Synthesis of two novel cysteine-functionalized thiophenes

被引:5
作者
Cagnoli, R
Lanzi, M
Mucci, A
Parenti, F
Schenetti, L
机构
[1] Univ Modena, Dipartimento Chim, I-41100 Modena, Italy
[2] Univ Bologna, Dipartimento Chim Ind & Mat, I-40136 Bologna, Italy
来源
SYNTHESIS-STUTTGART | 2005年 / 02期
关键词
cysteine; thiophenes; sulfur heterocycles; serine; nucleophilic substitution;
D O I
10.1055/s-2004-834930
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthetic approach to methyl N-(tert-butoxycarbonyl) -S- (3-thienyl)-L-cysteinate (1) and methyl N-(tert-butoxycarbonyl)-S-[2-(3-thienyl)ethyl]-L-eysteinate (2) through tosylate intermediates is reported and discussed. These compounds, which combine the properties of the cysteine side-chain with those of the thiophene ring represent both potential bioactive molecules and interesting synthons for the development of new materials.
引用
收藏
页码:267 / 271
页数:5
相关论文
共 44 条
[31]  
MORITA Y, 1987, Patent No. 62240663
[32]   A self-assembling polythiophene functionalised with a cysteine moiety [J].
Mucci, A ;
Parenti, F ;
Schenetti, L .
MACROMOLECULAR RAPID COMMUNICATIONS, 2003, 24 (09) :547-550
[33]   MERCAPTOACYL AMINO-ACID INHIBITORS OF ATRIOPEPTIDASE .1. STRUCTURE-ACTIVITY RELATIONSHIP STUDIES OF METHIONINE AND S-ALKYLCYSTEINE DERIVATIVES [J].
NEUSTADT, BR ;
SMITH, EM ;
NECHUTA, TL ;
BRONNENKANT, AA ;
HASLANGER, MF ;
WATKINS, RW ;
FOSTER, CJ ;
SYBERTZ, EJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (15) :2461-2476
[34]  
Ng SC, 1996, J CHEM RES-S, P232
[35]   Conformational transitions of a free amino-acid-functionalized polythiophene induced by different buffer systems [J].
Nilsson, KPR ;
Andersson, MR ;
Inganäs, O .
JOURNAL OF PHYSICS-CONDENSED MATTER, 2002, 14 (42) :10011-10020
[36]   SYNTHESIS OF N-ACETYL-S-TRIFLUOROMETHYLPHENYL-DL-CYSTEINE ESTERS [J].
ONDRUS, TA ;
CHRISTIE, BJ ;
GUY, RW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (10) :2313-2316
[37]   TERT-BUTYL GROUP AS THIOL PROTECTION IN PEPTIDE-SYNTHESIS [J].
PASTUSZAK, JJ ;
CHIMIAK, A .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (09) :1868-1873
[38]  
PITZELE BS, 1990, Patent No. 0361482
[39]   A concise formal synthesis of the potent HIV protease inhibitor nelfinavir mesylate [J].
Rieger, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8546-8548
[40]  
Shevchenko NE, 2003, SYNTHESIS-STUTTGART, P1191