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Synthesis of new analogs of AKBA and evaluation of their anti-inflammatory activities.

Abstract：

:A new series of 11-keto-β-boswellic acid and 3-O-acetyl-11-keto-β-boswellic acid analogs (5, 7, 8, 10, 13, 18a-d, 27a-c, 28a-d) were synthesized by modification of hydroxyl and acid functional moieties of boswellic acids. The structures of these analogs were confirmed by spectral data analysis (1H, 13C NMR and mass). Compounds 18b, 27a and 8 showed potent 5-lipoxygenase enzyme inhibitory activity (IC50: 19.53, 20.31 and 44.14μg/mL). The computational studies revealed that selectivity of AKBA is due to its fitment into the 5-LOX receptor, which is missing for the other enzymes like 12-LOX, COX-1 and COX-2. Our study found potentiating effects of 2-formyl and 3-keto substituents in reviving inactive AKBA analogues possessing essential COOH group at 4th position.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Meka B,Ravada SR,Murali Krishna Kumar M,Purna Nagasree K,Golakoti T

doi

10.1016/j.bmc.2016.12.045

subject

Has Abstract

pub_date

2017-02-15 00:00:00

pages

1374-1388

issue

4

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(16)31075-6

journal_volume

25

pub_type

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