N-benzyl-2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-benzyl-2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxamide
• 英文别名: N-benzyl-2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxamide
• 化学式: C₂₃H₂₃N₃O₂S
• 分子量: 405.521
• InChiKey: VGWIBNIYANSWJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-羟基硫代苯甲酰胺 在 盐酸羟胺 、 水 、 potassium carbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 sodium hydroxide 、 magnesium chloride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.67h， 生成 N-benzyl-2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxamide
  参考文献：
  名称：

  Synthesis, Molecular Docking, DFT Study of Novel N-Benzyl-2-(3-cyano-4-isobutoxyphenyl)- 4-methylthiazole-5-carboxamide Derivatives and their Antibacterial Activity

  摘要：

  使用微波方法合成了一系列基于非布索他的新化学实体，并通过核磁共振、质谱和傅里叶变换红外光谱研究进行了表征。非布索他酰胺核取代化合物8c（-7.91kcal/mol）、8g（-7.94 kcal/mol）的分子对接显示出高结合能对抗ALK受体。通过B3LYP/6-31G方法计算了MEPs、HOMO、LUMO和HOMO-LUMO能隙的理论研究。在测试的化合物中，甲氧基取代化合物8g对金黄色葡萄球菌和枯草杆菌显示出最高的抗菌活性。

  DOI：

  10.14233/ajchem.2020.22390

文献信息

• Febuxostat-based amides and some derived heterocycles targeting xanthine oxidase and COX inhibition. Synthesis, in vitro and in vivo biological evaluation, molecular modeling and in silico ADMET studies
  作者：Aya Y. Rashad、Shaymaa E. Kassab、Hoda G. Daabees、Ahmed E. Abdel Moneim、Sherif A.F. Rostom

  DOI：10.1016/j.bioorg.2021.104948

  日期：2021.8

  were further investigated for their in vitro COX-1 and COX-2 inhibitory activity, where fifteen analogs demonstrated recognizable COX-2 inhibitory potential (IC50 values range 0.04 – 0.1 µM), when correlated with celecoxib (IC50 0.05 µM), together with appreciable selectivity indices. Compounds 5a, 14b, 17, 19c, 19e and 21b that showed significant in vitro XO and/ or COX inhibitory potentials were further

  合成了包含羧酰胺官能团和不同取代杂环的各种非布司他衍生物，并评估了它们作为黄嘌呤氧化酶 (XO) 和环氧合酶 (COX) 抑制剂的生物活性。所有测试的化合物都表现出不同的体外XO 抑制活性（IC 50值 0.009–0.077 µM），其中类似物17已成为最有效的衍生物（IC 50 0.009 µM），几乎是非布司他效力的 3 倍（ IC 50 0.026 µM)。进一步研究了相同类似物的体外COX-1 和 COX-2 抑制活性，其中 15 种类似物显示出可识别的 COX-2 抑制潜力（IC 50值范围 0.04 – 0.1 µM)，当与塞来昔布 (IC 50 0.05 µM) 相关时，连同可观的选择性指数。化合物5a、14b、17、19c、19e和21b在体外显示出显着的XO 和/或 COX 抑制潜力，因此进一步研究了它们的体内降尿酸和抗炎活性。有趣的是，体内结果与收集的体外数据一致。化
• Design, synthesis, in silico and in vitro studies of novel 4-methylthiazole-5-carboxylic acid derivatives as potent anti-cancer agents
  作者：Ravendra Babu Kilaru、Koteswara Rao Valasani、Nanda Kumar Yellapu、Hari Prasad Osuru、Chandra Sekhar Kuruva、Bhaskar Matcha、Naga Raju Chamarthi

  DOI：10.1016/j.bmcl.2014.07.058

  日期：2014.9

  (S)ince inhibitors of mucin onco proteins are potential targets for breast cancer therapy, a series of novel 4-methylthiazole-5-carboxylic acid (1) derivatives 3a-k were synthesized by the reaction of 1 with SOCl2 followed by different bases/alcohols in the presence of triethylamine. Once synthesized and characterized, their binding modes with MUC1 were studied by molecular docking analysis using Aruglab 4.0.1 and QSAR properties were determined using HyperChem. All synthesized compounds were screened for in vitro anti-breast cancer activity against MDA-MB-231 breast adenocarcinoma cell lines by Trypan-blue cell viability assay and MTT methods. Compounds 1, 3b, 3d, 3e, 3i and 3f showed good anti-breast cancer activity. Since 1 and 3d exhibited high potent activity against MDA-MB-231 cell lines, they show could be effective mucin onco protein inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis, Molecular Docking, DFT Study of Novel N-Benzyl-2-(3-cyano-4-isobutoxyphenyl)- 4-methylthiazole-5-carboxamide Derivatives and their Antibacterial Activity
  作者：D. Sam Daniel Prabu、Sivalingam Lakshmanan、K. Thirumurugan、N. Ramalakshmi、S. Arul Antony

  DOI：10.14233/ajchem.2020.22390

  日期：2020.2.10

  A series of febuxostat based new chemical entities was synthesized using microwave method and characterized by NMR, mass and FT-IR spectral studies. Molecular docking of febuxostat amide nucleus substitution compounds 8c (-7.91kcal/mol), 8g (-7.94 kcal/mol) exhibiting high binding energy against ALK receptors. Theoretical investigation of MEPs, HOMO, LUMO and energy gap of HOMO-LUMO were calculated by B3LYP/6-31G method. Among the tested compounds, methoxy substituted compound 8g showed highest antibacterial activity against S. aereus and B. subtilis.

  使用微波方法合成了一系列基于非布索他的新化学实体，并通过核磁共振、质谱和傅里叶变换红外光谱研究进行了表征。非布索他酰胺核取代化合物8c（-7.91kcal/mol）、8g（-7.94 kcal/mol）的分子对接显示出高结合能对抗ALK受体。通过B3LYP/6-31G方法计算了MEPs、HOMO、LUMO和HOMO-LUMO能隙的理论研究。在测试的化合物中，甲氧基取代化合物8g对金黄色葡萄球菌和枯草杆菌显示出最高的抗菌活性。