺嘧啶
• 英文名称: 6-Hydroxydihydrothymine
• 英文别名: 6-hydroxy-5-methyl-dihydro-pyrimidine-2,4-dione；Thymine hydrate；6-hydroxy-5-methyl-1,3-diazinane-2,4-dione
• CAS: 13514-92-6
• 化学式: C₅H₈N₂O₃
• 分子量: 144.13
• InChiKey: IXLRNGYVHSNFAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  6-羟基-5,6-二氢胸腺嘧啶 在 氧气 作用下， 生成 5-甲基嘧啶-2,4,6(1H,3H,5H)-三酮
  参考文献：
  名称：

  Fahr, Egon; Fecher, Peter; Roth, Georg, Angewandte Chemie, 1980, vol. 92, # 10, p. 858 - 859

  摘要：

  DOI：
• 作为产物：
  描述：

  胸腺嘧啶 在 水 作用下， 生成 6-羟基-5,6-二氢胸腺嘧啶
  参考文献：
  名称：

  Fahr, Egon; Fecher, Peter; Roth, Georg, Angewandte Chemie, 1980, vol. 92, # 10, p. 858 - 859

  摘要：

  DOI：

文献信息

• RADIATION-INDUCED HYDROXYLATION OF THYMINE SENSITIZED BY NITRO COMPOUNDS IN N₂O-SATURATED AQUEOUS SOLUTION
  作者：Takeshi Wada、Hiroshi Ide、Sei-ichi Nishimoto、Tsutomu Kagiya

  DOI：10.1246/cl.1982.1041

  日期：1982.7.5

  Hydroxylation of thymine (1)to give thymine glycol (3) is remarkably promoted by the addition of nitro compounds (2a–f) in the γ-radiolysis of the N2O-saturated aqueous solution, although overall decomposition of 1 is depressed to some extent. The G-value of 3, increases linearly with increasing the one-electron reduction potential of 2a-f.

  通过在 N2O 饱和水溶液的 γ-辐射分解中添加硝基化合物 (2a-f) 显着促进了胸腺嘧啶 (1) 羟基化生成胸腺嘧啶乙二醇 (3)，尽管在一定程度上抑制了 1 的整体分解. G 值为 3，随着 2a-f 的单电子还原电位的增加而线性增加。
• PROMOTION EFFECT OF 2,2,6,6-TETRAMETHYLPIPERIDINE-1-OXYLS ON THE RADIOLYTIC HYDROXYLATION OF THYMINE IN DEAERATED AQUEOUS SOLUTION
  作者：Tsumotu Kagiya、Ryoji Kimura、Chikara Komuro、Koichi Sakano、Sei-ichi Nishimoto

  DOI：10.1246/cl.1983.1471

  日期：1983.9.5

  Remarkable promation of the hydroxylation of thimine to give thimine glycol with almost complete depression of side reactions by 2,2,6,6-tetramethylpiperidine-1-oxyl (TMPO·) derivatives was observed in the γ-radiolyses of the N2- and N2O-saturated aqueous solutions. In the O2-saturated solution, TMPO· depressed the thymine conversion close to the level under N2 while promoted the formation of thymine glycol to some extent by decreasing side reactions.

  在γ射线辐照下，N2和N2O饱和水溶液中观察到显著的胸腺嘧啶羟基化生成胸腺嘧啶二醇，同时几乎完全抑制了副反应，这一过程中2,2,6,6-四甲基哌啶-1-氧基（TMPO·）衍生物发挥了重要作用。在O2饱和溶液中，TMPO·虽抑制了胸腺嘧啶的转化至接近N2条件下的水平，但通过减少副反应在一定程度上促进了胸腺嘧啶二醇的生成。
• RADIATION-INDUCED REDUCTIVE CONVERSION OF 5-BROMO-6-HYDROXYTHYMINE TO THYMINE PROMOTED BY TRANSITION METAL SALTS IN DEAERATED AQUEOUS SOLUTION
  作者：Sei-ichi Nishimoto、Hiroshi Ide、Kikumi Nakamichi、Nobuaki Otsuki、Tsutomu Kagiya

