2-chloro-N-(6-iodobenzo[d]thiazol-2-yl)acetamide | 1372894-46-6

• 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-iodobenzo[d]thiazol-2-yl)acetamide
• 英文别名: 2-chloro-N-(6-iodo-1,3-benzothiazol-2-yl)acetamide
• CAS: 1372894-46-6
• 化学式: C₉H₆ClIN₂OS
• 分子量: 352.583
• InChiKey: IGRGSOVNRWRWCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(6-iodobenzo[d]thiazol-2-yl)acetamide 、 曲美他嗪 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以74%的产率得到N-(6-iodobenzo[d]thiazol-2-yl)-2-(4-(2,3,4-trimethoxybenzyl)piperazin-1-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
• 作为产物：
  描述：

  在 ammonium hydroxide 、 potassium carbonate 作用下， 以 水 、 苯 为溶剂， 生成 2-chloro-N-(6-iodobenzo[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

• 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。
• 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。
• Combination of bioactive moieties with different heteroatom(s): Application of the Suzuki cross-coupling reaction
  作者：Rahul V. Patel、Jigar K. Patel、Premlata Kumari、Kishor H. Chikhalia

  DOI：10.1002/hc.21027

  日期：——

  thiophene/benzothiophene-linked quinolinyl oxadiazoles condensed to the substituted N-benzothiazolyl acetamides have been synthesized via the Suzuki cross-coupling reaction. The ester derivative of 6-bromo-substituted quinoline was reacted via the Suzuki cross-coupling reaction with commercially available (benzo)thiophen-2-ylboronic acid at optimized temperature in 1,2-dimethoxy ethane and water in the presence

  已经通过 Suzuki 交叉偶联反应合成了两个系列的噻吩/苯并噻吩连接的喹啉基恶二唑，它们与取代的 N-苯并噻唑基乙酰胺缩合。6-溴取代喹啉的酯衍生物通过 Suzuki 交叉偶联反应与市售（苯并）噻吩-2-基硼酸在优化温度下在 1,2-二甲氧基乙烷和水中在碳酸钾和碳酸钾存在下反应。四氯化钯。然后使用 99% 的水合肼将所得衍生物肼化，然后在乙醇 KOH 中使用二硫化碳环化以提供相应的恶二唑，然后将其与各种取代的 2-氯-N-苯并噻唑基乙酰胺缩合以产生最终的支架，其中涉及四种杂环的独特组合，以检查它们对两种革兰氏阳性菌（金黄色葡萄球菌和蜡状芽孢杆菌）、三种革兰氏阳性菌的抗菌活性-阴性细菌（大肠杆菌、铜绿假单胞菌和肺炎克雷伯菌）和两种真菌（黑曲霉和白色念珠菌）。生物筛选数据的调查显示，与标准品相比，大多数测试的化合物对大多数微生物表现出优异的活性（最低抑制浓度；6.25-50 µg/mL），因此它们值得更多考虑作为未来的抗菌剂
• Synthesis of benzimidazolyl-1,3,4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents
  作者：Rahul V. Patel、Paresh K. Patel、Premlata Kumari、Dhanji P. Rajani、Kishor H. Chikhalia

  DOI：10.1016/j.ejmech.2012.03.033

  日期：2012.7

  To affiliate multiple bioactivities in a compact heteronuclei, two series of benzimidazole based 1,3,4-oxadiazoles were synthesized and assessed in vitro for their efficacy as antimicrobial agents against eight bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi, Proteus vulgaris, Shigella flexneri), four fungi (Aspergillus niger, Aspergillus fumigants, Aspergillus clavatus, Candida albicans) and Mycobacterium tuberculosis H37Rv and best results were observed amongst the N-benzothiazolylaetamide series. The lipophilicity (LogP) influence on the biological profile (MICs) of the prepared products was also discussed. Upon biological screening, it was observed that the majority of the compounds were found to possess a significant broad spectrum antimicrobial (3.12-25 mu g/mL of MIC) and antitubercular (6.25-25 mu g/mL of MIC) potential. The structural assignments of the new products were done on the basis of IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis of coumarin-based 1,3,4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides as antimicrobial and antituberculosis agents
  作者：Rahul V. Patel、Premlata Kumari、Dhanji P. Rajani、Kishor H. Chikhalia

  DOI：10.1007/s00044-012-0026-x

  日期：2013.1

  In an attempt to find new agents to fight against microbial infections, a series of coumarin-based 1,3,4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides was synthesized starting from coumarin-3-carboxylic acid ethyl ester obtained through Knoevenagel and Pinner reaction. In vitro antimicrobial activity against several bacteria (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, S. flexneri), fungi (A. niger, A. fumigatus, A. clavatus, C. albicans) and antimycobacterial activity against Mycobacterium tuberculosis H37Rv strain was assessed. This study shows to what extent the presence of various electron withdrawing/donating substituents on the phenyl or benzothiazole ring affects the activity profiles of the newer molecules. The relationship between activity profiles (MICs, 3.12-25 mu g/mL) and the lipophilic character (LogP) of the prepared products is also discussed and the MIC values of the active conjugates seem to correlate to some extent with the lipophilicity profiles. Two (5e and 6c) of the final analogues displayed promising antimycobacterial activity at 12.5 mu g/mL of MIC, half fold potent to the standard drug pyrazinamide (6.25 mu g/mL). Compounds were characterized by IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis.