5-(4-Bromophenyl)-3-(furan-2-yl)-3,4-dihydropyrazole-2-carbothioamide | 686725-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-Bromophenyl)-3-(furan-2-yl)-3,4-dihydropyrazole-2-carbothioamide
• CAS: 686725-74-6
• 化学式: C₁₄H₁₂BrN₃OS
• 分子量: 350.239
• InChiKey: KEFNLJYFYZJYLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  alpha-溴-4-甲氧基苯乙酮 、 5-(4-Bromophenyl)-3-(furan-2-yl)-3,4-dihydropyrazole-2-carbothioamide 以 乙醇 为溶剂， 反应 5.0h， 生成 2-(3-(4-bromophenyl)-5-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-(4-methoxyphenyl)thiazole
  参考文献：
  名称：

  Discovery and modification of sulfur-containing heterocyclic pyrazoline derivatives as potential novel class of β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors

  摘要：

  A series of sulfur-containing heterocyclic pyrazoline derivatives (C1-C18; D1-D9) have been synthesized and purified (all are new except one) to be screened for FabH inhibitory activity. Compound C14 showed the most potent biological activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis (MIC values: 1.56-3.13 mu g/mL), being comparable with the positive control, while D6 performed the best in the thiazolidinone series (MIC values: 3.13-6.25 mu g/mL). They also demonstrated strong broad-spectrum antimicrobial activity. Compounds C14 and D6 exhibited the most potent E. coli FabH inhibitory activity with IC50 of 4.6 and 8.4 mu M, respectively, comparable with the positive control DDCP (IC50 = 2.8 mu M). Docking simulation was performed to position compound C14 and D6 into the E. coli FabH structure active site to determine the probable binding model. The structurally modification of previous compounds and the attempt in innovative target have brought a positive progress. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.05.091
• 作为产物：
  描述：

  4-溴苯乙酮 以 乙醇 为溶剂， 反应 5.5h， 生成 5-(4-Bromophenyl)-3-(furan-2-yl)-3,4-dihydropyrazole-2-carbothioamide
  参考文献：
  名称：

  Discovery and modification of sulfur-containing heterocyclic pyrazoline derivatives as potential novel class of β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors

  摘要：

  A series of sulfur-containing heterocyclic pyrazoline derivatives (C1-C18; D1-D9) have been synthesized and purified (all are new except one) to be screened for FabH inhibitory activity. Compound C14 showed the most potent biological activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis (MIC values: 1.56-3.13 mu g/mL), being comparable with the positive control, while D6 performed the best in the thiazolidinone series (MIC values: 3.13-6.25 mu g/mL). They also demonstrated strong broad-spectrum antimicrobial activity. Compounds C14 and D6 exhibited the most potent E. coli FabH inhibitory activity with IC50 of 4.6 and 8.4 mu M, respectively, comparable with the positive control DDCP (IC50 = 2.8 mu M). Docking simulation was performed to position compound C14 and D6 into the E. coli FabH structure active site to determine the probable binding model. The structurally modification of previous compounds and the attempt in innovative target have brought a positive progress. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.05.091

文献信息

• Novel 3, 3a, 4, 5, 6, 7-Hexahydroindazole and Arylthiazolylpyrazoline derivatives as Anti-inflammatory Agents
  作者：Magda N. A. Nasr、Shehta A. Said

  DOI：10.1002/ardp.200300796

  日期：2003.12

  the other intermediates 3, 5‐diaryl‐1‐thiocarbamoyl‐2‐pyrazolines 7a—d were reacted with the previously‐mentioned reagents and gave the corresponding 3, 5‐diaryl‐1‐(4‐aryl‐2‐thiazolyl)‐2‐pyrazolines 8a—h, 3, 5‐diaryl‐1‐(5‐arylidene‐4, 5‐dihydro‐4‐oxo‐2‐thiazolyl)‐2‐pyrazolines 9a—d and 3, 5‐diaryl‐1‐(thiazolo[4, 5‐b]quinoxalin‐2‐yl)‐2‐pyrazoline derivatives 10a, b, respectively. Some of the newly prepared

  合成了2-位取代的7-亚苄基-3, 3a, 4, 5, 6, 7-六氢- 3-苯基- 2H-吲唑的新系列。2, 6-双-亚苄基环己酮 (1) 与氨基硫脲在 NaOH 存在下的反应得到 3-H、3a-H 反式 2 和顺式 2a 非对映异构体的混合物，这些非对映异构体已通过分级重结晶分离。在乙酸和乙酸酐的混合物存在下，第一个中间体 2 与取代苯甲酰溴、芳香醛和氯乙酸相互作用，2, 3-二氯喹喔啉产生相应的 7-亚苄基-3, 3a, 4, 5, 6 , 7-六氢-3-苯基-2H-吲唑衍生物在2-位被4-芳基-2-噻唑基3a、b、5-亚芳基-4、5-二氢-4-氧代-2-噻唑基-4-噻唑基取代b 和噻唑并 [4, 5-b] quinoxalin-2-yl 5，分别。而且，其他中间体3, 5-二芳基- 1-硫代氨基甲酰基- 2-吡唑啉7a - d 与前面提到的试剂反应得到相应的3, 5-二芳基- 1-