New 1,3‐Oxazole and 1,2,4‐Oxadiazole Derivatives as Novel Agents Against Human Rhinovirus and Cytomegalovirus

A library of 16 new five‐functionalized derivatives of 2‐undecyl‐ and 1,2,4‐oxadiazole‐containing 2‐aryl‐4‐cyano‐1,3‐oxazoles was synthesized using α ‐acylamino‐ β , β ‐dichloroacrylonitriles as key building blocks, enabling efficient formation of diverse 1,3‐oxazole, oxadiazole–oxazole, and sulfonamide–oxazole systems. The antiviral potential was evaluated in vitro against rhinovirus 8 (HRV8), cytomegalovirus (HCMV), parainfluenza virus type 3 (HPIV‐3), and zoonotic encephalomyocarditis virus (EMCV). Screening revealed distinct activity profiles: none of the compounds inhibited EMCV or HPIV‐3, while several demonstrated pronounced efficacy against HRV8 and HCMV. In concentration‐dependent assays, compounds 1, 7, 10, 13 , and 14 exhibited potent anti‐HCMV effects (IC 50 = 0.42–4.67 µM). Compound 7 showed remarkable selectivity (SI = 465), outperforming ganciclovir (GCV, SI = 326). Against HRV8, compound 2 was the most active (IC 50 = 1.67 µM, SI = 11), whereas compound 13 displayed weak activity (IC 50 = 21.0 µM, SI = 1). All molecules met drug‐likeness criteria with favorable ADMET‐predicted pharmacokinetic parameters. Molecular docking suggested that derivatives 7, 10, 13 , and 14 may target viral DNA polymerase, with binding energies from –8.8 to –9.7 kcal mol −1 . These findings demonstrate that 1,3‐oxazoles represent a promising chemotype for new antiviral candidates active against HCMV and HRV8.

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Publication Details

Journal
ChemMedChem
Published
2026-09-15
DOI
https://doi.org/10.1002/cmdc.70491
Primary Topic
Synthesis and biological activity
Type
article
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article

New 1,3‐Oxazole and 1,2,4‐Oxadiazole Derivatives as Novel Agents Against Human Rhinovirus and Cytomegalovirus

Stepan Pilyo, Agnieszka B. Olejniczak, Maryna Kachaeva, Victor Zhirnov et al.
ChemMedChem
Synthesis and biological activity
article

New 1,3‐Oxazole and 1,2,4‐Oxadiazole Derivatives as Novel Agents Against Human Rhinovirus and Cytomegalovirus

Stepan Pilyo, Agnieszka B. Olejniczak, Maryna Kachaeva, Victor Zhirnov, Marta Denel‐Bobrowska, Ivan Semenyuta, Yelyzaveta Yu. Rybina
article en

Abstract

A library of 16 new five‐functionalized derivatives of 2‐undecyl‐ and 1,2,4‐oxadiazole‐containing 2‐aryl‐4‐cyano‐1,3‐oxazoles was synthesized using α ‐acylamino‐ β , β ‐dichloroacrylonitriles as key building blocks, enabling efficient formation of diverse 1,3‐oxazole, oxadiazole–oxazole, and sulfonamide–oxazole systems. The antiviral potential was evaluated in vitro against rhinovirus 8 (HRV8), cytomegalovirus (HCMV), parainfluenza virus type 3 (HPIV‐3), and zoonotic encephalomyocarditis virus (EMCV). Screening revealed distinct activity profiles: none of the compounds inhibited EMCV or HPIV‐3, while several demonstrated pronounced efficacy against HRV8 and HCMV. In concentration‐dependent assays, compounds 1, 7, 10, 13 , and 14 exhibited potent anti‐HCMV effects (IC 50 = 0.42–4.67 µM). Compound 7 showed remarkable selectivity (SI = 465), outperforming ganciclovir (GCV, SI = 326). Against HRV8, compound 2 was the most active (IC 50 = 1.67 µM, SI = 11), whereas compound 13 displayed weak activity (IC 50 = 21.0 µM, SI = 1). All molecules met drug‐likeness criteria with favorable ADMET‐predicted pharmacokinetic parameters. Molecular docking suggested that derivatives 7, 10, 13 , and 14 may target viral DNA polymerase, with binding energies from –8.8 to –9.7 kcal mol −1 . These findings demonstrate that 1,3‐oxazoles represent a promising chemotype for new antiviral candidates active against HCMV and HRV8.

ChemMedChemVol. 21(18)
Institute of Bioorganic Chemistry and Petrochemistry V.P. Kukhar (UA), Polish Academy of Sciences (PL)
Openalex Percentile: Top 20%
Synthesis and biological activity
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