1-(1-β-D-arabinofuranosyl)-diketopiperazine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-β-D-arabinofuranosyl)-diketopiperazine
• 英文别名: 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]piperazine-2,5-dione；1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]piperazine-2,5-dione
• 化学式: C₉H₁₄N₂O₆
• 分子量: 246.22
• InChiKey: IIJFJAQUFQNBSB-LPJZALPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 盐酸 、 氢氧化钾 、 三(3,6-二氧杂庚基)胺 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 7.83h， 生成 1-(1-β-D-arabinofuranosyl)-diketopiperazine
  参考文献：
  名称：

  Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3‐Dideazaadenine, 4‐Nitro‐1, 3‐dideazaadenine and Diketopiperazine

  摘要：

  Different arabinosides and ribosides, viz. Ara-DDA or 9(1-beta-(D)-arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-beta-D-arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or I(1-beta-D-arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-beta-D-ribofuranosyl) 1,3-dideazaadenine (9) and Ribo-NDDP or 9(1-beta-D-ribofuranosyl) 4-nitro-1,3-dideazapurine (10) have been synthesized as probable antiviral agents. The arabinosides have been synthesized using the catalyst TDA-1 that causes stereospecific formation of beta-nucleosides while a one-pot synthesis procedure was adopted for the synthesis of the ribonucleosides where beta-anomers were obtained in higher yields. All the five nucleoside analogs have been screened for antiviral property against HIV-1 ((IIIB)), HSV-1 and 2, parainfluenza-3, reovirus-1 and many others. It was observed that arabinosides had greater inhibitory action than ribosides. The compound 7 or Ara-NDDP has shown maximum inhibition of HIV-1 replication than the rest of the molecules with an IC50 of 79.4 mug/mL.

  DOI：

  10.1081/ncn-200040614

文献信息

• Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3‐Dideazaadenine, 4‐Nitro‐1, 3‐dideazaadenine and Diketopiperazine
  作者：Sarika Sinha、Richa Srivastava、Erik De Clercq、Ramendra K. Singh

  DOI：10.1081/ncn-200040614

  日期：2004.1.12

  Different arabinosides and ribosides, viz. Ara-DDA or 9(1-beta-(D)-arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-beta-D-arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or I(1-beta-D-arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-beta-D-ribofuranosyl) 1,3-dideazaadenine (9) and Ribo-NDDP or 9(1-beta-D-ribofuranosyl) 4-nitro-1,3-dideazapurine (10) have been synthesized as probable antiviral agents. The arabinosides have been synthesized using the catalyst TDA-1 that causes stereospecific formation of beta-nucleosides while a one-pot synthesis procedure was adopted for the synthesis of the ribonucleosides where beta-anomers were obtained in higher yields. All the five nucleoside analogs have been screened for antiviral property against HIV-1 ((IIIB)), HSV-1 and 2, parainfluenza-3, reovirus-1 and many others. It was observed that arabinosides had greater inhibitory action than ribosides. The compound 7 or Ara-NDDP has shown maximum inhibition of HIV-1 replication than the rest of the molecules with an IC50 of 79.4 mug/mL.