N,N-Dimethyl-2-Nitro-5-Aminoaniline | 55851-38-2

• 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: N,N-Dimethyl-2-Nitro-5-Aminoaniline
• 英文别名: 3-(dimethylamino)-4-nitroaniline；3-dimethylamino-4-nitroaniline；3-N,3-N-dimethyl-4-nitrobenzene-1,3-diamine
• CAS: 55851-38-2
• 化学式: C₈H₁₁N₃O₂
• 分子量: 181.194
• InChiKey: OQBOMBGZJBBZLA-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  358.8±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

反应信息

• 作为反应物：
  描述：

  N,N-Dimethyl-2-Nitro-5-Aminoaniline 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 反应 4.25h， 生成 N-[4-(3,5-Dimethyl-acridin-9-ylamino)-3-dimethylamino-phenyl]-methanesulfonamide; hydrochloride
  参考文献：
  名称：

  Potential antitumor agents. 48. 3'-Dimethylamino derivatives of amsacrine: redox chemistry and in vivo solid tumor activity

  摘要：

  Structure-activity relationships for a series of acridine-substituted 3'-N(CH3)2 derivatives of the clinical antileukemic drug amsacrine (1) are reported. The parent (unsubstituted) compound 3 has activity against the Lewis lung solid tumor that is superior to amsacrine (1), the new clinical amsacrine analogue 4, and the recently developed 3'-NHCH3 derivative 2. Although the compounds generally bind less well to DNA and are less dose potent in vivo than either their amsacrine (3'-OCH3) or 3'-NHCH3 analogues, they show very high levels of antitumor activity, with the 4-OCH3 derivative capable of effecting 100% cures of the Lewis lung solid tumor. The broad structure-activity relationships for acridine substitution more closely resemble those of the amsacrine than the 3'-NHCH3 series, with 4-substituted and 4,5-disubstituted compounds showing the highest activity.

  DOI：

  10.1021/jm00387a012
• 作为产物：
  描述：

  3-chloro-4-nitroacetanilide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 N,N-Dimethyl-2-Nitro-5-Aminoaniline
  参考文献：
  名称：

  Potential antitumor agents. 48. 3'-Dimethylamino derivatives of amsacrine: redox chemistry and in vivo solid tumor activity

  摘要：

  Structure-activity relationships for a series of acridine-substituted 3'-N(CH3)2 derivatives of the clinical antileukemic drug amsacrine (1) are reported. The parent (unsubstituted) compound 3 has activity against the Lewis lung solid tumor that is superior to amsacrine (1), the new clinical amsacrine analogue 4, and the recently developed 3'-NHCH3 derivative 2. Although the compounds generally bind less well to DNA and are less dose potent in vivo than either their amsacrine (3'-OCH3) or 3'-NHCH3 analogues, they show very high levels of antitumor activity, with the 4-OCH3 derivative capable of effecting 100% cures of the Lewis lung solid tumor. The broad structure-activity relationships for acridine substitution more closely resemble those of the amsacrine than the 3'-NHCH3 series, with 4-substituted and 4,5-disubstituted compounds showing the highest activity.

  DOI：

  10.1021/jm00387a012

文献信息

• Potential antitumor agents. 52. Carbamate analogs of amsacrine with in vivo activity against multidrug-resistant P388 leukemia
  作者：Gordon W. Rewcastle、Bruce C. Baguley、Graham J. Atwell、William A. Denny

  DOI：10.1021/jm00392a009

  日期：1987.9

  provided increased activity against the multidrug-resistant P388/ADR leukemia subline in vivo. Since activity against such resistant tumors is of great clinical significance, a series of acridine-substituted carbamate derivatives were evaluated against both wild-type and ADR/resistant P388 leukemia and the Lewis lung solid tumor in vivo. Structure-activity relationships for all three tumor lines were similar

