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.
April-1 2022MDPI
Molecules
2022#27Issue 7
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 heterocycliza-tion 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 (ortho-nitrobezenesulfonate 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-nitrobenzenesul-fochlorination product. The antidiabetic screening of the new nitrobezenesulfochlorination ami-doximes 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.
nitrobezenesulfochlorination , spiropyrazolinium salts , X-ray diffraction , β-aminopropioamidoximes
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JSC A. B. Bekturov Institute of Chemical Sciences, 106 Shokan Ualikhanov St., Almaty, 050010, Kazakhstan
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., B-334, Moscow, 119991, Russian Federation
NRC “Kurchatov Institute”, 1, Akademika Kurchatova pl., Moscow, 123182, Russian Federation
RSE National Center for Biotechnology, Science Committee of ME&S RK, 13/5 Kurgalzhinskoe highway, Nur-Sultan, 010000, Kazakhstan
JSC International Research and Production Holding Phytochemistry, 4 M. Gazalieva St., Karaganda, 100009, Kazakhstan
National Scientific Laboratory, S. Amanzholov East Kazakhstan State University, 18/1 Amurskaya St., Ust-Kamenogorsk, 070002, Kazakhstan
JSC A. B. Bekturov Institute of Chemical Sciences
A. N. Nesmeyanov Institute of Organoelement Compounds
NRC “Kurchatov Institute”
RSE National Center for Biotechnology
JSC International Research and Production Holding Phytochemistry
National Scientific Laboratory
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