N‑(5‑acetyl‑4‑methylthiazol‑2‑yl)‑2‑chlorobenzamide | 303127-29-9

• 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)‑2‑chlorobenzamide
• 英文别名: N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-2-chlorobenzamide
• CAS: 303127-29-9
• 化学式: C₁₃H₁₁ClN₂O₂S
• 分子量: 294.762
• InChiKey: RQTVXCMTCQZIPK-UHFFFAOYSA-N

物化性质

• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 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：
  87.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N‑(5‑acetyl‑4‑methylthiazol‑2‑yl)‑2‑chlorobenzamide 在 氢溴酸 、 pyridinium hydrobromide perbromide 作用下， 以 溶剂黄146 为溶剂， 生成 N-[5-(2-bromoacetyl)-4-methyl-1,3-thiazol-2-yl]-2-chlorobenzamide
  参考文献：
  名称：

  4′-Methyl-4,5′-bithiazole-based correctors of defective ΔF508-CFTR cellular processing

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.03.037
• 作为产物：
  描述：

  3-溴戊烷-2,4-二酮 在 吡啶 作用下， 反应 0.17h， 生成 N‑(5‑acetyl‑4‑methylthiazol‑2‑yl)‑2‑chlorobenzamide
  参考文献：
  名称：

  Synthesis, Characterization, Crystal Structure and Biological Study of Carboxamides Obtained from 2-Aminothiazole Derivatives

  摘要：

  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。

  DOI：

  10.1007/s10870-019-00800-w

文献信息

• 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.
• 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。