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

被引:181
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
    Terjeson, RJ
    Willenbring, R
    Gard, GL
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1996, 76 (01) : 63 - 65
  • [92] NEW PENTAFLUOROTHIO(SF5)FLUOROPOLYMERS
    TERJESON, RJ
    GARD, GL
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1987, 35 (04) : 653 - 662
  • [93] Unusual reactivity of 3-chloro-1-pentafluorosulfanylpropene in nucleophilic substitution reactions
    Trushkov, IV
    Brel, VK
    [J]. 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
    Umemoto, Teruo
    Garrick, Lloyd M.
    Saito, Norimichi
    [J]. 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
    WANG, QC
    WHITE, HF
    GARD, GL
    [J]. 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
    Welch, John T.
    Lim, Dong Sung
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (21) : 6659 - 6666
  • [100] Aromatic pentafluoro-λ6-sulfanyl (SF5) surfactants:: m-SF5(CF2)nC6H4SO3K
    Winner, Scott W.
    Winter, Rolf W.
    Smith, Jeremy A.
    Gard, Gary L.
    Hannah, Nicole A.
    Rananavare, Shankar B.
    Piknova, Barbora
    Hall, Stephen B.
    [J]. MENDELEEV COMMUNICATIONS, 2006, 16 (03) : 182 - 184