N‑(5‑acetyl‑4‑methylthiazol‑2‑yl)‑4‑methoxybenzamide | 39884-16-7

• 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‑methoxybenzamide
• 英文别名: N-(5-acetyl-4-methylthiazol-2-yl)-4-methoxybenzamide；4-methyl-5-acetyl-2-(4-methoxybenzoylamino)thiazole；N-(5-acetyl-4-methyl-thiazol-2-yl)-4-methoxy-benzamide；N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-4-methoxybenzamide
• CAS: 39884-16-7
• 化学式: C₁₄H₁₄N₂O₃S
• 分子量: 290.343
• InChiKey: NEEXDKFZRZVLKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N‑(5‑acetyl‑4‑methylthiazol‑2‑yl)‑4‑methoxybenzamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 N-[5-(1-hydroxy-ethyl)-4-methyl-thiazol-2-yl]-4-methoxy-benzamide
  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：

  3-溴戊烷-2,4-二酮 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 N‑(5‑acetyl‑4‑methylthiazol‑2‑yl)‑4‑methoxybenzamide
  参考文献：
  名称：

  Design, synthesis and neuraminidase inhibitory activity of 4-methyl-5-(3-phenylacryloyl) thiazoles

  摘要：

  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。

  DOI：

  10.1007/s11030-023-10639-1

文献信息

• Synthesis, Characterization, Crystal Structure and Biological Study of Carboxamides Obtained from 2-Aminothiazole Derivatives
  作者：Sachin S. Wazalwar、Anita R. Banpurkar、Franc Perdih

  DOI：10.1007/s10870-019-00800-w

  日期：2020.12

  Two series of novel thiazolylcarboxamide derivatives were synthesized by the reaction of ethyl 2-amino-4-methylthiazole-5-carboxylate or 1-(2-amino-4-methylthiazol-5-yl)ethan-1-one with four substituted carbonyl chlorides at 0 °C in excellent yield. All products were characterized by FTIR, 1H NMR spectroscopy and mass spectrometry. Crystal structures of four compounds were studied by X-ray analysis. All the synthesized compounds were screened against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pyogenes for antibacterial activity and against Candida albicans, Aspergillusniger and Aspergillus clavatus for antifungal activity. Present study describes the biological activity and crystal structure study of carboxamides obtained from 2-aminothaizol derivatives. Owing to the insolubility of these amides in single volatile solvent, crystals were grown in a mixture of solvents.

  通过乙基2-氨基-4-甲基噻唑-5-羧酸盐或1-(2-氨基-4-甲基噻唑-5-基)乙烷-1-酮与四种取代的羰基氯在0°C下反应，合成了两系列新型噻唑基羧酰胺衍生物，产率极佳。所有产物均通过FTIR、1H NMR光谱和质谱进行了表征。通过X射线分析研究了四种化合物的晶体结构。对所有合成化合物进行了针对大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌和酿脓链球菌的抗菌活性筛选，以及针对白色念珠菌、黑曲霉和棒状曲霉的抗真菌活性筛选。本研究描述了由2-氨基噻唑衍生物获得的羧酰胺的生物活性和晶体结构研究。由于这些酰胺在单一挥发性溶剂中的不溶性，晶体是在混合溶剂中生长的。
• 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
• 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.