Correlation of anti-HIV potency with lipophilicity in a series of cosalane analogs having normal alkenyl and phosphodiester chains as cholestane replacements
In order to define the role of the cholestane moiety in the anti-HIV agent cosalane, a series of cosalane analogs was synthesized in which the cholestane ring system was replaced by normal alkenyl and phosphodiester substituents having varied chain lengths and lipophilicities. The compounds containing simple alkenyl substituents were found to be more potent as inhibitors of the cytopathic effect of HIV-1 in cell culture than the phosphodiesters. In addition, the potencies of the alkene congeners correlated positively with chain length and lipophilicity of the alkene. The results indicate that the cholestane moiety of cosalane functions as a lipophilic accessory appendage to escort the dichlorodisalicylmethane pharmacophore to a lipid environment.
Keyes, Robert F.,Golebiewski, W. Marek,Cushman, Mark
p. 508 - 514
(2007/10/03)
Quantitative Treatment of the Rotational Dynamics of Flexible-Chain Molecules. 13C NMR Relaxation Study of Hydrocarbon Chains Attached to the Fluorene Anchor
13C spin-lattice relaxation times (T1) and nuclear Overhauser enhancements (NOEs) were measured for individual carbons in flexible-chain molecules consisting of a hydrocarbon chain attached to fluorene moiety at position 3 through an ester bond.Quantitative treatment of the relaxation data of the ring carbons revealed an anisotropic motion for all the molecules studied.The relaxation times of the chain carbons were analysed in terms of a correlation function describing multiple internal rotations about successive C-C bonds.The results (rotational diffusion constants) were used to discuss features of the chain mobility as a function of chain length and chain unsaturation.The assumptions involved in the quantitative treatment were examined and the values were compared with those of n-alkanes and lipid bilayers. - Keywords: 13C NMR spin-lattice relaxation times Rotational diffusion constants Rotational dynamics Overall and internal motions Hydrocarbon-chain esters of fluorene-3-carboxylic acid
Pissas, D.,Dais, Photis,Mikros, E.
p. 263 - 275
(2007/10/02)
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