2-氯-N-(6-乙氧基苯并噻唑-2-基)-乙酰胺 | 3268-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-氯-N-(6-乙氧基苯并噻唑-2-基)-乙酰胺
• 中文别名: 2-氯-N-(6-乙氧基-苯并噻唑-2-基)-乙酰胺
• 英文名称: 2-chloro-N-(6-ethoxy-1,3-benzothiazol-2-yl)acetamide
• 英文别名: 2-chloro-N-(6-ethoxybenzo[d]thiazol-2-yl)acetamide
• CAS: 3268-74-4
• 化学式: C₁₁H₁₁ClN₂O₂S
• mdl: MFCD00445455
• 分子量: 270.74
• InChiKey: RTLJXLUAHMPBAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934200090

反应信息

• 作为反应物：
  描述：

  2-氯-N-(6-乙氧基苯并噻唑-2-基)-乙酰胺 在 哌啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-((6-((2,4-dioxothiazolidin-5-ylidene)methyl)naphthalen-2-yl)oxy)-N-(6-ethoxybenzo[d]thiazol-2-yl)acetamide
  参考文献：
  名称：

  Thiazolidinedione “Magic Bullets” Simultaneously Targeting PPARγ and HDACs: Design, Synthesis, and Investigations of their In Vitro and In Vivo Antitumor Effects

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00491
• 作为产物：
  描述：

  对乙氧基苯胺 在 溴 、 potassium carbonate 、 溶剂黄146 作用下， 以 苯 为溶剂， 生成 2-氯-N-(6-乙氧基苯并噻唑-2-基)-乙酰胺
  参考文献：
  名称：

  New Quinolinyl–1,3,4–Oxadiazoles: Synthesis, In Vitro Antibacterial, Antifungal and Antituberculosis Studies

  摘要：

  为了产生具有新作用模式的混合抗菌药物，合成了两个系列的喹啉基 1,3,4-恶二唑衍生物与 N-芳基/苯并噻唑基乙酰胺缩合物。金黄色葡萄球菌、蜡样芽孢杆菌、大肠杆菌、铜绿假单胞菌、肺炎双球菌、伤寒杆菌、脓疱疮菌、柔毛杆菌）、四种真菌（黑木耳、烟曲霉、克拉维氏菌、白僵菌）和结核分枝杆菌 H37Rv 的 MIC 值进行了体外检测。在回流甲醇中用亚硫酰氯处理喹啉-6-甲酸，得到相应的酯衍生物，然后用 99% 的水合肼在乙醇中进行肼解，生成肼中间体。羧酰肼前体在二硫化碳和乙醇 KOH 的作用下发生环化反应，生成 5-喹啉基-6-基-1,3,4-恶二唑-2-硫醇。然后，取代的 2-氯-N-苯基（苯并噻唑基）乙酰胺衍生物通过硫键与 1,3,4-恶二唑核缩合，得到所需的产物。含有 N-苯并噻唑基-2-氯乙酰胺的目标产品显示出良好的抑制潜力。生物筛选结果表明，许多最终类似物在 3.12-25 μg/mL 的 MIC 值下对微生物的生长有明显的抑制作用，与对照药物相当。研究还探讨了苯基/苯并噻唑环上存在的各种官能团对活性的影响。红外光谱、1H NMR、13C NMR 光谱和元素分析证实了新制备产品的拟议结构。这些结果可为设计新型生物活性模板库提供新的见解。

  DOI：

  10.2174/1573406411309040014

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。
• Synthesis and antimicrobial activity evaluation of new dithiocarbamate derivatives bearing thiazole/benzothiazole rings
  作者：Leyla Yurttaş、Yusuf Özkay、Murat Duran、Gülhan Turan-Zitouni、Ahmet Özdemir、Zerrin Cantürk、Kaan Küçükoğlu、Zafer Asım Kaplancıklı

  DOI：10.1080/10426507.2016.1150277

  日期：2016.8.2

  compounds were elucidated by 1H NMR, 13C NMR, MS spectral data, and elemental analysis. The antimicrobial activity of the thirty eight newly synthesized compounds were tested against 12 microorganism strains using the microdilution technique. Compounds 2-(4-ethoxycarbonylthiazol-2-ylamino)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (B12), 2-(3-fluorophenyl)-2-oxoethyl 4-(pyrimidin-2-yl)pipera

  图形摘要摘要 2-(取代苯基)-2-氧乙基4-(嘧啶-2-基)哌嗪-1-碳二硫代(A1-A24)衍生物和2-(4-取代的噻唑-2-基氨基)-的合成2-氧乙基4-(嘧啶-2-基)哌嗪-1-碳二硫代(B1-B14)衍生物从4-(2-嘧啶基)哌嗪二硫代氨基甲酸酯的钾盐开始进行。所得化合物的结构通过1H NMR、13C NMR、MS谱数据和元素分析阐明。使用微量稀释技术测试了 38 种新合成化合物对 12 种微生物菌株的抗菌活性。化合物 2-(4-ethoxycarbonylthiazol-2-ylamino)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (B12), 2-(3-fluorophenyl)-2-oxoethyl 4-(pyrimidin- 2-yl)piperazin-1-carbodithiodate (A18)
• 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。
• Synthesis of some novel 3,4,5-trisubstituted triazole derivatives bearing quinoline ring and evaluation of their antimicrobial activity
  作者：Leyla Yurttaş、Aslıhan Kubilay、Asaf Evrim Evren、İpek Kısacık、Hülya Karaca Gençer

  DOI：10.1080/10426507.2020.1756808

  日期：2020.9.1

  Abstract Some new 3,4,5-trisubstituted 1,2,4-triazole derivatives were synthesized and studied for their antimicrobial activity. The lead compounds were obtained starting from 8-hydroxyquinoline and ethyl 2-chloroacetate. The obtained ester compound (1) first reacted with hydrazine hydrate (2) then with phenyl isothiocyanate (3). Ring closure by KOH led to 3-mercapto-1,2,4-triazole derivative (4).

  摘要 合成了一些新的3,4,5-三取代1,2,4-三唑衍生物并研究了它们的抗菌活性。先导化合物是从 8-羟基喹啉和 2-氯乙酸乙酯开始获得的。所得酯化合物(1)首先与水合肼(2)反应，然后与异硫氰酸苯酯(3)反应。KOH 闭环产生 3-巯基-1,2,4-三唑衍生物 (4)。最后，它与 2-氯-N-（取代（苯并）/噻唑）乙酰胺衍生物反应得到最终化合物（5a-j）。通过1H NMR和13C NMR光谱和高分辨率质谱技术和元素分析进行​​化合物的结构解析。研究了合成的化合物对七种细菌和四种真菌的抗菌活性。作为活动研究的结果，观察到化合物 N-(6-nitrobenzothiazol-2-yl)-2-[[4-phenyl-5-((quinolin-8-yloxy)methyl)-4H-1,2,4-triazol-3-基]硫代]乙酰胺(5a)和N-(6-氟苯并噻唑-2-基)-2-[[4-苯基-5-((喹啉-8-基氧基)甲基)-4H-1