7-(trimethylsilyl)theophylline | 62374-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 7-(trimethylsilyl)theophylline
• 英文别名: Theophylline TMS derivative；1,3-dimethyl-7-trimethylsilylpurine-2,6-dione
• CAS: 62374-32-7
• 化学式: C₁₀H₁₆N₄O₂Si
• 分子量: 252.348
• InChiKey: KPBTTYFAGBODJB-UHFFFAOYSA-N

物化性质

• 沸点：
  402.9±37.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-(trimethylsilyl)theophylline 在 N-氯代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 13.0h， 生成 8-chloro-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)theophylline
  参考文献：
  名称：

  Synthesis of 8-Substituted Theophyllineβ-D-Ribofuranosides

  摘要：

  Methods for the synthesis of 8-chloro- and 8-bromotheophylline D-riboside triacetates by the chlorination of 7-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-theophylline with N-chlorosuccinimide or by the glycosylation of 8-bromotheo-phylline with 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose were found. Nucleophilic displacement of the halogen gave 8-amino-, 8-alkylamino-, 8-benzylamino-, and 8-hydrazinotheophylline beta-D-ribofuranosides.

  DOI：

  10.1080/07328319308018553
• 作为产物：
  描述：

  1-甲基黄嘌呤 在 sodium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 33.0h， 生成 7-(trimethylsilyl)theophylline
  参考文献：
  名称：

  Use of (pivaloyloxy)methyl as a protecting group in the synthesis of antigenic theophylline (1,3-dimethylxanthine) derivatives

  摘要：

  DOI：

  10.1021/jo01297a048

文献信息

• Synthesis of Theophylline and 6-Thiotheophylline 7-Ribosyl Nucleosides
  作者：Rodrigo Rico-Gómez、Angel Rodríguez-González、Josefa Ríos-Ruíz、Francisco Nájera、J. Manuel López-Romero

  DOI：10.1002/ejoc.200300377

  日期：2003.10

  The syntheses of theophylline and thiotheophylline 7-ribopyranose and 7-ribofuranose nucleosides, both by direct coupling of the base and the sugar and by construction of the imidazole ring, are reported. The conformational syn/anti equilibrium of the peracetyl derivatives was studied by molecular mechanics and by the low-temperature line-shape/1H NMR method. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  报告了茶碱和硫茶碱 7-吡喃核糖和 7-呋喃核糖核苷的合成，包括碱基和糖的直接偶联以及咪唑环的构建。通过分子力学和低温线形/1H NMR 方法研究了过乙酰基衍生物的构象同步/反平衡。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• STEREOSELECTIVE SYNTHESIS OF α-RIBONUCLEOSIDES FROM 1-HYDROXY SUGARS BY USING 2-FLUOROPYRIDINIUM TOSYLATE
  作者：Teruaki Mukaiyama、Yukihiko Hashimoto、Yujiro Hayashi、Shin-ichiro Shoda

  DOI：10.1246/cl.1984.557

  日期：1984.4.5

  A novel method for the preparation of α-ribonucleosides was developed by the use of 2-fluoro-1-methylpyridinium tosylate as a condensing reagent. Various α-ribonucleosides were synthesized from 1-hydroxy sugars and trimethylsilylated nitrogen compounds, such as nucleoside bases and azide, in good yields under mild conditions.

  通过使用甲苯磺酸 2-氟-1-甲基吡啶鎓作为缩合剂开发了一种制备 α-核糖核苷的新方法。在温和的条件下，从 1-羟基糖和三甲基硅烷化氮化合物（如核苷碱基和叠氮化物）合成了各种 α-核糖核苷，收率良好。
• The synthesis and biological evaluation of nucleobases/tetrazole hybrid compounds: A new class of phosphodiesterase type 3 (PDE3) inhibitors
  作者：Mohsen Shekouhy、Somaye Karimian、Ali Moaddeli、Zeinab Faghih、Yousef Delshad、Ali Khalafi-Nezhad

  DOI：10.1016/j.bmc.2020.115540

  日期：2020.6

  Spired by the chemical structure of Cilostazol, a selective phosphodiesterase 3A (PDE3A) inhibitor, several novel hybrid compounds of nucleobases (uracil, 6-azauracil, 2-thiuracil, adenine, guanine, theophylline and theobromine) and tetrazole were designed and successfully synthesized and their inhibitory effects on PDE3A as well as their cytotoxicity on HeLa and MCF-7 cancerous cell lines were studied

  受西洛他唑，选择性磷酸二酯酶3A（PDE3A）抑制剂的化学结构的刺激，设计并成功合成了几种新型核碱基（尿嘧啶，6-氮杂尿嘧啶，2-硫嘧啶，腺嘌呤，鸟嘌呤，茶碱和可可碱）和四唑的杂合化合物。研究了它们对PDE3A的抑制作用以及对HeLa和MCF-7癌细胞系的细胞毒性。所得结果表明合成化合物的抑制作用与其细胞毒性之间呈线性关系。在某些情况下，合成化合物对PDE3A的抑制作用高于西洛他唑。此外，与标准抗癌药甲氨蝶呤相比，一些合成的化合物对HeLa和MCF-7癌细胞具有更高的细胞毒性。
• An improved method for the preparation of 2′,3′-unsaturated nucleosides: Synthesis of stereospecifically labelled ketonucleosides
  作者：Jean Herscovici、Roland Montserret、Kostas Antonakis

  DOI：10.1016/0008-6215(88)80133-2

  日期：1988.5

  excellent yields under mild conditions by the condensation of acetylated glycals with purine or pyrimidine derivatives in the presence of trityl perchlorate. The synthesis of (α- and β-hex-2-enopyranosyl-4-ulose)theophylline nucleosides labelled at position 3′ with deuterium is described.

  摘要在高氯酸三苯酯存在下，乙酰化的糖基与嘌呤或嘧啶衍生物缩合，在温和条件下以极高的收率制备了2'，3'-不饱和核苷。描述了在3'位用氘标记的（α-和β-hex-2-enopyranosyl-4-ulose）茶碱核苷的合成。
• Nucleosides 9: Design and synthesis of new 8-nitro and 8-amino xanthine nucleosides of expected biological activity
  作者：Mosselhi A. N. M. Mohamed、Laila M. B. Abu-Alola、Nada M. G. Aljaied

  DOI：10.1080/15257770.2017.1395036

  日期：2017.12.2

  5-tri-O-benzoyl-β-D-ribofuranose afforded the corresponding protected nucleosides, respectively. Nitration of each of the theophylline and 3-benzy-1-methyllxanthine protected nucleosides yielded the corresponding 8-nitronucleosides derivatives, which were reduced to give the corresponding 8-aminonucleoside derivatives. Debenzoylation of protected nucleosides formed by using methanolic sodium methoxide afforded the

  摘要1,3-二甲基黄嘌呤（茶碱），3-苄基黄嘌呤和3-苄基-1-甲基黄嘌呤与1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖的偶联反应相应的被保护的核苷。茶碱和3-苄基-1-甲基黄嘌呤保护的核苷中的每一个的硝化产生相应的8-硝基核苷衍生物，将其还原以得到相应的8-氨基核苷衍生物。通过使用甲醇甲醇钠形成的被保护的核苷进行脱苯甲酰化，分别得到相应的游离N-核苷。已经阐明并报道了产品的结构，并且还筛选了一些产品的抗微生物活性。一些被测产品显示中等活性。图形概要

表征谱图