4-methyl-N-(3,4,5-trimethoxybenzylidene)aniline | 58896-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methyl-N-(3,4,5-trimethoxybenzylidene)aniline
• 英文别名: N-(3,4,5-trimethoxybenzylidene)-4-methylphenylamine；N-(4-methylphenyl)-1-(3,4,5-trimethoxyphenyl)methanimine
• CAS: 58896-42-7
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: RNRJWKBMBSZXOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(3,4,5-trimethoxybenzylidene)aniline 在 [Mn(CO)₃Br(κ²N,N-PyCH₂NH₂)] 、 potassium tert-butylate 、 异丙醇 作用下， 反应 18.0h， 以88%的产率得到苯甲胺,3,4,5-三甲氧基-N-(4-甲基苯基)-
  参考文献：
  名称：

  锰催化的醛亚胺转移加氢

  摘要：

  不含膦的锰（I）催化剂促进了通过转移氢化将亚胺还原为胺。使用异丙醇作为还原剂，在存在吨丁醇钾（4摩尔％）和锰配合物[锰（CO）3 Br（上κ 2 N，PyCH 2 NH 2）]（2摩尔％），大量的各种醛亚胺的（30个实施例）通常在80°C下经过3小时还原，收率良好至极佳。

  DOI：

  10.1002/cctc.201900314
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 乙烷,三氯氟- 在 1-butyl-1-methylpyrrolidinium hydrogen sulfate 作用下， 以 乙醇 为溶剂， 生成 4-methyl-N-(3,4,5-trimethoxybenzylidene)aniline
  参考文献：
  名称：

  1-Butyl-1-methylpyrrolidinium hydrogen sulfate-promoted preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives

  摘要：

  开发了一种便捷的制备方法，用于合成各种1,5-二芳基-3-(芳基氨基)-1H-吡咯-2(5H)-酮，这一方法由1-丁基-1-甲基吡咯烷铵氢磺酸促进，涉及醛与胺和乙基丙酮在常温条件下的环缩合反应。

  DOI：

  10.1007/s11164-012-0749-9

文献信息

• 3-Vinylazetidin-2-Ones: Synthesis, Antiproliferative and Tubulin Destabilizing Activity in MCF-7 and MDA-MB-231 Breast Cancer Cells
  作者：Wang、Malebari、Greene、O’Boyle、Fayne、Nathwani、Twamley、McCabe、Keely、Zisterer、Meegan

  DOI：10.3390/ph12020056

  日期：——

  Microtubule-targeted drugs are essential chemotherapeutic agents for various types of cancer. A series of 3-vinyl-β-lactams (2-azetidinones) were designed, synthesized and evaluated as potential tubulin polymerization inhibitors, and for their antiproliferative effects in breast cancer cells. These compounds showed potent activity in MCF-7 breast cancer cells with an IC50 value of 8 nM for compound 7s 4-[3-Hydroxy-4-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-3-vinylazetidin-2-one) which was comparable to the activity of Combretastatin A-4. Compound 7s had minimal cytotoxicity against both non-tumorigenic HEK-293T cells and murine mammary epithelial cells. The compounds inhibited the polymerisation of tubulin in vitro with an 8.7-fold reduction in tubulin polymerization at 10 M for compound 7s and were shown to interact at the colchicine-binding site on tubulin, resulting in significant G2/M phase cell cycle arrest. Immunofluorescence staining of MCF-7 cells confirmed that β-lactam 7s is targeting tubulin and resulted in mitotic catastrophe. A docking simulation indicated potential binding conformations for the 3-vinyl-β-lactam 7s in the colchicine domain of tubulin. These compounds are promising candidates for development as antiproiferative microtubule-disrupting agents.

