N-<3,4-Dichlor-phenyl>-ameisensaeureimid-aethylester | 22363-14-0

• 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: N-<3,4-Dichlor-phenyl>-ameisensaeureimid-aethylester
• 英文别名: N-(3,4-Dichlor-phenyl)-ameisensaeureimid-aethylester；Ethyl (3,4-dichlorophenyl)imidoformate；ethyl N-(3,4-dichlorophenyl)methanimidate
• CAS: 22363-14-0
• 化学式: C₉H₉Cl₂NO
• 分子量: 218.083
• InChiKey: TYDIEUACUMZKHK-UHFFFAOYSA-N

物化性质

• 沸点：
  128-139 °C(Press: 0.35-0.75 Torr)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 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 、 N-<3,4-Dichlor-phenyl>-ameisensaeureimid-aethylester 以 乙腈 为溶剂， 反应 26.0h， 以32%的产率得到N-(3,4-dichlorophenyl)-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 、 3,4-二氯苯胺 以 乙腈 为溶剂， 反应 0.5h， 生成 N-<3,4-Dichlor-phenyl>-ameisensaeureimid-aethylester
  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

• 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.