Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

被引:188
作者
Altomonte, Stefano [1 ,2 ]
Zanda, Matteo [1 ,2 ,3 ]
机构
[1] Univ Aberdeen, Inst Med Sci, Kosterlitz Ctr Therapeut, Aberdeen AB25 2ZD, Scotland
[2] Univ Aberdeen, John Mallard Scottish PET Ctr, Aberdeen AB25 2ZD, Scotland
[3] CNR Ist Chim Riconoscimento Mol, I-20131 Milan, Italy
关键词
Pentafluorosulphanyl group; Review; Synthesis; Biological properties; FALCIPARUM DIHYDROOROTATE DEHYDROGENASE; VICARIOUS NUCLEOPHILIC-SUBSTITUTION; SULFUR CHLORIDE PENTAFLUORIDE; FACILE PREPARATION; LEAD OPTIMIZATION; DERIVATIVES; TRIFLUOROMETHYL; INHIBITORS; FLUORINE; SALTS;
D O I
10.1016/j.jfluchem.2012.06.030
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The pentafluorosulphanyl group (SF5) is a highly stable chemical function which has been attracting a great deal of interest owing to its peculiar chemical, structural, physicochemical and biological properties. Progress in the area of SF5-compounds has been somewhat hindered by the lack of straightforward lab-scale synthetic methods for introducing the SF5-group into organic molecules. However, recent synthetic progress, the availability of some SF5-building blocks from commercial suppliers and the discovery of interesting properties of SF5-substituted molecules in materials science, biology and drug discovery are giving new momentum to research in this fascinating area of fluorine chemistry. Synthesis, reactivity and biological properties of SF5-substituted organic molecules are herein reviewed with an emphasis on the work published after year 2000. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:57 / 93
页数:37
相关论文
共 123 条
[1]   5-(1,2,3-Triazol-1-yl)tetrazole Derivatives of an Azidotetrazole via Click Chemistry [J].
Abe, Takashi ;
Tao, Guo-Hong ;
Joo, Young-Hyuk ;
Winter, Rolf W. ;
Gard, Gary L. ;
Shreeve, Jean'ne M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (38) :9897-9904
[2]   New and convenient method for incorporation of pentafluorosulfanyl (SF5) substituents into aliphatic organic compounds [J].
Aït-Mohand, S ;
Dolbier, WR .
ORGANIC LETTERS, 2002, 4 (17) :3013-3015
[3]  
Altomonte S., UNPUB
[4]  
[Anonymous], 2011, CORRIGENDUM SYNTHESI, P827
[5]   Hydroxylation of nitro-(pentafluorosulfanyl)benzenes via vicarious nucleophilic substitution of hydrogen [J].
Beier, Petr ;
Pastyrikova, Tereza .
TETRAHEDRON LETTERS, 2011, 52 (34) :4392-4394
[6]   Preparation of SF5 Aromatics by Vicarious Nucleophilic Substitution Reactions of Nitro(pentafluorosulfanyl)benzenes with Carbanions [J].
Beier, Petr ;
Pastyrikova, Tereza ;
Iakobson, George .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (11) :4781-4786
[7]   SNAr Reactions of Nitro-(pentafluorosulfanyl)benzenes To Generate SF5 Aryl Ethers and Sulfides [J].
Beier, Petr ;
Pastyrikova, Tereza ;
Vida, Norbert ;
Iakobson, George .
ORGANIC LETTERS, 2011, 13 (06) :1466-1469
[8]   REACTIONS OF PENTAFLUOROSULFUR HALIDES WITH SILANES AND VINYLSILANES [J].
BERRY, AD ;
FOX, WB .
JOURNAL OF FLUORINE CHEMISTRY, 1975, 6 (02) :175-180
[9]   REACTION OF PENTAFLUOROSULFUR BROMIDE WITH CIS-1,2-DIFLUOROETHYLENE AND TRANS-1,2-DIFLUOROETHYLENE [J].
BERRY, AD ;
FOX, WB .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) :365-367
[10]   SYNTHESIS AND CHARACTERIZATION OF (PENTAFLUOROSULFUR)ACETYLENES [J].
BERRY, AD ;
DEMARCO, RA ;
FOX, WB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (03) :737-738