4-(dimethylamino)-3-nitroaniline | 5367-54-4

• 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: 4-(dimethylamino)-3-nitroaniline
• 英文别名: N¹,N¹-Dimethyl-2-nitro-p-phenylendiamin；1-N,1-N-dimethyl-2-nitrobenzene-1,4-diamine
• CAS: 5367-54-4
• 化学式: C₈H₁₁N₃O₂
• 分子量: 181.194
• InChiKey: CYSDOQWFKCYUSN-UHFFFAOYSA-N

物化性质

• 熔点：
  137 °C
• 沸点：
  339.1±27.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2921590090

反应信息

• 作为反应物：
  描述：

  4-(dimethylamino)-3-nitroaniline 在 sodium sulfite 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Van Beek,L.K.H. et al., Recueil des Travaux Chimiques des Pays-Bas, 1968, vol. 87, p. 737 - 745

  摘要：

  DOI：
• 作为产物：
  描述：

  1-N-2,4-二硝基苯基二甲胺 在 sodium sulfide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以42%的产率得到N~1~,N~1~-二甲基-4-硝基-1,2-苯二胺
  参考文献：
  名称：

  Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine

  摘要：

  The nitroacridine derivative 9-[[3-(dimethylamino)propyl]amino]-1-nitroacridine (nitracrine) is selectively cytotoxic to hypoxic tumor cells in culture. However, the compound undergoes reductive metabolism too rapidly, with the reduction not being sufficiently inhibited by molecular oxygen in aerobic tissues, for it to demonstrate the same activity in vivo. In a search for derivatives with lower reduction potentials, we have synthesized and evaluated a series of derivatives bearing 4-substituents with a wide range of electronic properties. The one-electron reduction potentials (E(1] of these compounds, when compared under conditions of equivalent ionization, were highly correlated with sigma p values. However, at pH 7 the influence of substituent electronic properties was modified by prototrophic equilibria, with the basic nature of the acridine limiting the extent to which ring substituent electronic effects can be used to modulate reduction potential of the 1-nitro group. Nevertheless, comparison of the kinetics of the killing of AA8 cells under hypoxia suggests that some metabolic stabilization of the compounds can be achieved by the use of electron-donating substituents, with such compounds retaining the hypoxia-selective toxicity of nitracrine in cell culture. However, the 4-substituted nitracrines show no clear relationship between E(1) and cytotoxic potency, in distinct contrast to simpler nitroheterocycles such as nitroimidazoles.

  DOI：

  10.1021/jm00121a006

文献信息

• OXIDATION DYES
  申请人：Andreas J. Bittner

  公开号：US20010005914A1

  公开（公告）日：2001-07-05

  The invention relates to oxidation colorants which are particularly suitable for coloring keratin fiber and to a method of coloring such fiber. The colorants contain as the preliminary oxidation dye at least one diamino aniline of the general formula (I), in which R 1 to R 6 independently of each other are hydrogen, a (C 1- C 4 )-alkyl group, a hydroxy-(C 2- C 3 )-alkyl group, a (C 1- C 4 )-alkoxy-(C 2- C 3 )-alkyl group, an amino-(C 2- C 3 )-alkyl group in which the amino group can also have one or two (C 1- C 4 )-alkyl radicals, or a 2,3-dihydroxypropyl group provided that not all substituents R 1 to R 6 are simultaneously hydrogen, and R 1 and R 2 and/or R 3 and R 4 and/or R 5 and R 6 along with the nitrogen atom to which they are attached are also an aziridine ring, an azetidine ring, a pyrrolidine ring, a piperidine ring, an azepane ring, an azocine ring or a morpholino group, thiomorpholino group or piperazino group which has another substituent R 7 on the nitrogen atom which is selected from hydrogen, a (C 1- C 4 )-alkyl group, a hydroxy-(C 2- C 3 )-alkyl group, a (C 1- C 4 )-alkoxy-(C 2- C 3 )-alkyl group, an amino-(C 2- C 3 )-alkyl group, or a 2,3-dihydroxypropyl group, and the three remaining hydrogen atoms on the benzol ring can also be replaced independently of each other by a halogen atom or a (C 1- C 4 )-alkyl group, or the physiologically tolerable salts thereof with inorganic and organic acids. Shades of color are obtained which have a high level of brilliancy and color fastness.

