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
[91]   New pentafluorothio (SF5)-containing alkyl dibromides [J].
Terjeson, RJ ;
Willenbring, R ;
Gard, GL .
JOURNAL OF FLUORINE CHEMISTRY, 1996, 76 (01) :63-65
[92]   NEW PENTAFLUOROTHIO(SF5)FLUOROPOLYMERS [J].
TERJESON, RJ ;
GARD, GL .
JOURNAL OF FLUORINE CHEMISTRY, 1987, 35 (04) :653-662
[93]   Unusual reactivity of 3-chloro-1-pentafluorosulfanylpropene in nucleophilic substitution reactions [J].
Trushkov, IV ;
Brel, VK .
TETRAHEDRON LETTERS, 2005, 46 (28) :4777-4779
[94]  
Umemoto T., 2010, [No title captured], Patent No. [Patent US 2011/0301382 A1, 20110301382]
[95]   Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): Beginning of a new era of "super-trifluoromethyl" arene chemistry and its industry [J].
Umemoto, Teruo ;
Garrick, Lloyd M. ;
Saito, Norimichi .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :461-471
[96]  
Verma R.D., 1994, ADV INORG CHEM, V41, P125, DOI DOI 10.1016/S0898-8838(08)60171-3
[97]   ADDITION OF SF5BR TO PROPYNE AND 3,3,3-TRIFLUOROPROPYNE [J].
WANG, QC ;
WHITE, HF ;
GARD, GL .
JOURNAL OF FLUORINE CHEMISTRY, 1979, 13 (05) :455-461
[98]  
Welch J. T., 2012, FLUORINE PHARM MED C, P175
[99]   The synthesis and biological activity of pentafluorosulfanyl analogs of fluoxetine, fenfluramine, and norfenfluramine [J].
Welch, John T. ;
Lim, Dong Sung .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (21) :6659-6666
[100]   Aromatic pentafluoro-λ6-sulfanyl (SF5) surfactants:: m-SF5(CF2)nC6H4SO3K [J].
Winner, Scott W. ;
Winter, Rolf W. ;
Smith, Jeremy A. ;
Gard, Gary L. ;
Hannah, Nicole A. ;
Rananavare, Shankar B. ;
Piknova, Barbora ;
Hall, Stephen B. .
MENDELEEV COMMUNICATIONS, 2006, 16 (03) :182-184