2-氰基-N-(2,4-二甲氧基苯基)乙酰胺 | 133550-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氰基-N-(2,4-二甲氧基苯基)乙酰胺
• 英文名称: 2-cyano-N-(2,4-dimethoxyphenyl) acetamide
• 英文别名: 2-cyano-N-(2,4-dimethoxyphenyl)acetamide
• CAS: 133550-46-6
• 化学式: C₁₁H₁₂N₂O₃
• mdl: MFCD00019841
• 分子量: 220.228
• InChiKey: DNTNHFNYAPVBQU-UHFFFAOYSA-N

物化性质

• 沸点：
  431.8±40.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-氰基-N-(2,4-二甲氧基苯基)乙酰胺 在 高氯酸 、 一水合肼 作用下， 以 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 24.0h， 生成 2-(tert-butyl)-N-(2,4-dimethoxyphenyl)-3-((2,4,4-trimethylpentan-2-yl)amino)-1H-imidazo[1,2-b]pyrazole-7-carboxamide
  参考文献：
  名称：

  咪唑并[1,2-b]吡唑-7-甲酰胺的合成、细胞毒性表征和合成孔径雷达研究

  摘要：

  研究了新型咪唑并[1,2-b]吡唑-7-甲酰胺的合成和体外细胞毒特性。在利用 MCF-7 人乳腺、4T1 乳腺和 HL-60 人早幼粒细胞白血病癌细胞系的 2D 和 3D 培养物进行先导优化后，构建了一个 67 元文库，并构建了构效关系（SAR ) 确定。七个合成的类似物表现出亚微摩尔活性，其中化合物 63 发挥最显着的效力，具有显着的 HL-60 敏感性（IC50 = 0.183 μM）。

  DOI：

  10.1002/ardp.201800062
• 作为产物：
  描述：

  氰乙酸乙酯 、 2,4-二甲氧基苯胺 反应 0.5h， 生成 2-氰基-N-(2,4-二甲氧基苯基)乙酰胺
  参考文献：
  名称：

  Synthesis of New 8-Formyl-4-methyl-7-hydroxy Coumarin Derivatives

  摘要：

  8-甲醛-4-甲基-7-羟基香豆素衍生物通过Penchem缩合反应及Duffs反应合成。将其与N,N-二取代氰基乙酰胺在哌啶存在下处理，得到了新的8-甲醛-4-甲基-7-羟基香豆素衍生物（7a-o）。其结构通过红外光谱、^1H NMR、^13C NMR、质谱以及元素分析数据进行了表征。

  DOI：

  10.5012/jkcs.2012.56.4.459

文献信息

• Isatin-Schiff's base and chalcone hybrids as chemically apoptotic inducers and EGFR inhibitors; design, synthesis, anti-proliferative activities and in silico evaluation
  作者：Eman A. Fayed、Rogy R. Ezz Eldin、Ahmed B. M. Mehany、Ashraf H. Bayoumi、Yousry A. Ammar

  DOI：10.1016/j.molstruc.2021.130159

  日期：2021.6

  effect is concerned. Moreover, up-regulation of BAX and Caspase-3 and down-regulation of Bcl-2 resulted in the induction of apoptosis from those active compounds. Further work has shown that the most potent derivative 8b, caused cell cycle arrest at the G2/M phase. Also, EGFR inhibitory activity for 8b showed IC50 0.014 µM versus wild EGFRWT and 12.66 nM versus the mutant type, Lapatinib, and Erlotinib

