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E-Journal of Chemistry
Volume 8 (2011), Issue 2, Pages 703-710
http://dx.doi.org/10.1155/2011/731090

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

Jose Isagani B. Janairo,1,2 Gerardo C. Janairo,1 and Derrick Ethelbhert C. YU3

1Materials Science and Nanotechnology Unit, Center for Natural Sciences and Environmental Research, De La Salle University, 2401 Taft Avenue, Manila, Philippines
2Department of Physics, De La Salle University, 2401 Taft Avenue, Manila, Philippines
3Department of Chemistry, De La Salle University, 2401 Taft Avenue, Manila, Philippines

Received 25 July 2010; Accepted 2 October 2010

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.

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.