2-chloro-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-chloro-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
• 英文别名: 2-chloro-N-(6-nitro-1,3-benzothiazol-2-yl)acetamide
• 化学式: C₉H₆ClN₃O₃S
• mdl: MFCD00520425
• 分子量: 271.684
• InChiKey: FSKHTMXWCNEWMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、150.0 kPa 条件下， 以59%的产率得到N-(6-aminobenzothiazol-2-yl)-2-chloroacetamide
  参考文献：
  名称：

  具有抗菌活性的双重大肠杆菌DNA促旋酶A和B抑制剂。

  摘要：

  耐多药细菌的出现是对全球健康的威胁，因此有必要发现新的抗菌素和与细菌感染作斗争的新策略。我们报告一流的DNA回旋酶B（GyrB）抑制剂/环丙沙星杂种，对大肠杆菌表现出抗菌活性。尽管DNA旋转酶ATPase抑制实验，DNA旋转酶超螺旋测定和体外抗菌测定表明杂合体与大肠杆菌GyrA和GyrB亚基结合，但与GyrA氟喹诺酮结合位点的相互作用似乎是其抗菌活性的唯一原因。我们的研究结果为通过与高渗透性GyrA抑制剂环丙沙星结合促进非渗透性GyrB抑制剂进入细菌的新概念奠定了基础。

  DOI：

  10.1002/cmdc.201900607
• 作为产物：
  描述：

  6-nitrobenzo[d]thiazol-2-amine hydrobromide 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 水 、 苯 为溶剂， 生成 2-chloro-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
  参考文献：
  名称：

  In vitroBiological Investigations of Novel Piperazine Based Heterocycles

  摘要：

  本研究采用简单高效的方法合成了 11 种 N-苯基和 11 种 N-苯并噻唑基-2-(4-(2,3,4-三甲氧基苄基)哌嗪-1-基)乙酰胺。测试了这 22 种新型化合物对两种革兰氏阳性菌、三种革兰氏阴性菌、两种真菌和结核分枝杆菌 H37Rv 的体外生物效力。生物测定结果表明，大多数 N-苯并噻唑取代的哌嗪衍生物具有中等至良好的生物效力，其 MIC 值令人鼓舞。本文讨论了芳基乙酰胺分子上是否存在各种吸电子或供电子官能团对不同生物测定结果的影响。

  DOI：

  10.3184/174751914x14116443659287

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。
• Design and Synthesis of New 1,3,4-Oxadiazole – Benzothiazole and Hydrazone Derivatives as Promising Chemotherapeutic Agents
  作者：Betül Kaya、Weiam Hussin、Leyla Yurttaş、Gülhan Turan-Zitouni、Hülya Gençer、Merve Baysal、Abdullah Karaduman、Zafer Kaplancıklı

  DOI：10.1055/s-0042-119070

  日期：2017.5

  Looking for new cytotoxic and antimicrobial agents with improved antitumor activity, a series of hydrazide and oxadiazole derivatives were designed and synthesized using 3-methoxyphenol as starting substance. Novel N'-(arylidene)-2-(3-methoxyphenoxy)acetohydrazide derivatives (4a-f)/1-(4-substitutedphenyl)-2-[(5-[(3-methoxyphenoxy)methyl]-1,3,4-oxadiazol-2-yl)thio]ethan-1-one derivatives (6a-f)/N-

  为了寻找具有改善的抗肿瘤活性的新的细胞毒性和抗菌剂，以3-甲氧基苯酚为起始原料设计并合成了一系列酰肼和恶二唑衍生物。新的N'-（亚芳基）-2-（3-甲氧基苯氧基）乙酰肼衍生物（4a-f）/ 1-（4-取代的苯基）-2-[（5-[（3-甲氧基苯氧基）甲基] -1,3， 4-恶二唑-2-基）硫]乙烷-1-酮衍生物（6a-f）/ N-（6-取代的苯并噻唑-2-基）-2-[（5-[（3-甲氧基苯氧基）甲基] -1获得了，3，4-恶二唑-2-基）硫代]乙酰胺衍生物（7a-e），并评价了它们对各种革兰氏阳性，革兰氏阴性细菌和真菌的体外抗菌活性。与抗革兰氏阳性细菌的潜力相比，发现该化合物对革兰氏阴性细菌的抗菌潜力更高。还，筛选化合物对作为健康细胞系的两种选定的人类肿瘤细胞系，A549肺，MCF7乳腺癌细胞系和小鼠胚胎成纤维细胞系，NIH / 3T3的抗增殖活性。在所评估的化合物中，与1,3,3,3T3细胞系相反，具有1
• 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。