8-bromotubercidin | 78000-56-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 8-bromotubercidin
• 英文别名: 6-Bromotubercidin；(2R,3R,4S,5R)-2-(4-amino-6-bromopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 78000-56-3
• 化学式: C₁₁H₁₃BrN₄O₄
• 分子量: 345.153
• InChiKey: KKSZEMHICOMLHV-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-bromotubercidin 在 吡啶 、 磷酸三乙酯 、 水 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 反应 170.25h， 生成 [[(2R,3S,4R,5R)-5-(4-amino-6-bromopyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
  参考文献：
  名称：

  Synthesis of 7-deaza-8-bromo cyclic adenosine 5′-diphosphate ribose: the first hydrolysis resistant antagonist at the cADPR receptor

  摘要：

  7-Deaza-8-bromo cyclic adenosine 5â²-diphosphate ribose 是由 7-deazaadenosine 通过 7-deaza-8-bromo nicotinamide adenine dinucleotide 合成的；它比 8-bromo 衍生物具有更强的拮抗作用，并具有化学和酶水解稳定性的优势。

  DOI：

  10.1039/a700336f
• 作为产物：
  描述：

  杀结核菌素 在 N-溴代丁二酰亚胺(NBS) 、 potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以40%的产率得到8-bromotubercidin
  参考文献：
  名称：

  Synthesis of 7-deaza-8-bromo cyclic adenosine 5′-diphosphate ribose: the first hydrolysis resistant antagonist at the cADPR receptor

  摘要：

  7-Deaza-8-bromo cyclic adenosine 5â²-diphosphate ribose 是由 7-deazaadenosine 通过 7-deaza-8-bromo nicotinamide adenine dinucleotide 合成的；它比 8-bromo 衍生物具有更强的拮抗作用，并具有化学和酶水解稳定性的优势。

  DOI：

  10.1039/a700336f

文献信息

• Chemical synthesis and biological activity of novel brominated 7-deazaadenosine-3′,5′-cyclic monophosphate derivatives
  作者：Marco Lelle、Maik Otte、Susanne Thon、Daniela Bertinetti、Friedrich W. Herberg、Klaus Benndorf

  DOI：10.1016/j.bmc.2019.03.024

  日期：2019.4

  Synthetic derivatives of cyclic adenosine monophosphate, such as halogenated or other more hydrophobic analogs, are widely used compounds, to investigate diverse signal transduction pathways of eukaryotic cells. This inspired us to develop cyclic nucleotides, which exhibit chemical structures composed of brominated 7-deazaadenines and the phosphorylated ribosugar. The synthesized 8-bromo- and 7-br

  环状腺苷单磷酸的合成衍生物，例如卤代或其他更疏水的类似物，是广泛使用的化合物，用于研究真核细胞的多种信号转导途径。这启发了我们开发环状核苷酸，该环状核苷酸具有由溴化7-脱氮基腺嘌呤和磷酸化核糖组成的化学结构。合成的8-溴和7-溴7-脱氮杂腺苷3'，5'-环单磷酸酯是环核苷酸调节的离子通道以及cAMP依赖性蛋白激酶的最有效激活剂。而且，这些物质紧密结合以交换被cAMP直接激活的蛋白质。
• Chemoenzymatic Synthesis of 7-Deaza Cyclic Adenosine 5‘-Diphosphate Ribose Analogues, Membrane-Permeant Modulators of Intracellular Calcium Release
  作者：Bo Zhang、Victoria C. Bailey、Barry V. L. Potter

  DOI：10.1021/jo071236p

  日期：2008.3.1

  [Graphics]An optimized synthetic route to 7-deaza-8-bromo-cyclic adenosine 5'-diphosphate ribose (7-deaza-8-bromo-cADPR 3), an established cell-permeant, hydrolysis-resistant cyclic adenosine 5'-diphosphate ribose (cADPR) antagonist, is presented. Using NMR analysis, we found that 3 adopted a C-2'endo conformation in the N9-linked ribose and a syn conformation about the N9-glycosyl linkage, which are similar to that of cADPR. The synthetic route was also employed to produce 7-deaza-2'-deoxy-cADPR 4, a potential cell-permeant cADPR analogue. 3 and 4 were more stable to chemical hydrolysis, consistent with the observation that 7-deaza-cADPR analogues are more stable than their parent adenosine derivatives. 3 was also found to be stable to enzyme-mediated hydrolysis using CD38 ectoenzyme.
• 7-Deazainosine Derivatives: Synthesis and Characterization of 7- and 7,8-Substituted Pyrrolo [2,3-<i>d</i>]Pyrimidine Ribonucleosides
  作者：Nunzia Ciliberti、Elisa Durini、Stefano Manfredini、Silvia Vertuani