  对一系列与抗白血病药物氨苯磺酸有关的苯胺取代的9-苯胺基cr啶的研究表明，1'-氨基甲酸酯基团在体内对多药耐药的P388 / ADR白血病亚系提供增强的活性。由于针对这种抗药性肿瘤的活性具有重要的临床意义，因此在体内针对野生型和ADR /抗药性P388白血病以及Lewis肺实体瘤评估了一系列of啶取代的氨基甲酸酯衍生物。所有三个肿瘤细胞系的结构活性关系相似，其中3-卤代-5-甲基和3-卤代5-甲氧基化合物被证明是活性最高的。这种取代模式还提供了最高的DNA结合。此类化合物（尤其是3-氯-5-甲基和3-氯-5-甲氧基）对野生型P388和Lewis肺具有体内活性，其活性与先前开发的最佳氨水analogue类似物相当（治愈率超过50％） ，以及P388 / ADR活动。这项工作从根本上完成了amsacrine系列抗肿瘤药的开发。
• DYES
  申请人：——

  公开号：US20010052156A1

  公开（公告）日：2001-12-20

  A colorant for coloring keratin fibers wherein the colorant contains a substantive dye which is a 4-nitroaniline derivative corresponding to formula (I): 1 in which R 1 , R 2 , R 3 and R 4 independently of one another represent a hydrogen atom, an alkyl, hydroxyalkyl, alkoxyalkyl, carbamyl alkyl, mesylaminoalkyl, acetylaminoalkyl, ureidoalkyl, carbalkoxyaminoalkyl, sulfalkyl, piperidinoalkyl, morpholinoalkyl or phenyl radical optionally substituted by an amino group in the para position, the alkyl or alkoxy groups containing 1 to 4 carbon atoms, with the proviso that the four substituents R 1 , R 2 , R 3 and R 4 do not simultaneously represent hydrogen, and the groups —NR 1 R 2 and —NR 3 R 4 may also represent an aziridine, acetidine, pyrrolidine, piperidine, azepan, azocine, morpholine, thiomorpholine or piperazine ring which may also bear another substituent R 8 at the nitrogen atom, R 8 being a hydrogen atom, a (C 1-4 )-alkyl, hydroxy-(C 2-3 )-alkyl, (C 1-4 )-alkoxy-(C 2-3 )-alkyl, amino-(C 2-3 )-alkyl or 2,3-dihydroxypropyl group, and R 5 , R 6 and R 7 independently of one another represent ahydrogen atom, a halogen atom, a (C 1-4 )-alkyl, (C 1-4 )-alkoxy, carboxy, sulfo or (C 2-4 )-hydroxyalkyl group, or a physiologically compatible salt of the compounds with an inorganic or organic acid.

  一种用于给角蛋白纤维着色的着色剂，其中该着色剂含有一种实质性染料，该染料是与式(I)相对应的4-硝基苯胺衍生物，式中R1、R2、R3和R4分别独立地代表氢原子、烷基、羟基烷基、烷氧基烷基、氨基甲酰基烷基、甲磺基氨基烷基、乙酰氨基烷基、脲基烷基、羰基氨基烷基、磺基烷基、哌啶基烷基、吗啉基烷基或苯基基团，该苯基基团在对位可能被氨基取代，烷基或烷氧基基团含有1至4个碳原子，但R1、R2、R3和R4的四个取代基不能同时代表氢，而基团—NR1R2和—NR3R4也可以表示一个氮杂环丙烷、乙酸丙烷、吡咯烷、哌啶、氮丙烷、氮环己烷、吗啉、硫吗啉或哌嗪环，该环也可以在氮原子处带有另一个取代基R8，R8为氢原子、(C1-4)-烷基、羟基-(C2-3)-烷基、(C1-4)-烷氧基-(C2-3)-烷基、氨基-(C2-3)-烷基或2,3-二羟基丙基基团，而R5、R6和R7分别独立地代表氢原子、卤原子、(C1-4)-烷基、(C1-4)-烷氧基、羧基、磺酸基或(C2-4)-羟基烷基，或者是与无机或有机酸形成的生理相容盐。
• 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。
• Structure-based discovery of IHMT-IDH1-053 as a potent irreversible IDH1 mutant selective inhibitor
  作者：Qianmao Liang、Beilei Wang、Fengming Zou、Gongrui Guo、Wenliang Wang、Wei Wang、Qingwang Liu、Lijuan Shen、Chen Hu、Wenchao Wang、Aoli Wang、Tao Huang、Yuying He、Ruixiang Xia、Jian Ge、Jing Liu、Qingsong Liu

