盐酸土霉素兽药 | 73-39-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 盐酸土霉素兽药
• 英文名称: C⁵-(allyl)-2'-deoxyuridine
• 英文别名: 5-allyl-2'-deoxyuridine；5'-allyluridine；5-allyl-2'-deoxy-uridine；5-Allyl-2'-deoxyuridin；Uridine, 5-allyl-2'-deoxy-；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-prop-2-enylpyrimidine-2,4-dione
• CAS: 73-39-2
• 化学式: C₁₂H₁₆N₂O₅
• 分子量: 268.269
• InChiKey: XUAFMQXKGPTTJN-IVZWLZJFSA-N

物化性质

• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  盐酸土霉素兽药 在 Grubbs catalyst first generation 吡啶 、 四氮唑 、 叔丁基过氧化氢 、 ammonium hydroxide 、 对甲苯磺酸 、 silver nitrate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 Phosphoric acid (2R,3S,5R)-5-[5-((E)-4-amino-but-2-enyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Tandem ring-closing metathesis and hydrogenation towards cyclic dinucleotides

  摘要：

  含有丁烯核碱基-磷酸三酯连接的环状二核苷酸是通过串联闭环复分解和氢化反应合成的。

  DOI：

  10.1039/b206560f
• 作为产物：
  描述：

  5-(chloromercuri)-2'-deoxyuridine 、 3-氯丙烯 在 palladium dichloride 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以78%的产率得到盐酸土霉素兽药
  参考文献：
  名称：

  二硫键交联 DNA 三螺旋的结构和动力学

  摘要：

  介绍了两个二硫化物交联分子内pyr·pur-pyr 三螺旋（IV 和V）的设计、合成和表征。从 Hoogsteen 链到 Watson-Crick 双链的共价交联的放置在交联的 DNA 中相对于亲本序列产生了两个基本变化。首先，交联的形成导致 Hoogsteen 胞嘧啶的表观 pKa 增加 1.5 pKa 单位（IV 和 V 分别增加到 8.6 和 8.3），同时在 pH 值下热稳定性增加约 40 °C 7.4. 其次，交联在广泛的溶液条件下增强了三重结构，包括与生理相关的条件（例如，pH 7.4、155 mM Na+、37 °C）。CD 和 NMR 测量表明，交联不会显着扰乱 IV 和 V 相对于其未改性对应物的几何形状。因为二硫化物交联有效地防止了与 pyr·pur-pyr 三重螺旋相关的构象异质性...

  DOI：

  10.1021/ja963285h

文献信息

• SYNTHESIS AND STUDY OF THE FLUORESCEIN CONJUGATE OF THE NUCLEOTIDE dPTP
  作者：W. J. Cummins、A. L. Hamilton、C. L. Smith、M. S. J. Briggs

  DOI：10.1081/ncn-100002489

  日期：2001.3.31

  The synthesis of a fluorescein conjugate on the non-natural base P is described. The ability of the newly synthesised fluorescein--dPTP and of a fluorescein-11-dUTP to compete with the natural nucleotide TTP was also studied. Overall the efficiency of labelling a nucleic acid with a fluorescein moiety was found to be approximately equal.

  描述了在非天然碱基P上的荧光素缀合物的合成。还研究了新合成的荧光素-dPTP和荧光素-11-dUTP与天然核苷酸TTP竞争的能力。总的来说，发现用荧光素部分标记核酸的效率大致相等。
• Photoinduced reactions. 169. Photochemistry of 5- and 6-iodouracils in the presence of alylsilanes and alkenes. A convenient route to (C5)- and (C6)-substituted uracils
  作者：Isao Saito、Hideyuki Ikehira、Teruo Matsuura

  DOI：10.1021/jo00376a018

  日期：1986.12
• A facile photochemical route to C-5 and C-6 allyl-substituted uracil nucleosides
  作者：Isao Saito、Hideyuki Ikehira、Teruo Matsuura

  DOI：10.1016/s0040-4039(00)98361-8

  日期：1985.1
• Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity
  作者：John Goodchild、Roderick A. Porter、Robert H. Raper、Iain S. Sim、Roger M. Upton、Julie Viney、Harry J. Wadsworth

  DOI：10.1021/jm00363a009

  日期：1983.9

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.
• Dinucleotides containing two allyl groups by combinations of allyl phosphotriesters, 5-allyl-, 2′-O-allyl- and 2′-arabino-O-allyl uridine derivatives as substrates for ring-closing metathesis
  作者：Philip Børsting、Morten Freitag、Poul Nielsen

  DOI：10.1016/j.tet.2004.09.023

  日期：2004.11

  Five different dinucleotides, each containing two allyl groups in various positions, were prepared and studied as substrates for ring-closing metathesis reactions. These dinucleotides were designed from appropriate nucleoside building blocks combining four different positions for the allyl group; the allyl phosphotriester linkage, 5-allyl-2' -deoxyuridine, and ribo- as well as arabino-configured 2'-O-allyluridine. Thus, convenient procedures for these building blocks were developed. From the dinucleotides, two new cyclic nucleotide structures were obtained; one connecting two adjacent nucleobase moieties and the other forming an unsaturated four-carbon linkage between the phosphate moiety and the adjacent pyrimidine nucleobase. The latter cyclic dinucleotide was also prepared with a saturated four-carbon linkage using a tandem ring-closing metathesis-hydrogenation procedure. This compound was found to be significantly more stable towards a nucleophilic ring-opening than its unsaturated counterpart. (C) 2004 Elsevier Ltd. All rights reserved.