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Volumn 132, Issue 2, 2011, Pages 88-93

Extreme modulation properties of aromatic fluorine

(2) Gakh, Andrei A a Burnett, Michael N a

a OAK RIDGE NATIONAL LABORATORY (United States)

Author keywords

Aromatic fluorine; Biological activity; Free Wilson analysis; Modular chemical descriptor language (MCDL); Modulation; NCI database; Singular value decomposition

Indexed keywords

EID: 79551562195 PISSN: 00221139 EISSN: None Source Type: Journal
DOI: 10.1016/j.jfluchem.2010.11.009 Document Type: Article

Times cited : (17)

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- The maximum observed positive modulation of biological activity for aromatic chlorine and bromine reported in these 167 individual papers was 1145 times (compounds 10c and 15c, OVCAR-4 cell line, Ref. [22]) and about 75 times (compounds 11g and 11i, heparanase, in: S.M. Courtney, P.A. Hay, R.T. Buck, C.S. Colville, D.J. Phillips, D.I.C. Scopes, F.C. Pollard, M.J. Page, J.M. Bennett, M.L. Hircock, E.A. McKenzie, M. Bhaman, R. Felix, C.R. Stubberfield, P.R. Turner, Bioorg. Med. Chem. Lett. 15 (2005) 2295-2299), respectively. These effects were substantially smaller than the extreme modulation reported for aromatic fluorine in the same set of 167 papers. It is important to note that the maximum positive modulation properties of bromine are probably similar or slightly higher compared to chlorine in a larger data set [32,33]. Even higher positive modulation properties are expected for aromatic iodine due to its size and polarizability. Unfortunately, very low relative abundance of aromatic iodine compounds makes it difficult to draw any statistically significant conclusions.
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