  DOI：10.1016/j.ejmech.2023.115411

  日期：2023.8

  Through a structure-based irreversible drug design approach, we have discovered a highly potent IDH1-mutant inhibitor compound 16 (IHMT-IDH1-053) (IC50 = 4.7 nM), which displays high selectivity against IDH1 mutants over IDH1 wt and IDH2 wt/mutants. The crystal structure demonstrates that 16 binds to the IDH1 R132H protein in the allosteric pocket adjacent to the NAPDH binding pocket through a covalent

  通过基于结构的不可逆药物设计方法，我们发现了一种高效的 IDH1 突变体抑制剂化合物16 (IHMT-IDH1-053)（IC 50  = 4.7 nM），它对 IDH1 突变体的选择性高于 IDH1 wt 和 IDH2 wt /突变体。晶体结构表明16通过与残基 Cys269 的共价键结合到与 NAPDH 结合口袋相邻的变构口袋中的 IDH1 R132H 蛋白。16在 IDH1 R132H 突变体转染的 293T 细胞中抑制 2-羟基戊二酸 (2-HG) 的产生 (IC 50  = 28 nM)。此外，它还能抑制 HT1080 细胞系和原代 AML 细胞的增殖，这两种细胞都带有 IDH1 R132 突变体。体内，16在 HT1080 异种移植小鼠模型中抑制 2-HG 水平。我们的研究表明，16将成为研究 IDH1 突变体相关病理学的新药理学工具，共价结合模式为设计不可逆 IDH1 抑制剂提供了一种新方法。
• Substituted o-phenylenediamine compounds
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0095355A1

  公开（公告）日：1983-11-30

  The novel class of compounds of the present invention represented by the general formula (I): in which R1 represents A and B each represent H or a lower alkane optionally substituted with amino and/or hydroxyl functions, except that A and B are not both H; R3 represents H, OCH3, CH3, halogen, NH2, NO2, NHCH3, N3(CH3)2, N3, NHCOCH3, NHCOOCH3, N(CH3)COOCH3, CONH2 or CONHCH3,R4 represents H, alkyl, O-alkyl, CONH2, CONHCH3 or CONHCH2CONHCH3, except that R3 and R4, taken together can represent -C = CH -CN = N-; R5 represents H, alkyl, O-alkyl, CONH2, CONHCH3 or CONH2CH2 CONHCH3; Re represents lower alkyl; R7 represents CH3 or C5H6 (phenyl); R8 repn3sents lower alkyl or C8H6 (phenyl); R9 represents H, NHCOCH3, NH2 or N=CHN(CH3)2 and R10 represents H or NH2; and the acid addition salts thereof, possess antibacterial and antitumour properties.

  本发明的新型化合物由通式(I)代表： 其中 R1 代表 A 和 B 分别代表 H 或任选被氨基和/或羟基取代的低级烷烃，但 A 和 B 不能都是 H； R3 代表 H、OCH3、CH3、卤素、NH2、NO2、NHCH3、N3(CH3)2、N3、NHCOCH3、NHCOOCH3、N(CH3)COOCH3、CONH2 或 CONHCH3；R4 代表 H、烷基、O-烷基、CONH2、CONHCH3 或 CONHCH2CONHCH3，但 R3 和 R4 合在一起可代表 -C = CH -CN = N-；R5 代表 H、烷基、O-烷基、CONH2、CONHCH3 或 CONH2CH2CONHCH3；R6 代表 H、烷基、O-烷基、CONH2、CONHCH3 或 CONH2CH2CONHCH3。 CONH2CH2 CONHCH3； Re 代表低级烷基； R7 代表 CH3 或 C5H6（苯基）； R8 代表低级烷基或 C8H6（苯基）； R9 代表 H、NHCOCH3、NH2 或 N=CHN(CH3)2，R10 代表 H 或 NH2； 及其酸加成盐具有抗菌和抗肿瘤特性。