N-(2,2,2-trichloro-1-hydroxyethyl)furan-2-carboxamide | 6945-02-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2,2,2-trichloro-1-hydroxyethyl)furan-2-carboxamide
• 英文别名: furan-2-carboxylic acid-(2,2,2-trichloro-1-hydroxy-ethylamide)；Furan-2-carbonsaeure-(2,2,2-trichlor-1-hydroxy-aethylamid)；(+/-)-N-(2,2,2-Trichlor-1-hydroxy-aethyl)-furan-2-carbamid
• CAS: 6945-02-4
• 化学式: C₇H₆Cl₃NO₃
• mdl: MFCD00033637
• 分子量: 258.489
• InChiKey: GRGOQUBKQQMSQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  62.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  N-(2,2,2-trichloro-1-hydroxyethyl)furan-2-carboxamide 在 五氯化磷 作用下， 生成 N-(2,2,2-trichloro-1-piperidino-ethyl)-furan-2-carboxamide
  参考文献：
  名称：

  Studies in the Furan Series. Chloralfuramides and Some of their Reactions

  摘要：

  DOI：

  10.1021/ja01106a025
• 作为产物：
  描述：

  糠酰胺 、 水合氯醛 反应 1.0h， 生成 N-(2,2,2-trichloro-1-hydroxyethyl)furan-2-carboxamide
  参考文献：
  名称：

  Concise and regioselective synthesis of 5H-imidazo[1,2-e][1,3,5]triazepines

  摘要：

  DOI：

  10.24820/ark.5550190.p011.689

文献信息

• Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides
  作者：Pavlo V. Zadorozhnii、Ihor O. Pokotylo、Vadym V. Kiselev、Aleksandr V. Kharchenko、Oxana V. Okhtina

  DOI：10.1515/hc-2019-0020

  日期：2019.11.28

  Based on readily available N-(2,2,2-trichloro-1-hydroxyethyl)carboxamides, N-(2,2,2-trichloro-1-(3-(3-mercapto-4H-1,2,4-triazol-4-yl)thioureido)ethyl) carboxamides, dehydrosulfurization–under the influence of excess HgO–led to the formation of N-(1-([1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides. The reaction was carried out in boiling glacial acetic acid for 1-1.5 hours. The cyclization products were obtained in 42-62% yields and easily isolated from the reaction mixture. The structure of all synthesized compounds was confirmed by complex spectral studies.

  基于易得的N-(2,2,2-三氯-1-羟乙基)羧酰胺，N-(2,2,2-三氯-1-(3-(3-巯基-4H-1,2,4-三唑-4-基)硫脲基)乙基)羧酰胺，通过过量HgO的脱硫化作用，在沸腾的冰乙酸中反应1-1.5小时，形成了N-(1-([1,2,4]三唑[3,4-b][1,3,4]噻二唑-6-基氨基)-2,2,2-三氯乙基)羧酰胺。环化产物以42-62%的产率得到，并且可以很容易地从反应混合物中分离。所有合成化合物的结构都通过复杂的光谱研究得到了确认。

• In silico and in vitro studies of a number PILs as new antibacterials against MDR clinical isolate <i>Acinetobacter baumannii</i>
  作者：Maria M. Trush、Vasyl Kovalishyn、Diana Hodyna、Olexandr V. Golovchenko、Svitlana Chumachenko、Igor V. Tetko、Volodymyr S. Brovarets、Larysa Metelytsia

  DOI：10.1111/cbdd.13678

  日期：2020.6

  AbstractQSAR analysis of a set of previously synthesized phosphonium ionic liquids (PILs) tested against Gram‐negative multidrug‐resistant clinical isolate Acinetobacter baumannii was done using the Online Chemical Modeling Environment (OCHEM). To overcome the problem of overfitting due to descriptor selection, fivefold cross‐validation with variable selection in each step of the model development was applied. The predictive ability of the classification models was tested by cross‐validation, giving balanced accuracies (BA) of 76%–82%. The validation of the models using an external test set proved that the models can be used to predict the activity of newly designed compounds with a reasonable accuracy within the applicability domain (BA = 83%–89%). The models were applied to screen a virtual chemical library with expected activity of compounds against MDR Acinetobacter baumannii. The eighteen most promising compounds were identified, synthesized, and tested. Biological testing of compounds was performed using the disk diffusion method in Mueller‐Hinton agar. All tested molecules demonstrated high anti‐A. baumannii activity and different toxicity levels. The developed classification SAR models are freely available online at http://ochem.eu/article/113921 and could be used by scientists for design of new more effective antibiotics.