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3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors.
- Source :
-
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2017 Apr 01; Vol. 25 (7), pp. 2074-2083. Date of Electronic Publication: 2017 Feb 10. - Publication Year :
- 2017
-
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 (IC <subscript>50</subscript> 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.<br /> (Copyright © 2017 Elsevier Ltd. All rights reserved.)
- Subjects :
- Antiviral Agents chemistry
Benzopyrans chemistry
Carbon-13 Magnetic Resonance Spectroscopy
HeLa Cells
Humans
Microbial Sensitivity Tests
Proton Magnetic Resonance Spectroscopy
Spectrophotometry, Infrared
Structure-Activity Relationship
Antiviral Agents pharmacology
Benzopyrans pharmacology
Rhinovirus drug effects
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3391
- Volume :
- 25
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 28242170
- Full Text :
- https://doi.org/10.1016/j.bmc.2017.02.012