N-(6-acetamidobenzo[d]thiazol-2-yl)-2-chloroacetamide | 874590-17-7

• 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: N-(6-acetamidobenzo[d]thiazol-2-yl)-2-chloroacetamide
• 英文别名: N-(6-Acetylamino-benzothiazol-2-yl)-2-chloro-acetamide；N-(6-acetamido-1,3-benzothiazol-2-yl)-2-chloroacetamide
• CAS: 874590-17-7
• 化学式: C₁₁H₁₀ClN₃O₂S
• mdl: MFCD06753084
• 分子量: 283.738
• InChiKey: JRUJUWJCYPWFQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  99.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  N-(6-acetamidobenzo[d]thiazol-2-yl)-2-chloroacetamide 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 N-(5-((4-isopropylpiperazin-1-yl)methylene)-4-oxothiazolidin-2-ylideneaminobenzo[d]thiazol-6-yl)acetamide
  参考文献：
  名称：

  Catalytic N-formylation for synthesis of 6-substituted-2-benzothiazolylimino-5-piperazinyl-4-thiazolidinone antimicrobial agents

  摘要：

  利用温和的异相催化剂硫酸化钨酸盐，通过高度加速 N-异丙基哌嗪的 N-甲酰化反应，高效地制备了一类新的哌嗪基 2-苯并噻唑亚氨基-4-噻唑烷酮。在回流条件下，使用 NH4SCN 在乙醇中对 N-(苯并[d]噻唑-2-基)-2-氯乙酰胺（3a-j）进行异环化，可以有效地生成中间体 2-苯并噻唑基亚氨基噻唑烷-4-酮（4a-j）。这些中间产物经 4-异丙基哌嗪-1-甲醛（2）处理后，制备出最终产物 5a-j。元素分析和光谱数据（傅立叶变换红外光谱和 1H NMR）证实了新衍生物的结构。在体外检测细菌和真菌时，确定了它们作为有前途的抗菌剂的药理潜力；观察到的最低抑菌浓度（MIC）在 4-8 µg/mL 范围内。

  DOI：

  10.1007/s11164-014-1684-8
• 作为产物：
  描述：

  4′-氨基乙酰苯胺 在 溴 、 potassium carbonate 、 溶剂黄146 作用下， 生成 N-(6-acetamidobenzo[d]thiazol-2-yl)-2-chloroacetamide
  参考文献：
  名称：

  Catalytic N-formylation for synthesis of 6-substituted-2-benzothiazolylimino-5-piperazinyl-4-thiazolidinone antimicrobial agents

  摘要：

  利用温和的异相催化剂硫酸化钨酸盐，通过高度加速 N-异丙基哌嗪的 N-甲酰化反应，高效地制备了一类新的哌嗪基 2-苯并噻唑亚氨基-4-噻唑烷酮。在回流条件下，使用 NH4SCN 在乙醇中对 N-(苯并[d]噻唑-2-基)-2-氯乙酰胺（3a-j）进行异环化，可以有效地生成中间体 2-苯并噻唑基亚氨基噻唑烷-4-酮（4a-j）。这些中间产物经 4-异丙基哌嗪-1-甲醛（2）处理后，制备出最终产物 5a-j。元素分析和光谱数据（傅立叶变换红外光谱和 1H NMR）证实了新衍生物的结构。在体外检测细菌和真菌时，确定了它们作为有前途的抗菌剂的药理潜力；观察到的最低抑菌浓度（MIC）在 4-8 µg/mL 范围内。

  DOI：

  10.1007/s11164-014-1684-8

文献信息

• Access to a new class of biologically active quinoline based 1,2,4-triazoles
  作者：Rahul V. Patel、Se Won Park

  DOI：10.1016/j.ejmech.2013.10.059

  日期：2014.1

  found to possess a good spectrum of antifungal potency, which eventually suggested the azole template as an essential pharmacophore to diversify the biological occupations of the attendant molecules. However, it was noticed that the potency of final analogs against each strain placed reliance on the type of substituent present on benzothiazole ring. The structures of final compounds were confirmed with

  作为我们正在进行的寻找新的抗菌武器库的研究的一个方面，构建了一系列1,2,4-三唑-3-基硫代乙酰胺，并对其体外对几种细菌和真菌的抗菌活性进行了分析。为了建立更高的效价，将生物测定结果与之前使用的1,3,4-恶二唑进行了比较。值得注意的是，发现1,2,4-三唑具有良好的抗真菌效力谱，这最终表明吡咯模板是使伴随分子的生物学职业多样化的必不可少的药效团。然而，注意到最终类似物针对每种菌株的效力依赖于苯并噻唑环上存在的取代基的类型。借助红外光谱确定了最终化合物的结构，1 H NMR，13 C NMR光谱和CHN分析。
• <i>In vitro</i>Biological Investigations of Novel Piperazine Based Heterocycles
  作者：Nirmal M. Chhatriwala、Amit B. Patel、Rahul V. Patel、Premlata Kumari

  DOI：10.3184/174751914x14116443659287

  日期：2014.10

  Eleven N-phenyl- and 11 N-benzothiazolyl-2-(4-(2,3,4-trimethoxybenzyl)piperazin-1-yl)acetamides have been synthesised by a simple and efficient method. The 22 novel compounds were tested for their in vitro biological efficacy against two Gram-positive bacteria, three Gram-negative bacteria, two fungi and Mycobacterium tuberculosis H37Rv. The bioassay results revealed that the majority of the N -benzothiazole-substituted piperazine derivatives exhibited moderate to good bioefficacies with encouraging MICs. The influence of the presence or absence of various electron-withdrawing or -donating functional groups on the aryl acetamide moiety on the different bioassay results is discussed.

