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（）-和（）-奥沙西泮琥酸半酯的水解和对映体选择性研究：NMR 研究。

Hydrolysis and Enantiodiscrimination of ()- and ()-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation.

机构信息

Dipartimento di Scienze Chimiche, Università di Padova, Via Marzolo 1, 35131 Padova, Italy.

Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Moruzzi 13, 56124 Pisa, Italy.

出版信息

Molecules. 2021 Oct 20;26(21):6347. doi: 10.3390/molecules26216347.

DOI:10.3390/molecules26216347
PMID:34770758
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8587842/
Abstract

Partially and exhaustively methylated β-cyclodextrins [(2-methyl)-β-CD (MCD), heptakis-(2,6-di--methyl)-β-CD (DIMEB), and heptakis-(2,3,6-tri--methyl)-β-CD (TRIMEB)] have been compared in the hydrolysis and enantiodiscrimination of benzodiazepine derivative ()- or ()-oxazepam hemisuccinate (OXEMIS), using nuclear magnetic resonance (NMR) spectroscopy as an investigation tool. After 6 h, MCD induced an 11% hydrolysis of OXEMIS, remarkably lower in comparison with underivatized β-CD (48%), whereas no hydrolysis was detected in the presence of DIMEB or TRIMEB after 24 h. DIMEB showed greater ability to differentiate OXEMIS enantiomers in comparison to TRIMEB, by contrast MCD did not produce any splitting of racemic OXEMIS resonances. Both enantiomers of OXEMIS underwent deep inclusion of their phenyl pendant into cyclodextrins cavities from their wider rims, but tighter complexes were formed by DIMEB with respect to TRIMEB.

摘要

部分和完全甲基化的β-环糊精[（2-甲基）-β-CD（MCD），七（2,6-二-O-甲基）-β-CD（DIMEB）和七（2,3,6-三-O-甲基）-β-CD（TRIMEB）]已在苯并二氮杂卓衍生物（）-或（）-奥沙西泮半琥珀酸酯（OXEMIS）的水解和对映体识别中进行了比较，使用核磁共振（NMR）光谱作为研究工具。6 小时后，MCD 诱导 OXEMIS 的水解率为 11％，与未衍生化的β-CD（48％）相比明显降低，而在 DIMEB 或 TRIMEB 存在下 24 小时后未检测到水解。与 TRIMEB 相比，DIMEB 显示出更大的区分 OXEMIS 对映体的能力，相比之下，MCD 不会导致外消旋 OXEMIS 共振的任何分裂。OXEMIS 的两种对映体都从其较宽的边缘将其苯基侧链深入地纳入环糊精腔中，但 DIMEB 与 TRIMEB 相比形成了更紧密的复合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/98ff9b9d1b38/molecules-26-06347-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/648633381506/molecules-26-06347-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/cfc641952de3/molecules-26-06347-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/2f312bfcbb6e/molecules-26-06347-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/792669f38b56/molecules-26-06347-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/a2fda22d029e/molecules-26-06347-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/5e307228952c/molecules-26-06347-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/98ff9b9d1b38/molecules-26-06347-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/648633381506/molecules-26-06347-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/cfc641952de3/molecules-26-06347-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/2f312bfcbb6e/molecules-26-06347-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/792669f38b56/molecules-26-06347-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/a2fda22d029e/molecules-26-06347-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/5e307228952c/molecules-26-06347-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2dbd/8587842/98ff9b9d1b38/molecules-26-06347-g007.jpg

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