2-hydroxy-N-(6-nitro-1,3-benzothiazol-2-yl)benzamide | 301165-41-3

• 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: 2-hydroxy-N-(6-nitro-1,3-benzothiazol-2-yl)benzamide
• 英文别名: 2-hydroxy-N-(6-nitrobenzo[d]thiazol-2-yl)benzamide
• CAS: 301165-41-3
• 化学式: C₁₄H₉N₃O₄S
• 分子量: 315.309
• InChiKey: VSEYMBZJMCMEAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxy-N-(6-nitro-1,3-benzothiazol-2-yl)benzamide 、 乙酸酐 在 硫酸 作用下， 反应 0.33h， 以84%的产率得到2-{[(6-nitro-1,3-benzothiazol-2-yl)amino]carbonyl}phenyl acetate
  参考文献：
  名称：

  Nitazoxanide类似物作为针对医院病原体的抗菌剂。

  摘要：

  背景技术抗菌剂的频繁使用和患者暴露于挽救生命的干预过程一直与医院感染机会的增加和医院环境中多药耐药性微生物的出现有关。因此，新的抗微生物剂对于治疗由这些对目前可获得的抗药性具有抗性的推定病原体引起的严重的医院感染是没有必要的。方法描述了硝唑尼特（NTZ）的类似物的设计，合成和生物学评估，后者是FDA批准的噻唑类抗寄生虫药，可作为对抗医院病原体的新型抗菌剂。在增加噻唑类内酯部分的电子共振效应或改善整个NTZ结构的阴离子形式的基础上，合理地研究了NTZ类似物。结果测量了这些NTZ类似物对流行的医院病原体的MIC和MBC值。苯并类似物3a和4a以及对氯苯磺酰胺8d和9d表现出巨大的抗菌活性，其效力比NTZ和环丙沙星强100至2000倍。结论结果表明，对NTZ核心结构的精细操作可导致有希望的针对医院病原体的抗菌剂。

  DOI：

  10.2174/1573406412666160129105719
• 作为产物：
  描述：

  2-{[(6-nitro-1,3-benzothiazol-2-yl)amino]carbonyl}phenyl acetate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 2-hydroxy-N-(6-nitro-1,3-benzothiazol-2-yl)benzamide
  参考文献：
  名称：

  Synthesis of benzologues of Nitazoxanide and Tizoxanide: A comparative study of their in vitro broad-spectrum antiprotozoal activity

  摘要：

  We have synthesized two new benzologues of Nitazoxanide (NIT) and Tizoxanide (TIZ), using a short synthetic route. Both compounds were tested in vitro against six protozoa (Giardia intestinalis, Trichomonas vaginalis, Entamoeba histolytica, Plasmodium berghei, Leishmania mexicana and Trypanosoma cruzi). Compound 1 (benzologue of NIT) showed broad antiprotozoal effect against all parasites tested, showing IC(50)'s <5 mu M. This compound was five-times more active than NIT, and 18-times more potent than metronidazole against G. intestinalis. It was 10-times more active than pentamidine against L. mexicana, and it was sevenfold more potent than benznidazole versus T. cruzi. This compound could be considered as a new broad spectrum antiprotozoal agent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.100

文献信息

• NOVEL HYDRAZONE DERIVATIVE WITH ARYL OR HETEROARYL GROUP SUBSTITUTED AT TERMINAL AMINE GROUP THEREOF AND USE THEREOF
  申请人：Korea Institute of Science and Technology

  公开号：EP3901139A1

  公开（公告）日：2021-10-27

  The present invention relates to novel hydrazone derivatives in which a terminal amine group is substituted with an aryl group or a heteroaryl group, and uses thereof.

  本发明涉及末端胺基被芳基或杂芳基取代的新型腙衍生物及其用途。
• EP3901139
  申请人：——

  公开号：——

  公开（公告）日：——
• NOVEL HYDRAZONE DERIVATIVE IN WHICH TERMINAL AMINE GROUP IS SUBSTITUTED WITH ARYL GROUP OR HETEROARYL GROUP, AND USE THEREOF
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20220396553A1

  公开（公告）日：2022-12-15

  The present invention relates to novel hydrazone derivatives in which a terminal amine group is substituted with an aryl group or a heteroaryl group, and uses thereof.
• Nitazoxanide Analogues as Antimicrobial Agents Against Nosocomial Pathogens
  作者：Jia-Suey Gau、Wen-Pao Lin、Li-Ching Kuo、Ming-Kuan Hu

  DOI：10.2174/1573406412666160129105719

  日期：2016.7.29

  putative pathogens resistant to currently available agents. METHOD Design, synthesis, and biological evaluation of analogues of nitazoxanide (NTZ), an FDA approved thiazolide antiparasitic, as new antimicrobial agents against nosocomial pathogens were described. The NTZ analogues were rationally explored on the basis of either increasing the electronic resonance effects at the nitrothiazolide moiety or improving

  背景技术抗菌剂的频繁使用和患者暴露于挽救生命的干预过程一直与医院感染机会的增加和医院环境中多药耐药性微生物的出现有关。因此，新的抗微生物剂对于治疗由这些对目前可获得的抗药性具有抗性的推定病原体引起的严重的医院感染是没有必要的。方法描述了硝唑尼特（NTZ）的类似物的设计，合成和生物学评估，后者是FDA批准的噻唑类抗寄生虫药，可作为对抗医院病原体的新型抗菌剂。在增加噻唑类内酯部分的电子共振效应或改善整个NTZ结构的阴离子形式的基础上，合理地研究了NTZ类似物。结果测量了这些NTZ类似物对流行的医院病原体的MIC和MBC值。苯并类似物3a和4a以及对氯苯磺酰胺8d和9d表现出巨大的抗菌活性，其效力比NTZ和环丙沙星强100至2000倍。结论结果表明，对NTZ核心结构的精细操作可导致有希望的针对医院病原体的抗菌剂。
• Synthesis of benzologues of Nitazoxanide and Tizoxanide: A comparative study of their in vitro broad-spectrum antiprotozoal activity
  作者：Gabriel Navarrete-Vazquez、Fabiola Chávez-Silva、Rocío Argotte-Ramos、María del Carmen Rodríguez-Gutiérrez、Manuel Jesús Chan-Bacab、Roberto Cedillo-Rivera、Rosa Moo-Puc、Emanuel Hernández-Nuñez

  DOI：10.1016/j.bmcl.2011.02.100

  日期：2011.5

  We have synthesized two new benzologues of Nitazoxanide (NIT) and Tizoxanide (TIZ), using a short synthetic route. Both compounds were tested in vitro against six protozoa (Giardia intestinalis, Trichomonas vaginalis, Entamoeba histolytica, Plasmodium berghei, Leishmania mexicana and Trypanosoma cruzi). Compound 1 (benzologue of NIT) showed broad antiprotozoal effect against all parasites tested, showing IC(50)'s <5 mu M. This compound was five-times more active than NIT, and 18-times more potent than metronidazole against G. intestinalis. It was 10-times more active than pentamidine against L. mexicana, and it was sevenfold more potent than benznidazole versus T. cruzi. This compound could be considered as a new broad spectrum antiprotozoal agent. (C) 2011 Elsevier Ltd. All rights reserved.