methyl 4-(cyanomethyl)-1-(3,5-di-O-p-toluyl-α-D-erythro-pentosyl)imidazole-5-carboxylate | 91713-24-5

• 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 4-(cyanomethyl)-1-(3,5-di-O-p-toluyl-α-D-erythro-pentosyl)imidazole-5-carboxylate
• 英文别名: methyl 4-(cyanomethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)imidazole-5-carboxylate；methyl 5-(cyanomethyl)-3-[(2S,4S,5R)-4-(4-methylbenzoyl)oxy-5-[(4-methylbenzoyl)oxymethyl]oxolan-2-yl]imidazole-4-carboxylate
• CAS: 91713-24-5
• 化学式: C₂₈H₂₇N₃O₇
• 分子量: 517.538
• InChiKey: KSYYJMFOFKDMLR-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 4-(cyanomethyl)-1-(3,5-di-O-p-toluyl-α-D-erythro-pentosyl)imidazole-5-carboxylate 在 氨 作用下， 反应 18.0h， 生成 4-(cyanomethyl)-1-(2-deoxy-α-D-erythro-pentofuranosyl)imidazole-5-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
• US5457191A
  申请人：——

  公开号：US5457191A

  公开（公告）日：1995-10-10
• US5587470A
  申请人：——

  公开号：US5587470A

  公开（公告）日：1996-12-24
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  申请人：——

  公开号：US5750692A

  公开（公告）日：1998-05-12
• US5948903A
  申请人：——

  公开号：US5948903A

  公开（公告）日：1999-09-07