Efficient synthesis of 5-alkyl amino and thioether substituted pyrazoles

被引：48

作者：

Sakya, SM ^{[1
]}

Rast, B ^{[1
]}

机构：

[1] Pfizer Inc, Vet Med Res & Dev, Groton, CT 06340 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 41期

关键词：

D O I：

10.1016/j.tetlet.2003.08.054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic substitution reactions of 1-(4-methylsulfonyl-2-pyridyl)-5-chloropyrazoles with various substitutions at the 4 position with amine nucleophiles and thiols occur under mild conditions to provide the 5-alkyl amino and thioether pyrazoles in high yields. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7629 / 7632

页数：4

共 11 条

[1] Synthesis and antimicrobial activity of some new pyrazoles and thieno[2,3-c]pyrazoles [J].

Bakhite, EA ;

Geies, AA ;

El-Kashef, HS .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2000, 157 :107-122

[2]

Carty T.J., 1999, CURR OPIN ANTIINFLAM, V1, P89

[3] Structural approaches to explain the selectivity of COX-2 inhibitors: Is there a common pharmacophore? [J].

Dannhardt, G ;

Laufer, S .

CURRENT MEDICINAL CHEMISTRY, 2000, 7 (11) :1101-1112

[4] HETARYLPYRAZOLES .4. SYNTHESIS AND REACTIONS OF 1,5'-BIPYRAZOLES [J].

KHAN, MA ;

FREITAS, ACC .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (02) :277-279

[5] Synthesis and biological evaluation of 3-heteroarizoxy-4-phenyl-2(5H)-furanones as selective COX-2 inhibitors [J].

Lau, CK ;

Brideau, C ;

Chan, CC ;

Charleson, S ;

Cromlish, WA ;

Ethier, D ;

Gauthier, JY ;

Gordon, R ;

Guay, J ;

Kargman, S ;

Li, CS ;

Prasit, P ;

Riendeau, D ;

Thérien, M ;

Visco, DM ;

Xu, LJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (22) :3187-3192

[6] Sar in the alkoxy lactone series:: The discovery of DFP, a potent and orally active COX-2 inhibitor [J].

Leblanc, Y ;

Roy, P ;

Boyce, S ;

Brideau, C ;

Chan, CC ;

Charleson, S ;

Gordon, R ;

Grimm, E ;

Guay, J ;

Léger, S ;

Li, CS ;

Riendeau, D ;

Visco, D ;

Wang, Z ;

Webb, J ;

Xu, LJ ;

Prasit, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (15) :2207-2212

[7] SYNTHESIS AND C-13 NMR OF (TRIFLUOROMETHYL)HYDROXYPYRAZOLES [J].

LEE, LF ;

SCHLEPPNIK, FM ;

SCHNEIDER, RW ;

CAMPBELL, DH .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (02) :243-245

[8] A new structural variation on the methanesulfonylphenyl class of selective cyclooxygenase-2 inhibitors [J].

Li, CS ;

Black, WC ;

Brideau, C ;

Chan, CC ;

Charleson, S ;

Cromlish, WA ;

Claveau, D ;

Gauthier, JY ;

Gordon, R ;

Greig, G ;

Grimm, E ;

Guay, J ;

Lau, CK ;

Riendeau, D ;

Thérien, M ;

Visco, DM ;

Wong, E ;

Xu, LJ ;

Prasit, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (22) :3181-3186

[9] FUSED PYRIMIDINES BY A TANDEM AZA-WITTIG ELECTROCYCLIC RING-CLOSURE STRATEGY - SYNTHESIS OF PYRAZOLO[3,4-D]PYRIMIDINE, [1,2,3]TRIAZOLO[4,5-D]PYRIMIDINE, AND THIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES [J].

MOLINA, P ;

ARQUES, A ;

VINADER, MV ;

BECHER, J ;

BRONDUM, K .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4654-4663

[10] 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

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