N-(benzothiazol-2-yl)-2-(2,6-dimethylpiperidin-1-yl)acetamide | 731790-06-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(benzothiazol-2-yl)-2-(2,6-dimethylpiperidin-1-yl)acetamide
• 英文别名: N-(1,3-benzothiazol-2-yl)-2-(2,6-dimethylpiperidin-1-ium-1-yl)ethanimidate
• CAS: 731790-06-0
• 化学式: C₁₆H₂₁N₃OS
• 分子量: 303.428
• InChiKey: PIUABQJWXQXZJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯基硫脲 在 溴 、 溶剂黄146 、 三乙胺 作用下， 以 苯 为溶剂， 反应 16.0h， 生成 N-(benzothiazol-2-yl)-2-(2,6-dimethylpiperidin-1-yl)acetamide
  参考文献：
  名称：

  Kumar, Arun; Shakya, Ashok K.; Siddiqui, Indian Journal of Heterocyclic Chemistry, 2016, vol. 25, # 3-4, p. 243 - 249

  摘要：

  DOI：

文献信息

• Synthesis and Biological Evaluation of some Amide Derivatives Bearing Benzothiazole and Piperidine Moieties as Antimicrobial Agents
  作者：Mehlika Dilek Altintop、Ahmet Ozdemir、Zafer Asim Kaplancikli、Gulhan Turan-Zitouni、Gokalp Iscan、Gulsen Akalin Ciftci

  DOI：10.2174/1570180811310050013

  日期：2013.4.1

  In this study, N-(benzothiazol-2-yl)-2-(piperidin-1-yl)acetamide derivatives (1-24) were obtained by the reaction of 2-chloro-N-(benzothiazole-2-yl)acetamides with piperidine derivatives. The structures of the compounds were elucidated by 1H-NMR and mass spectral data and elemental analysis. The compounds were screened for their antimicrobial activities against pathogenic bacteria and Candida species. The compounds were also investigated for their cytotoxic properties using MTT assay. The microbiological results revealed that the compounds were more effective against fungi than bacteria. Among Candida species, C. utilis was the most susceptible fungus to compounds 7 and 11. It is apparent that 2,6-dimethylpiperidine group and chloro and methyl substituents on benzothiazole ring have an important impact on anticandidal activity. MTT assay indicated that the effective doses of these derivatives were lower than their cytotoxic doses.

  在本研究中，通过2-氯-N-(苯并噻唑-2-基)乙酰胺与哌啶衍生物的反应，合成了N-(苯并噻唑-2-基)-2-(哌啶-1-基)乙酰胺衍生物(1-24)。通过1H-NMR、质谱数据和元素分析阐明了化合物的结构。筛选了这些化合物对病原菌和念珠菌的抗微生物活性。还利用MTT法研究了它们的细胞毒性。微生物学结果显示，这些化合物对真菌的活性强于细菌。在念珠菌属中，对化合物7和11，新型隐球酵母最为敏感。显然，哌啶环上的2,6-二甲基及苯并噻唑环上的氯和甲基取代基对杀念珠菌活性具有重要作用。MTT法结果表明，这些衍生物的有效剂量低于其细胞毒剂量。
• Biological Evaluation of Some Antimicrobial Nano-Materials
  作者：Bahram Mokhtari、Kobra Pourabdollah

  DOI：10.1002/jccs.201200531

  日期：2013.6

  zole‐2‐yl)acetamides with piperidine derivatives. The structures of the compounds were elucidated by 1H‐NMR and mass spectral data and elemental analysis. The compounds were screened for their antimicrobial activities against pathogenic bacteria and Candida species. The compounds were also investigated for their cytotoxic properties using MTT assay. The microbiological results revealed that the compounds

  通过2-氯-N-（苯并噻唑-2-基）乙酰胺与哌啶衍生物的反应获得N-（苯并噻唑-2-基）-2-（哌啶-1-基）乙酰胺衍生物（1-24）。通过1 H-NMR，质谱数据和元素分析阐明了化合物的结构。筛选化合物对病原菌和念珠菌的抗菌活性。还使用MTT测定法研究了化合物的细胞毒性。微生物学结果表明，该化合物比真菌对真菌更有效。间念珠菌物种，C.产朊假丝是最敏感真菌的化合物7和11。显然，苯并噻唑环上的2,6-二甲基哌啶基团和氯和甲基取代基对抗候选活性有重要影响。MTT测定表明这些衍生物的有效剂量低于其细胞毒性剂量。
• Biological evaluation of a series of benzothiazole derivatives as mosquitocidal agents
  作者：Belgin Sever、Mehlika Dilek Altıntop、Ahmet Özdemir、Nurhayat Tabanca、Alden S. Estep、James J. Becnel、Jeffrey R. Bloomquist

  DOI：10.1515/chem-2019-0027

  日期：2019.6.7

  Aedes aegypti is associated with the transmission of numerous human and animal diseases, such as yellow fever, dengue fever, chikungunya, and more recently Zika virus. Emerging insecticide resistance has created a need to develop new mosquitocidal agents for effective control operations. A series of benzothiazole-piperidine derivatives (1-24) were investigated for their larvicidal and adulticidal effects on Ae. aegypti It was observed that compounds 2, 4, 6, 7, 8, 11 and 13 showed notable larvicidal activity. Furthermore, compounds 6 and 10 showed promising adulticidal activity. Based on the mosquitocidal properties of these compounds, docking studies were also carried out in the active site of the AeSCP2 enzyme to explore any insights into further in vitro enzyme studies. Docking results indicated that all these active compounds showed reasonable interactions with critical residues in the active site of this enzyme. This outcome suggested that these compounds might show their larvicidal and adulticidal effects via the inhibition of AeSCP2. According to in vitro and in silico studies, compounds 2, 4, 6, 7, 8, 10, 11 and 13 stand out as candidates for further studies.

  《摘要》 Aedes aegypti与许多人类和动物疾病的传播有关，如黄热病、登革热、基孔肯亚病毒，以及最近的寨卡病毒。新兴的杀虫剂抗性已经导致需要开发新的蚊虫杀灭剂来进行有效的控制操作。对一系列苯并噻唑-哌啶衍生物（1-24）进行了研究，以评估它们对Ae. aegypti的幼虫和成虫的杀虫效果。观察到化合物2、4、6、7、8、11和13显示出显著的幼虫毒性活性。此外，化合物6和10显示出有希望的成虫毒性活性。基于这些化合物的杀蚊特性，还在AeSCP2酶的活性位点进行了对接研究，以探索进一步体外酶研究的任何见解。对接结果表明，所有这些活性化合物与该酶的活性位点中的关键残基有合理的相互作用。这一结果表明，这些化合物可能通过抑制AeSCP2来展现它们的幼虫毒性和成虫毒性效果。根据体外和体内研究，化合物2、4、6、7、8、10、11和13被认为是进一步研究的候选化合物。