  DOI：10.1080/15257770802089009

  日期：2008.4.18

  The synthesis of model 7 deazapurine derivatives related to tubercidin and toyocamycin has been performed. Tubercidin derivatives were obtained by simple conversion of the amino group of the heterocyclic moiety of the starting 7-deazadenosine compounds, into a hydroxyl group. Preparation of toyocamycin derivatives was accomplished by treatment of the silylated 6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-4-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose. The glycosylation reaction afforded a mixture of 8-bromo 7-cyano 2',3',5' tri-O-benzoyl 7-deazainosine and 6-bromo-5-cyano-3-(2',3',5'-tri-O-benzoyl-beta-D-ribofuranosyl)pyrrolo[2,3-d]-pyrimidin-4-one isomers: The structures were assigned on the basis of NMR spectroscopy studies. Next deprotection treatment gave the novel 7-deazainosine ribonucleosides.
• Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide–alkyne click reactions and direct C H bond functionalization
  作者：Sam Kavoosi、Ramanjaneyulu Rayala、Brenna Walsh、Maria Barrios、Walter G. Gonzalez、Jaroslava Miksovska、Logesh Mathivathanan、Raphael G. Raptis、Stanislaw F. Wnuk

  DOI：10.1016/j.tetlet.2016.08.053

  日期：2016.9

  8-bromotoyocamycin with sodium azide provided novel 8-azidotoyocamycin. Strain promoted click reactions of the latter with cyclooctynes resulted in the formation of the 1,2,3-triazole products. Iodine-mediated direct C8-H bond functionalization of tubercidin with benzotriazoles in the presence of tert-butyl hydroperoxide gave the corresponding 8-benzotriazolyltubercidin derivatives. The 8-(1,2,3-triazol-1-yl)-7-deazapurine

  用甲醇中的1,3-二溴-5,5-二甲基乙内酰脲（rt / 30分钟）处理Toyocamycin或sangivamycin（产率为30分钟），得到的8-溴代霉素和8-broangangivamycin收率很高。用叠氮化钠对8-溴代霉素进行亲核芳香取代，从而提供了新型的8-阿奇多卡霉素。后者与环辛炔的应变促进的点击反应导致形成1,2,3-三唑产物。在叔丁基氢过氧化物的存在下，碘介导的结核菌素与苯并三唑的直接C8-H键官能化得到相应的8-苯并三唑基tubercidin衍生物。8-（1,2,3-三唑-1-基）-7-脱氮嘌呤衍生物显示出适度的量子产率和〜100 nm的大斯托克斯位移。
• Synthesis of 7-deaza-8-bromo cyclic adenosine 5′-diphosphate ribose: the first hydrolysis resistant antagonist at the cADPR receptor
  作者：Victoria C. Bailey、Jaswinder K. Sethi、Antony Galione、Barry V. L. Potter

  DOI：10.1039/a700336f

  日期：——

  7-Deaza-8-bromo cyclic adenosine 5′-diphosphate ribose is synthesised from 7-deazaadenosine via 7-deaza-8-bromo nicotinamide adenine dinucleotide; it is both a more potent antagonist than the 8-bromo derivative and has the advantage of chemical and enzymatic hydrolytic stability.

  7-Deaza-8-bromo cyclic adenosine 5â²-diphosphate ribose 是由 7-deazaadenosine 通过 7-deaza-8-bromo nicotinamide adenine dinucleotide 合成的；它比 8-bromo 衍生物具有更强的拮抗作用，并具有化学和酶水解稳定性的优势。