6-(3,4-Dimethyl-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion | 59776-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(3,4-Dimethyl-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion
• 英文别名: 3-Methyl-6-(3,4-dimethylphenylamino)uracil；3-methyl-6-(3,4-xylidino)uracil；6-(3,4-dimethyl-anilino)-3-methyl-1H-pyrimidine-2,4-dione；1-Methyl-6-(3,4-dimethylanilin)-uracil；6-[(3,4-dimethylphenyl)amino]-3-methylpyrimidine-2,4(1H,3H)-dione；6-(3,4-dimethylanilino)-3-methyl-1H-pyrimidine-2,4-dione
• CAS: 59776-24-8
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: GRCBYCDNGBXOKU-UHFFFAOYSA-N

物化性质

• 熔点：
  309-312 °C
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(3,4-Dimethyl-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion 以 环丁砜 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 3,7,8-trimethyl-5-phenyl-1H-pyrimido[4,5-b]quinoline-2,4-dione
  参考文献：
  名称：

  Yoneda, Fumio; Tsukuda, Kinshiro; Shinozuka, Kazuo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 10, p. 3049 - 3056

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲基苯胺 、 6-氯-3-甲基尿嘧啶 在 sodium hydroxide 作用下， 反应 0.5h， 以92%的产率得到6-(3,4-Dimethyl-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion
  参考文献：
  名称：

  取代的 5-去氮杂黄素，第 4 版。供体取代的 5-去氮杂恶嗪的合成

  摘要：

  供体 - 取代的 6 - 苯胺尿嘧啶衍生物 6 与 Vilsmeier 试剂的反应导致三种不同的反应，具体取决于取代：a) m 位的供体导致 8- 取代的 5- 脱氮杂恶嗪 8，b) p- 中的供体5-甲酰衍生物 11 在第 1 位获得，c) 与强间位二甲氨基供体，额外的甲酰化和原位环化成 6-二甲氨基-9-甲酰-5-脱氮杂恶嗪 9 与形成8. 使用乙烯基脒7 作为中间体来解释这些反应。

  DOI：

  10.1002/ardp.19823151111

文献信息

• A new, general, and convenient synthesis of 5-deazaflavins (5-deazaisoalloxazines)
  作者：Tomohisa Nagamatsu、Yuko Hashiguchi、Mastsugu Higuchi、Fumio Yoneda

  DOI：10.1039/c39820001085

  日期：——

  The condensation of 6-substituted-aminouracils with o-halogenobenzaldehydes in dimethylformamide led to the formation of the corresponding 5-deazaflavins in a single step.

  6-取代的氨基尿嘧啶与邻卤代苯甲醛在二甲基甲酰胺中的缩合导致一步形成相应的5-脱氮黄素。
• Nagamatsu, Tomohisa; Yamato, Hirotake; Ono, Masami, Journal of the Chemical Society. Perkin transactions I, 1992, # 16, p. 2101 - 2110
  作者：Nagamatsu, Tomohisa、Yamato, Hirotake、Ono, Masami、Takarada, Shigeki、Yoneda, Fumio

  DOI：——

  日期：——
• Flavins as potential antimalarials. 2. 3-Methyl-10-(substituted-phenyl)flavins
  作者：William B. Cowden、Peter K. Halladay、Ross B. Cunningham、Nicholas H. Hunt、Ian A. Clark

  DOI：10.1021/jm00110a009

  日期：1991.6

  A series of 3-methyl-10-(substituted-phenyl)flavins was prepared and tested for antimalarial activity against the lethal parasite Plasmodium vinckei in mice. Several of these analogues were found to be effective antimalarial agents. A quantitative structure-activity relationship study was undertaken with 44 analogues and no satisfactory relationship could be established.
• Synthesis, biological active molecular design, and molecular docking study of novel deazaflavin–cholestane hybrid compounds
  作者：Ajaya R. Shrestha、Takashi Shindo、Noriyuki Ashida、Tomohisa Nagamatsu

  DOI：10.1016/j.bmc.2008.07.089

  日期：2008.9

  Novel deazaflavin-cholestane hybrid compounds, 3',8'-disubstituted-5'-deazacholest-2,4-dieno[2,3g] pteridine-2',4'(3'H, 8'H)-diones, have been synthesized by condensation reaction between 6-(monosubstituted amino)-pyrimidin-2,4(1H,3H)-diones and 2-hydroxymethylenecholest-4-en-3-one in presence of p-toluenesulfonic acid monohydrate and diphenyl ether. The antitumor activities against human tumor cell lines (CCRF-HSB-2 and KB cells) have been investigated in vitro, and many of these compounds showed promising antitumor activities. Furthermore, molecular docking study using LigandFit within the software package Discovery Studio 1.7 was done for lead optimization of these compounds as potential PTK inhibitors. In general, all of the synthesized steroid-hybrid compounds showed good binding affinities into PTK (PDB code: 1t46). (C) 2008 Elsevier Ltd. All rights reserved.
• Nagamatsu, Tomohisa; Hashiguchi, Yuko; Yoneda, Fumio, Journal of the Chemical Society. Perkin transactions I, 1984, # 3, p. 561 - 565
  作者：Nagamatsu, Tomohisa、Hashiguchi, Yuko、Yoneda, Fumio

  DOI：——

  日期：——