  该发明涉及氧化着色剂，特别适用于着色角蛋白纤维，并提供了一种着色这种纤维的方法。这些着色剂包含至少一种二氨基苯胺的初级氧化染料，其通式为（I），其中R1到R6独立地是氢，（C1-C4）烷基，羟基（C2-C3）烷基，（C1-C4）烷氧基（C2-C3）烷基，氨基（C2-C3）烷基，其中氨基团也可以有一个或两个（C1-C4）烷基基团，或2,3-二羟基丙基基团，前提是R1到R6的所有取代基不同时是氢，且R1和R2和/或R3和R4和/或R5和R6连同它们连接的氮原子也是氮杂环丙烷环，氮杂环丁烷环，吡咯烷环，哌啶环，氮杂庚烷环，氮杂环庚烷环或吗啉基，硫代吗啉基或哌嗪基，其在氮原子上还有另一个取代基R7，选自氢，（C1-C4）烷基，羟基（C2-C3）烷基，（C1-C4）烷氧基（C2-C3）烷基，氨基（C2-C3）烷基，或2,3-二羟基丙基基团，苯环上的其余三个氢原子也可以独立地被卤原子或（C1-C4）烷基取代，或其与无机和有机酸的生理耐受盐。获得的色彩具有高度的光泽度和色牢度。
• [EN] N-(4-(4-METHYLTHIAZOL-5-YL) PYRIMIDIN-2-YL) -N-PHENYLAMINES AS ANTIPROLIFERATIVE COMPOUNDS<br/>[FR] N-(4-(4-METHYLTHIAZOL-5-YL) PYRIMIDINE-2-YL) -N-PHENYLAMINES COMME COMPOSES A ACTION ANTIPROLIFERANTE
  申请人：CYCLACEL LTD

  公开号：WO2003029248A1

  公开（公告）日：2003-04-10

  The present invention relates to 2-substituted 4-heteroaryl-pyrimidines, their preparation, pharmaceutical compositions containing them and their use as inhibitors of cyclin-dependent kinases (CDKs) and hence their use in the treatment of proliferative disorders such as cancer, leukaemia, psoriasis and the like.

  本发明涉及2-取代的4-杂环芳基嘧啶，它们的制备，包含它们的药物组合物以及它们作为细胞周期依赖性激酶（CDKs）的抑制剂的用途，因此可用于治疗增生性疾病，如癌症、白血病、牛皮癣等。
• N-(4-(4-methylthiazol-5-yl)pyrimidin-2-yl)-N-phenylamines as antiproliferative compounds
  申请人：——

  公开号：US20040259894A1

  公开（公告）日：2004-12-23

  The present invention relates to 2-substituted 4-heteroaryl-pyrimidines, their preparation, pharmaceutical compositions containing them and their use as inhibitors of cyclin-dependent kinases (CDKs) and hence their use in the treatment of proliferative disorders such as cancer, leukemia, psoriasis and the like.

  本发明涉及2-取代的4-杂环芳基嘧啶、它们的制备、含有它们的药物组合物以及它们作为细胞周期蛋白依赖性激酶（CDKs）的抑制剂的用途，因此可用于治疗增殖性疾病，如癌症、白血病、牛皮癣等。
• Anti-viral compounds
  申请人：Wang Shudong

  公开号：US20050288307A1

  公开（公告）日：2005-12-29

  The present invention relates to the use of 2-substituted 4-heteroaryl-pyrimidines and related compounds in the treatment of viral disorders.

  本发明涉及使用2-取代的4-杂环基嘧啶和相关化合物治疗病毒性疾病。
• N-(4-(4-methylthiazol-5-yl) pyrimidin-2-yl)-N-phenylamines as antiproliferative compounds
  申请人：Wang Shudong

  公开号：US20060199830A1

  公开（公告）日：2006-09-07

  The present invention relates to 2-substituted 4-heteroaryl-pyrimidines, their preparation, pharmaceutical compositions containing them and their use as inhibitors of cyclin-dependent kinases (CDKs) and hence their use in the treatment of proliferative disorders such as cancer, leukaemia, psoriasis and the like.

  本发明涉及2-取代的4-杂环芳基嘧啶，它们的制备，含有它们的药物组合物以及它们作为细胞周期蛋白依赖性激酶（CDKs）抑制剂的用途，因此可用于治疗增殖性疾病，如癌症、白血病、银屑病等。