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Crystal structure and antidiabetic activity of 2-aminospiropyrazolinium tosylates and the product of O-tosylation of beta-(benzimidazol-1-yl)propioamidoximeстатья Исследовательская статья
- Авторы: Kayukova Lyudmila A., Vologzhanina Anna V., Yergaliyeva Elmira M., Baitursynova Gulnur P., Shulgau Zarina T., Sergazy Shynggys
- Журнал: ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
- Том: 78
- Номер: 10
- Год издания: 2022
- Издательство: John Wiley & Sons Inc.
- Местоположение издательства: United States
- Первая страница: 542
- Последняя страница: 551
- DOI: 10.1107/s2053229622008464
- Аннотация: 2-Amino-1,5-diazaspiro[4.5]dec-1-en-5-ium salts possess bioactivity tuned bythe nature of the heteroatoms in the six-membered ring and the counter-ion.The molecular environment of these cations in solids provides an opportunity toestablish the conformations and hydrogen-bonding patterns typical for this family.-Aminopropioamidoxime tosylation products [2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium tosylates and the product of theO-tosylation of-(benzimidazol-1-yl)propioamidoxime, namely, 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium tosylate, (C8H16N3)(C7H7O3S) (6), 2-amino-8-oxa-1,5-diazaspiro[4.5]dec-1-en-5-ium tosylate, (C7H14N3O)(C7H7O3S)(7), the monohydrate of 7, (C7H14N3O)(C7H7O3S)H2O (7a), 2-amino-8-thia-1,5-diazaspiro[4.5]dec-1-en-5-ium tosylate, (C7H14N3S)(C7H7O3S) (8), 2-amino-8-phenyl-1,5,8-triazaspiro[4.5]dec-1-en-5-ium tosylate, (C13H19N4)(C7H7O3S) (9), and 3-(1H-benzimidazol-1-yl)-N0-(tos-yloxy)propanimidamide, C17H18N4O3S (10)] were investigated using X-raydiffraction to study peculiarities of their molecular geometry and intermolecularinteractions. In vitro antitubercular and antidiabetic screening of the amino-propioamidoxime tosylation products was also carried out. It was revealed that this series of compounds does not have activity against drug-sensitive and multidrug-resistant M. tuberculosis strains, and exhibits high and moderate antidiabetic-amylase and-glucosidase activity. Using the hydrogen-bond propensity tool, we found that the inclination of counter-ions and atoms to act as acceptors of hydrogen bonds for the amino group decreases passing from tosylate O atoms to water molecules and the N atoms of five-membered rings. This fact is probably the reason for the formation in the solids of hydrogen-bonded tetramers consisting of two anions and two cations, and the rareoccurrence of 2-aminospiropyrazolinium salt hydrates.
- Добавил в систему: Вологжанина Анна Владимировна
Прикрепленные файлы
| № | Имя | Описание | Имя файла | Размер | Добавлен |
|---|---|---|---|---|---|
| 2. | экспертное заключение | ActaCrystC_expt.pdf | 388,9 КБ | 16 сентября 2022 [VologzhaninaAV] |