1-(O²,O³-isopropylidene-β-D-ribofuranosyl)-6,7-diphenyl-1H-pteridine-2,4-dione | 60915-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 1-(O²,O³-isopropylidene-β-D-ribofuranosyl)-6,7-diphenyl-1H-pteridine-2,4-dione
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6,7-diphenylpteridine-2,4-dione
• CAS: 60915-86-8
• 化学式: C₂₆H₂₄N₄O₆
• 分子量: 488.5
• InChiKey: ZEUCENZYQZIZRE-FZGCSJHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(O²,O³-isopropylidene-β-D-ribofuranosyl)-6,7-diphenyl-1H-pteridine-2,4-dione 在 盐酸 、 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 以75%的产率得到6,7-diphenyl-1-β-D-ribofuranosyl-1H-pteridine-2,4-dione
  参考文献：
  名称：

  Novel and Facil Synthesis and Evaluation of Antitumor Activities of 6,7-Bisaryl-1-(β-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones

  摘要：

  Novel 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4( 1H,3H)-dione derivatives were synthesized by condensation of 5,6-diamino-2',3'-O-isopropylideneuridine, which was derived from uridine, with an appropriate alpha,beta-diketon, followed by acidic hydrolysis allowing removal of the isopropylidene group of the sugar moiety as a protecting group. Moreover, several N-3 alkyl derivatives of the 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones were obtained by alkylation of the 6,7-bisaryl-l-(2',3'-O-isopropylidene-beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones with alkyl halides and by their acidic hydrolysis for deprotection. The antitumor activities of all synthesized compounds against CCRF-HSB-2 and KB cell lines were also investigated in vitro and some of the compounds showed prospective antitumor activities.

  DOI：

  10.3987/com-09-s(s)77
• 作为产物：
  描述：

  5,6-diamino-2',3'-O-isopropylideneuridine 、 联苯甲酰 以 乙醇 为溶剂， 反应 18.0h， 以70%的产率得到1-(O²,O³-isopropylidene-β-D-ribofuranosyl)-6,7-diphenyl-1H-pteridine-2,4-dione
  参考文献：
  名称：

  Novel and Facil Synthesis and Evaluation of Antitumor Activities of 6,7-Bisaryl-1-(β-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones

  摘要：

  Novel 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4( 1H,3H)-dione derivatives were synthesized by condensation of 5,6-diamino-2',3'-O-isopropylideneuridine, which was derived from uridine, with an appropriate alpha,beta-diketon, followed by acidic hydrolysis allowing removal of the isopropylidene group of the sugar moiety as a protecting group. Moreover, several N-3 alkyl derivatives of the 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones were obtained by alkylation of the 6,7-bisaryl-l-(2',3'-O-isopropylidene-beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones with alkyl halides and by their acidic hydrolysis for deprotection. The antitumor activities of all synthesized compounds against CCRF-HSB-2 and KB cell lines were also investigated in vitro and some of the compounds showed prospective antitumor activities.

  DOI：

  10.3987/com-09-s(s)77

文献信息

• Novel and Facil Synthesis and Evaluation of Antitumor Activities of 6,7-Bisaryl-1-(β-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones
  作者：Tomohisa Nagamatsu、Rafiya Khan Kandahary、Abugafar M. L. Hossion、Noriyuki Ashida

  DOI：10.3987/com-09-s(s)77

  日期：——

  Novel 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4( 1H,3H)-dione derivatives were synthesized by condensation of 5,6-diamino-2',3'-O-isopropylideneuridine, which was derived from uridine, with an appropriate alpha,beta-diketon, followed by acidic hydrolysis allowing removal of the isopropylidene group of the sugar moiety as a protecting group. Moreover, several N-3 alkyl derivatives of the 6,7-bisaryl-1-(beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones were obtained by alkylation of the 6,7-bisaryl-l-(2',3'-O-isopropylidene-beta-D-ribofuranosyl)pteridine-2,4(1H,3H)-diones with alkyl halides and by their acidic hydrolysis for deprotection. The antitumor activities of all synthesized compounds against CCRF-HSB-2 and KB cell lines were also investigated in vitro and some of the compounds showed prospective antitumor activities.