Solid phase synthesis of benzothiazolyl compounds

被引:54
作者
Mourtas, S [1 ]
Gatos, D [1 ]
Barlos, K [1 ]
机构
[1] Univ Patras, Dept Chem, Patras, Greece
关键词
benzothiazoles; benzothiazole equivalent; solid phase synthesis; trityl resin;
D O I
10.1016/S0040-4039(01)00109-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Aminobenzenethiol, bound through its thiol function to the 2-chlorotrityl (Clt)-, trityl (Trt)-, 4-methyltrityl (Mtt)- and 4-methoxytrityl (Mmt)-resins, was acylated at the amino-function by aliphatic and aromatic acids. The obtained 2-N-acylaminobenzenethiols were cleaved from the resin by treatment with trifluoroacetic acid solutions in dichloromethane. The 2-N-acyl-aminobenzenethiols released from the resin were cyclised to the corresponding 2-substituted benzothiazoles, by standing in a solution of dithiothreitol in DMF or methanol for 1-3 h at room temperature. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2201 / 2204
页数:4
相关论文
共 23 条
[1]  
BALROS K, 1993, PEPTIDES 1992, P281
[2]  
Barlos K, 1996, INT J PEPT PROT RES, V47, P148
[3]   SYNTHESIS OF PROTECTED PEPTIDE-FRAGMENTS USING SUBSTITUTED TRIPHENYLMETHYL RESINS [J].
BARLOS, K ;
GATOS, D ;
KALLITSIS, J ;
PAPAPHOTIU, G ;
SOTIRIU, P ;
YAO, WQ ;
SCHAFER, W .
TETRAHEDRON LETTERS, 1989, 30 (30) :3943-3946
[4]   Novel synthesis of 2-arylbenzothiazoles - Microwave-activated electron transfer [J].
BenAlloum, A ;
Bakkas, S ;
Soufiaoui, M .
TETRAHEDRON LETTERS, 1997, 38 (36) :6395-6396
[5]   2-(4-aminophenyl)benzothiazoles: novel agents with selective profiles of in vitro anti-tumour activity [J].
Bradshaw, TD ;
Wrigley, S ;
Shi, DF ;
Schultz, RJ ;
Paull, KD ;
Stevens, MFG .
BRITISH JOURNAL OF CANCER, 1998, 77 (05) :745-752
[6]   INHIBITION OF INTERLEUKIN-1 (IL-1) INDUCED NEUTRAL PROTEASES FROM RABBIT ARTICULAR CHONDROCYTES BY WY-46,135 AND WY-48,989 [J].
CACCESE, RG ;
DIJOSEPH, JF ;
SKOTNICKI, JS ;
BORELLA, LE ;
ADAMS, LM .
AGENTS AND ACTIONS, 1991, 34 (1-2) :223-225
[7]  
FRECHET JMJ, 1975, TETRAHEDRON LETT, P30255
[8]  
Hadjipavlou-Litina D. J., 1997, DRUG DES DISCOV, V15, P199
[9]  
Hall IH, 1999, ARCH PHARM, V332, P115
[10]   The regiospecific synthesis of 5-and 7-monosubstituted and 5,6-disubstituted 2-arylbenzothiazoles [J].
Hutchinson, I ;
Stevens, MFG ;
Westwell, AD .
TETRAHEDRON LETTERS, 2000, 41 (03) :425-428