1-β-D-ribofuranosyl-1H-pteridine-2,4-dione | 35777-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-β-D-ribofuranosyl-1H-pteridine-2,4-dione
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pteridine-2,4-dione；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pteridine-2,4-dione
• CAS: 35777-56-1
• 化学式: C₁₁H₁₂N₄O₆
• 分子量: 296.239
• InChiKey: UEXJVZRHJPPDOU-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,4-二羟基蝶啶 在 ammonium sulfate 、 三甲基氯硅烷 、 三氟甲磺酸三甲基硅酯 、 氨 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 31.0h， 生成 1-β-D-ribofuranosyl-1H-pteridine-2,4-dione
  参考文献：
  名称：

  熔融嘧啶类。7。嘧啶嘧啶二酮和蝶啶二酮的核苷可作为潜在的化学治疗剂

  摘要：

  嘧啶的几个核苷衍生物[4,5- d ]嘧啶-2,4（1 ħ，3 ħ） -二酮1和2,4- {1 ħ，3 ħ -pteridinedione 2制备。在三甲基甲硅烷基膨胀酸酯的存在下，用1 - O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-核呋喃糖-鼻子3处理适当的甲硅烷基化的核碱基，得到4和8，在脱苯甲酰化后，得到5和分别为9。用五硫化二磷处理4得到硫取代的化合物6。同样，脱保护得到7。通过用甲硅烷基化的核碱基处理1- O-乙酰基-2,3,5-三-O-苯甲酰基-D-阿拉伯呋喃糖10得到阿拉伯糖衍生物，得到11和13。脱苯甲酰化分别得到游离的阿拉伯核苷12和14。脱氧衍生物16是通过1与1-氯-3，5-二-O-乙酰基-2-脱氧-D-呋喃呋喃糖15反应制备的。用甲醇氨将16脱乙酰，得到α-端基异构体17。

  DOI：

  10.1002/jhet.5570340532

文献信息

• Vorbrueggen, Helmut; Krolikiewicz, Konrad; Bennua, Baerbel, Chemische Berichte, 1981, vol. 114, # 4, p. 1234 - 1255
  作者：Vorbrueggen, Helmut、Krolikiewicz, Konrad、Bennua, Baerbel

  DOI：——

  日期：——
• 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.
• Fused pyrimidines.<b>7</b>. Nucleosides of pyrimidopyrimidinediones and pteridinediones as potential chemotherapeutic agents
  作者：A. Nagarajan、Bernard R. Meltsner、Thomas J. Delia

  DOI：10.1002/jhet.5570340532

  日期：1997.9

  Several nucleoside derivatives of pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione 1 and 2,41H,3H-pteridinedione 2 were prepared. Treating the appropriate silylated nucleobase with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofura-nose 3 in the presence of trimethylsilyl Inflate gave 4 and 8 which, upon debenzoylation, gave 5 and 9, respectively. Treatment of 4 with phosphorus pentasulfide afforded the sulfur

  嘧啶的几个核苷衍生物[4,5- d ]嘧啶-2,4（1 ħ，3 ħ） -二酮1和2,4- 1 ħ，3 ħ -pteridinedione 2制备。在三甲基甲硅烷基膨胀酸酯的存在下，用1 - O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-核呋喃糖-鼻子3处理适当的甲硅烷基化的核碱基，得到4和8，在脱苯甲酰化后，得到5和分别为9。用五硫化二磷处理4得到硫取代的化合物6。同样，脱保护得到7。通过用甲硅烷基化的核碱基处理1- O-乙酰基-2,3,5-三-O-苯甲酰基-D-阿拉伯呋喃糖10得到阿拉伯糖衍生物，得到11和13。脱苯甲酰化分别得到游离的阿拉伯核苷12和14。脱氧衍生物16是通过1与1-氯-3，5-二-O-乙酰基-2-脱氧-D-呋喃呋喃糖15反应制备的。用甲醇氨将16脱乙酰，得到α-端基异构体17。