Sunday, 29 July 2012

Imidazole lipophilicity revisited

It's almost three months since I arrived in Brasil to spend year in São Carlos at Universidade de São Paulo. One of the advantages of being back in academia is that access to literature is a lot better and I managed to dig up some cyclohexane/water partition coefficients for a couple of the compounds that featured last year's Lipophilicity Teaser. While octanol/water doesn't appear to 'see' the hydrogen bond donor that is unmasked by moving the methyl group, the cyclohexane/water partitioning system certainly does. Readers with an interest in Physical-Organic Chemistry might like to think about how tautomerism might affect partition coefficients. There are also a couple of lipophilicity-based items (logP versus logD for ADMET discussion and poll on correlation of pharmacological promiscuity) that are current in the FBDD LinkedIn group so why not drop by and join the fun there.


Literature cited

Abraham, Chadha, Whiting & Mitchell, Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the Δlog P parameter of Seiler. J. Pharm. Sci. 1994, 83, 1085-1100. DOI

Radzicka & Wolfenden, Comparing the polarities of the amino acids: side-chain distribution coefficients between the vapor phase, cyclohexane, 1-octanol, and neutral aqueous solution. Biochem. 1988, 27, 1664-1670. DOI