Synthesis and Antibacterial Activity of N-Alkyl-Substituted 4-Aryldiazenylpyrazoles

被引：8

作者：

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

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

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

机构：

[1] Russian Acad Sci, I Ya Postovskii Inst Organ Synth, Ural Branch, Ekaterinburg 620990, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2013年 / 49卷 / 08期

基金：

俄罗斯基础研究基金会;

关键词：

pyrazoles; regioisomers; alkylation; deacylation; tuberculostatic and antibacterial activity; 1,2,3-TRIKETONES; NUCLEOSIDES; INHIBITORS; PYRAZOLES; ANALOGS;

D O I：

10.1007/s10593-013-1353-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylation of 4-aryldiazenylpyrazoles using (4-bromobutyl)acetate and [(2-acetoxyethoxy)methyl]-acetate gave the corresponding 1-(4-acetoxybutyl)- and 1-[(2-acetoxyethoxy)methyl]pyrazoles. 3-Fluoroalkyl-4-aryldiazenylpyrazoles react with (4-bromobutyl)acetate to form a mixture of the regio-isomeric 1-(4-acetoxybutyl)-3- and 1-(4-acetoxybutyl)-5-fluoroalkylpyrazoles. Several of the acetoxy- pyrazole derivatives were deacylated and isolated using HPLC. Modest activity towards the ATCC 6633 strain of bacteria Bacillus subtilis has been found for 1-(4-hydroxybutyl)-5-methyl-4-[(4-methyl-phenyl)diazenyl]-3-(octafluorobutyl)-1H-pyrazole.

引用

页码：1128 / 1135

页数：8

共 21 条

[1] Synthesis and antitumor activity of 5-trifluoromethyl-2,4-dihydropyrazol-3-one nucleosides [J].

Abdou, IM ;

Saleh, AM ;

Zohdi, HF .

MOLECULES, 2004, 9 (03) :109-116

[2]

[Anonymous], 2009, Methods for Measuring the Mass Fraction of Fluorine in Organic Compounds Using a Spectroscopic Method, No. 88-16358-95-2009, Patent No. 2198165

[3] N-ALKYLATION AND N-ARYLATION OF UNSYMMETRICAL PYRAZOLES [J].

GRIMMETT, MR ;

LIM, KHR ;

WEAVERS, RT .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (10) :2203-2213

[4] SYNTHESIS AND ANTIMICROBIAL EVALUATION OF NOVEL PYRAZOLONES AND PYRAZOLONE NUCLEOSIDES [J].

Hassan, Abdalla E. A. ;

Moustafa, Ahmed H. ;

Tolbah, Mervat M. ;

Zohdy, Hussein F. ;

Haikal, Abdelfattah Z. .

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2012, 31 (11) :783-800

[5]

Ivanova A. E., 2011, IZV AKAD NAUK K, V2349

[6]

Khabriev R. U., 2005, GUIDEBOOK EXPT PRECL, P217

[7] Synthesis and the reactions of trifluoromethylated 1,2,3-triketones 2-(het)arylhydrazones and 4,7-dihydroazolo[5,1-c]triazines [J].

Khudina, OG ;

Shchegol'kov, EV ;

Burgart, YV ;

Kodess, MI ;

Kazheva, ON ;

Chekhlov, AN ;

Shilov, GV ;

Dyachenko, OA ;

Saloutin, VI ;

Chupakhin, ON .

JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (08) :1230-1238

[8]

Mashkovskii M. D., 2002, DRUGS, V1, P159

[9] 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) [J].

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 .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (09) :1347-1365

[10]

Pimenova E. V., 2003, RU Pat. Appl., Patent No. [2198165, 5434178]

← 1 2 3 →