N-(5-acetyl-4-methylthiazol-2-yl)-4-nitrobenzamide | 39884-15-6

• 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-(5-acetyl-4-methylthiazol-2-yl)-4-nitrobenzamide
• 英文别名: 4-methyl-5-acetyl-2-(4-nitrobenzoylamino)thiazole；1-[4-methyl-2-(4-nitro-benzoylamino)-thiazol-5-yl]-ethanone；N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-4-nitrobenzamide
• CAS: 39884-15-6
• 化学式: C₁₃H₁₁N₃O₄S
• 分子量: 305.314
• InChiKey: WPMURQRZFHQAJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(5-acetyl-4-methylthiazol-2-yl)-4-nitrobenzamide 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 2-bromo-1-[4-methyl-2-(4-nitro-benzoylamino)-thiazol-5-yl]-ethanone
  参考文献：
  名称：

  Suciu,D., Journal fur praktische Chemie (Leipzig 1954), 1972, vol. 314, p. 961 - 964

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯甲酰异硫氰酸盐 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 生成 N-(5-acetyl-4-methylthiazol-2-yl)-4-nitrobenzamide
  参考文献：
  名称：

  Chalcone-Thiazole Hybrids: Rational Design, Synthesis, and Lead Identification against 5-Lipoxygenase

  摘要：

  A hybrid pharmacophore approach is used to design and synthesize novel chalcone-thiazole hybrid molecules. Herein, thiazole has been hybridized with chalcone to obtain a new class of 5-LOX inhibitors. In vitro biological evaluation showed that most of the compounds were better 5-LOX inhibitors than the positive control, Zileuton (IC50 = 1.05 +/- 0.03 mu M). The best compounds in the series, namely, 4k, 4n, and 4v (4k: IC50 = 0.07 +/- 0.02 mu M, 4n: IC50 = 0.08 +/- 0.05 mu M, 4v: 0.12 +/- 0.04 mu M) are found to be 10 times more active than previously reported 2-amino thiazole (2m: IC50 = 0.9 +/- 0.1 mu M) by us. Further, 4k has redox (noncompetitive) while 4n and 4v act through a competitive inhibition mechanism. SAR indicated that the presence of methoxy/methyl either in the vicinity of chalcone or both thiazole and chalcone contributed to the synergistic inhibitory effect.

  DOI：

  10.1021/acsmedchemlett.9b00193

文献信息

• N-(5-acetyl-4-methylthiazol-2-yl)arylamide derivatives as multi-target-directed ligands: design, synthesis, biochemical evaluation and computational analysis
  作者：Rabail Ujan、Hafiz Mohammad Kashif Mahmood、Pervaiz Ali Channar、Syeda Abida Ejaz、Shomaila Saeed、Aamer Saeed、Amna Saeed、Mamoona Rafiq、Kashif Ali Channar、Hafiz Abdul Bari Indher、Hammad Ismail

  DOI：10.1007/s12039-021-01998-z

  日期：2022.3

  analysis) and further tested for biological activities (antioxidant, antibacterial, antifungal and α-glucosidase). The anti-oxidant properties of compound 3h (IC50 ± SEM = 141.9 ± 1.12 µg/mL) were found maximum in comparison to the rest of the derivatives. The antibacterial results showed the compounds 3d and 3h as a significant bacterial inhibitor. The significant fungicidal activity was observed by compound

  在本研究中，我们报告了 N-(5-acetyl-4-methylthiazol-2-yl) 芳酰胺衍生物 ( 3a-h )的总共八种衍生物的合成。以良好至优异的产率获得的产品代表具有良好结构-活性关系的药物样分子。所有合成的化合物都进一步进行了化学表征（NMR、FTIR 和元素分析），并进一步测试了生物活性（抗氧化、抗菌、抗真菌和 α-葡萄糖苷酶）。与其他衍生物相比，化合物3h (IC 50 ± SEM = 141.9 ± 1.12 µg/mL)的抗氧化特性最大。抗菌结果显示化合物3d和3h作为一种重要的细菌抑制剂。与阳性对照(特比萘芬)的结果相比，化合物3a观察到显着的杀真菌活性，抑制区高达24mm。当观察对 α-葡萄糖苷酶活性的影响时，酶抑制活性最高的是3h (IC 50 ± SEM 134.4 ± 1.01 µg/mL)，其次是3c (IC 50± SEM = 157.3 ± 1.11
• Design, synthesis and neuraminidase inhibitory activity of 4-methyl-5-(3-phenylacryloyl) thiazoles
  作者：Yu-Yang Liu、Yang-Jie Yi、Jiao Ye、Ai-Xi Hu

