1-(2-deoxy-β-D-erythro-pentofuranosyl)quinozaline-2,4(3H)-dione | 15135-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-(2-deoxy-β-D-erythro-pentofuranosyl)quinozaline-2,4(3H)-dione
• 英文别名: 1-(2'-Desoxy-β-D-ribofuranosyl)-chinazolin-2,4-dion；1-(β-D-erythro-2-deoxy-pentofuranosyl)-1H-quinazoline-2,4-dione；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]quinazoline-2,4-dione
• CAS: 15135-29-2
• 化学式: C₁₃H₁₄N₂O₅
• 分子量: 278.265
• InChiKey: DFACGHXLVLNQEL-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-β-D-erythro-pentofuranosyl)quinozaline-2,4(3H)-dione 、 对甲基苯甲酰氯 在 吡啶 作用下， 生成 1-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)quinozaline-2,4(3H)-dione
  参考文献：
  名称：

  An Improved Synthesis of 1-(2-Deoxy-β-D-erythro-pentofuranosyl)quinazoline-2,4(3H)-dione and Its Incorporation Into G-Rich Triple Helix Forming Oligonucleotides

  摘要：

  A convenient synthesis of 1-(2-deoxy-beta-D-erythro-pentofuranosyl)quinazoline-2,4(3H)-dione (6) has been accomplished. The structural conformation of (6) was derived by 2D NMR, COSY and NOESY experiments. Nucleoside (6) was incorporated into G-rich tripler forming oligonucleotides (TFOs) by solid-support, phosphoramidite method. The tripler forming capabilities of modified TFOs (S2, S3 and S4) has been evaluated in antiparallel motif with a target duplex (duplex-31) 5'd(GTCACTGGCCCTTCCTCCTTCCCGGTCTCAG)3'-5'd(CAGTGACCGGGAAGGAGGAAGGGCCAGAGTC)3' (D1) at pH 7.6. The parallel tripler formation of a shorter TFO (S6) containing Q has also been studied with a target duplex-11 (D2) at PH 5.0.

  DOI：

  10.1080/15257779508014652
• 作为产物：
  描述：

  1-(2-deoxy-D-erythro-pentofuranosyl)quinozaline-2,4(3H)-dione 在 吡啶 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 1-(2-deoxy-β-D-erythro-pentofuranosyl)quinozaline-2,4(3H)-dione
  参考文献：
  名称：

  An Improved Synthesis of 1-(2-Deoxy-β-D-erythro-pentofuranosyl)quinazoline-2,4(3H)-dione and Its Incorporation Into G-Rich Triple Helix Forming Oligonucleotides

  摘要：

  A convenient synthesis of 1-(2-deoxy-beta-D-erythro-pentofuranosyl)quinazoline-2,4(3H)-dione (6) has been accomplished. The structural conformation of (6) was derived by 2D NMR, COSY and NOESY experiments. Nucleoside (6) was incorporated into G-rich tripler forming oligonucleotides (TFOs) by solid-support, phosphoramidite method. The tripler forming capabilities of modified TFOs (S2, S3 and S4) has been evaluated in antiparallel motif with a target duplex (duplex-31) 5'd(GTCACTGGCCCTTCCTCCTTCCCGGTCTCAG)3'-5'd(CAGTGACCGGGAAGGAGGAAGGGCCAGAGTC)3' (D1) at pH 7.6. The parallel tripler formation of a shorter TFO (S6) containing Q has also been studied with a target duplex-11 (D2) at PH 5.0.

  DOI：

  10.1080/15257779508014652

文献信息

• An Improved Synthesis of 1-(2-Deoxy-β-D-erythro-pentofuranosyl)quinazoline-2,4(3<i>H</i>)-dione and Its Incorporation Into G-Rich Triple Helix Forming Oligonucleotides
  作者：Birendra K. Bhattacharya、Mohan V. Chari、Ross H. Durland、Ganapathi R. Revankar

  DOI：10.1080/15257779508014652

  日期：1995.2

  A convenient synthesis of 1-(2-deoxy-beta-D-erythro-pentofuranosyl)quinazoline-2,4(3H)-dione (6) has been accomplished. The structural conformation of (6) was derived by 2D NMR, COSY and NOESY experiments. Nucleoside (6) was incorporated into G-rich tripler forming oligonucleotides (TFOs) by solid-support, phosphoramidite method. The tripler forming capabilities of modified TFOs (S2, S3 and S4) has been evaluated in antiparallel motif with a target duplex (duplex-31) 5'd(GTCACTGGCCCTTCCTCCTTCCCGGTCTCAG)3'-5'd(CAGTGACCGGGAAGGAGGAAGGGCCAGAGTC)3' (D1) at pH 7.6. The parallel tripler formation of a shorter TFO (S6) containing Q has also been studied with a target duplex-11 (D2) at PH 5.0.