5-氨基-6-氯-1,3-二甲基嘧啶-2,4-二酮 | 1128-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-氨基-6-氯-1,3-二甲基嘧啶-2,4-二酮
• 英文名称: 5-amino-6-chloro-1,3-dimethyluracil
• 英文别名: 5-Amino-6-chloro-1,3-dimethylpyrimidine-2,4(1h,3h)-dione；5-amino-6-chloro-1,3-dimethylpyrimidine-2,4-dione
• CAS: 1128-14-9
• 化学式: C₆H₈ClN₃O₂
• 分子量: 189.601
• InChiKey: MIRRVPSJMQEWTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氨基-6-氯-1,3-二甲基嘧啶-2,4-二酮 在 tris(dibenzylideneacetone)dipalladium (0) copper(l) iodide 、 caesium carbonate 、 三苯基膦 、 lithium chloride 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 3,5-Dimethyl-3,5,8,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),10,12-tetraene-4,6-dione
  参考文献：
  名称：

  Synthesis of hybrid molecules of caffeine and eudistomin D and its effects on adenosine receptors

  摘要：

  Four hybrid molecules (1 and 12-14) of caffeine and eudistomin D, a beta-carboline alkaloid from a marine tunicate, were synthesized, and their affinity and selectivity for adenosine receptors A(1), A(2A), and A(3) were examined. It was found that all the compounds showed better potency as adenosine receptor ligands as compared with caffeine. Among them, a compound (13) possessing a nitrogen at the delta-position of the pyridine ring (delta-N type) showed the most potent affinity for adenosine receptor A(3) subtype, while N-methylation (14) of a pyrrole ring in 13 significantly lowered the potency as adenosine receptor ligands. Compounds (1 and 12) having a nitrogen at the beta-position of the pyridine ring (beta-N type) showed lower affinity than the corresponding delta-N type compounds (13 and 14), while compounds (10, 11, and 17) lacking a pyrrole ring between the pyridine and pyrimidine rings exhibited almost no affinity to the adenosine receptor subtypes examined. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.043
• 作为产物：
  描述：

  6-氯-1,3-二甲基-5-硝基嘧啶-2,4-二酮 在 铁粉 、 溶剂黄146 作用下， 反应 4.0h， 以77%的产率得到5-氨基-6-氯-1,3-二甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  通过铃木交叉偶联和区域选择性氮插入反应合成某些重氮基稠合的三环系统

  摘要：

  将5-氯-2-甲基-6-苯基哒嗪-3（2 H）-1、6-氯-1,3-二甲基尿嘧啶和2-氯吡嗪与受保护的氨基芳基硼酸进行Suzuki偶联反应，得到相应的新戊酰氨基苯基二嗪，将其转化重氮基稠合的吲哚和cinnoline衍生物。5-氨基-6-氯-1,3-二甲基尿嘧啶与2-甲酰基苯基硼酸的Suzuki偶联在一个反应​​釜中提供了一种新型的嘧啶异喹啉环系统。

  DOI：

  10.1016/s0040-4020(02)01400-x

文献信息

• Hirota, Kosaku; Maruhashi, Kazuo; Asao, Tetsuji, Heterocycles, 1981, vol. 15, # 1, p. 285 - 288
  作者：Hirota, Kosaku、Maruhashi, Kazuo、Asao, Tetsuji、Senda, Shigeo

  DOI：——

  日期：——
• SENDA SHIGEO; HIROTA KOSAKU; ASAO TETSUJI; MARUHASHI KAZUO, J. CHEM. SOC. CHEM. COMMUN., 1978, NO 8, 367
  作者：SENDA SHIGEO、 HIROTA KOSAKU、 ASAO TETSUJI、 MARUHASHI KAZUO

  DOI：——

  日期：——
• Synthesis of hybrid molecules of caffeine and eudistomin D and its effects on adenosine receptors
  作者：Kengo Ohshita、Haruaki Ishiyama、Koshi Oyanagi、Hiroyasu Nakata、Jun’ichi Kobayashi

  DOI：10.1016/j.bmc.2007.02.043

  日期：2007.5

  Four hybrid molecules (1 and 12-14) of caffeine and eudistomin D, a beta-carboline alkaloid from a marine tunicate, were synthesized, and their affinity and selectivity for adenosine receptors A(1), A(2A), and A(3) were examined. It was found that all the compounds showed better potency as adenosine receptor ligands as compared with caffeine. Among them, a compound (13) possessing a nitrogen at the delta-position of the pyridine ring (delta-N type) showed the most potent affinity for adenosine receptor A(3) subtype, while N-methylation (14) of a pyrrole ring in 13 significantly lowered the potency as adenosine receptor ligands. Compounds (1 and 12) having a nitrogen at the beta-position of the pyridine ring (beta-N type) showed lower affinity than the corresponding delta-N type compounds (13 and 14), while compounds (10, 11, and 17) lacking a pyrrole ring between the pyridine and pyrimidine rings exhibited almost no affinity to the adenosine receptor subtypes examined. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of some diazino-fused tricyclic systems via Suzuki cross-coupling and regioselective nitrene insertion reactions
  作者：Pál Tapolcsányi、Gábor Krajsovszky、Rómeó Andó、Péter Lipcsey、Gyula Horváth、Péter Mátyus、Zsuzsanna Riedl、György Hajós、Bert U.W Maes、Guy L.F Lemière

  DOI：10.1016/s0040-4020(02)01400-x

  日期：2002.12

  diazino-fused indole and cinnoline derivatives. Suzuki coupling of 5-amino-6-chloro-1,3-dimethyluracil with 2-formylphenyl boronic acid afforded a novel pyrimidoisoquinoline ring system in a one-pot reaction.

  将5-氯-2-甲基-6-苯基哒嗪-3（2 H）-1、6-氯-1,3-二甲基尿嘧啶和2-氯吡嗪与受保护的氨基芳基硼酸进行Suzuki偶联反应，得到相应的新戊酰氨基苯基二嗪，将其转化重氮基稠合的吲哚和cinnoline衍生物。5-氨基-6-氯-1,3-二甲基尿嘧啶与2-甲酰基苯基硼酸的Suzuki偶联在一个反应​​釜中提供了一种新型的嘧啶异喹啉环系统。