From Chemistry Towards Technology Step-By-Step From Chemistry Towards Technology Step-By-Step От химии к технологии шаг за шагом 2782-1900 92389 10.52957/2782-1900-2024-5-4-88-95 Научные статьи Scientific articles Научные статьи O-alkylation of 4-hydroxybenzolsulfonamide by N-substituted 2-chloroacetamides and 5-(chloromethyl)-3-aryl-1,2,4-oxadiazoles O-alkylation of 4-hydroxybenzolsulfonamide by N-substituted 2-chloroacetamides and 5-(chloromethyl)-3-aryl-1,2,4-oxadiazoles Васильева Елена Андреевна Vasil'eva Elena Andreevna Полунина Полина Владимировна Polunina Polina Vladimirovna Балбуцкий Егор Александрович Balbuckiy Egor Aleksandrovich Проскурина Ирина Константиновна Proskurina Irina Konstantinovna

кандидат биологических наук;

candidate of sciences in biology;

 Ивановский Сергей Александрович Ivanovskiy Sergey Aleksandrovich s.ivanovskiy@yspu.org

кандидат химических наук;

candidate of chemical sciences;

 Шетнев Антон Андреевич Shetnev Anton Andreevich

кандидат химических наук;

candidate of chemical sciences;

 Корсаков Михаил Константинович Korsakov Mikhail Konstantinovich

доктор химических наук;

doctor of chemical sciences;

 Российский государственный университет им. А.Н. Косыгина Россия Российский государственный университет им. А.Н. Косыгина Russian Federation Ярославский государственный педагогический университет им. К.Д. Ушинского Yaroslavl State Pedagogical University named after K.D. Ushinsky Московский физико-технический институт (государственный университет) Moscow Institute of Physics and Technology (State University) 23 12 2024 23 12 2024 5 4 88 95 01 11 2024 19 11 2024 https://chemintech.ru/en/nauka/article/92389/view

The paper presents a method for the synthesis of new representatives of the primary benzenesulfonamides class. They are promising agents for the treatment of open-angle glaucoma and neurodegenerative diseases. The authors have developed a mechanism for the O-alkylation of 4-hydroxybenzene sulfonamide with alkylating agents of different nature. The method provides mild conditions and selectivity of the process. The paper shows the necessity of activation of N-substituted 2-chloroacetamides and 5-(chloromethyl)-3-aryl-1,2,4-oxadiazoles by catalytic addition of potassium iodide in O-alkylation reactions of phenols. The authors demonstrated the applicability of the developed methodology on 12 examples of O-alkyl derivatives of 4-hydroxybenzene sulfonamide obtained in yields from 28 to 86%. The research proved the purity and structure of the new compounds by the combined methods of 1H NMR, 13C NMR, and elemental analysis.

The paper presents a method for the synthesis of new representatives of the primary benzenesulfonamides class. They are promising agents for the treatment of open-angle glaucoma and neurodegenerative diseases. The authors have developed a mechanism for the O-alkylation of 4-hydroxybenzene sulfonamide with alkylating agents of different nature. The method provides mild conditions and selectivity of the process. The paper shows the necessity of activation of N-substituted 2-chloroacetamides and 5-(chloromethyl)-3-aryl-1,2,4-oxadiazoles by catalytic addition of potassium iodide in O-alkylation reactions of phenols. The authors demonstrated the applicability of the developed methodology on 12 examples of O-alkyl derivatives of 4-hydroxybenzene sulfonamide obtained in yields from 28 to 86%. The research proved the purity and structure of the new compounds by the combined methods of 1H NMR, 13C NMR, and elemental analysis.

 sulphonamide oxadiazole O-alkylation carboanhydrase monoamine oxidase The study was performed within the framework of the State assignment of Yaroslavl State Pedagogical University named after K. D. Ushinsky for 2024 from the Ministry of Education of the Russian Federation on the topic "Development of a new drug for the treatment of neurodegenerative diseases based on a monoamine oxidase inhibitor" (registry entry number 720000F.99.1.BN62AAA12000).

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