Synthesis and Biological Evaluation of  N -Aminoalkil Derivatives of Sulfanilamide Reaction

Elena A. Vasilyeva; Васильева Елена Андреевна; Irina K. Proskurina; Проскурина Ирина Константиновна; Anton А. Shetnev; Шетнев Антон Андреевич; Anna A. Romanycheva; Романычева Анна Александровна; Alyona V. Korovina; Коровина Алёна Вадимовна; Maria V. Belchenko; Бельченко Мария Владимировна; Ekaterina O. Grunina; Грунина Екатерина Олеговна; Anelle Petzer; Петцер Анель; Alexander D. Kotov; Котов Александр Дмитриевич; Jacob Petzer; Петцер Яков

doi:10.31857/S0044460X25030013

Synthesis and Biological Evaluation of N-Aminoalkil Derivatives of Sulfanilamide Reaction

Authors: Vasilyeva E.A.¹^,2, Proskurina I.K.¹, Shetnev A.А.¹^,3, Romanycheva A.A.¹, Korovina A.V.¹, Belchenko M.V.¹, Grunina E.O.¹, Petzer A.⁴, Kotov A.D.¹, Petzer J.⁴
Affiliations:
1. Ushinsky Yaroslavl State Pedagogical University
2. Kosygin Russian State University
3. Moscow Institute of Physics and Technology
4. North-West University
Issue: Vol 95, No 3-4 (2025)
Pages: 80-91
Section: Articles
URL: https://rjmseer.com/0044-460X/article/view/686598
DOI: https://doi.org/10.31857/S0044460X25030013
EDN: https://elibrary.ru/DCOCLA
ID: 686598

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Abstract

A series of 19 derivatives of sulfanilamide was synthesized by the reaction of chloroacetamide, trichloroacetamide and chloropropionamide with N-nucleophiles. It was shown that N-trichloroacetylsulfanilamide in reactions with amines forms products of substitution of the trichloromethyl group, while N-chloroacetylsulfanilamide and N-chloropropionylsulfanilamide react with substitution of the halogen atom. An assessment of the antibacterial properties of the synthesized structures was carried out, showing the absence of activity with respect to E. coli and St. aureus strains. Two aminoalkyl-containing sulfonamides – 2-(4-benzylpiperidin-1-yl)-N-(4-sulfamoylphenyl)acetamide and 2-(4-nitropyrazol-1-yl)-N-(4-sulfamoylphenyl)acetamide – showed inhibitory properties against the human monoamine oxidase enzyme, comparable in IC₅₀ value to the drug zonisamide.

Keywords

sulfonamide, N-alkylation, monoamine oxidase, inhibitor, antimicrobial activity

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References

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