1,3-Dimethyl-6-naphthalen-1-yl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione | 90994-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-Dimethyl-6-naphthalen-1-yl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione
• 英文别名: 1,3-dimethyl-6-naphthalen-1-yl-5H-pyrrolo[3,2-d]pyrimidine-2,4-dione
• CAS: 90994-81-3
• 化学式: C₁₈H₁₅N₃O₂
• 分子量: 305.336
• InChiKey: SREBOUCLOPUWNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-Dimethyl-6-naphthalen-1-yl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以74%的产率得到1,3,5-Trimethyl-6-naphthalen-1-yl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of Deazaxanthines: Analogs of Potent A1- and A2-Adenosine Receptor Antagonists

  摘要：

  A set of 22 9-deazaxanthines (pyrrolo[3,2-d]pyrimidine-2,4-diones) and three 7-deazaxanthines (pyrrolo[2,3-d] pyrimidine-2,4-diones) with various substituents in the 1-, 3-, 7- or 9-, and 8-positions was synthesized and investigated in A1 and A2a adenosine receptor binding assays at rat brain cortical membranes and rat brain striatal membranes, respectively. 9-Deazaxanthines showed structure-activity relationships that were similar to those of xanthines. They were about equipotent to the corresponding xanthines at A2a adenosine receptors. 9-Deazaxanthines were generally at least 2-3-fold more potent than xanthines at A1 receptors and therefore exhibited higher A1 selectivities compared to the xanthines. 1,3-Dimethyl-8-(2-naphthyl)-9-deazaxanthine (19e) showed high affinty (K-i = 26 nM) and selectivity for A1 adenosine receptors. A hydroxyl function at N7 of 9-deazaxanthines was unfavorable for A1 and A2a receptor binding. 7-Deazaxanthines were considerably less potent compared to xanthines and to 9-deazaxanthines at both receptor subtypes.

  DOI：

  10.1021/jm00036a019
• 作为产物：
  描述：

  1,3,4-三甲基尿嘧啶 在 氢氧化钾 、 硫酸 、 硝酸 、 sodium methylate 、 N,N-二甲基甲酰胺 、 potassium iodide 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 1,3-Dimethyl-6-naphthalen-1-yl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of Deazaxanthines: Analogs of Potent A1- and A2-Adenosine Receptor Antagonists

  摘要：

  A set of 22 9-deazaxanthines (pyrrolo[3,2-d]pyrimidine-2,4-diones) and three 7-deazaxanthines (pyrrolo[2,3-d] pyrimidine-2,4-diones) with various substituents in the 1-, 3-, 7- or 9-, and 8-positions was synthesized and investigated in A1 and A2a adenosine receptor binding assays at rat brain cortical membranes and rat brain striatal membranes, respectively. 9-Deazaxanthines showed structure-activity relationships that were similar to those of xanthines. They were about equipotent to the corresponding xanthines at A2a adenosine receptors. 9-Deazaxanthines were generally at least 2-3-fold more potent than xanthines at A1 receptors and therefore exhibited higher A1 selectivities compared to the xanthines. 1,3-Dimethyl-8-(2-naphthyl)-9-deazaxanthine (19e) showed high affinty (K-i = 26 nM) and selectivity for A1 adenosine receptors. A hydroxyl function at N7 of 9-deazaxanthines was unfavorable for A1 and A2a receptor binding. 7-Deazaxanthines were considerably less potent compared to xanthines and to 9-deazaxanthines at both receptor subtypes.

  DOI：

  10.1021/jm00036a019

文献信息

• Pyrimidine derivatives and related compounds. Part 47. A new synthesis of xanthines and pyrrolo[3,2-d]pyrimidines by intramolecular cyclisation of 6-substituted 5-nitrouracil derivatives
  作者：Kosaku Hirota、Tadashi Sugiyama、Yukio Kitade、Shigeo Senda、Yoshifumi Maki

  DOI：10.1039/p19840000583

  日期：——

  of 6-[2-(ethoxycarbonyl, acetyl, and cyano) ethyl] uracil (8h–j) with triethylamine led to the formation of the corresponding 6-vinyluracil (11 a–c). A one-step synthesis of the 7-hydroxy-9-deazaxanthines (9a–e) was accomplished by the treatment of the sodium salt (7) with arylalkyl chlorides in the presence of potassium carbonate in dry DMF. Deoxygenation of the 7-hydroxy-9-deazaxanthines (9a–e) smoothly

  通过在三乙胺存在下使6-氯-1,3-二甲基-5-硝基尿嘧啶（1）与芳基烷基胺反应，制得6-芳烷基氨基-1,3-二甲基-5-硝基尿嘧啶（2a–f）。其中，在氮原子和6-芳基烷基氨基部分中的苄基位置不具有取代基的6-芳基烷基氨基尿嘧啶（2a–d）在转化为相应的8-芳基-1,3-二甲基黄嘌呤（3a–d）时在二甲基甲酰胺（DMF）中加热回流。钠盐（反应7 1,3,6-三甲基-5- nitrouracil（的）6）用在无水DMF烷基和芳基烷基卤化物，得到相应的6-（取代甲基）-1,3-二甲基-5-硝基尿嘧啶（8a–j）。其中，对6-（2-芳基乙基）尿嘧啶（8b-f）进行碱催化的环化反应，得到8-芳基-7-羟基-9-脱氮黄嘌呤（9a-e）。另一方面，用三乙胺处理6- [2-（乙氧羰基，乙酰基和氰基）乙基]尿嘧啶（8h-j）导致形成相应的6-乙烯基尿嘧啶（11a-c）。在干燥的DMF中，在碳酸钾的存在下
• HIROTA, KOSAKU;SUGIYAMA, TADASHI;KITADE, YUKIO;SENDA, SHIGEO;MAKI, YOSHIF+, J. CHEM. SOC. PERKIN TRANS., 1984, N 4, 583-588
  作者：HIROTA, KOSAKU、SUGIYAMA, TADASHI、KITADE, YUKIO、SENDA, SHIGEO、MAKI, YOSHIF+

  DOI：——

  日期：——
• Synthesis and Structure-Activity Relationships of Deazaxanthines: Analogs of Potent A1- and A2-Adenosine Receptor Antagonists
  作者：Bettina Grahner、Susanne Winiwarter、Wolfgang Lanzner、Christa E. Mueller

  DOI：10.1021/jm00036a019

  日期：1994.5

  A set of 22 9-deazaxanthines (pyrrolo[3,2-d]pyrimidine-2,4-diones) and three 7-deazaxanthines (pyrrolo[2,3-d] pyrimidine-2,4-diones) with various substituents in the 1-, 3-, 7- or 9-, and 8-positions was synthesized and investigated in A1 and A2a adenosine receptor binding assays at rat brain cortical membranes and rat brain striatal membranes, respectively. 9-Deazaxanthines showed structure-activity relationships that were similar to those of xanthines. They were about equipotent to the corresponding xanthines at A2a adenosine receptors. 9-Deazaxanthines were generally at least 2-3-fold more potent than xanthines at A1 receptors and therefore exhibited higher A1 selectivities compared to the xanthines. 1,3-Dimethyl-8-(2-naphthyl)-9-deazaxanthine (19e) showed high affinty (K-i = 26 nM) and selectivity for A1 adenosine receptors. A hydroxyl function at N7 of 9-deazaxanthines was unfavorable for A1 and A2a receptor binding. 7-Deazaxanthines were considerably less potent compared to xanthines and to 9-deazaxanthines at both receptor subtypes.