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Effective discrimination of antimalarial potency of artemisinin compounds based on quantum chemical calculations of their reaction mechanism.

Abstract：

:The reaction mechanism of 12 antimalarial artemisinin compounds with two competitive pathways was studied by means of quantum chemical calculations using the IMOMO(B3LYP/6-31(d,p):HF/3-21G) method. The oxygen-centered radicals, carbon-centered radicals, and transition states (TS) in both pathways were geometrically optimized. The obtained kinetic and thermodynamic energy profiles show that homolytic C-C cleavage reaction (pathway 2) is energetically more preferable than an intramolecular 1,5-hydrogen shift process (pathway 1), which is consistent with the docking calculations. However, compounds that can easily proceed along the pathway 1 have high activity. Therefore, both pathways are important for antimalarial activity. Moreover, effective discrimination between high and low activity compounds using EA1, deltaE1, and deltaE(1A-2A) was accomplished.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Tonmunphean S,Parasuk V,Kokpol S

doi

10.1016/j.bmc.2005.07.003

subject

Has Abstract

pub_date

2006-04-01 00:00:00

pages

2082-8

issue

7

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(05)00653-X

journal_volume

14

pub_type

杂志文章

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