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Synthesis and highly potent anti-inflammatory activity of licofelone- and ketorolac-based 1-arylpyrrolizin-3-ones.

Abstract：

:Since NSAIDs are commonly used anti-inflammatory agents that produce adverse effects, there have been ongoing efforts to develop more effective and less toxic compounds. Based on the structure of the anti-inflammatory pyrrolizines licofelone and ketorolac, a series of 1-arylpyrrolizin-3-ones was synthesized. Also prepared was a series of substituted pyrroles, mimicking similar known anti-inflammatory agents. The anti-inflammatory activity of the test compounds was determined with a phorbol ester (TPA)-induced murine ear edema protocol. For the most active derivatives, 19b-c/20b-c, the anti-inflammatory effect was the same as that of the reference compound (indomethacin) and was dose-dependent. These compounds have an aryl ring at the C-1 position and a methoxycarbonyl group at the C-2 position of the pyrrolizine framework, which represent plausible pharmacophore groups with anti-inflammatory activity. The anti-inflammatory activity of 1-substituted analogs containing a five- or six-membered heterocycles was lower but still good, while that of the pyrroles was only moderate. Although the docking studies suggests that the effect of analogs 19a-c/20a-c is associated with the inhibition of cyclooxygenase-2, experimental assays did not corroborate this idea. Indeed, a significant inhibition of NO was found experimentally as a plausible mechanism of action.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Madrigal DA,Escalante CH,Gutiérrez-Rebolledo GA,Cristobal-Luna JM,Gómez-García O,Hernández-Benitez RI,Esquivel-Campos AL,Pérez-Gutiérrez S,Chamorro-Cevallos GA,Delgado F,Tamariz J

doi

10.1016/j.bmc.2019.115053

subject

Has Abstract

pub_date

2019-10-15 00:00:00

pages

115053

issue

20

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(19)30503-6

journal_volume

27

pub_type

杂志文章

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