Quantum molecular modeling of melatonin

Molecular modeling of melatonin was conducted using AM1 and ab initio quantum computations. Our study shows that four minimal energy conformations (noted I to IV) with a folded ethylamido side-chain are possible. These conformations are in correspondance (form I with form II, and form III with form...

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Bibliographic Details
Published in:Journal of molecular structure. Theochem 1999-02, Vol.460 (1), p.191-205
Main Authors: Vasilescu, D., Broch, H.
Format: Article
Language:English
Subjects:
Melatonin
Pharmacophore models
Quantum molecular modeling
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Summary:Molecular modeling of melatonin was conducted using AM1 and ab initio quantum computations. Our study shows that four minimal energy conformations (noted I to IV) with a folded ethylamido side-chain are possible. These conformations are in correspondance (form I with form II, and form III with form IV) and are characterized by equivalent orbital frontiers and electrostatic properties. Conformations II and IV are in good agreement with pharmacophore models proposed by Jansen et al. [Bioorganic Med. Chem. 4 (1996) 1321] or by Sicsic et al. [J. Med. Chem. 40 (1997) 739]. The localization of molecular electrostatic potential and of the H omo and L umo onto the indole may explain a dominant role of this ring in the free radical scavenging mechanism.
ISSN:0166-1280
1872-7999
DOI:10.1016/S0166-1280(98)00317-0