Journal of Chemistry

Journal of Chemistry / 2011 / Article

Open Access

Volume 8 |Article ID 731090 | https://doi.org/10.1155/2011/731090

Jose Isagani B. Janairo, Gerardo C. Janairo, Derrick Ethelbhert C. YU, "Semi-Empirical Predictions on the Structure and Properties of ent-Kaurenoic Acid and Derivatives", Journal of Chemistry, vol. 8, Article ID 731090, 8 pages, 2011. https://doi.org/10.1155/2011/731090

Semi-Empirical Predictions on the Structure and Properties of ent-Kaurenoic Acid and Derivatives

Received25 Jul 2010
Accepted02 Oct 2010

Abstract

The physicochemical properties of ent- kaurenoic acid model derivatives, which possibly influence its therapeutic application, were calculated. Results revealed that the molecule possess favourable attributes which renders it possible to be considered as a drug lead only that its very hydrophobic nature can result to poor bioavailabilty, low absorption and poor systemic circulation. In silico simulations revealed that this setback can be overcome by introduction of hydroxyl group to the tertiary carbon of ent-kaurenoic acid employing m-CPBA catalyzed hydroxylation, thus, unleashing its full drug potency. Moreover, molecular similarity analyses derived from semi-empirical calculations between ent-kaurenoic acid and a set of kaurane diterpenoids showed differences in hydrophobic complementarity, size and electronic properties despite possessing nearly identical molecular frameworks, thus, arriving in a generalization for their observed mechanistic differences on acting on different targets.

Copyright © 2011 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


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