Synthesis of polyfluoroalkyl-containing 1-(4-acetoxybutyl)- and 1-(4-hydroxybutyl)pyrazoles and their tuberculostatic activity

被引：3

作者：

Ivanova, A. E. ^{[1
]}

Khudina, O. G. ^{[1
]}

Burgart, Ya. V. ^{[1
]}

Saloutin, V. I. ^{[1
]}

Kravchenko, M. A. ^{[2
]}

机构：

[1] Russian Acad Sci, Ural Branch, I Ya Postovsky Inst Organ Synth, Ekaterinburg 620041, Russia

[2] Minist Healthcare & Social Dev Russian Federat, Ural Res Inst Phthisiopulmonol, Ekaterinburg 620039, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2011年 / 60卷 / 11期

基金：

俄罗斯基础研究基金会;

关键词：

pyrazoles; alkylation; deacylation; tuberculostatic activity; IDENTIFICATION;

D O I：

10.1007/s11172-011-0368-4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkylation of polyfluoroalkyl-containing pyrazoles with 4-bromobutyl acetate in acetone in the presence of potassium carbonate leads to a mixture of isomeric 1-(4-acetoxybutyl)-3-fluoroalkyl- and 1-(4-acetoxybutyl)-5-fluoroalkylpyrazoles, which in a number of cases were successfully separated by HPLC. Deacylation in acidic medium with gaseous hydrogen chloride and in basic medium with gaseous ammonia leads to 1-(4-hydroxybutyl)pyrazoles, which manifest moderate tuberculostatic activity.

引用

页码：2396 / 2400

页数：5

共 8 条

[1] One-pot synthesis of trifluoromethyl- and nitroso-substituted pyrazolines and pyrazoles and their tuberculostatic activity
Khudina, O. G.
Burgart, Ya. V.
Saloutin, V. I.
Kravchenko, M. A.
[J]. RUSSIAN CHEMICAL BULLETIN, 2010, 59 (10) : 1967 - 1973
[2] Synthesis and the reactions of trifluoromethylated 1,2,3-triketones 2-(het)arylhydrazones and 4,7-dihydroazolo[5,1-c]triazines
Khudina, OG
Shchegol'kov, EV
Burgart, YV
Kodess, MI
Kazheva, ON
Chekhlov, AN
Shilov, GV
Dyachenko, OA
Saloutin, VI
Chupakhin, ON
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (08) : 1230 - 1238
[3] Mashkovskii M. D., 1993, LEKARSTVENNYE SREDST, V1, P160
[4] Synthesis and anti-HSV activity of new N1-acyclic C4 and C6-disubstituted pyrazolo[3,4-d]pyrimidine nucleosides
Moukha-Chafiq, Omar
Taha, Mohamed Labd
Mouna, Abdelmalek
[J]. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (8-9) : 1107 - 1110
[5] PEGLION JL, 1980, B SOC CHIM FR II-CH, P309
[6] Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)
Penning, TD
Talley, JJ
Bertenshaw, SR
Carter, JS
Collins, PW
Docter, S
Graneto, MJ
Lee, LF
Malecha, JW
Miyashiro, JM
Rogers, RS
Rogier, DJ
Yu, SS
Anderson, GD
Burton, EG
Cogburn, JN
Gregory, SA
Koboldt, CM
Perkins, WE
Seibert, K
Veenhuizen, AW
Zhang, YY
Isakson, PC
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (09) : 1347 - 1365
[7] Synthesis of fluoroalkyl-containing 1,2,3-triketone 2-hetarylhydrazones and their reactions with hydrazines
Shchegol'kov, EV
Burgart, YV
Khudina, OG
Saloutin, VI
Chupakhin, ON
[J]. RUSSIAN CHEMICAL BULLETIN, 2004, 53 (11) : 2584 - 2590
[8] Vasilev V. N., 1971, MIKOBAKTERIOZY MIKOZ, P377

← 1 →