2',3'-O-isopropylidene-5'-O-phenoxycarbonyluridine | 42021-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2',3'-O-isopropylidene-5'-O-phenoxycarbonyluridine
• 英文别名: O^{2'_,O3'_{-isopropylidene-O}5'}-phenoxycarbonyl-uridine；2',3'-Isopropyliden-5'-O-carbophenoxyuridin
• CAS: 42021-79-4
• 化学式: C₁₉H₂₀N₂O₈
• 分子量: 404.376
• InChiKey: MBYMHZHASAOWKD-DTZQCDIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  118.08
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2',3'-O-isopropylidene-5'-O-phenoxycarbonyluridine 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Design and synthesis of chitin synthase inhibitors as potent fungicides

  摘要：

  Chitin is a structural component of fungal cell walls but is absent in vertebrates, mammals, and humans. Chitin synthase is thus an attractive molecular target for developing fungicides. Based on the structure of its donor substrate, UDP-N-acetyl-glucosamine, as well as the modelled structure of the bacterial chitin synthase NodC, we designed a novel scaffold which was then further optimized into a series of chitin synthase inhibitors. The most potent inhibitor, compound 13, exhibited high chitin synthase inhibitory activity with an IC50 value of 64.5 mu mol/L. All of the inhibitors exhibited antifungal activities against the growth of agriculturally-destructive fungi, Fusarium graminearum,Botrytis cinerea, and Colletotrichum lagenarium. This work presents a new scaffold which can be used for the development of novel fungicides. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.03.030
• 作为产物：
  描述：

  尿嘧啶核苷 在 吡啶 、 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 二氯甲烷 为溶剂， 生成 2',3'-O-isopropylidene-5'-O-phenoxycarbonyluridine
  参考文献：
  名称：

  Design and synthesis of chitin synthase inhibitors as potent fungicides

  摘要：

  Chitin is a structural component of fungal cell walls but is absent in vertebrates, mammals, and humans. Chitin synthase is thus an attractive molecular target for developing fungicides. Based on the structure of its donor substrate, UDP-N-acetyl-glucosamine, as well as the modelled structure of the bacterial chitin synthase NodC, we designed a novel scaffold which was then further optimized into a series of chitin synthase inhibitors. The most potent inhibitor, compound 13, exhibited high chitin synthase inhibitory activity with an IC50 value of 64.5 mu mol/L. All of the inhibitors exhibited antifungal activities against the growth of agriculturally-destructive fungi, Fusarium graminearum,Botrytis cinerea, and Colletotrichum lagenarium. This work presents a new scaffold which can be used for the development of novel fungicides. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.03.030

文献信息

• SYSTEMATIC SYNTHESIS OF PURINE 8,5′-IMINO AND SUBSTITUTED IMINO CYCLONUCLEOSIDES
  作者：Tadashi Sasaki、Katsumaro Minamoto、Yasumi Fujiki

  DOI：10.1246/cl.1983.1017

  日期：1983.7.5

  To achieve a systematic synthesis of purine 8,5'-imino and substituted imino cyclonucleosides, 2',3'-O-isopropylidene-purinenucleosides substituted with a methylamino (4a,b), benzyl-amino (4c,d,g and h) and allylamino group (4e,f,i and j) at the C8 were synthesized. With these substrates in hand, extensive 8,5'-cyclization reactions were carried out using diphenyl carbonate/Et3N (Method A), N,N'-carbonyldiimidazole

  为了实现嘌呤 8,5'-亚氨基和取代亚氨基环核苷的系统合成，2',3'-O-异亚丙基-嘌呤核苷被甲氨基 (4a,b)、苄基氨基 (4c,d,g 和 h ) 和 C8 处的烯丙氨基 (4e,f,i 和 j) 被合成。使用这些底物，使用碳酸二苯酯/Et3N（方法 A）、N,N'-羰基二咪唑（方法 B）和 Mitsunobu 反应（方法 C）进行广泛的 8,5'-环化反应，得到 8,5 '-取代的亚氨基环核苷（5a、c、d、e、f和g）。方法C的环化产率一般高于其他两种方法。5a、b、c、d、e、f、g和h通过一或两步脱保护为相应的母体化合物8。在鸟苷系列中，一个新的循环系统包括一个 8,5'
• Versatile Site-Specific Conjugation of Small Molecules to siRNA Using Click Chemistry
  作者：Takeshi Yamada、Chang Geng Peng、Shigeo Matsuda、Haripriya Addepalli、K. Narayanannair Jayaprakash、Md. Rowshon Alam、Kathy Mills、Martin A. Maier、Klaus Charisse、Mitsuo Sekine、Muthiah Manoharan、Kallanthottathil G. Rajeev

  DOI：10.1021/jo101761g

  日期：2011.3.4

  We have previously demonstrated that conjugation of small molecule ligands to small interfering RNAs (siRNAs) and anti-microRNAs results in functional siRNAs and antagomirs in vivo. Here we report on the development of an efficient chemical strategy to make oligoribonucleotide-ligand conjugates using the copper-catalyzed azide-alkyne cycloaddition (CuAAC) or click reaction. Three click reaction approaches were evaluated for their feasibility and suitability for high-throughput synthesis: the CuAAC reaction at the monomer level prior to oligonucleotide synthesis, the solution-phase postsynthetic "click conjugation", and the "click conjugation" on an immobilized and cornpletely protected alkyne-oligonucleotide scaffold. Nucleosides bearing 5'-alkyne moieties were used for conjugation to the 5'-end of the oligonucleotide. Previously described 2'- and 3'-O-propargylated nucleosides were prepared to introduce the alkyne moiety to the 3' and 5' termini and to the internal positions of the scaffold. Azido-functionalized ligands bearing lipophilic long chain alkyls, cholesterol, oligoamine, and carbohydrate were utilized to study the effect of physicochemical characteristics of the incoming azide on click conjugation to the alkyne-oligonucleotide scaffold in solution and on immobilized solid support. We found that microwave-assisted click conjugation of azido-functionalized ligands to a fully protected solid-support bound alkyne-oligonucleotide prior to deprotection was the most efficient "click conjugation" strategy for site-specific, high-throughput oligonucleotide conjugate synthesis tested. The siRNA conjugates synthesized using this approach effectively silenced expression of a luciferase gene in a stably transformed HeLa cell line.