5,6-diamino-1-(2-chlorophenyl)-3-methyl-2,4 (1H, 3H)-pyrimidinedione | 176379-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5,6-diamino-1-(2-chlorophenyl)-3-methyl-2,4 (1H, 3H)-pyrimidinedione
• 英文别名: 1-(2-chlorophenyl)-5,6-diamino-3-methyluracil；5,6-diamino-1-(2-chlorophenyl)-3-methylpyrimidine-2,4-dione
• CAS: 176379-66-1
• 化学式: C₁₁H₁₁ClN₄O₂
• 分子量: 266.687
• InChiKey: XXZRGQJKFRAVEA-UHFFFAOYSA-N

物化性质

• 沸点：
  372.5±52.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  奎诺二甲基丙烯酸酯 、 5,6-diamino-1-(2-chlorophenyl)-3-methyl-2,4 (1H, 3H)-pyrimidinedione 在 三乙胺 、 二苯基次膦酰氯 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以34%的产率得到N-[6-amino-1-(2-chlorophenyl)-3-methyl-2,4-dioxopyrimidin-5-yl]-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide
  参考文献：
  名称：

  Structure and activity relationships of novel uracil derivatives as topical anti-inflammatory agents

  摘要：

  In order to create novel, topical anti-inflammatory compounds exhibiting more potent activities than lead compound CX-659S (1), we designed and synthesized various derivatives of 1 focusing on the uracil N(l)- and N(3)-substituents, and evaluated their anti-inflammatory activities via inhibition of the picryl chloride-induced contact hypersensitivity reaction (CHR) in mice. In the course of our structure and activity relationship study, we found that compounds 6k, 6q, and 6r inhibited by approximately 50% the CHR, at 0.1 mg/ear. These activities were essentially equipotent with that of Tacrolimus, a strong immunosuppressant. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.012
• 作为产物：
  描述：

  1-(2-氯苯基)-3-甲基脲 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 乙酸酐 、 sodium nitrite 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 13.0h， 生成 5,6-diamino-1-(2-chlorophenyl)-3-methyl-2,4 (1H, 3H)-pyrimidinedione
  参考文献：
  名称：

  Structure and activity relationships of novel uracil derivatives as topical anti-inflammatory agents

  摘要：

  In order to create novel, topical anti-inflammatory compounds exhibiting more potent activities than lead compound CX-659S (1), we designed and synthesized various derivatives of 1 focusing on the uracil N(l)- and N(3)-substituents, and evaluated their anti-inflammatory activities via inhibition of the picryl chloride-induced contact hypersensitivity reaction (CHR) in mice. In the course of our structure and activity relationship study, we found that compounds 6k, 6q, and 6r inhibited by approximately 50% the CHR, at 0.1 mg/ear. These activities were essentially equipotent with that of Tacrolimus, a strong immunosuppressant. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.012

文献信息

• 1-arylpyrimidine derivatives and pharmaceutical use thereof
  申请人：Japan Energy Corporation

  公开号：US05661153A1

  公开（公告）日：1997-08-26

  The present invention relates to 1-arylpyrimidine derivatives represented by general formula (I): ##STR1## wherein R.sub.1 is H, alkyl or aralkyl; Ar is 1-naphthyl, or a substituted or unsubstituted phenyl group; R.sub.4 is a substituted phenyl, a substituted styryl, 1-methylcyclohexyl, 4-methylcyclohexyl, 4-oxo-4H-pyran-2-yl or 2-oxo-2H-pyran-5-yl group; R.sub.5 and R.sub.6 are each independently H or alkyl; R.sub.3 is H, and R.sub.7 and R.sub.8 are combined together to be oxo, or else R.sub.3 and R.sub.7 are combined together to be another direct bond, and R.sub.5 and R.sub.8 are combined together to be a direct bond, or pharmaceutically acceptable salts thereof; and methods for treating allergic diseases with such compounds.

  本发明涉及通式(I)所表示的1-芳基嘧啶衍生物：##STR1## 其中，R.sub.1是氢、烷基或芳基烷基；Ar是1-萘基，或取代或未取代的苯基；R.sub.4是取代的苯基，取代的苯乙烯基，1-甲基环己烷基，4-甲基环己烷基，4-氧代-4H-吡喃-2-基或2-氧代-2H-吡喃-5-基；R.sub.5和R.sub.6各自独立地为氢或烷基；R.sub.3是氢，R.sub.7和R.sub.8结合在一起是氧代，否则R.sub.3和R.sub.7结合在一起是另一个直接键，R.sub.5和R.sub.8结合在一起是一个直接键，或其药学上可接受的盐；以及使用这些化合物治疗过敏性疾病的方法。
• 1-Arylpyrimidine derivatives and pharmaceutical use thereof
  申请人：JAPAN ENERGY CORPORATION

  公开号：EP0700908A1

  公开（公告）日：1996-03-13

  The present invention relates to pyrimidine derivatives of the formula (I): wherein    R₁ is H, alkyl or aralkyl;    Ar is 1-naphthyl, or a substituted or unsubstituted phenyl group;    R₄ is a substituted phenyl, a substituted styryl, 1-methylcyclohexyl, 4-methylcyclohexyl, 4-oxo-4H-pyran-2-yl or 2-oxo-2H-pyran-5-yl group;    R₅ and R₆ are each independently H or alkyl;    R₃ is H, and R₇ and R₈ are combined together to be oxo, or else R₃ and R₇ are combined together to be another direct bond, and R₅ and R₈ ar combined together to be a direct bond, or pharmaceutically acceptable salts thereof; and the use of such compounds in the treatment of an allergic disease.

  本发明涉及式（I）的嘧啶衍生物： 其中 R₁ 是 H、烷基或芳烷基； Ar 是 1-萘基或取代或未取代的苯基； R₄ 是取代的苯基、取代的苯乙烯基、1-甲基环己基、4-甲基环己基、4-氧代-4H-吡喃-2-基或 2-氧代-2H-吡喃-5-基； R₅ 和 R₆ 各自独立地为 H 或烷基； R₃为H，且R₇和R₈结合在一起为氧代，或者R₃和R₇结合在一起为另一个直接键，且R₅和R₈结合在一起为一个直接键，或其药学上可接受的盐；以及此类化合物在治疗过敏性疾病中的用途。
• US5661153A
  申请人：——

  公开号：US5661153A

  公开（公告）日：1997-08-26
• Structure and activity relationships of novel uracil derivatives as topical anti-inflammatory agents
  作者：Yoshiaki Isobe、Masanori Tobe、Yoshifumi Inoue、Masakazu Isobe、Masami Tsuchiya、Hideya Hayashi

  DOI：10.1016/j.bmc.2003.09.012

  日期：2003.11

  In order to create novel, topical anti-inflammatory compounds exhibiting more potent activities than lead compound CX-659S (1), we designed and synthesized various derivatives of 1 focusing on the uracil N(l)- and N(3)-substituents, and evaluated their anti-inflammatory activities via inhibition of the picryl chloride-induced contact hypersensitivity reaction (CHR) in mice. In the course of our structure and activity relationship study, we found that compounds 6k, 6q, and 6r inhibited by approximately 50% the CHR, at 0.1 mg/ear. These activities were essentially equipotent with that of Tacrolimus, a strong immunosuppressant. (C) 2003 Elsevier Ltd. All rights reserved.