Fluorination in medicinal chemistry: Methods, strategies, and recent developments

被引:1082
作者
Kirk, Kenneth L. [1 ]
机构
[1] NIDDK, Bioorgan Chem Lab, NIH, Bethesda, MD 20892 USA
关键词
D O I
10.1021/op700134j
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Methods for introducing fluorine into organic molecules are reviewed, with an emphasis on preparation of compounds designed for biomedicinal applications. Electrophilic fluorination, nucleophilic fluorination, and enantioselective monofluorination procedures are discussed. This is followed by a review of the development of nucleophilic and electrophilic trifluoromethylation procedures. The final sections highlight recent applications of fluorine chemistry in drug development with selected examples.
引用
收藏
页码:305 / 321
页数:17
相关论文
共 115 条
[91]   Highly enantioselective catalytic fluorination and chlorination reactions of carbonyl compounds capable of two-point binding [J].
Shibata, N ;
Kohno, J ;
Takai, K ;
Ishimaru, T ;
Nakamura, S ;
Toru, T ;
Kanemasa, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) :4204-4207
[92]   First enantio-flexible fluorination reaction using metal-bis(oxazoline) complexes [J].
Shibata, N ;
Ishimaru, T ;
Nagai, T ;
Kohno, J ;
Toru, T .
SYNLETT, 2004, (10) :1703-1706
[93]   A fundamentally new approach to enantioselective fluorination based on cinchona alkaloid derivatives/selectfluor combination [J].
Shibata, N ;
Suzuki, E ;
Takeuchi, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (43) :10728-10729
[94]   Modern synthetic methods for fluorine-substituted target molecules [J].
Shimizu, M ;
Hiyama, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (02) :214-231
[95]  
Singh R.P., 2002, SYNTHESIS-STUTTGART, V17, P2561, DOI DOI 10.1055/S-2002-35626
[96]   Nucleophilic trifluoromethylation reactions of organic compounds with (trifluoromethyl)trimethylsilane [J].
Singh, RP ;
Shreeve, JM .
TETRAHEDRON, 2000, 56 (39) :7613-7632
[97]   N-FLUOROPERFLUOROALKYLSULFONIMIDES - REMARKABLE NEW FLUORINATION REAGENTS [J].
SINGH, S ;
DESMARTEAU, DD ;
ZUBERI, SS ;
WITZ, M ;
HUANG, HN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7194-7196
[98]   INHIBITION OF HUMAN-LEUKOCYTE ELASTASE (HLE) BY N-SUBSTITUTED PEPTIDYL TRIFLUOROMETHYL KETONES [J].
SKILES, JW ;
FUCHS, V ;
MIAO, C ;
SORCEK, R ;
GROZINGER, KG ;
MAULDIN, SC ;
VITOUS, J ;
MUI, PW ;
JACOBER, S ;
CHOW, G ;
MATTEO, M ;
SKOOG, M ;
WELDON, SM ;
POSSANZA, G ;
KEIRNS, J ;
LETTS, G ;
ROSENTHAL, AS .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (04) :641-662
[99]   ENANTIOSELECTIVE SYNTHESIS OF N-BOC AND N-FMOC PROTECTED DIETHYL 4-PHOSPHONO(DIFLUOROMETHYL)-L-PHENYLALANINE - AGENTS SUITABLE FOR THE SOLID-PHASE SYNTHESIS OF PEPTIDES CONTAINING NONHYDROLYZABLE ANALOGS OF O-PHOSPHOTYROSINE [J].
SMYTH, MS ;
BURKE, TR .
TETRAHEDRON LETTERS, 1994, 35 (04) :551-554
[100]   The unexpected diaxial orientation of cis-3,5-difluoropiperidine in water:: A potent CF---NHcharge-dipole effect [J].
Snyder, JP ;
Chandrakumar, NS ;
Sato, H ;
Lankin, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (03) :544-545