  微管靶向药物是各种癌症的重要化疗药物。一系列3-乙烯基-β-内酰胺（2-氮杂环丙酮）被设计、合成并评估为潜在的微管聚合抑制剂，以及它们在乳腺癌细胞中的抗增殖效应。这些化合物在MCF-7乳腺癌细胞中表现出强大的活性，其中化合物7s（4-[3-羟基-4-甲氧基苯基]-1-(3,4,5-三甲氧基苯基)-3-乙烯基氮杂环丙酮）的IC50值为8 nM，与康布雷他定A-4的活性相当。化合物7s对非肿瘤性HEK-293T细胞和小鼠乳腺上皮细胞均具有最小的细胞毒性。这些化合物在体外抑制了微管的聚合，在10 μM的浓度下，化合物7s使微管聚合减少了8.7倍，并且显示出它们与微管上的秋水仙碱结合位点相互作用，导致显著的G2/M期细胞周期阻滞。MCF-7细胞的免疫荧光染色证实了β-内酰胺7s靶向微管，并导致有丝分裂灾难。对于3-乙烯基-β-内酰胺7s在微管秋水仙碱结合区域的潜在结合构象进行的对接模拟表明了潜在的结合构象。这些化合物是作为抗增殖微管破坏剂的发展有前途的候选药物。
• NHC-carbene cyclopentadienyl iron based catalyst for a general and efficient hydrosilylation of imines
  作者：Luis C. Misal Castro、Jean-Baptiste Sortais、Christophe Darcel

  DOI：10.1039/c1cc14403k

  日期：——

  A general and efficient hydrosilylation of imines catalysed by a well defined NHC-carbene cyclopentadienyl iron complex has been developed. Both aldimines and ketimines are converted to the corresponding amines under mild conditions, and under visible light activation.

  已经开发出一种通用且高效的由明确的NHC-卡宾环戊二烯基铁络合物催化的亚胺的水硅化反应。醛亚胺和酮亚胺在温和条件下以及可见光激活下转化为相应的胺。
• Cyclopentadienyl N-heterocyclic carbene–nickel complexes as efficient pre-catalysts for the hydrosilylation of imines
  作者：Linus P. Bheeter、Mickaël Henrion、Michael J. Chetcuti、Christophe Darcel、Vincent Ritleng、Jean-Baptiste Sortais

  DOI：10.1039/c3cy00514c

  日期：——

  The in situ generated nickel hydride complex, [Ni(Mes2NHC)HCp], and its cationic analogue, [Ni(Mes2NHC)(NCMe)Cp](PF6), are efficient and chemoselective pre-catalysts for the hydrosilylation of both aldimines and ketimines under mild conditions.

  原位生成的镍氢化物[Ni(Mes2NHC)HCp]及其阳离子类似物[Ni(Mes2NHC)(NCMe)Cp](PF6)是在温和条件下进行醛亚胺和酮亚胺氢化反应的高效化学选择性前催化剂。
• Stilbene derivatives as anticancer agents
  申请人：Research Corporation Technologies, Inc.

  公开号：US05430062A1

  公开（公告）日：1995-07-04

  The present invention relates to stilbene derivatives which possess utility as anti-cancer agents. The compounds can be used to treat cancers which are susceptible to treatment therewith, and can be utilized in a method of treating such cancers. Pharmaceutical compositions containing the compounds are disclosed. Three preferred compounds among those disclosed are (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, (Z)-1-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, and 4-methyl-3',4',5'-trimethoxybenzylaniline hydrochloride.

  本发明涉及一种具有抗癌作用的苯乙烯衍生物。该化合物可用于治疗易受其治疗的癌症，并可用于治疗此类癌症的方法。本发明还揭示了含有该化合物的制药组合物。在所披露的化合物中，有三种优选化合物，分别为（Z）-1-（4-甲氧基苯基）-2-（3,4,5-三甲氧基苯基）乙烯，（Z）-1-（4-甲基苯基）-2-（3,4,5-三甲氧基苯基）乙烯和4-甲基-3'，4'，5'-三甲氧基苯乙胺盐酸盐。
• Gopalakrishnan, Mannathusamy; Sureshkumar, Purushothaman; Kanagarajan, Vijayakumar, Journal of Chemical Research, 2005, # 5, p. 299 - 303
  作者：Gopalakrishnan, Mannathusamy、Sureshkumar, Purushothaman、Kanagarajan, Vijayakumar、Thanusu, Jeyaraman、Govindaraju, Ramalingam

  DOI：——

  日期：——