Synthesis and Analgesic Activity of 5-Aryl-4-Heteroyl-3-Hydroxy-1-(2-Thiazolyl)-3-Pyrrolin-2-Ones and their Derivatives

被引：6

作者：

Gein, V. L. ^{[1
]}

Mar'yasov, M. A. ^{[1
]}

Silina, T. A. ^{[1
]}

Makhmudov, R. R. ^{[2
]}

机构：

[1] Perm State Pharmaceut Acad, Perm 614990, Russia

[2] Perm State Univ, Perm 614990, Russia

来源：

PHARMACEUTICAL CHEMISTRY JOURNAL | 2014年 / 47卷 / 10期

关键词：

5-aryl-4-heteroyl-3-hydroxy-1-(2-thiazolyl)-3-pyrrolin-2-ones; synthesis; dinucleophiles; 4-aryl-5-(2-thiazolyl)-3-(2-thienoyl)-1,4-dihydropyrrolo[3,4]pyrazol-6-ones; analgesic activity; acute toxicity;

D O I：

10.1007/s11094-014-1000-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The three-component reaction of methyl 2-heteroylpyruvates with aromatic aldehydes and 2-aminothiazole was used to synthesize 5-aryl-4-(2-heteroyl)-3-hydroxy-1-(2-thiazolyl)-3-pyrrolin-2-ones. The corresponding 3-amino derivatives were obtained from the synthesized compounds by nucleophilic substitution with o-aminophenol, m-phenylenediamine, hydroxylamine, and urea; the corresponding pyrrolo[3, 4]pyrazoles, with hydrazine hydrate and phenylhydrazine. The structures of the new compounds were established using IR, PMR, and mass spectra and qualitative reactions. The acute toxicity and analgesic activity of the synthesized compounds were studied.

引用

页码：539 / 543

页数：5

共 50 条

[1] Synthesis and Analgesic Activity of 5-Aryl-4-Heteroyl-3-Hydroxy-1-(2-Thiazolyl)-3-Pyrrolin-2-Ones and their Derivatives
V. L. Gein
M. A. Mar’yasov
T. A. Silina
R. R. Makhmudov
Pharmaceutical Chemistry Journal, 2014, 47 : 539 - 543
[2] Synthesis and antimicrobial activity of 5-aryl-4-acyl(heteroyl)-3-hydroxy-1- (3-ethoxypropyl)-3-pyrrolin-2-ones
V. L. Gein
A. A. Bobyleva
E. B. Levandovskaya
T. F. Odegova
M. I. Vakhrin
Pharmaceutical Chemistry Journal, 2012, 46 : 23 - 25
[3] Synthesis and antimicrobial activity of 5-aryl-4-acyl(heteroyl)-3-hydroxy-1-(3-ethoxypropyl)-3-pyrrolin-2-ones
Gein, V. L.
Bobyleva, A. A.
Levandovskaya, E. B.
Odegova, T. F.
Vakhrin, M. I.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2012, 46 (01) : 23 - 25
[4] Synthesis and antibacterial and analgesic activity of 5-aryl-4-acyl-3-hydroxy-1(2,2-dimethoxyethyl)-3-pyrrolin-2-ones
V. L. Gein
V. N. Vychegzhanina
E. B. Levandovskaya
B. Ya. Syropyatov
M. I. Vakhrin
E. V. Voronina
N. V. Danilova
Pharmaceutical Chemistry Journal, 2010, 44 : 370 - 373
[5] SYNTHESIS AND ANTIBACTERIAL AND ANALGESIC ACTIVITY OF 5-ARYL-4-ACYL-3-HYDROXY-1(2,2-DIMETHOXYETHYL)-3-PYRROLIN-2-ONES
Gein, V. L.
Vychegzhanina, V. N.
Levandovskaya, E. B.
Syropyatov, B. Ya.
Vakhrin, M. I.
Voronina, E. V.
Danilova, N. V.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2010, 44 (07) : 370 - 373
[6] Synthesis and biological activity of 4-acyl-5-aryl-3-hydroxy-1-(2- hydroxyethylaminoethyl)-3-pyrrolin-2-ones
Gein V.L.
Kasimova N.N.
Moiseev A.L.
Sheptukha M.A.
Syropyatov B.Ya.
Ismailova N.G.
Voronina E.V.
Ivanenko O.I.
Pharmaceutical Chemistry Journal, 2007, 41 (9) : 476 - 479
[7] Synthesis and antibacterial activity of 5-aryl-4-acyl-3-hydroxy-1-(2-hydroxyethyl)-3-pyrrolin-2-ones
Gein, V. L.
Odegova, T. F.
Korol', A. N.
Varkentin, L. I.
Bobyleva, A. A.
Gein, L. F.
Vakhrin, M. I.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2014, 47 (10) : 536 - 538
[8] Synthesis and antibacterial activity of 5-aryl-4-acyl-3-hydroxy-1-(2-hydroxyethyl)-3-pyrrolin-2-ones
V. L. Gein
T. F. Odegova
A. N. Korol’
L. I. Varkentin
A. A. Bobyleva
L. F. Gein
M. I. Vakhrin
Pharmaceutical Chemistry Journal, 2014, 47 : 536 - 538
[9] Synthesis of 5-Aryl-4-acyl-3-hydroxy-1-(2-furylmethyl)-3-pyrrolin-2-ones
Gein, V. L.
Nosova, N. V.
Shishkin, A. P.
Gein, L. F.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (03) : 598 - 601
[10] Synthesis of 5-Aryl-4-acyl-3-hydroxy-1-(2-furylmethyl)-3-pyrrolin-2-ones
V. L. Gein
N. V. Nosova
A. P. Shishkin
L. F. Gein
Russian Journal of General Chemistry, 2018, 88 : 598 - 601

← 1 2 3 4 5 →