Reaction Products of β-Aminopropioamidoximes Nitrobenzenesulfochlorination: Linear and Rearranged to Spiropyrazolinium Salts with Antidiabetic Activity

Kayukova, L.; Vologzhanina, A.; Dorovatovskii, P.; Baitursynova, G.; Yergaliyeva, E.; Kurmangaliyeva, A.; Shulgau, Z.; Adekenov, S.; Shaimerdenova, Z.; Akatan, K.

Авторы: Kayukova Lyudmila, Vologzhanina Anna, Dorovatovskii Pavel, Baitursynova Gulnur, Yergaliyeva Elmira, Kurmangaliyeva Ayazhan, Shulgau Zarina, Adekenov Sergazy, Shaimerdenova Zhanar, Akatan Kydymolla
Журнал: Molecules
Том: 27
Год издания: 2022
Издательство: MDPI
Местоположение издательства: Basel, Switzerland
Номер статьи: 2181
DOI: 10.3390/molecules27072181
Аннотация: Nitrobenzenesulfochlorination of β-aminopropioamidoximes leads to a set of products depending on the structure of the initial interacting substances and reaction conditions. Amidoximes, functionalized at the terminal C atom with six-membered N-heterocycles (piperidine, morpholine, thiomorpholine and phenylpiperazine), as a result of the spontaneous intramolecular heterocyclization of the intermediate reaction product of an SN2 substitution of a hydrogen atom in the oxime group of the amidoxime fragment by a nitrobenzenesulfonyl group, produce spiropyrazolinium ortho- or para-nitrobenzenesulfonates. An exception is ortho-nitrobenzenesulfochlorination of β-thiomorpholin-1-yl)propioamidoxime, which is regioselective at room temperature, producing two spiropyrazolinium salts (orthonitrobezenesulfonate and chloride), and regiospecific at the boiling point of the solvent, when only chloride is formed. The para-Nitrobezenesulfochlorination of β-(benzimidazol-1-yl)propioamidoxime, due to the reduced nucleophilicity of the aromatic β-amine nitrogen atom, is regiospecific at both temperatures, and produces the O-para-nitrobenzenesulfochlorination product. The antidiabetic screening of the new nitrobezenesulfochlorination amidoximes found promising samples with in vitro α-glucosidase activity higher than the reference drug acarbose. 1H-NMR spectroscopy and X-ray analysis revealed the slow inversion of six-membered heterocycles, and experimentally confirmed the presence of an unfavorable stereoisomer with an axial N–N bond in the pyrazolinium heterocycle.
Добавил в систему: Вологжанина Анна Владимировна

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№	Имя	Описание	Имя файла	Размер	Добавлен
1.	Полный текст		Kayukova_molecules.pdf	3,3 МБ	29 марта 2022 [VologzhaninaAV]
2.	экспертное заключение		220329160336_0001.pdf	213,6 КБ	29 марта 2022 [VologzhaninaAV]

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Интеллектуальная Система Тематического Исследования НАукометрических данных

Reaction Products of β-Aminopropioamidoximes Nitrobenzenesulfochlorination: Linear and Rearranged to Spiropyrazolinium Salts with Antidiabetic Activityстатья

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