2-chloro-N-(6-chlorobenzo[d]thiazol-2-yl)acetamide | 3268-75-5

• 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-chlorobenzo[d]thiazol-2-yl)acetamide
• 英文别名: 2-chloro-N-(6-chloro-1,3-benzothiazol-2-yl)acetamide；2-chloro-N-(6-chlorobenzothiazol-2-yl)-acetamide；6-Chlor-2-chloracetylamino-benzthiazol
• CAS: 3268-75-5
• 化学式: C₉H₆Cl₂N₂OS
• mdl: MFCD02668183
• 分子量: 261.131
• InChiKey: XUVJLNSGXUWBNT-UHFFFAOYSA-N

物化性质

• 熔点：
  218 °C
• 密度：
  1.605±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934200090

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(6-chlorobenzo[d]thiazol-2-yl)acetamide 在 哌啶 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 6.0h， 生成 5-(4-chlorobenzylidene)-2-(6-chlorobenzo[d]thiazol-2-ylimino)thiazolidin-4-one
  参考文献：
  名称：

  Deodhar, Meenakshi N.; Dongre, Ashishkumar C.; Kudale, Sayali D., Asian Journal of Chemistry, 2012, vol. 24, # 6, p. 2747 - 2752

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯基硫脲 在 吡啶 、 溴 作用下， 以 氯仿 、 苯 为溶剂， 反应 2.5h， 生成 2-chloro-N-(6-chlorobenzo[d]thiazol-2-yl)acetamide
  参考文献：
  名称：

  Deodhar, Meenakshi N.; Dongre, Ashishkumar C.; Kudale, Sayali D., Asian Journal of Chemistry, 2012, vol. 24, # 6, p. 2747 - 2752

  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。
• 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 Oxadiazole-Thiadiazole Hybrids and Their Anticandidal Activity
  作者：Serkan Levent、Betül Kaya Çavuşoğlu、Begüm Sağlık、Derya Osmaniye、Ulviye Acar Çevik、Özlem Atlı、Yusuf Özkay、Zafer Kaplancıklı

  DOI：10.3390/molecules22112004

  日期：——

  compounds (6a-6s) and evaluate their antifungal activity. The structures of synthesized compounds were elucidated by various methods including FT-IR, ¹H-NMR, 13C-NMR and HR-MS spectral data. Compounds were tested against four Candida species by broth microdilution assay. Compounds 6e, 6k and 6r, bearing a nitro group, showed significant antifungal activity against all fungi with minimum inhibitory concentration

  在感染管理领域，由于耐药菌株的出现，发现一种有效而安全的抗真菌剂是一项重大挑战。因此，本文的目的是设计和合成新型恶二唑-噻二唑杂化化合物（6a-6s）并评估其抗真菌活性。通过多种方法阐明了合成化合物的结构，包括FT-IR，1 H-NMR，13 C-NMR和HR-MS光谱数据。通过肉汤微稀释测定法针对四种念珠菌对化合物进行了测试。带有硝基的化合物6e，6k和6r对所有真菌均表现出显着的抗真菌活性，其最小抑菌浓度（MIC）在0.78-3.12 µg / mL范围内。还通过MTT测定法筛选了这些化合物的体外细胞毒性作用，并以其对假丝酵母菌株的活性浓度检测为无毒。为了检查这些化合物对麦角固醇生物合成的影响，进行了LC-MS-MS方法，该方法基于定量克鲁维酵母中麦角固醇水平。最后，最活跃的分子（6e）停靠在羊毛甾醇14α-脱甲基酶的活性位点，并确定该化合物与该酶之间有很强的相互作用。