  DOI：10.1007/s11030-023-10639-1

  日期：——

  A series of 4-methyl-5-(3-phenylacryloyl)thiazoles based on chalcones were designed, synthesized and evaluated for their influenza neuraminidase (NA) inhibitory activity in vitro. A preliminary structure–activity relationship (SAR) analysis showed that thiazoles bearing amide had greater potency. It also showed that mono-hydroxyl group at 4-position on phenyl ring was more effective than other electron-releasing groups or electron-withdraw groups. Compounds A2 and A26 were more potent against NA with IC50 values of 8.2 ± 0.5 μg/mL and 6.2 ± 1.4 μg/mL, respectively. Molecular docking study demonstrated that thiazoles skeleton was benefit for the NA inhibitory activity.

  研究人员设计、合成了一系列基于查耳酮的 4-甲基-5-(3-苯基丙烯酰基)噻唑，并在体外评估了它们对流感神经氨酸酶（NA）的抑制活性。初步的结构-活性关系（SAR）分析表明，含酰胺的噻唑类化合物具有更强的效力。分析还表明，苯环 4 位上的单羟基比其他释放电子的基团或撤回电子的基团更有效。化合物 A2 和 A26 对 NA 更有效，IC50 值分别为 8.2 ± 0.5 μg/mL 和 6.2 ± 1.4 μg/mL。分子对接研究表明，噻唑骨架有利于NA的抑制活性。
• Suciu,D., Journal fur praktische Chemie (Leipzig 1954), 1972, vol. 314, p. 961 - 964
  作者：Suciu,D.

  DOI：——

  日期：——
• 4′-Methyl-4,5′-bithiazole-based correctors of defective ΔF508-CFTR cellular processing
  作者：Choong Leol Yoo、Gui Jun Yu、Baoxue Yang、Lori I. Robins、A.S. Verkman、Mark J. Kurth

  DOI：10.1016/j.bmcl.2008.03.037

  日期：2008.4

  The synthesis and Delta F508-CFTR corrector activity of a 148-member methylbithiazole-based library are reported. Synthetic routes were devised and optimized to generate methylbithiazole analogs in four steps. Corrector potency and efficacy were assayed using epithelial cells expressing human Delta F508-CFTR. These structure-activity data establish that the bithiazole substructure plays a critical function; eight novel methylbithiazole correctors were identified with low micromolar potencies. (c) 2008 Elsevier Ltd. All rights reserved.
• Chalcone-Thiazole Hybrids: Rational Design, Synthesis, and Lead Identification against 5-Lipoxygenase
  作者：Shweta Sinha、S. L. Manju、Mukesh Doble

  DOI：10.1021/acsmedchemlett.9b00193

  日期：2019.10.10

  A hybrid pharmacophore approach is used to design and synthesize novel chalcone-thiazole hybrid molecules. Herein, thiazole has been hybridized with chalcone to obtain a new class of 5-LOX inhibitors. In vitro biological evaluation showed that most of the compounds were better 5-LOX inhibitors than the positive control, Zileuton (IC50 = 1.05 +/- 0.03 mu M). The best compounds in the series, namely, 4k, 4n, and 4v (4k: IC50 = 0.07 +/- 0.02 mu M, 4n: IC50 = 0.08 +/- 0.05 mu M, 4v: 0.12 +/- 0.04 mu M) are found to be 10 times more active than previously reported 2-amino thiazole (2m: IC50 = 0.9 +/- 0.1 mu M) by us. Further, 4k has redox (noncompetitive) while 4n and 4v act through a competitive inhibition mechanism. SAR indicated that the presence of methoxy/methyl either in the vicinity of chalcone or both thiazole and chalcone contributed to the synergistic inhibitory effect.