methyl 5-(cyanomethyl)-1-(3,5-di-O-p-toluyl-α-D-erythro-pentosyl)imidazole-4-carboxylate | 91713-26-7

• 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: methyl 5-(cyanomethyl)-1-(3,5-di-O-p-toluyl-α-D-erythro-pentosyl)imidazole-4-carboxylate
• 英文别名: methyl 5-(cyanomethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)imidazole-4-carboxylate；methyl 5-(cyanomethyl)-1-[(2S,4S,5R)-4-(4-methylbenzoyl)oxy-5-[(4-methylbenzoyl)oxymethyl]oxolan-2-yl]imidazole-4-carboxylate
• CAS: 91713-26-7
• 化学式: C₂₈H₂₇N₃O₇
• 分子量: 517.538
• InChiKey: ITEPQBZLIVNHQY-VXNXHJTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 5-(cyanomethyl)-1-(3,5-di-O-p-toluyl-α-D-erythro-pentosyl)imidazole-4-carboxylate 在 氨 作用下， 反应 6.0h， 生成 5-(cyanomethyl)-1-(2-deoxy-α-D-erythro-pentofuranosyl)imidazole-4-carboxamide
  参考文献：
  名称：

  Syntheses and antitumor activity of 2-deoxyribofuranosides of 3-deazaguanine

  摘要：

  Synthesis of 2-deoxyribofuranosides of 3-deazaguanine (IX-XII) has been achieved by a base-catalyzed ring closure of appropriate 2-deoxyribofuranosides of methyl 5(4)-(cyanomethyl)imidazole-4(5)-carboxalate (IV-VII). The separation of isomers and anomers were accomplished by column chromatography and HPLC. The site of glycosidic linkage and the anomeric configurations were established on the basis of C-13 and proton magnetic resonance spectroscopy, as well as UV absorption characteristics. Preliminary results of the antitumor activity of these derivatives, in vitro and in vivo, are described.

  DOI：

  10.1021/jm00356a034
• 作为产物：
  描述：

  Hoffer's chlorosugar 、 4-(氰基甲基)-1H-咪唑-5-羧酸甲酯 在 ammonium sulfate 、 四氯化锡 、 六甲基二硅氮烷 作用下， 生成 methyl 5-(cyanomethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)imidazole-4-carboxylate 、 methyl 4-(cyanomethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)imidazole-5-carboxylate 、 methyl 4-(cyanomethyl)-1-(3,5-di-O-p-toluyl-α-D-erythro-pentosyl)imidazole-5-carboxylate 、 methyl 5-(cyanomethyl)-1-(3,5-di-O-p-toluyl-α-D-erythro-pentosyl)imidazole-4-carboxylate
  参考文献：
  名称：

  Syntheses and antitumor activity of 2-deoxyribofuranosides of 3-deazaguanine

  摘要：

  Synthesis of 2-deoxyribofuranosides of 3-deazaguanine (IX-XII) has been achieved by a base-catalyzed ring closure of appropriate 2-deoxyribofuranosides of methyl 5(4)-(cyanomethyl)imidazole-4(5)-carboxalate (IV-VII). The separation of isomers and anomers were accomplished by column chromatography and HPLC. The site of glycosidic linkage and the anomeric configurations were established on the basis of C-13 and proton magnetic resonance spectroscopy, as well as UV absorption characteristics. Preliminary results of the antitumor activity of these derivatives, in vitro and in vivo, are described.

  DOI：

  10.1021/jm00356a034

文献信息

• Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides
  作者：Ganapathi R. Revankar、Pranab K. Gupta、Alexander D. Adams、N. Kent Dalley、Patricia A. McKernan、P. Dan Cook、Peter G. Canonico、Roland K. Robins

  DOI：10.1021/jm00377a002

  日期：1984.11

  3-deazaguanosine (2) has been developed by reacting methyl 5(4)-(cyanomethyl) imidazole-4(5)-carboxylate (4) and 5-(cyanomethyl)-1- (2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)imidazole-4-carboxylate (6), respectively, with hydrazine. The 3-deazaguanosine 3',5'-cyclic phosphate (13) was prepared from 5-(cyanomethyl)-1-beta-D-ribofuranosyl-imidazole-4-carboxamide 5'-phosphate. Glycosylation of the trimethylsilyl 4

  通过使5（4）-（氰基甲基）咪唑-4（5）-羧酸甲酯反应，开发了一种制备抗病毒和抗肿瘤药3-deazaguanine（1）及其代谢物3-deazaguanosine（2）的新方法。 4）和5-（氰基甲基）-1-（2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖基）咪唑-4-羧酸酯（6）与肼。由5-（氰基甲基）-1-β-D-呋喃呋喃糖基-咪唑-4-羧酰胺5'-磷酸制备3-脱氮鸟苷3'，5'-环状磷酸酯（13）。在三甲基甲硅烷基三氟甲磺酸酯存在下，用1-O-甲基-2-脱氧-3,5-二-Op-甲苯甲酰基-D-呋喃呋喃糖将三甲基甲硅烷基4糖基化，得到相应的N-1和N-3糖基衍生物，其中α-配置（18和20）作为主要产品，以及少量的β-端基异构体（19和21）。然而，4的钠盐与1-氯-2-脱氧-3,5-二-Op-甲苯甲酰-α-D-赤型五氟呋喃糖（17）的糖基化反应仅产生良好的β-端基异构体（19和2
• Compositions and methods for detecting and modulating rna activity and gene expression
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP1418179A2

  公开（公告）日：2004-05-12

  Compositions and methods for modulating the activity of RNA and DNA are disclosed. In accordance with preferred embodiments, antisense compositions are prepared comprising targeting and reactive portions. Reactive portions which act, alternatively, through phosphorodiester bond cleavage, through backbone sugar bond cleavage or through base modification are preferably employed. Groups which improve the pharmacodynamic and pharmacokinetic properties of the oligonucleotides are also useful in accordance with certain embodiments of this invention. Delivery of the reactive or non-reactive functionalities into the minor groove formed by the hybridization of the composition with the target RNA is also preferably accomplished. Therapeutics, diagnostics and research methods are also disclosed. Synthetic nucleosides and nucleoside fragments are also provided useful for elaboration of oligonucleotides and oligonucleotide analogs for such purposes.

  本文公开了调节 RNA 和 DNA 活性的组合物和方法。根据优选的实施方案，反义组合物由靶向部分和反应部分组成。反应部分最好通过磷酸二酯键裂解、骨架糖键裂解或碱基修饰起作用。根据本发明的某些实施方案，改善寡核苷酸药效学和药代动力学特性的基团也是有用的。最好还能将反应性或非反应性官能团输送到组合物与目标 RNA 杂交形成的次凹槽中。本发明还公开了治疗、诊断和研究方法。本发明还提供了合成核苷和核苷片段，可用于制备用于上述目的的寡核苷酸和寡核苷酸类似物。
• EP0604409A4
  申请人：——

  公开号：EP0604409A4

  公开（公告）日：1996-06-12
• COMPOSITIONS AND METHODS FOR DETECTING AND MODULATING RNA ACTIVITY AND GENE EXPRESSION
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0604409A1

  公开（公告）日：1994-07-06
• OLIGONUCLEOTIDE ANALOGS FOR DETECTING AND MODULATING RNA ACTIVITY AND GENE EXPRESSION
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0604409B1

  公开（公告）日：2004-07-14