2',3',5'-tri-O-acetyl-8-(trifluoromethyl)inosine | 76513-93-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2',3',5'-tri-O-acetyl-8-(trifluoromethyl)inosine
• 英文别名: 8-trifluoromethyl-2',3',5'-tri-O-acetylinosine；8-(Trifluoromethyl)inosine 2',3',5'-triacetate；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[6-oxo-8-(trifluoromethyl)-1H-purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 76513-93-4
• 化学式: C₁₇H₁₇F₃N₄O₈
• 分子量: 462.339
• InChiKey: HVMZZOPURHGVIH-SDBHATRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  氟磺酰基二氟乙酸甲酯 、 2',3',5'-tri-O-acetyl-8-bromoinosine 在 六甲基磷酰三胺 、 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2',3',5'-tri-O-acetyl-8-(trifluoromethyl)inosine
  参考文献：
  名称：

  Trifluoromethylated cyclic-ADP-ribose mimic: synthesis of 8-trifluoromethyl-N1-[(5′′-O-phosphorylethoxy)methyl]-5′-O-phosphorylinosine-5′,5′′-cyclic pyrophosphate (8-CF3-cIDPRE) and its calcium release activity in T cells

  摘要：

  首先应用了一种便捷的三氟甲基化方法合成8-三氟甲基嘌呤核苷。在此基础上,研发了新颖的保护和去保护策略,顺利合成了三氟甲基化环状ADP核糖模拟物,即8-CF\({}_{3}\)-cIDPRE 1。利用完整、装载了fura-2的Jurkat T细胞,化合物1和2′,3′-O-异亚丙基-8-CF\({}_{3}\)-cIDPRE 14被鉴定为膜渗透性cADPR激动剂。与主要作为细胞内cADPR拮抗剂的8-取代cADPR类似物相反,8-取代cIDPRE衍生物显示为钙动员激动剂。本文报道,即使化合物1,即含有强吸电子CF\({}_{3}\)基团的8-取代cIDPRE,在T细胞中亦表现激动剂性质。有趣的是,部分保护的2′,3′-O-异亚丙基-8-CF\({}_{3}\)-cIDPRE也激活了钙信号,表明cADPR南侧核糖上的羟基对其生物活性仅有微小作用。据我们所知,8-CF\({}_{3}\)-cIDPRE 1是首个报道的含氟cADPR模拟物,而8-CF\({}_{3}\)-cIDPRE 1及化合物14则是阐明cADPR作用机制的有前景的分子探针。

  DOI：

  10.1039/c0ob00090f

文献信息

• Studies on organic fluorine compounds. Part 35. Trifluoromethylation of pyrimidine- and purine-nucleosides with trifluoromethyl–copper complex
  作者：Yoshiro Kobayashi、Kenjiro Yamamoto、Toyohira Asai、Masanori Nakano、Itsumaro Kumadaki

  DOI：10.1039/p19800002755

  日期：——

  Halogenated nucleoside derivatives were trifluoromethylated using a solution of a trifluoromethyl–copper complex, which was prepared by shaking trifluoromethyl iodide and copper powder in hexamethylphosphoric triamide and filtering off the excess of copper powder. The following trifluoromethylated nucleosides were obtained in moderate to good yields: 5-trifluoromethyl-uridine, -deoxyuridine, -cytidine

  使用三氟甲基-铜络合物的溶液将卤代的核苷衍生物进行三氟甲基化，该溶液是通过将三氟甲基碘和铜粉在六甲基磷酸三酰胺中振摇并滤出过量的铜粉而制得的。以中等至良好的产率获得以下三氟甲基化的核苷：5-三氟甲基-尿苷，-脱氧尿苷，-胞苷，-脱氧胞苷和-阿拉伯糖基胞嘧啶；8-三氟甲基-腺苷，-脱氧腺苷和-肌苷；和6-三氟甲基核呋喃呋喃糖基嘌呤。该程序提供了许多三氟甲基化合物的简单合成方法。
• Nucleobase Having Perfluoroalkyl Group and Process for Producing the Same
  申请人：Yamakawa Tetsu

  公开号：US20090124796A1

  公开（公告）日：2009-05-14

  Provided is a simple and efficient production process of a nucleobase having a perfluoroalkyl group. A nucleobase (for example, uracils, cytosines, adenines, guanines, hypoxanthines, xanthines, or the like) is reacted with a perfluoroalkyl halide in the presence of a sulfoxide, a peroxide and an iron compound to produce a perfluoroalkyl-substituted nucleobase, which is useful as an intermediate for medical drugs, economically.

  提供一种具有全氟烷基的核碱的简单高效的生产工艺。将核碱（例如尿嘧啶、胞嘧啶、腺嘌呤、鸟嘌呤、次黄嘌呤、黄嘌呤等）与全氟烷基卤化物在亚砜、过氧化物和铁化合物的存在下反应，制得全氟烷基取代的核碱，该中间体在医药制剂中具有经济价值。
• Nucleobase having perfluoroalkyl group and process for producing the same
  申请人：Tosoh Corporation

  公开号：US07884202B2

  公开（公告）日：2011-02-08

  Nucleobases are perfluoroalkylated in a one step process with a perfluoroalkyl halide in the presence of a sulfoxide, a peroxide and an iron compound. Compounds so produced are useful as medicinal drugs, intermediates for medicinal drugs and agricultural chemicals.

  核碱基可以在有亚砜、过氧化物和铁化合物的存在下，通过一步法与全氟烷基卤化物进行全氟烷基化。这样产生的化合物可用作药物、药物中间体和农药。
• NUCLEIC ACID BASE HAVING PERFLUOROALKYL GROUP AND METHOD FOR PRODUCING THE SAME
  申请人：Tosoh Corporation

  公开号：EP1947092A1

  公开（公告）日：2008-07-23

  Provided is a simple and efficient production process of a nucleobase having a perfluoroalkyl group. A nucleobase (for example, uracils, cytosines, adenines, guanines, hypoxanthines, xanthines, or the like) is reacted with a perfluoroalkyl halide in the presence of a sulfoxide, a peroxide and an iron compound to produce a perfluoroalkyl-substituted nucleobase, which is useful as an intermediate for medical drugs, economically.

  本发明提供了一种具有全氟烷基的核碱基的简单而高效的生产工艺。 核碱基（例如尿嘧啶、胞嘧啶、腺嘌呤、鸟嘌呤、次黄嘌呤、黄嘌呤或类似物）在亚砜、过氧化物和铁化合物的存在下与全氟烷基卤化物反应，生成全氟烷基取代的核碱基，该核碱基可经济地用作医疗药物的中间体。
• Method for producing nucleic acid base having perfluoroalkyl group
  申请人：Tosoh Corporation

  公开号：EP1947092B1

  公开（公告）日：2015-04-15