Effect of Chirality on the Compression of 2-(2-Oxo-1-pyrrolidinyl)butyramide: A Tale of Two Crystals.
Effect of Chirality on the Compression of 2-(2-Oxo-1-pyrrolidinyl)butyramide: A Tale of Two Crystals.
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DOI：
10.1021/acs.cgd.0c00871
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发表时间：
2020-10-07
影响因子：
3.8
通讯作者：
Oswald IDH
中科院分区：
文献类型：
--
作者：
Bebiano SS;Ter Horst JH;Oswald IDH
了解用于药物制造的手性系统的多态对于避免不良的治疗效果是至关重要的。通常，通过改变温度和溶液浓度来研究多态现象。一种不太常见的方法是施加压力。本工作的目的是研究压力对左乙拉西坦(纯对映体)和乙乙拉西坦(外消旋化合物)的影响。左乙拉西坦和依特拉西坦的各向异性压缩压力分别为5.26和6.29 GPa.两者最可压缩的方向被确定为垂直于结构的各层。拉曼光谱和分子间相互作用分析表明，左乙拉西坦(∼2 Gpa)和依特拉西坦(∼1.5 Gpa)存在微妙的相变。乙拉西坦相对于左乙拉西坦在压缩时的稳定性增加；因此，该体系的手性拆分在压力下是不利的。这项工作有助于理解手性体系的稳定性。用拉曼光谱和单晶X射线衍射法研究了压力对2-(2-氧代-1-吡咯烷基)丁酰胺的手性晶体和外消旋晶体的影响。在计算方法的支持下，观察到了每种晶型中潜在的向新高压相的微妙相变。
Understanding polymorphism in chiral systems for drug manufacturing is essential to avoid undesired therapeutic effects. Generally, polymorphism is studied through changes in temperature and solution concentration. A less common approach is the application of pressure. The goal of this work is to investigate the effect of pressure on levetiracetam (pure enantiomer) and etiracetam (racemic compound). Anisotropic compressions of levetiracetam and etiracetam are observed to 5.26 and 6.29 GPa, respectively. The most compressible direction for both was identified to be perpendicular to the layers of the structure. Raman spectroscopy and an analysis of intermolecular interactions suggest subtle phase transitions in levetiracetam (∼2 GPa) and etiracetam (∼1.5 GPa). The stability of etiracetam increases with respect to levetiracetam on compression; hence, the chiral resolution of this system is unfavorable using pressure. This work contributes to the ongoing efforts in understanding the stability of chiral systems. The effect of pressure on the chiral and racemic crystals of 2-(2-oxo-1-pyrrolidinyl)butyramide was performed using Raman and single-crystal X-ray diffraction measurements. Potential subtle phase transitions to new high-pressure phases in each crystal form were observed with the support of computational approaches.
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影响因子：
3.7
作者：
Cai, Weizhao;Marciniak, Jedrzej;Katrusiak, Andrzej
通讯作者：
Katrusiak, Andrzej
DOI：
10.1107/s0567740882009431
发表时间：
1982-01-01
期刊：
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE
影响因子：
--
作者：
ADMIRAAL, G;EIKELENBOOM, JC;VOS, A
通讯作者：
VOS, A
影响因子：
15
作者：
Bordallo, Heloisa N.;Kolesov, Boris A.;Juranyi, Fanni
通讯作者：
Juranyi, Fanni
DOI：
10.1107/s2052520614026389
发表时间：
2015-02-01
影响因子：
1.9
作者：
Connor, Lauren E.;Delori, Amit;Oswald, Iain D. H.
通讯作者：
Oswald, Iain D. H.
影响因子：
6.1
作者：
Dawson, A;Allan, DR;Ruf, M
通讯作者：
Ruf, M