Synthesis and Antiviral Bioactivity of Novel 3-((2-((1E,4E)-3-Oxo-5-arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3H)-quinazolinone Derivatives

Abstract

A series of novel 3-((2-((1E,4E)-3-oxo-5-arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3H)-quinazolinone derivatives were designed and synthesized. Antiviral bioassays indicated that a few of the compounds exhibited higher antiviral activities against tobacco mosaic virus (TMV) in vivo than the commercial agent ningnanmycin. In particular, compounds A5, A12, A25, and A27 possessed appreciable curative bioactivities on TMV in vivo, with 50% effective concentration values ranging from 132.25 to 156.10 μg/mL. These values are superior to that of ningnanmycin (281.22 μg/mL) and suggest that novel 4(3H)-quinazolinone derivatives containing 1,4-pentadien-3-one moiety can effectively control TMV. Evaluation of the antiviral properties in field studies and the mechanisms underlying the enhanced antiviral activities of these derivatives are an interesting topic for future investigation.

Antiviral activity and interaction mechanisms study of novel glucopyranoside derivatives

“…Notably, a number of quinazolin-1,4-pentadien-3-one derivatives 33 and 4(3H)-quinazolinone-1,4-pentadien-3-one derivatives exhibited better protection and curative effects in vivo against TMV than Ningnanmycin. 34 However, all of the synthesized compounds poorly inactivated TMV. Thus, the development of an excellent antiviral agent with a simple structure is needed.…”

“…Additionally, curcumin and its derivatives have been also found to possess fine activities against plant virus. [31][32][33][34] For example, our research group has synthesized a series of 1,4-pentadiene-3-one derivatives containing pyrazole, oxime ester, and quinazoline groups with good antiviral activities. Notably, a number of quinazolin-1,4-pentadien-3-one derivatives 33 and 4(3H)-quinazolinone-1,4-pentadien-3-one derivatives exhibited better protection and curative effects in vivo against TMV than Ningnanmycin.…”

“…Using 2 or 4-hydroxybenzaldehydes as the starting materials, the key intermediates d1-d32 were obtained via two consecutive condensation reactions. 34 Then, a mixture of the intermediates d1-d32, compound e, tetrabutylammonium bromide and NaOH were reacted in dichloromethane (DCM) for 6-12 h at 35°C, and generated the title compounds f1-f32 in 36-87% yields. To optimize the reaction conditions for the preparation of compound f1, the synthesis was carried out with different concentrations of NaOH (3%, 4%, 5%, and 6%).…”

Design, synthesis, antiviral bioactivity and three‐dimensional quantitative structure–activity relationship study of novel ferulic acid ester derivatives containing quinazoline moiety

“…Quinazoline is an important nitrogenous heterocyclic compound because of its antiviral, antibacterial and herbicidal activities . Previous studies have demonstrated quinazoline derivatives as potential medicinal drugs, and some of them have been used in clinical settings .…”

Comparison of three cell-based drug screening platforms for HSV-1 infection

“…A selected group of nostodiones were also tested, as nostodione A possesses proteasome inhibitory activity (Shim et al, 2008) and proteosome inhibitors exhibit antiviral activity, including effects against HSV-1 infection (La Frazia et al, 2006). We also tested a group of quinazolinones, because several derivatives have potential antiviral activity against influenza (Liu et al, 2015), HIV (Corbett et al, 2000), and TMV (Ma et al, 2014). Additionally, quinazolinone analogs can interfere with epigenetic regulation through inhibition of bromodomains (BET) (Gilham et al, 2016).…”