Publication: New racemosol derivatives as potent cyclooxygenase (COX) inhibitors
Issued Date
2005-12-01
Resource Type
ISSN
16121880
16121872
16121872
Other identifier(s)
2-s2.0-30344455603
Rights
Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
Chemistry and Biodiversity. Vol.2, No.12 (2005), 1635-1647
Suggested Citation
Saiphon Songarsa, Shuleewan Rajviroongit, Darinee Sae-Tang, Supa Hannongbua, Kanyawim Kirtikara, Prasat Kittakoop New racemosol derivatives as potent cyclooxygenase (COX) inhibitors. Chemistry and Biodiversity. Vol.2, No.12 (2005), 1635-1647. doi:10.1002/cbdv.200590133 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/16263
Research Projects
Organizational Units
Authors
Journal Issue
Thesis
Title
New racemosol derivatives as potent cyclooxygenase (COX) inhibitors
Abstract
Racemosol (1) and 10-O-demethylracemosol (2), natural products from Bauhinia malabarica Roxb., exhibit potent in vitro anti-inflammatory activities against cyclooxygenase-1 and -2 (COX-1 and -2) enzymes. To investigate the structure - activity relationship (SAR) of these molecules, we prepared and fully characterized 17 derivatives by functionalizing one, two, or all three OH group(s) of 2 (Scheme). Both the size and polarity of the substituents as well as the substitution pattern in compounds 3a-q were found to be critical for anti-inflammatory activity. The orientation of the drugs and their mode of binding were studied by molecular docking based on the known 3D structure of the complex between COX-2 and the drug SC-558. Whereas the monoacetoxy derivative 3h exhibited an equally potent inhibitory activity towards both COX-1 and -2 (Table 1), its diacetoxy congener 3i was slightly more selective toward COX-2. In vivo anti-inflammatory tests showed that 3i and 2 are slightly more active than the reference compound phenylbutazone (Table 2). © 2005 Verlag Helvetica Chimica Acta AG, Zürich.