O-alkylation of 4-hydroxybenzolsulfonamide by N-substituted 2-chloroacetamides and 5-(chloromethyl)-3-aryl-1,2,4-oxadiazoles

Elena Vasil&#039;eva; Polina Polunina; Egor Balbuckiy; Irina K. Proskurina; Sergey Ivanovskiy; Anton Shetnev; Mikhail Korsakov

doi:doi:10.52957/2782-1900-2024-5-4-88-95

UDC 547.793

O-alkylation of 4-hydroxybenzolsulfonamide by N-substituted 2-chloroacetamides and 5-(chloromethyl)-3-aryl-1,2,4-oxadiazoles

Published в From Chemistry Towards Technology Step-By-Step · Volume 5, Issue 4, 2024 · Pages 88–95 · Rubrics: Scientific articles

DOI 10.52957/2782-1900-2024-5-4-88-95

Received: 01.11.2024 Accepted: 19.11.2024 Published: 23.12.2024 Language of publication: ENG

Authors

Elena Vasil'eva ¹ · Polina Polunina ² · Egor Balbuckiy ³ · Irina K. Proskurina ⁴ · Sergey Ivanovskiy ⁵ · Anton Shetnev ⁶ · Mikhail Korsakov ⁷

1 Rossiyskiy gosudarstvennyy universitet im. A.N. Kosygina
graduate student
Moscow, Moscow, Russian Federation

2 Yaroslavl State Pedagogical University named after K.D. Ushinsky
student
Yaroslavl, Yaroslavl, Russian Federation

3 Yaroslavl State Pedagogical University named after K.D. Ushinsky
student
Yaroslavl, Yaroslavl, Russian Federation

4 Yaroslavl State Pedagogical University named after K.D. Ushinsky
Yaroslavl, Yaroslavl, Russian Federation

5 Yaroslavl State Pedagogical University named after K.D. Ushinsky (Associate Professor)
Yaroslavl, Yaroslavl, Russian Federation

6 Yaroslavl State Pedagogical University named after K.D. Ushinsky (Associate Professor)
, Moscow Institute of Physics and Technology (State University)
from 01.01.2024 until now Yaroslavl, Yaroslavl, Russian Federation

7 Yaroslavl State Pedagogical University named after K.D. Ushinsky (Professor)
Yaroslavl, Yaroslavl, Russian Federation

ABSTRACT

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.

KEYWORDS

sulphonamide oxadiazole O-alkylation carboanhydrase monoamine oxidase

Information Text

Authors:

1. Rossiyskiy gosudarstvennyy universitet im. A.N. Kosygina
graduate student

Moscow, Moscow, Russian Federation

2. Yaroslavl State Pedagogical University named after K.D. Ushinsky
student

Yaroslavl, Yaroslavl, Russian Federation

3. Yaroslavl State Pedagogical University named after K.D. Ushinsky
student

Yaroslavl, Yaroslavl, Russian Federation

4. Yaroslavl State Pedagogical University named after K.D. Ushinsky

Yaroslavl, Yaroslavl, Russian Federation

5. Yaroslavl State Pedagogical University named after K.D. Ushinsky (Associate Professor)

Yaroslavl, Yaroslavl, Russian Federation

6. Yaroslavl State Pedagogical University named after K.D. Ushinsky (Associate Professor)

Moscow Institute of Physics and Technology (State University)
from 01.01.2024 until now
Yaroslavl, Yaroslavl, Russian Federation

7. Yaroslavl State Pedagogical University named after K.D. Ushinsky (Professor)

Yaroslavl, Yaroslavl, Russian Federation

Type:

Article

Pages:

from 88 to 95

Status:

Published

Subject area:

UDC 547.793

Language:

English

Keywords:

sulphonamide, oxadiazole, O-alkylation, carboanhydrase, monoamine oxidase

Funding

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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