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Enantioselective Separation of Chiral N1-Substituted-1H-pyrazoles: Greenness Profile Assessment and Chiral Recognition Analysis
ACS Omega ( IF 3.7 ) Pub Date : 2021-09-23 , DOI: 10.1021/acsomega.1c04613 Mohammed Farrag El-Behairy 1 , Rasha M Hassan 2 , Inas A Abdallah 3
ACS Omega ( IF 3.7 ) Pub Date : 2021-09-23 , DOI: 10.1021/acsomega.1c04613 Mohammed Farrag El-Behairy 1 , Rasha M Hassan 2 , Inas A Abdallah 3
Affiliation
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Two commercialized polysaccharide-based chiral stationary phases, Lux cellulose-2 and Lux amylose-2, were examined for their chiral recognition ability on a set of 18 biologically active racemic 4,5-dihydro-1H-pyrazole derivatives by applying normal and polar organic elution modes. The results showed that all compounds were baseline-resolved with at least one of the used elution modes. The cellulose-based column was superior using polar organic mobile-phase compositions with analysis times close to 5 min and resolutions up to 18, while the enantiomer-resolving ability of amylose-based columns was greater using the normal elution mode with analysis times close to 30 min and resolutions up to 30. The competition between the analytes and the mobile phase constituents on H-bond interactions with the stationary phase has been discussed, and the impact of this competition on chiral recognition has been investigated. It was found that the polar organic mode is very beneficial for short run times and sharp peaks. The developed enantioselective high-performance liquid chromatography (HPLC) methods will be applied to monitor the stereoselective synthesis of compounds 1–18 or to develop preparative HPLC techniques for compounds 1–18, followed by stereospecific pharmacological studies for each enantiomer separately. Greenness profile assessment of the different elution solvents was carried out using the AGREE metric approach.
中文翻译：
手性 N1-取代-1H-吡唑的对映选择性分离：绿度分布评估和手性识别分析
研究了两种商业化的基于多糖的手性固定相 Lux 纤维素-2 和 Lux amylose-2 对一组 18 种生物活性外消旋 4,5-dihydro-1 H的手性识别能力-吡唑衍生物通过应用正常和极性有机洗脱模式。结果表明，所有化合物都使用至少一种所用的洗脱模式实现了基线分离。使用极性有机流动相组合物时，纤维素基色谱柱性能优越，分析时间接近 5 分钟，分辨率高达 18 30 分钟和高达 30 的分辨率。已经讨论了分析物和流动相成分之间对氢键与固定相相互作用的竞争，并研究了这种竞争对手性识别的影响。发现极性有机模式对于短运行时间和尖峰非常有利。1-18或为化合物1-18开发制备型 HPLC 技术，然后分别对每个对映异构体进行立体特异性药理学研究。使用 AGREE 度量方法对不同洗脱溶剂进行绿度分布评估。
更新日期：2021-10-06
中文翻译：
手性 N1-取代-1H-吡唑的对映选择性分离：绿度分布评估和手性识别分析
研究了两种商业化的基于多糖的手性固定相 Lux 纤维素-2 和 Lux amylose-2 对一组 18 种生物活性外消旋 4,5-dihydro-1 H的手性识别能力-吡唑衍生物通过应用正常和极性有机洗脱模式。结果表明，所有化合物都使用至少一种所用的洗脱模式实现了基线分离。使用极性有机流动相组合物时，纤维素基色谱柱性能优越，分析时间接近 5 分钟，分辨率高达 18 30 分钟和高达 30 的分辨率。已经讨论了分析物和流动相成分之间对氢键与固定相相互作用的竞争，并研究了这种竞争对手性识别的影响。发现极性有机模式对于短运行时间和尖峰非常有利。1-18或为化合物1-18开发制备型 HPLC 技术，然后分别对每个对映异构体进行立体特异性药理学研究。使用 AGREE 度量方法对不同洗脱溶剂进行绿度分布评估。
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