Synthesis and Anti-Rhinovirus Activity of 2-Styrylchromones

Abstract

2-Styrylchromones were synthesized as vinylogues of 2-phenylchromones (flavones), a broad class of anti-rhinovirus compounds. The antiviral activity of 2-styrylchromones and 3-hydroxy-1-(2-hydroxyphenyl)-5-phenyl-2,4-pentadien-1-ones, which are intermediates in the synthesis, was evaluated against two selected serotypes of human rhinovirus, 1B and 14, by a plaque reduction assay in HeLa cell cultures. All of the compounds interfered with HRV 1B replication, with the exception of 3-hydroxy-1-(2-hydroxyphenyl)-5-(4-methoxyphenyl)-2,4-pentadien-1-one. The majority of derivatives were also found to be effective against serotype 14, often with a higher potency.

Epoxidation studies of 2-styrylchromones using jacobsen's catalyst and hydrogen peroxide and iodosylbenzene as oxidants

“…A detailed analysis of the 1 H, 13 C, HSQC and HMBC NMR spectra of all epoxides 3a-h allowed the assignment of the 6-H, 8 epoxides 3a-h was confirmed by the connectivities found in their HMBC spectra, the most important C-H connectivities are shown by Figure 1. …”

Synthesis of New Hydroxy‐2‐styrylchromones.

“…[12] Prior to the isolation of these natural 2-styrylchromones, studies had already been carried out on numerous synthetic derivatives, [13] which also showed promising antitumour and anti-allergic activities. [14] More recently, it has been demonstrated that certain synthetic derivatives are inhibitors of the replication of both 1B and 14 serotypes of the human anti-rhinovirus, [15] while we have found that 3Ј-allyl-5,7,4Ј-trimethoxy-2-styrylchromone uncouples oxidative phosphorylation, [16] and that some hydroxy-2-styrylchromones act as potent xanthine oxidase inhibitors. [17] The mechanism of action of polyphenolic compounds as antioxidants can include the suppression of the formation of reactive oxygen species, either by the inhibition of enzymes (e.g.…”

2-Styrylchromones: Novel strong scavengers of reactive oxygen and nitrogen species

“…Several analogues of these compounds have been synthesized and tested in different biological systems, showing different activities with potential therapeutic application, even before the first isolation of natural 2-styrylchromones from the green algae Chrysophaem taylori in 1986. 1,2 The natural derivatives were demonstrated to possess cytotoxic activity against leukemia cells, 1,2 and those obtained by synthesis exhibited antiallergic, 3 antiviral, 4 antitumor, 5 antagonism of A3 adenosine receptor, 6 xanthine oxidase inhibitor, 7 hepatoprotective against pro-oxidant agents, 8 and antioxidant properties. 9 The antioxidant behavior of these compounds is a matter of particular interest, as previously demonstrated by their strong protective effects against pro-oxidant agents observed in cellular systems 8 and in non-cellular systems.…”