1-(2-deoxy-2-isocyano-β-D-arabinofuranosyl)cytosine | 153265-57-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2-deoxy-2-isocyano-β-D-arabinofuranosyl)cytosine
• 英文别名: Ncdac；4-amino-1-[(2R,3S,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-isocyanooxolan-2-yl]pyrimidin-2-one
• CAS: 153265-57-7
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: SSDLPLWBMNUNRB-VCGXYPBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-<2-deoxy-2-isocyano-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl>uracil 在 ammonium hydroxide 、 triisopropylbenzenesulfonyl chloride 、 四丁基氟化铵 、 四丁基溴化铵 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 1-(2-deoxy-2-isocyano-β-D-arabinofuranosyl)cytosine
  参考文献：
  名称：

  Matsuda; Dan; Minakawa, Journal of Medicinal Chemistry, 1993, vol. 36, # 26, p. 4190 - 4194

  摘要：

  DOI：

文献信息

• SYNTHESIS OF ARA-2'-O-METHYL-NUCLEOSIDES, CORRESPONDING PHOSPHORAMIDITES AND OLIGONUCLEOTIDES INCORPORATING NOVEL MODIFICATIONS FOR BIOLOGICAL APPLICATION IN THERAPEUCTICS, DIAGNOSTICS, G- TETRAD FORMING OLIGONUCLEOTIDES AND APTAMERS
  申请人：Srivastava Suresh C.

  公开号：US20120149888A1

  公开（公告）日：2012-06-14

  The present invention relates to synthesis, purification and methods to obtain high purity novel 2′-arabino-O-methyl nucleosides and the corresponding phosphoramidites of various arabinonucleoside bases and introduction of such units into defined sequence synthetic DNA and RNA. Various synthetic oligonucleotides, such as HIV integrase inhibitor 14-mer and thrombin binding oligonucleotide, thrombin-1, bearing ara-2′-omethyl modification have been synthesized. It is anticipated the oligonucleotides incorporating these monomers will exhibit biological activities related to antisense approach approach, design of better SiRNA's, diagnostic agents. Similarly, it is anticipated that oligonucleotides incorporating such novel nucleosides will be useful to develop therapeutic candidates designing stable G-quadruplexes and Aptamers for oligonucleotide structure, folding topology, evaluation of biochemical properties and design and develop as therapeutic agents. It is further anticipated that the nucleosides, phosphates and triphosphates of this invention could develop as therapeutic agents.

  本发明涉及合成、纯化和获取高纯度新型2'-阿拉伯核苷-O-甲基核苷和各种阿拉伯核苷基的相应磷酰胺酯的方法，并将这些单元引入到定义的序列合成DNA和RNA中。已合成了各种合成寡核苷酸，例如HIV整合酶抑制剂14-mer和凝血酶结合寡核苷酸，凝血酶-1，带有ara-2'-omethyl修饰。预计包含这些单体的寡核苷酸将展示与反义方法、更好的SiRNA设计、诊断剂相关的生物学活性。同样，预计包含这些新型核苷的寡核苷酸将有助于开发稳定的G四链体和寡核苷酸结构的Aptamers，用于寡核苷酸结构、折叠拓扑、生化特性的评估和设计和开发为治疗剂。进一步预计，本发明的核苷、磷酸盐和三磷酸盐可作为治疗剂开发。
• SYNTHESIS OF ARA-2'-O-METHYL-NUCLEOSIDES, CORRESPONDING PHOSPHORAMIDITES AND OLIGONUCLEOTIDES INCORPORATING NOVEL MODIFICATIONS FOR BIOLOGICAL APPLICATION IN THERAPEUTICS, DIAGNOSTICS, G- TETRAD FORMING OLIGONUCLEOTIDES AND APTAMERS
  申请人：Chemgenes Corporation

  公开号：EP2398815A2

  公开（公告）日：2011-12-28
• [EN] SYNTHESIS OF ARA-2'-O-METHYL-NUCLEOSIDES, CORRESPONDING PHOSPHORAMIDITES AND OLIGONUCLEOTIDES INCORPORATING NOVEL MODIFICATIONS FOR BIOLOGICAL APPLICATION IN THERAPEUTICS, DIAGNOSTICS, G- TETRAD FORMING OLIGONUCLEOTIDES AND APTAMERS<br/>[FR] SYNTHÈSE DE ARA-2'-O-MÉTHYL-NUCLÉOSIDES, PHOSPHORAMIDITES CORRESPONDANTS ET OLIGONUCLÉOTIDES INCORPORANT DE NOUVELLES MODIFICATIONS POUR UNE APPLICATION BIOLOGIQUE EN THÉRAPEUTIQUE, DIAGNOSTIC, OLIGONUCLÉOTIDES FORMANT UN G-TÉTRADE ET APTAMÈRES
  申请人：CHEMGENES CORP

  公开号：WO2010096201A2

  公开（公告）日：2010-08-26

  The present invention relates to synthesis, purification and methods to obtain high purity novel 2'-arabino-O-methyl nucleosides and the corresponding phosphoramidites of various arabinonucleoside bases and introduction of such units into defined sequence synthetic DNA and RNA. Various synthetic oligonucleotides, such as HIV integrase inhibitor 14-mer and thrombin binding oligonucleotide, thrombin -1, bearing ara-2'-omethyl modification have been synthesized. It is anticipated the oligonucleotides incorporating these monomers will exhibit biological activities related to antisense approach approach, design of better SiRNA's, diagnostic agents. Similarly, it is anticipated that oligonucleotides incorporating such novel nucleosides will be useful to develop therapeutic candidates designing stable G-quadruplexes and Aptamers for oligonucleotide structure, folding topology, evaluation of biochemical properties and design and develop as therapeutic agents. It is further anticipated that the nucleosides, phosphates and triphosphates of this invention could develop as therapeutic agents.