4-amino-6-bromo-7-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile | 183882-19-1

• 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: 4-amino-6-bromo-7-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• 英文别名: [(2R,3S,5R)-5-(4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-7-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 183882-19-1
• 化学式: C₂₈H₂₄BrN₅O₅
• 分子量: 590.433
• InChiKey: MWHSPJRVPFQVLQ-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-amino-6-bromo-7-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile 在 palladium on activated charcoal 吡啶 、 sodium hypophosphite 、 氢气 、 镍 、 溶剂黄146 、 三乙胺 、 异丁酸 作用下， 以 1,4-二氧六环 为溶剂， 50.0~65.0 ℃ 、344.73 kPa 条件下， 反应 10.0h， 生成
  参考文献：
  名称：

  2‘-Deoxy-7-(hydroxymethyl)-7-deazaadenosine:  A New Analogue to Model Structural Water in the Major Groove of DNA

  摘要：

  A novel deoxynucleoside, 2'-deoxy-7-(hydroxymethyl)-7-deazaadenosine, was synthesized with the intent of using the analogue to mimic the role of ''structural'' waters in the major groove of DNA. The target compound was synthesized in four steps starting from 2-((ethoxymethylene)amino)-5-bromo-1-(2'-deoxy-3',5'-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)pyrrole-3,4-dicarbonitrile. The structure was characterized by X-ray diffraction and proton NMR spectroscopic analyses. The crystal structure shows an intramolecular hydrogen bond between an amino proton on N6 and the oxygen of the hydroxymethyl group. When superimposed onto particular adenines in the structure of the tryptophan (trp) repressor/operator complex, the analogue places the oxygen of the hydroxymethyl group very near the oxygen contributed by the water in the protein/DNA complex. This analogue may be useful for probing the role of structural waters in other specific protein/DNA complexes and in DNA bending.

  DOI：

  10.1021/ja961540s
• 作为产物：
  描述：

  2-[(ethoxymethylene)amino]-5-bromo-1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)pyrrole-3,4-dicarbonitrile 在 氨 作用下， 以 甲醇 为溶剂， 以70%的产率得到4-amino-6-bromo-7-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile
  参考文献：
  名称：

  2‘-Deoxy-7-(hydroxymethyl)-7-deazaadenosine:  A New Analogue to Model Structural Water in the Major Groove of DNA

  摘要：

  A novel deoxynucleoside, 2'-deoxy-7-(hydroxymethyl)-7-deazaadenosine, was synthesized with the intent of using the analogue to mimic the role of ''structural'' waters in the major groove of DNA. The target compound was synthesized in four steps starting from 2-((ethoxymethylene)amino)-5-bromo-1-(2'-deoxy-3',5'-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)pyrrole-3,4-dicarbonitrile. The structure was characterized by X-ray diffraction and proton NMR spectroscopic analyses. The crystal structure shows an intramolecular hydrogen bond between an amino proton on N6 and the oxygen of the hydroxymethyl group. When superimposed onto particular adenines in the structure of the tryptophan (trp) repressor/operator complex, the analogue places the oxygen of the hydroxymethyl group very near the oxygen contributed by the water in the protein/DNA complex. This analogue may be useful for probing the role of structural waters in other specific protein/DNA complexes and in DNA bending.

  DOI：

  10.1021/ja961540s