  DOI：10.1246/cl.1983.1441

  日期：1983.9.5

  The radiation-induced reduction of 5-bromo-6-hydroxythymine to produce thymine (2) in deaerated aqueous solution was remarkably promoted by the addition of lower-valent transition metal salts (K4Fe(CN)6 (3a), CuCl (3b), K2PtCl6 (3c), and FeSO4(3d)). It is suggested that the possible intermediate hydroxythymine-5-yl radical undergoes one-electron reduction by 3a-d to the corresponding anion which eliminates

  添加低价过渡金属盐（K4Fe（CN）6（3a）、CuCl（3b））显着促进了5-溴-6-羟基胸腺嘧啶在脱气水溶液中的辐射诱导还原生成胸腺嘧啶（2） 、K2PtCl6 (3c) 和 FeSO4(3d))。这表明可能的中间体羟基胸腺嘧啶-5-基自由基通过 3a-d 进行单电子还原，生成相应的阴离子，从而消除 OH- 产生 2。
• Effect of Fe(III) Ions on the γ-Radiolysis of Thymine
  作者：S. N. Bhattacharyya、P. C. Mandal、S. Chakrabarti

  DOI：10.1246/bcsj.63.3001

  日期：1990.10

  Aqueous solutions of thymine (T) in the presence of Fe(III) were irradiated under deaerated conditions at pH ≈2. The products of radiolysis were separated by two dimensional thin-layer chromatography. In the absence of any metal ion, the G(-T) is 2.6 but when Fe(III) is present during radiolysis, the G(-T) increases significantly and reaches a limiting value of 3.2. The yields of the hydroxylated products

  胸腺嘧啶 (T) 在 Fe(III) 存在下的水溶液在 pH ≈2 的脱气条件下进行辐照。辐射分解产物通过二维薄层色谱分离。在没有任何金属离子的情况下，G(-T) 为 2.6，但当在辐射分解过程中存在 Fe(III) 时，G(-T) 显着增加并达到 3.2 的极限值。在 Fe(III) 存在下，胸腺嘧啶的羟基化产物的产率也会增加。结果由一种机制解释，该机制涉及 Fe(III) 与胸腺嘧啶的瞬态加合物的相互作用。
• Hydroxyl radical-induced cross-linking of thymine and lysine: Identification of the primary structure and mechanism
  作者：Syota Morimoto、Hiroshi Hatta、Shin-ichi Fujita、Tomochika Matsuyama、Tôru Ueno、Sei-ichi Nishimoto

  DOI：10.1016/s0960-894x(98)00124-3

  日期：1998.4

  Hydroxyl radical-induced formation of a cross-link of thymine (Thy) and lysine (Lys) in the gamma-radiolysis of N2O-saturated aqueous solution was studied. A Thy-Lys cross-link (I) of the formal structure that OH radical and 4-carbon-centered Lys radical added respectively to C(5) and C(6) positions of Thy was isolated by a preparative HPLC and identified by a FAB-HRMS. The primary cross-link I was dehydrated by treatment with HCl at 120 degrees C to yield the secondary structure (II) possessing a C(5)-C(6) double bond in the Thy moiety: the latter structure II was reported previously (Dizdaroglu, M.; Gajewski, E. Cancer Res. 1989, 49, 3463-3467). A pulse radiolysis study with a redox titration method indicated that 4-carbon centered Lys radical intermediate was of neutral redox reactivity in contrast to reducing reactivity of 5-hydroxy-5,6-dihydrothymin-6-yl radical intermediate. The cross-link I could be formed by a conventional radical recombination mechanism, but not by an ionic recombination mechanism involving a redox reaction between the radical intermediates. (C) 1998 Elsevier Science Ltd. All rights reserved.