Synthesis of Substituted Thienopyrimidinones Based on 2-Amino-4-(1,4-benzodioxan-2-yl) Thiophene-3-carboxylic Acid Ethyl Ester

S. O. Vardanyan; Вартанян С. О.; A. S. Avagyan; Авакян А. С.; A. B. Sargsyan; Саргсян А. Б.; S. A. Harutyunyan; Арутюнян С. А.; H. V. Gasparyan; Гаспарян Г. В.; A. A. Aghekyan; Агекян А. А.

doi:10.31857/S0514749225040109

Synthesis of Substituted Thienopyrimidinones Based on 2-Amino-4-(1,4-benzodioxan-2-yl) Thiophene-3-carboxylic Acid Ethyl Ester

Authors: Vardanyan S.O.¹, Avagyan A.S.¹, Sargsyan A.B.¹, Harutyunyan S.A.¹, Gasparyan H.V.¹, Aghekyan A.A.¹
Affiliations:
1. The Scienctific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Issue: Vol 61, No 4 (2025)
Pages: 447-452
Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://journal-vniispk.ru/0514-7492/article/view/307896
DOI: https://doi.org/10.31857/S0514749225040109
EDN: https://elibrary.ru/SEAFNB
ID: 307896

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract
About the authors
References
Supplementary files
Statistics

Abstract

The previously obtained N-arylamides of 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylic acid ethyl ester were cyclized to 2-aryl-substituted 3-aminothienopyrimidin-4-ones by the action of hydrazine hydrate. By condensation of the starting amino ester with chloroacetic acid chloride was obtained chloramide, which was converted by the action of piperidine and morpholine into the corresponding aminomethylamides. The latters were also subjected to cyclization with hydrazine hydrate to 3-aminothienopyrimidin-4-one derivatives with aminomethyl substituents in the second position. The antihypoxic activity of the synthesized compounds was studied.

Keywords

1,4-benzodioxane, chloramide, 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylic acid ethyl ester, thienopyrimidin-4-one, cyclization

References

The use of stems in the selection of International Nonprietary Names (INN) for pharmaceutical substances. Geneva, WHO, 2018.
Giri R.S., Thaker H. M., Giordano T., Williams J., Rogers D, Vasu K.K., Sudarsanam V. Bioorg. Med. Chem. 2010, 18, 2796. doi: 10.1016/j.bmc.2010.01.007
Tang J., Huber A.D, Pineda D. L., Boschert K.N., Wolf J.J., Kankanala J., Xie J., Sarafianos S.G., Wang Zh. Eur. J. Med. Chem. 2019, 164, 179. doi: 10.1016/j.ejmech.2018.12.047
Jin X., Merrett J., Tong Sh., Flower B., Xie J., Yu R., Tian Sh., Gao L., Zhao J., .Wang X, Jiang T., Proud Ch.G. Eur. J. Med. Chem. 2019, 162, 735–751. doi 10.1016/j. ejmech. 2018.10.070
Vardanyan S.O., Aghekyan A.A., Avagyan A.S., Harutyunyan S.A., Gasparyan H.V. Russ. J. Org. Chem. 2019, 55, 598–601. doi: 10.1134/S1070428019050038
Арутюнян С.А. Вестник МАНЭБ. 2005, 10, 169–173.

Supplementary files

Supplementary Files

Action

1. JATS XML

Download

Username
Password
Remember me

Forgot password?	Register

Username
Password
Remember me

Forgot password?	Register

Synthesis of Substituted Thienopyrimidinones Based on 2-Amino-4-(1,4-benzodioxan-2-yl) Thiophene-3-carboxylic Acid Ethyl Ester

Full Text

Abstract

Keywords

About the authors

References

Supplementary files