Microwave-assisted synthesis of sodium sulfonates precursors of sulfonyl chlorides and fluorides

被引:14
作者
Alapafuja, Shakiru O. [1 ]
Nikas, Spyros P. [1 ]
Shukla, Vidyanand G. [1 ]
Papanastasiou, Ioannis [1 ]
Makriyannis, Alexandros [1 ]
机构
[1] Northeastern Univ, Ctr Drug Discovery, Boston, MA 02115 USA
关键词
Sodium sulfonates; Microwave; Sulfonyl chlorides; Sulfonyl fluorides; ACID AMIDE HYDROLASE; MOLECULAR CHARACTERIZATION; ENDOCANNABINOID SYSTEM; FACILE SYNTHESIS; DERIVATIVES; ANANDAMIDE; THIOLS; ENZYME;
D O I
10.1016/j.tetlet.2009.09.167
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe the use of a microwave reaction for the conversion of various bromides to sodium sulfonates that have been further elaborated to sulfonyl chlorides. This new approach leads to much improved yields and shorter reaction times. Representative sulfonyl chlorides serve as precursors for the respective sulfonyl fluorides that are potent inhibitors of the fatty acid amide hydrolase. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7028 / 7031
页数:4
相关论文
共 53 条
[1]   SOLUTION AND FLASH VACUUM PYROLYSES OF BETA-(3,5-DISUBSTITUTED-PHENYL)ETHANESULFONYL AZIDES - SULTAM, PYRINDINE, AND AZEPINE FORMATION [J].
ABRAMOVITCH, RA ;
HOLCOMB, WD ;
THOMPSON, WM ;
WAKE, S .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5124-5131
[2]   CONVENIENT GENERAL-METHOD FOR THE PREPARATION OF PRIMARY ALKYLLITHIUMS BY LITHIUM IODINE EXCHANGE [J].
BAILEY, WF ;
PUNZALAN, ER .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) :5404-5406
[3]   A new, mild preparation of sulfonyl chlorides [J].
Blotny, G .
TETRAHEDRON LETTERS, 2003, 44 (07) :1499-1501
[4]  
BLOTNY G, 1963, LIEBIGS ANN CHEM, V663, P194
[5]  
Boger DL, 1998, CURR PHARM DESIGN, V4, P303
[6]   Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling [J].
Bracey, MH ;
Hanson, MA ;
Masuda, KR ;
Stevens, RC ;
Cravatt, BF .
SCIENCE, 2002, 298 (5599) :1793-1796
[7]   DEHYDRATIONS WITH AROMATIC SULFONYL HALIDES IN PYRIDINE .2. A CONVENIENT METHOD FOR THE PREPARATION OF ESTERS [J].
BREWSTER, JH ;
CIOTTI, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (23) :6214-6215
[8]   N-sulfonyl homoserine lactones as antagonists of bacterial quorum sensing [J].
Castang, S ;
Chantegrel, B ;
Deshayes, C ;
Dolmazon, R ;
Gouet, P ;
Haser, R ;
Reverchon, S ;
Nasser, W ;
Hugouvieux-Cotte-Pattat, N ;
Doutheau, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (20) :5145-5149
[9]   Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides [J].
Cravatt, BF ;
Giang, DK ;
Mayfield, SP ;
Boger, DL ;
Lerner, RA ;
Gilula, NB .
NATURE, 1996, 384 (6604) :83-87
[10]   Fatty acid amide hydrolase: an emerging therapeutic target in the endocannabinoid system [J].
Cravatt, BF ;
Lichtman, AH .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2003, 7 (04) :469-475