ethyl 4-[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-bis(4-methylphenyl)-2,4-dioxopteridin-3-yl]butanoate | 1213253-00-9

• 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: ethyl 4-[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-bis(4-methylphenyl)-2,4-dioxopteridin-3-yl]butanoate
• CAS: 1213253-00-9
• 化学式: C₃₄H₃₈N₄O₈
• 分子量: 630.698
• InChiKey: DXFZJQFWYJCRGK-CGAVVAMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 4-[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-bis(4-methylphenyl)-2,4-dioxopteridin-3-yl]butanoate 在 盐酸 、 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 以24%的产率得到ethyl 4-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,7-bis(4-methylphenyl)-2,4-dioxopteridin-3-yl]butanoate
  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：

  4-溴丁酸乙酯 、 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-bis(4-methylphenyl)pteridine-2,4-dione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以21%的产率得到ethyl 4-[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-bis(4-methylphenyl)-2,4-dioxopteridin-3-yl]butanoate
  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