  已经发现，伊斯汀衍生物对不同的人类癌细胞系具有抗增殖作用。合成了一系列isatin-schiff碱和查尔酮，并筛选了它们对三种人类细胞系MCF-7，HepG-2和HCT-116的抗癌活性。与作为参考标准的伊马替尼相比，所有测试的化合物均显示出中度至高度的抗肿瘤活性，IC 50为0.68–35.60μM。化合物2b，5、8b，12、13a和13b的活性最高，三种细胞系的IC 50为0.68至5.85μM。选择了最活跃的结构用于进一步研究。首先，IC 50已对正常人细胞（WI-38）的值进行了研究以确保命中的安全性，这表明就细胞毒性作用而言，我们的新化合物已表现出（IC 50 > 165.98μM）。此外，BAX和Caspase-3的上调和Bcl-2的下调导致了这些活性化合物的凋亡诱导。进一步的工作表明，最有效的衍生物8b导致细胞周期停滞在G2 / M期。此外，针对8b的EGFR抑制活性显示，与野生型EGFR
• Identification of a promising hit from a new series of pyrazolo[1,5-a]pyrimidine based compounds as a potential anticancer agent with potent CDK1 inhibitory and pro-apoptotic properties through a multistep in vitro assessment
  作者：Hossam R. Elgiushy、Sameh H. Mohamed、Heba Taha、Hussein Sawaf、Zeinab Hassan、Nageh A. Abou-Taleb、Eman M. El-labbad、Ashraf S. Hassan、Khaled A.M. Abouzid、Sherif F. Hammad

  DOI：10.1016/j.bioorg.2022.105646

  日期：2022.3

  cytochrome c, caspases (-3,-8, and-9), and decreased expression of Bcl-2. This suggests that the pro-apoptotic effect is exerted through the intrinsic pathway. The molecular docking study revealed a unique binding mode at the ATP binding pocket of CDK1/Cyc B/Cks2 through its 2,4-dimethoxyphenyl-amino. These results suggest that compound 7a could be a promising hit as a targeted protein kinase inhibitor which

  设计合成了16种新型2-芳氨基-5,7-二取代-N-芳基-吡唑并[1,5 - a ]嘧啶-3-甲酰胺衍生物系列。新化合物的抗肿瘤活性最初是通过 NCI-USA 60 细胞系小组的发展治疗计划筛选的。2-((2,4-二甲氧基苯基)氨基)-5,7-二苯基吡唑并[1,5 - a ]嘧啶-3-甲酰胺 ( 7a)被确定为潜在的打击物，平均生长抑制百分比为 48.5% 60-NCI 癌细胞系，而其他 15 种化合物的范围从 0.5 到 10.72%。在 MTT 测定中，化合物7a表现出 IC 50对 HCT-116 结肠直肠癌和 WI-38 人肺成纤维细胞正常细胞系分别为 6.28 ± 0.26 µM 和 17.7 ± 0.92 µM。在细胞周期分析中，化合物7a使细胞周期停滞在 G2/M 期。它能够以 IC 50 161.2 ± 2.7 nM 抑制 CDK1（细胞周期蛋白依赖性激酶 1）/Cyc B（细胞周期蛋白
• Development of Potent MALT1 Inhibitors Featuring a Novel “2-Thioxo-2,3-dihydrothiazolo[4,5-<i>d</i>]pyrimidin-7(6<i>H</i>)-one” Scaffold for the Treatment of B Cell Lymphoma
  作者：Xuewu Liang、Haolan Yu、Renwen Liang、Zhuanghui Feng、Abdusaid Saidahmatov、Chenxia Sun、Hairu Ren、Xiaohui Wei、Jiayan Zhao、Chenghua Yang、Hong Liu

  DOI：10.1021/acs.jmedchem.3c02031

  日期：2024.2.22

  reported a new class of MALT1 inhibitors featuring a novel “2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidin-7(6H)-one” scaffold developed by structure-based drug design. Structure–activity relationship studies finally led to the discovery of MALT1 inhibitor 10m, which covalently and potently inhibited MALT1 protease with the IC50 value of 1.7 μM. 10m demonstrated potent and selective antiproliferative

