Synthesis and Enantiomeric Resolution of Medetomidine

被引:6
作者
Fakhraian, H. [1 ]
Toulabi, H. [1 ]
Choobdari, E. [2 ]
Peyrovi, M. H. [2 ]
Ghanbary, H. Hadj [1 ]
机构
[1] Imam Hossein Univ, Dept Chem, Tehran, Iran
[2] Shahid Beheshti Univ, Dept Chem, Tehran, Iran
关键词
ADRENERGIC ACTIVITIES; ANALOGS; DEXMEDETOMIDINE; LIGANDS; DESIGN; OXIDE;
D O I
10.1080/00304948.2015.1005985
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Medetomidine {4-[l-(2,3-dimethylphenyl)ethyl]-3H-imidazole], 5} is a selective α2-adrenoceptor agonist used in veterinary medicine for its analgesic and sedative properties. It is also an alternative and environmentally acceptable anti-fouling biocide which impedes the settlement of barnacles at nanomolar concentrations and replaces toxic antifouling coatings based on heavy metals. Several syntheses of medetomidine have been reported. The first method for the preparation of 5 and of other related 4-benzylimidazoles was described in a patent starting from 2,3-dimethylbromobenzene as shown in Scheme 1; unfortunately the yields were not reported. Copyright © Taylor & Francis Group, LLC.
引用
收藏
页码:141 / 148
页数:8
相关论文
共 26 条
[1]   SYNTHESIS AND ALPHA-ADRENERGIC ACTIVITIES OF 2-SUBSTITUTED AND 4-SUBSTITUTED IMIDAZOLINE AND IMIDAZOLE ANALOGS [J].
AMEMIYA, Y ;
HONG, SS ;
VENKATARAMAN, BV ;
PATIL, PN ;
SHAMS, G ;
ROMSTEDT, K ;
FELLER, DR ;
HSU, FL ;
MILLER, DD .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (04) :750-755
[2]   Efficient synthesis of (S)-4(5)-[1-(2,3-dimethylphenyl)ethyl]imidazole tartrate, the potent alpha(2) adrenoceptor agonist dexmedetomidine [J].
Cordi, AA ;
Persigand, T ;
Lecouve, JP .
SYNTHETIC COMMUNICATIONS, 1996, 26 (08) :1585-1593
[3]  
Evich E. O. G., 2010, RU patent, Patent No. 2448094
[4]  
Gertler R, 2001, Proc (Bayl Univ Med Cent), V14, P13
[5]   Bioaccumulation of the new antifoulant medetomidine in marine organisms [J].
Hilvarsson, Annelie ;
Ohlauson, Cecilia ;
Blanck, Hans ;
Granmo, Ake .
MARINE ENVIRONMENTAL RESEARCH, 2009, 68 (01) :19-24
[6]   RESOLUTION AND ADRENERGIC ACTIVITIES OF THE OPTICAL ISOMERS OF 4-[1-(1-NAPHTHYL)ETHYL]-1H-IMIDAZOLE [J].
HONG, SS ;
ROMSTEDT, KJ ;
FELLER, DR ;
HSU, FL ;
GEORGE, C ;
CUPPS, TL ;
LYON, RA ;
MILLER, DD .
CHIRALITY, 1992, 4 (07) :432-438
[7]   A STRUCTURE-ACTIVITY RELATIONSHIP STUDY OF BENZYLIC MODIFICATIONS OF 4-[1-(1-NAPHTHYL)ETHYL]-1H-IMIDAZOLES ON ALPHA(1)-ADRENERGIC AND ALPHA(2)-ADRENERGIC RECEPTORS [J].
HONG, SS ;
ROMSTEDT, KJ ;
FELLER, DR ;
HSU, FL ;
CUPPS, TL ;
LYON, RA ;
MILLER, DD .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (15) :2328-2333
[8]  
Kannan T., 2011, WO Patent, Patent No. 070069
[9]  
Karjalainen A. J., 1983, CHEM ABSTR, Patent No. 4,544,664
[10]  
Karjalainen A. J., 1982, CHEM ABSTR, Patent No. 2,069,481