Synthesis of a new, highly fluorescent amino acid derivative:: N-[(tert-butoxy)carbonyl]-3-[2-(1H-indol-3-yl)benzoxazol-5-yl]-L-alanine methyl ester

被引:0
作者
Guzow, K [1 ]
Szabelski, M [1 ]
Malicka, J [1 ]
Wiczk, W [1 ]
机构
[1] Univ Gdansk, Fac Chem, PL-80952 Gdansk, Poland
关键词
D O I
10.1002/1522-2675(20010516)84:5<1086::AID-HLCA1086>3.0.CO;2-D
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple method of synthesis of a new. highly fluorescent amino acid derivative from the simple and generally available substrates 3-nitro-L-tyrosine and 1H-indole-3-carbaldehyde is described. The obtained compound, N-[(tert-butoxy)carbonyl]-3-[2-(1H-indol-3-yl)benzoxazol-5-yl]-L-alanine methyl ester (4), possesses a high fluorescence quantum yield. The described method illustrates a new possibility of synthesis of amino acid derivatives possessing desirable photophysical properties.
引用
收藏
页码:1086 / 1092
页数:7
相关论文
共 50 条
[21]   N′-(2-hydroxy-5-nitrobenzylidene)-2-(1H-indol-3-yl)acetohydrazide [J].
Puvaneswary, Subramaniam ;
Ali, Hapipah M. ;
Robinson, Ward T. ;
Ng, Seik Weng .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 :O1777-U2123
[22]   Synthesis of [3-[2-(dimethylamino)ethyl]-2[[3-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1H-indol-5-yl]-N-methylmethanesulfonamide -: the main sumatriptane impurity [J].
Skwierawska, A ;
Paluszkiewicz, E .
POLISH JOURNAL OF CHEMISTRY, 2003, 77 (03) :329-332
[23]   2-{3-[2-(1H-Indol-3-yl)vinyl]-5,5-dimethylcyclohex-2-enylidene}malononitrile [J].
Kolev, T ;
Glavcheva, Z ;
Yancheva, D ;
Schürmann, M ;
Kleb, DC ;
Preut, H ;
Bleckmann, P .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2001, 57 :O760-O761
[24]   Synthesis, Pharmacological Evaluation and Molecular Docking Studies of N-[2-(1H-indol-3-yl)Acetyl]Arylsulfonohydrazides [J].
K. Rubab ;
M. A. Abbasi ;
S. Z. Aziz-ur-Rehman ;
S. A. A. Siddiqui ;
M. Shah ;
M. A. Ashraf ;
F. A. Qurat-ul-Ain ;
M. Lodhi ;
Hina Khan ;
I. Shahid .
Pharmaceutical Chemistry Journal, 2021, 55 :665-678
[25]   Synthesis and biological evaluation of 3-(1H-indol-3-yl)pyrazole-5-carboxylic acid derivatives [J].
Datong Zhang ;
Guangtian Wang ;
Chubing Tan ;
Weiren Xu ;
Yuan Pei ;
Lingyan Huo .
Archives of Pharmacal Research, 2011, 34 :343-355
[26]   Synthesis and Biological Evaluation of 3-(1H-indol-3-yl)pyrazole-5-carboxylic Acid Derivatives [J].
Zhang, Datong ;
Wang, Guangtian ;
Tan, Chubing ;
Xu, Weiren ;
Pei, Yuan ;
Huo, Lingyan .
ARCHIVES OF PHARMACAL RESEARCH, 2011, 34 (03) :343-355
[27]   Synthesis, Pharmacological Evaluation and Molecular Docking Studies of N-[2-(1H-indol-3-yl)Acetyl]Arylsulfonohydrazides [J].
Rubab, K. ;
Abbasi, M. A. ;
Aziz-ur-Rehman ;
Siddiqui, S. Z. ;
Shah, S. A. A. ;
Ashraf, M. ;
Qurat-ul-Ain ;
Lodhi, M. A. ;
Khan, F. A. ;
Shahid, M. ;
Fatima, Hina ;
Ahmad, I .
PHARMACEUTICAL CHEMISTRY JOURNAL, 2021, 55 (07) :665-678
[28]   N-(2-(1H-Indol-3-yl)ethyl)-2-(2-fluoro[1,1′-biphenyl]-4-yl)propanamide [J].
Manolov, Stanimir ;
Ivanov, Iliyan ;
Bojilov, Dimitar .
MOLBANK, 2021, 2021 (01) :1-4
[29]   Synthesis, Crystal Structure and Antitumor Activities of N-(2-(1H-indol-3-yl)ethyl)-2-nitroaniline [J].
He Dian ;
Yang Zhu-Qing ;
Hou Meng .
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2014, 33 (12) :1784-1788
[30]   New fluorescent probes based on 3-(2-benzoxazol-5-yl)alanine skeleton -: Synthesis and photophysical properties [J].
Guzow, Katarzyna ;
Szmigiel, Dagmara ;
Wroblewski, Dominik ;
Milewska, Magda ;
Karolczak, Jerzy ;
Wiczk, Wieslaw .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2007, 187 (01) :87-96