Ethyl N-(p-bromophenyl)formimidate | 443754-60-7

• 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: Ethyl N-(p-bromophenyl)formimidate
• 英文别名: ethyl N-(4-bromophenyl)methanimidate
• CAS: 443754-60-7
• 化学式: C₉H₁₀BrNO
• 分子量: 228.088
• InChiKey: MKCJPQBPEYJMBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  异烟肼 、 Ethyl N-(p-bromophenyl)formimidate 以 乙腈 为溶剂， 反应 26.0h， 以49%的产率得到N-(4-bromophenyl)-N'-(pyridin-4-ylcarbonyl)hydrazonoformamide
  参考文献：
  名称：

  New series of isoniazid hydrazones linked with electron-withdrawing substituents

  摘要：

  A series of new isoniazid hydrazones was synthesized by two procedures. In the first isoniazid was activated with diethoxymethyl acetate and condensed with the appropriate anilines. Alternatively, substituted anilines were activated by diethoxymethyl acetate and subsequently condensed with isoniazid. NMR study confirmed that both synthetic approaches gave the same tautomer. All compounds were screened for in vitro antimycobacterial activity. Most of them exhibited the same activity against Mycobacterium tuberculosis (MIC 1 mu mol L-1) as isoniazid (INH), better activity against Mycobacterium kansasii 325/80 (MIC 0.125-0.250 mu mol L-1), high value of selectivity index (SI) and IC50 between 0.0218 and 0.326 mmol L-1. Compound 2o with the best SI was used as a model compound for the stability test and was found to be stable at neutral pH, but under acidic conditions it slowly hydrolysed. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.054
• 作为产物：
  描述：

  乙酸二乙氧基甲酯 、 4-溴苯胺 以 乙腈 为溶剂， 反应 0.5h， 生成 Ethyl N-(p-bromophenyl)formimidate
  参考文献：
  名称：

  New series of isoniazid hydrazones linked with electron-withdrawing substituents

  摘要：

  A series of new isoniazid hydrazones was synthesized by two procedures. In the first isoniazid was activated with diethoxymethyl acetate and condensed with the appropriate anilines. Alternatively, substituted anilines were activated by diethoxymethyl acetate and subsequently condensed with isoniazid. NMR study confirmed that both synthetic approaches gave the same tautomer. All compounds were screened for in vitro antimycobacterial activity. Most of them exhibited the same activity against Mycobacterium tuberculosis (MIC 1 mu mol L-1) as isoniazid (INH), better activity against Mycobacterium kansasii 325/80 (MIC 0.125-0.250 mu mol L-1), high value of selectivity index (SI) and IC50 between 0.0218 and 0.326 mmol L-1. Compound 2o with the best SI was used as a model compound for the stability test and was found to be stable at neutral pH, but under acidic conditions it slowly hydrolysed. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.054

文献信息

• Antimicrobial and Antiquorum-Sensing Studies. Part 3: Synthesis and Biological Evaluation of New Series of [1,3,4]Thiadiazoles and Fused [1,3,4]Thiadiazoles
  作者：Nadia S. El-Gohary、Mona I. Shaaban

  DOI：10.1002/ardp.201400381

  日期：2015.4

  New series of [1,3,4]thiadiazoles and fused [1,3,4]thiadiazoles were synthesized. The newly synthesized compounds were screened for their antibacterial activity against Staphylococcus aureus, Bacillus cereus, and Escherichia coli. Compounds 3b and 10a displayed the highest activity against E. coli with MIC value of 78.125 μg/mL. In addition, compound 10a exhibited the highest activity against B. cereus

  合成了新系列的[1,3,4]噻二唑和稠合[1,3,4]噻二唑。筛选了新合成的化合物对金黄色葡萄球菌、蜡样芽孢杆菌和大肠杆菌的抗菌活性。化合物 3b 和 10a 对大肠杆菌的活性最高，MIC 值为 78.125 μg/mL。此外，化合物10a对蜡样芽孢杆菌表现出最高的活性，MIC值为156.25 μg/mL。还测试了这些化合物对白色念珠菌和黄曲霉 3375 的抗真菌活性。化合物 3b、5a、10a 和 12b 对黄曲霉 3375 的活性最好，MIC 值为 19.531 μg/mL。检测了相同化合物对紫罗兰色杆菌 ATCC 12472 的抗群体感应活性，而化合物 3b、5a 和 12b 表现出中等活性。进行了化合物 3b、c、5a、6a、10a 和 12a、b 对人正常肺成纤维细胞 (W138) 细胞系的体外细胞毒性测试。还测试了相同化合物的体内急性毒性，所得结果表明化合物10a是毒性最小的类似物。研究了相同化合物的
• New series of isoniazid hydrazones linked with electron-withdrawing substituents
  作者：Eva Vavříková、Slovenko Polanc、Marijan Kočevar、Janez Košmrlj、Kata Horváti、Szilvia Bősze、Jiřina Stolaříková、Aleš Imramovský、Jarmila Vinšová

  DOI：10.1016/j.ejmech.2011.09.054

  日期：2011.12

  A series of new isoniazid hydrazones was synthesized by two procedures. In the first isoniazid was activated with diethoxymethyl acetate and condensed with the appropriate anilines. Alternatively, substituted anilines were activated by diethoxymethyl acetate and subsequently condensed with isoniazid. NMR study confirmed that both synthetic approaches gave the same tautomer. All compounds were screened for in vitro antimycobacterial activity. Most of them exhibited the same activity against Mycobacterium tuberculosis (MIC 1 mu mol L-1) as isoniazid (INH), better activity against Mycobacterium kansasii 325/80 (MIC 0.125-0.250 mu mol L-1), high value of selectivity index (SI) and IC50 between 0.0218 and 0.326 mmol L-1. Compound 2o with the best SI was used as a model compound for the stability test and was found to be stable at neutral pH, but under acidic conditions it slowly hydrolysed. (C) 2011 Elsevier Masson SAS. All rights reserved.