3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors.

Abstract:

:Following our studies on structure-activity relationships of anti-rhinovirus chromene and chroman derivatives, we designed and synthesized new series of 3-phenylalkyl-2H-chromenes and -chromans bearing differently sized, aliphatic linker chains between the two cycles. The cytotoxicity and the antiviral activity of the new compounds on human rhinovirus (HRV) serotype 1B and 14 infection were evaluated in HeLa cell cultures. Most of the tested compounds interfered with HRV1B multiplication in the micromolar or submicromolar concentrations while HRV14 was less susceptible. 3-[3-(4-Chlorophenyl)propyl]chroman (9c) was selected for preliminary mechanism of action studies due to its potent activity against both serotypes (IC50 of 0.48μM and 1.36μM towards HRV1B and 14, respectively) coupled with high selectivity (SI=206.18 and 73.26, respectively). Results of time of addition/removal studies suggest that 9c, similarly to related derivatives, behaves as a capsid binder interfering with some early events of the HRV1B infectious cycle.

journal_name

Bioorg Med Chem

authors

Conti C,Proietti Monaco L,Desideri N

doi

10.1016/j.bmc.2017.02.012

subject

Has Abstract

pub_date

2017-04-01 00:00:00

pages

2074-2083

issue

7

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(16)30899-9

journal_volume

25

pub_type

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