  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。
• Design, Synthesis and Computational Studies of New Benzothiazole Substituted Quinazolines as Potential Antimicrobial Agents
  作者：Amit B. Patel、Premlata Kumari、Suban K. Sahoo、Kishor H. Chikhalia

  DOI：10.2174/15701808113109990025

  日期：2013.10.1

  four fungi (Aspergillus niger MTCC 282, Aspergillus fumigatus MTCC 343, Aspergillus clavatus MTCC 1323, and Candida albicans MTCC 183). Some of the synthesized analogs have demonstrated excellent antimicrobial activity (MICs: 3.12-25 μg/mL) as compared with the standards (MICs: 6.25-25 μg/mL). Density Functional Theory (DFT) calculations at the B3LYP/6-31G(d,p) level were performed to predict the molecular

  已经合成了一些新颖的N-（苯并[d]噻唑-2-基）-2-（（4-（4-（间甲苯基氧基）喹唑啉-2基）苯基）氨基）乙酰胺类似物（7a-j）。该合成方法利用了基于对喹唑啉环的铃木偶联反应的合并方案。测试了类似物对八种细菌（金黄色葡萄球菌MTCC 96，蜡状芽孢杆菌MTCC 619，大肠杆菌MTCC 739，铜绿假单胞菌MTCC 741，肺炎克雷伯菌肺炎MTCC 109，鼠伤寒沙门氏菌MTCC MTCC 733，变形杆菌1寻常型）的微生物活性。 ）和四种真菌（黑曲霉MTCC 282，烟曲霉MTCC 343，克拉维曲霉MTCC 1323和白色念珠菌MTCC 183）。与标准品（MIC：6.25-25μg/ mL）相比，某些合成的类似物已显示出优异的抗菌活性（MIC：3.12-25μg/ mL）。在B3LYP / 6-31G（d，p）水平进行密度泛函理论（DFT）计算以预测类似物的分子结构和电子性质
• Access to antimycobacterial and anticancer potential of some fused quinazolines
  作者：Amit B. Patel、Kishor H. Chikhalia、Premlata Kumari

  DOI：10.1007/s11164-014-1542-8

  日期：2015.7

  Two series of some various N-phenyl/benzothiazolyl acetamide-fused quinazoline derivatives were synthesized and tested for their antimycobacterial activity against M. tuberculosis H37Rv. Moreover, the synthesized analogs were also screened against human PC3 cells in order to explore their anticancer activity. The in vitro antimycobacterial screening revealed that, among the synthesized analogs, N-benzothiazolyl acetamide derivatives showed remarkable antimycobacterial activity. However, the best anticancer results were observed amongst the N-phenyl acetamide-substituted quinazoline derivatives. The newly synthesized compounds were characterized through IR, 1H NMR, 13C NMR, MS, and elemental analysis.

  合成了两系列不同的N-苯基/苯噻唑乙酰胺融合喹唑啉衍生物，并测试了它们对结核分枝杆菌H37Rv的抗分枝杆菌活性。此外，还对合成的类似物进行了对人PC3细胞的检测，以探讨其抗癌活性。体外抗分枝杆菌筛选结果显示，在合成的类似物中，N-苯噻唑乙酰胺衍生物表现出显著的抗分枝杆菌活性。然而，在N-苯基乙酰胺取代的喹唑啉衍生物中观察到了最佳的抗癌结果。新合成的化合物通过红外光谱、1H NMR、13C NMR、质谱和元素分析进行了表征。
• New Quinolinyl–1,3,4–Oxadiazoles: Synthesis, In Vitro Antibacterial, Antifungal and Antituberculosis Studies
  作者：Rahul V. Patel、Premlata Kumari、Kishor H. Chikhalia

  DOI：10.2174/1573406411309040014

  日期：2013.4.1

  In order to generate hybrid antimicrobial remedies with novel mode of action, two series of quinoline based 1,3,4-oxadiazole derivatives condensed with N-aryl/benzothiazolyl acetamides were synthesized and the MIC values of the compounds towards eight reference bacterial strains (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, S. flexneri), four fungi (A. niger, A. fumigatus, A. clavatus, C. albicans) and Mycobacterium tuberculosis H37Rv were assayed in vitro. Quinoline–6–carboxlic acid was treated with thionyl chloride in refluxing methanol to obtain the corresponding ester derivative to be hydrazinolyzed by 99% hydrazine hydrate in ethanol to produce carbohydrazide intermediate. The carbohydrazide precursor underwent cyclization by carbon disulfide and ethanolic KOH to construct 5–quinolinyl–6–yl–1,3,4–oxadiazol–2–thiol. Substituted 2–chloro–N–phenyl(benzothiazolyl)aceta-mide derivatives were then condensed to 1,3,4-oxadiazole nucleus via sulphur linkage to yield the desired products. Target products bearing N–benzothiazolyl–2–chloroacetamides displayed good inhibitory potential. The biological screening identified that many final analogues exhibited a significant inhibition of the growth of microorganisms at 3.12-25 μg/mL of MIC, which were comparable to control drugs. The influence of the presence of various functional groups to the phenyl/benzothiazolyl ring on activity profiles was investigated. The proposed structures of the newly prepared products were confirmed with the aid of IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. These results may provide new insights in the design of a novel pool of bioactive templates.

  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。