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Exploration of benzamidochromenone derivatives with conformational restrictor as interleukin-5 inhibitors.

Abstract：

:Novel amidochromen-4-one analogs 8a-k and 9a-f were prepared and studied for their IL-5 inhibitory activity. Among the synthesized compounds, (6-benzamido-2-cyclohexyl-4-oxo-4H-chromen-3-yl)methyl acetate (8a, 95% inhibition at 30 μM, IC50=6.1 μM) exhibited potent IL-5 inhibitory activity. The conformational restrictor at position 2 like bulky cyclohexyl group is favorable for the formation of effective conformer of side chain small ester like acetoxymethyl at position 3 of these chromenone analogs 8. In addition the hydrophobic planarity of benzamido group at position 6 should be important for the potent IL-5 inhibitory activity. Since replacing acetoxymethyl moiety with hydroxymethyl group at position 3 of chromenone decreases the activity, which indicates that the location of hydrogen bonding group should be near 4 atom distances away from chromenone ring is more optimum for the activity. Therefore, these benzamidochromen-4-one analogs 8 are novel scaffold for finding potent interleukin-5 inhibitors.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Venkateswararao E,Manickam M,Boggu P,Kim Y,Jung SH

doi

10.1016/j.bmc.2015.03.045

subject

Has Abstract

pub_date

2015-05-15 00:00:00

pages

2498-504

issue

10

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(15)00241-2

journal_volume

23

pub_type

杂志文章

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