2,4-dimethyl-5-methoxyaniline | 380844-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4-dimethyl-5-methoxyaniline
• 英文别名: 5-methoxy-2,4-dimethyl-aniline；5-Methoxy-2,4-dimethyl-anilin；5-Methoxy-2,4-dimethylaniline
• CAS: 380844-06-4
• 化学式: C₉H₁₃NO
• mdl: MFCD20694442
• 分子量: 151.208
• InChiKey: NBSCXIYYCHVKDV-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  261.2±35.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-5-methoxyaniline 在 硫酸 作用下， 生成 Methyl-(5-hydroxy-2.4-dimethyl-phenyl)-aether
  参考文献：
  名称：

  Tea as a Potential Chemopreventive Agent in PhIP Carcinogenesis: Effects of Green Tea and Black Tea on PhIP-DNA Adduct Formation in Female F-344 Rats

  摘要：

  The heterocyclic amine 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) is formed during the cooking of proteinaceous animal foods (meat, chicken, and fish). PhIP is a carcinogen in the Fischer 344 (F-344) rat; it induces mammary tumors in female rats and lymphomas and colon and prostate rumors in male rats. In F-344 rats, PhIP forms DNA adducts in various organs, including the target organs. Inhibition of PhIP-DNA adduct formation is likely to lead to inhibition of PhIP tumorigenicity. We have examined the chemopreventive properties of green tea and black tea in PhIP carcinogenesis by evaluating their effects on PhIP-DNA adduct formation in the female F-344 rat. Young adult animals were maintained on powdered AIN-76A diet while receiving regular drinking water or 2% (wt/vol) infusions of green tea or black tea for a total of six weeks. During Weeks 3, 4, and 5, all animals received PhIP by gavage (1 mg/kg/day). Three rats per group were euthanized on Days 1 and 8 after termination of PhIP exposure. DNA was isolated from a number of organs and analyzed for PhIP-DNA adducts by P-32-postlabeling assays. Compared with animals on regular drinking wafer, PhIP-DMA adduct formation was inhibited in small intestine, colon, liver, and mammary epithelial cells (MECS) of animals receiving green tea or black tea as the sole source of drinking fluid. Green tea inhibited adduct formation in colon, liver, and MECs (33.3-80.0%) on both days, but only on Day 8 (54.4%) in small intestine. Black tea inhibited adduct formation on both days in liver (71.4-80.0%), on Day 1 in colon (40.0%), and on Day 8 in small intestine (81.8%); it had no effect on MEC adducts. Neither green tea nor black tea had an effect on adduct levels in pancreas: lungs, white blood cells, heart, kidneys, spleen, cecum, or stomach. Similarly, these teas did not affect the rate of adduct removal (percent change from Day 1 to Day 8) in any organ. It is concluded that green tea and black tea are potential chemopreventive agents in PhIP-induced tumorigenesis in the F-344 rat.

  DOI：

  10.1207/s15327914nc3601_8
• 作为产物：
  描述：

  2,4-二甲基-5-硝基-苯酚 在 10percent Pd/C 氢气 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.0h， 生成 2,4-dimethyl-5-methoxyaniline
  参考文献：
  名称：

  Optimization of 4-Phenylamino-3-quinolinecarbonitriles as Potent Inhibitors of Src Kinase Activity

  摘要：

  Subsequent to the discovery of 4-[(2,4-dichlorophenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile (1a) as an inhibitor of Src kinase activity (IC50 = 30 nM), several additional analogues were prepared. Optimization of the C-4 anilino group of la led to le, which contains a 2,4-dichloro-5-methoxy-substituted aniline. Replacement of the methoxy group at C-7 of le with a 3-(morpholin-4-yl)propoxy group provided 2c, resulting in increased inhibition of both Src kinase activity and Src-mediated cell proliferation. Analogues of 2c, with other trisubstituted anilines at C-4 were also potent Src inhibitors, and the propoxy group of 2c was preferred over ethoxy, butoxy, or pentoxy. Replacement of the morpholine group of 2c with a 4-methylpiperazine group provided 31a, which had an IC50 of 1.2 nM in the Src enzymatic assay, an IC50 of 100 nM for the inhibition of Src-dependent cell proliferation and was selective for Src over non-Src family kinases. Compound 31a, which had higher 1 and 4 h plasma levels than 2c, effectively inhibited tumor growth in xenograft models.