  粘膜相关淋巴组织淋巴瘤易位蛋白 1 （MALT1） 已成为治疗淋巴瘤和自身免疫性疾病的新型且有前途的治疗靶点。在此，我们报道了一类新的MALT1抑制剂，其特点是通过基于结构的药物设计开发的新型“2-噻氧代-2,3-二氢噻唑并[4,5-d]嘧啶-7（6H）-one”支架。构效关系研究最终导致 MALT1 抑制剂 10m 的发现，它共价有效抑制 MALT1 蛋白酶，IC50 值为 1.7 μM。10m 显示出对 ABC-DLBCL 的有效和选择性抗增殖活性以及诱导 HBL1 细胞凋亡的强大能力。10m 还有效地下调了 MALT1 及其下游信号通路的活性。此外，10m 诱导 mTOR 和 PI3K-Akt 信号上调，并与 HBL1 细胞中的雷帕霉素表现出协同抗肿瘤作用。更重要的是，10m 在植入的 HBL1 和 TMD8 异种移植模型中都显着抑制了肿瘤生长。总的来说，这项工作提供了具有独特核心结构的有价值的
• Tyrphostins. II. Heterocyclic and .alpha.-substituted benzylidenemalononitrile tyrphostins as potent inhibitors of EGF receptor and ErbB2/neu tyrosine kinases
  作者：Aviv Gazit、Nir Osherov、Israel Posner、Pnina Yaish、Enrique Poradosu、Chaim Gilon、Alexander Levitzki

  DOI：10.1021/jm00110a022

  日期：1991.6

  We have previously described a novel series of low molecular weight protein tyrosine kinase inhibitors which we named tyrphostins. The characteristic active pharmacophore of these compounds was the hydroxy-cis-benzylidenemalononitrile moiety. In this article we describe three novel groups of tyrphostins: (i) one group has the phenolic moiety of the cis-benzylidenemalononitrile replaced either with other substituted benzenes or with heteroaromatic rings, (ii) another is a series of conformationally constrained derivatives of hydroxy-cis-benzylidenemalononitriles in which the malononitrile moiety is fixed relative to the aromatic ring, and (iii) two groups of compounds in which the position trans to the benzenemalononitrile has been substituted by ketones and amides. Among the novel tyrphostins examined we found inhibitors which discriminate between the highly homologous EGF receptor kinase (HER1) and ErbB2/neu kinase (HER2). These findings may lead to selective tyrosine kinase blockers for the treatment of diseases in which ErbB2/neu is involved.
• Synthesis, binding and bioactivity of γ-methylene γ-lactam ecdysone receptor ligands: Advantages of QSAR models for flexible receptors
  作者：Woldeamanuel Birru、Ross T. Fernley、Lloyd D. Graham、Julian Grusovin、Ronald J. Hill、Albert Hofmann、Linda Howell、Peter J. James、Karen E. Jarvis、Wynona M. Johnson、Dionne A. Jones、Christa Leitner、Andris J. Liepa、George O. Lovrecz、Louis Lu、Roland H. Nearn、Brian J. O’Driscoll、Tram Phan、Matthew Pollard、Kathleen A. Turner、David A. Winkler

  DOI：10.1016/j.bmc.2010.06.020

  日期：2010.8

  Nuclear hormone receptors, such as the ecdysone receptor, often display a large amount of induced fit to ligands. The size and shape of the binding pocket in the EcR subunit changes markedly on ligand binding, making modelling methods such as docking extremely challenging. It is, however, possible to generate excellent 3D QSAR models for a given type of ligand, suggesting that the receptor adopts a relatively restricted number of binding site configurations or 'attractors'. We describe the synthesis, in vitro binding and selected in vivo toxicity data for gamma-methylene gamma-lactams, a new class of high-affinity ligands for ecdysone receptors from Bovicola ovis (Phthiraptera) and Lucilia cuprina (Diptera). The results of a 3D QSAR study of the binding of methylene lactams to recombinant ecdysone receptor protein suggest that this class of ligands is indeed recognised by a single conformation of the EcR binding pocket. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.