6-Chloro-1,3-benzothiazol-2-amine;hydrobromide | 1367199-79-8

• 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: 6-Chloro-1,3-benzothiazol-2-amine;hydrobromide
• CAS: 1367199-79-8
• 化学式: BrH*C₇H₅ClN₂S
• 分子量: 265.561
• InChiKey: WJQDIZXRQUMOKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Chloro-1,3-benzothiazol-2-amine;hydrobromide 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 水 、 丙酮 、 苯 为溶剂， 生成 N-(6-chlorobenzo[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：

  对氯苯胺 在 盐酸 、 溴 作用下， 以 氯仿 、 水 为溶剂， 反应 8.5h， 生成 6-Chloro-1,3-benzothiazol-2-amine;hydrobromide
  参考文献：
  名称：

  1,4-噻嗪杂环系统的结构柔性杂环的合成及其抗菌活性

  摘要：

  在这项工作中，通过有效的合成方法，在一个步骤中就合成了4H-1,4-苯并噻嗪，该步骤涉及将取代的2-氨基苯硫醇与β-酮酸酯杂环化。合成化合物的结构由其分析和光谱数据证实。评估合成的化合物对细菌物种的抗菌活性。 Ë 。 大肠杆菌 和 蜡状芽孢杆菌 。合成的化合物显示出对微生物的显着活性，这可以与特权杂环结构支架相关。

  DOI：

  10.1007/s11164-011-0320-0

文献信息

• Benzothiazole Incorporated Barbituric Acid Derivatives: Synthesis and Anticonvulsant Screening
  作者：Nadeem Siddiqui、Waquar Ahsan

  DOI：10.1002/ardp.200900002

  日期：2009.8

  3‐benzothiazol‐2‐yl)‐3‐(substituted phenyl)hexahydro‐2,4,6‐pyrimidinetriones 4a–t were synthesized starting from substituted anilines. These compounds contained two active anticonvulsant pharmacophores, benzothiazole and barbituric acid. Structures of the compounds were confirmed on the basis of different spectroscopic techniques. All the compounds were evaluated for their anticonvulsant activity. Three

  以取代苯胺为原料合成了一系列1-(6-取代-1,3-苯并噻唑-2-基)-3-(取代苯基)六氢-2,4,6-嘧啶三酮4a-t。这些化合物含有两种活性抗惊厥药效团，苯并噻唑和巴比妥酸。基于不同的光谱技术确认了化合物的结构。评价所有化合物的抗惊厥活性。三种化合物 4c、4d 和 4s 在最大电击癫痫试验 (MES) 和皮下戊四唑试验 (scPTZ) 中显示出有希望的抗惊厥活性。在进行最小运动损伤测试时，它们还显示出广泛的安全性。
• 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.
• Synthesis, cytotoxic evaluation, and in silico studies of substituted N-alkylbromo-benzothiazoles
  作者：Rupinder Kaur Gill、Gagandeep Singh、Anuradha Sharma、P. M. S. Bedi、A. K. Saxena

  DOI：10.1007/s00044-012-0424-0

  日期：2013.9

  In efforts to develop a new class of anticancer agents with improved efficacy and selective action, a series of N-alkylbromo-benzothiazoles were synthesized and evaluated for in vitro cytotoxic activity against various human cancer cell lines such as lung (A-549), prostate (PC-3), leukemia (THP-1), and colon (Caco-2). They were found to be highly active against prostate (PC-3) and leukemia (THP-1) cancer cells, moderately active against colon (Caco-2) cancer cells and less active against lung (A-549) cancer cells. Of the 12 compounds, two (11d, 11j) exhibit IC50 values of a parts per thousand currency sign 1 mu M against leukemia (THP-1) cancer cell lines. Compound 11l showed significant cytotoxic activity against the PC-3 (IC50 = 0.6 mu M), THP-1 (IC50 = 3 mu M) and Caco-2 cell lines (IC50 = 9.9 mu M), respectively. Docking study of the synthesized ligand was done on epidermal growth factor receptor using ArgusLab flexible docking, to determine their observed activity. Further QSAR investigations with stepwise multiple linear regression analysis were applied to find correlation between various physicochemical parameters and anticancer activity. The QSAR results showed that anticancer activity could be modeled with descriptors. The predictive ability of models was cross-validated by observation of the low residual activity values and adjusted coefficient of variation () obtained by leave-one-out technique.