  DOI：

  10.1021/jm0102250

文献信息

• MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS
  申请人：Sheth Urvi

  公开号：US20120309758A1

  公开（公告）日：2012-12-06

  The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

  本发明涉及调节ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节蛋白，以及相关的组合物和方法。本发明还涉及使用这些调节剂治疗ABC转运蛋白介导的疾病的方法。
• Substituted arylamide diazepinopyrimidone derivatives for the treatment of neurodegenerative diseases caused by abnormal activity of GSK3-beta
  申请人：Sanofi-Aventis

  公开号：EP2090578A1

  公开（公告）日：2009-08-19

  A pyrimidone derivative represented by formula (I) or a salt thereof, or a solvate thereof or a hydrate thereof: wherein: Y represents two hydrogen atoms, a sulphur atom, an oxygen atom or a C1-2 alkyl group and a hydrogen atom; Z represents a bond, an oxygen atom, a nitrogen atom substituted by a hydrogen atom or a C1-3 alkyl group, a sulphur atom, a methylene group optionally substituted by one or two groups chosen from a C1-6 alkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-2 perhalogenated alkyl group or an amino group; R1 represents a 2, 3 or 4-pyridine ring or a 2, 4 or 5-pyrimidine ring, the ring being optionally substituted by a C1-6 alkyl group, a C1-6 alkoxy group or a halogen atom; R2 represents a hydrogen atom, a C1-6 alkyl group or a halogen atom; R3 represents a benzene ring or a naphthalene ring; the rings being optionally substituted R4 represents a hydrogen atom, a C1-4 alkyl group, a C3-7 cycloalkyl group, a C3-7 cycloalkyl-C1-6 alkyl group, a COO (C1-6-alkyl) group, these group being optionally substituted; R5 represents a hydrogen atom or a C1-6 alkyl group and n represents 0 to 3 and their therapeutic use in the treatment of neurodegenerative diseases caused by abnormal activity of GSK3β.

  公式（I）表示的嘧啶酮衍生物或其盐，或其溶剂或水合物：其中：Y代表两个氢原子，硫原子，氧原子或C1-2烷基和一个氢原子；Z代表键，氧原子，氮原子，被氢原子或C1-3烷基，硫原子，亚甲基基团替代的一个或两个基团，选自C1-6烷基，羟基，C1-6烷氧基，C1-2全氟烷基或氨基；R1代表2,3或4-吡啶环或2,4或5-嘧啶环，环可选择地被C1-6烷基，C1-6烷氧基或卤原子替代；R2代表氢原子，C1-6烷基或卤原子；R3代表苯环或萘环；环可选择地被替代R4代表氢原子，C1-4烷基，C3-7环烷基，C3-7环烷基-C1-6烷基，COO（C1-6-烷基）基团，这些基团可选择地被替代；R5代表氢原子或C1-6烷基和n代表0到3及其在治疗由GSK3β异常活性引起的神经退行性疾病中的治疗用途。
• Modulators of ATP-Binding Cassette Transporters
  申请人：Hadida-Ruah Sara

  公开号：US20130035327A1

  公开（公告）日：2013-02-07

  The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.

  本发明涉及ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜导电调节器，以及其组成物和使用这些调节剂的方法。本发明还涉及使用这些调节剂治疗ABC转运蛋白介导的疾病的方法。
• Divergent Synthesis of Anisidines by Controlling Cu‐Catalyzed [1,3]‐Methoxy Rearrangement
  作者：Itaru Nakamura、Riku Konta、Yasuhiro Ishida、Mai Tachibana、Masahiro Terada

  DOI：10.1002/adsc.202301160

  日期：2023.12.19

  with good product selectivity through a [1,3]-rearrangement of the methoxy group to the unsubstituted ortho position. In contrast, the reactions of N- methoxyanilines having a benzyloxycarbonyl group on the nitrogen atom using IPrCuBr and AgBF4 as catalysts afforded 3-substituted 2-anisidines via a domino process involving a [1,3]-rearrangement of the methoxy group to the EDG-substituted ortho position

  通过控制Cu催化的[1,3]-甲氧基重排实现了邻甲氧基苯胺的不同合成。在催化量的 IPr Me CuCl 和 AgNTf 2存在下，邻位具有给电子基团（EDG）（例如烷基或茴香基）和氮原子上的新戊酰基的N-烷氧基苯胺的反应得到通过甲氧基的[1,3]-重排至未取代的邻位，相应的6-取代的2-茴香胺具有良好的产物选择性。相反，使用IPrCuBr和AgBF 4作为催化剂，在氮原子上具有苄氧基羰基的N-甲氧基苯胺的反应通过涉及甲氧基的[1,3]-重排的多米诺过程得到3-取代的2-茴香胺。 EDG 取代邻位，然后对所得邻羟基喹啉亚胺中间体的 EDG 进行 [1,2]-重排。
• 7-Alkoxy-4-phenylamino-3-quinolinecar-bonitriles as Dual Inhibitors of Src and Abl Kinases
  作者：Diane H. Boschelli、Yanong D. Wang、Steve Johnson、Biqi Wu、Fei Ye、Ana Carolina Barrios Sosa、Jennifer M. Golas、Frank Boschelli

  DOI：10.1021/jm0499458

  日期：2004.3.1

  We previously reported that several 7-alkoxy-4-phenylamino-3-quinolinecarbonitriles were potent inhibitors of Src kinase activity. We disclose here a new highly efficient and versatile route to these compounds, which are also potent inhibitors of Abl kinase.