Synthesis and Hypotensive Activity of Pyrimidine-2,4-(1H,3H)-Dione Derivatives Containing Thietane Rings with Sulfur in Various Oxidation States

被引：4

作者：

Kataev, V. A. ^{[1
]}

Tyurenkov, I. N. ^{[2
]}

Meshcheryakova, S. A. ^{[1
]}

Perfilova, V. N. ^{[2
]}

Munasipova, D. A. ^{[1
]}

Borodin, D. D. ^{[2
]}

机构：

[1] Bashkir State Med Univ, Ufa 450074, Bashkortostan, Russia

[2] Volgograd State Med Univ, Volgograd 400131, Russia

来源：

PHARMACEUTICAL CHEMISTRY JOURNAL | 2014年 / 48卷 / 07期

关键词：

thietanepyrimidine-2,4-(1H,3H)-dione; oxidation; N-alkylation; CH-aminomethylation; hypotensive activity;

D O I：

10.1007/s11094-014-1126-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Oxo- and dioxothietane derivatives of 6-methyl-1-(thietan-3-yl)pyrimidine-2,4-(1H,3H)-dione were synthesized by oxidation. N-Alkylation and CH-aminomethylation produced 3-alkyl- and 5-aminomethyl-substituted 6-methyl-1-(thietan-3-yl)pyrimidine-2,4-(1H,3H)-dione, 6-methyl-1-(1-oxothietan-3-yl)pyrimidine-2,4-(1H,3H)-dione, and 1-(1,1-dioxothietan-3-yl)-6-methylpyrimidine-2,4-(1H,3H)-dione. The synthesized compounds showed hypotensive activity. Compounds causing pronounced, prolonged, and dose-dependent hypotensive effects that were comparable with those of reference drugs nebivolol (2 mg/kg), lisinopril (10 mg/kg), and amlodipine (1 mg/kg) were discovered.

引用

页码：434 / 438

页数：5

共 14 条

[1] Synthesis and Hypotensive Activity of Pyrimidine-2,4-(1H,3H)-Dione Derivatives Containing Thietane Rings with Sulfur in Various Oxidation States
V. A. Kataev
I. N. Tyurenkov
S. A. Meshcheryakova
V. N. Perfilova
D. A. Munasipova
D. D. Borodin
Pharmaceutical Chemistry Journal, 2014, 48 : 434 - 438
[2] Synthesis of pyrinidine-2,4(1H,3H)-dione derivatives containing N-alkyl substituents
Raskildina, G. Z.
Valiev, V. F.
Ozden, I. V.
Meshcheryakova, S. A.
Spirikhin, L. V.
Zlotskii, S. S.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (08) : 1872 - 1875
[3] Synthesis of pyrinidine-2,4(1H,3H)-dione derivatives containing N-alkyl substituents
G. Z. Raskildina
V. F. Valiev
I. V. Ozden
S. A. Meshcheryakova
L. V. Spirikhin
S. S. Zlotskii
Russian Journal of General Chemistry, 2017, 87 : 1872 - 1875
[4] Synthesis and structural analysis of 3-phenylethyl-2,4(1H,3H)-quinazolinediones
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Velez, Yormari
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JOURNAL OF MOLECULAR STRUCTURE, 2017, 1147 : 676 - 681
[5] An NMR Spectral Study of the Structure of 5,5,6-trihydroxy-6-methyldihydropyrimidine-2,4-(1H,3H)-dione in DMSO-d6
Petrova, S. F.
Nugumanov, T. R.
Lobov, A. N.
Spirikhin, L., V
Ivanov, S. P.
JOURNAL OF APPLIED SPECTROSCOPY, 2022, 89 (02) : 225 - 231
[6] STUDIES ON HYPOTENSIVE AGENTS - SYNTHESIS OF 1-SUBSTITUTED 3-(2-CHLOROPHENYL)-6-ETHOXYCARBONYL-5,7-DIMETHYL-2,4(1H,3H)-QUINAZOLINEDIONES
EGUCHI, Y
SASAKI, F
SUGIMOTO, A
EBISAWA, H
ISHIKAWA, M
CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (07) : 1753 - 1759
[7] Acid-Base Equilibrium of 5,5,6-Trihydroxy-6-Methyldihydropyrimidine-2,4(1H,3H)-Dione in the Gas Phase and in Water
Petrova, Svetlana F.
Khamitov, Edward M.
Nugumanov, Timur R.
Ivanov, Sergey P.
JOURNAL OF PHYSICAL CHEMISTRY A, 2025, 129 (03) : 661 - 666
[8] New Strategy for the Synthesis of 5-Aryl-1H,1′H-spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]2,2′,4,4′,6′(3H,3′H,5H)-pentaones and Their Sulfur Analogues
Jalilzadeh, Mohammad
Pesyan, Nader Noroozi
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (09): : 3382 - 3388
[9] PYRIMIDINE-DERIVATIVES .8. ONE-STEP SYNTHESIS OF 3,4-DIHYDRO-PYRIMIDO[6,1-C][1,4]OXAZINE DERIVATIVES BY REACTIONS OF 5-BROMO-1-(2-BROMOETHYL)-6-BROMOMETHYL-2,4(1H,3H)-PYRIMIDINEDIONE WITH SODIUM ALKOXIDES AND 2-NITROPROPANE
KINOSHITA, T
UGA, M
TANIMOTO, Y
OHISHI, K
FURUKAWA, S
CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (10) : 2668 - 2670
[10] Synthesis of Furo[3,2-c]pyridine-2,4-dione Derivatives by the Reaction of 1-Methyl-4-phenyl-5,6-dihydropyridin-2(1H)-one with Carboxylic Acids in the Presence of Manganese Triacetate
A. T. Soldatenkov
K. B. Polyanskii
S. A. Soldatova
Chemistry of Heterocyclic Compounds, 2002, 38 (3) : 368 - 369

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