Influenza antiviral activity of F- and OH-containing isopulegol-derived octahydro-2H-chromenes

Heterogeneous Catalytic Conversion of Citronellal into Isopulegol and Menthol: Literature Review

“…Isopulegol has been reported as a good antioxidant and anti-in ammatory (Ramos et al, 2020) , antihyperlipidemic (Kalaivani and Sankaranarayanan, 2019) , analgesic (Kalaivani and Sankaranarayanan, 2019) , and antitumor agent (Jaafari et al, 2012) . Isopulegol is also the intermediate for the synthesis of the anti-in uenza compound octahydro-2Hchromenes Ilyina et al, 2021 and bioactive 2H-chromene alcohols as an antiviral agent (Laluc et al, 2020). Exclusively, isopulegol, especially (-)-isopulegol, is the starting compound in the production of menthol, which is a compound in high demand throughout the world (Coman et al, 2009;Plößer et al, 2014).…”

Enantiomeric Isopulegol as the Chiral Pool in the Total Synthesis of Bioactive Agents

“…[67] Subsequently, the research group of Salakhutdinov synthesised fluoro-and hydroxy-containing octahydro-2H-chromenes by the Prins reaction starting from (À )-isopulegol 2 with carbonyl compounds of various types (aromatic, aliphatic, heteroaromatic aldehydes and aliphatic ketones) in the presence of the BF 3 • Et 2 O/H 2 O system in 2020 (Scheme 7). [68,69] The activity of the produced compounds against the influenza A/Puerto Rico/8/34 (H1 N1) virus was studied. The highest activity was demonstrated by hydroxy-and fluorocontaining derivatives of 2,4,6-trimethoxybenzaldehyde [(12 i) and (13 i)].…”

Through-Space Charge-Transfer-Based Aggregation-Induced Emission and Thermally Activated Delayed Fluorescence in Fused 2H-Chromene Coumarin Congener Generating ROS for Antiviral (SARS-CoV-2) Approach

“…34 Recent studies have also demonstrated that 2H-chromene-3-carbohydrazide derivatives have potential as HIV-1 integrase inhibitor 35 and isopulegol-derived octahydro-2H-chromenes possess antiinfluenza activity. 36 Coumarin or 2H-chromen-2-one is a compound widely found in plants with a plethora of applications in the pharmaceutical and cosmetic industry, particularly as fluorescent probes of pH, enzymes, biothiols, chemical warfare agents, metal ions, hydroxyl radicals, polymeric micelles, nitric oxide, anions, oxygen, DNA and RNA, hydrogen peroxide, amino acids, and proteins. 37 In the photophysical domain, coumarin exhibits a diverse range of analytical aspects, viz large Stokes shift, high fluorescence quantum yield, excellent light stability, and so on, which demonstrate its potential in energyefficient lighting, electronic displays, and light harvesting devices.…”

“…Their underlying properties have been exploited as an anticonvulsant, antidiabetic, antimicrobial, antituberculosis, anticholinesterase, anticancer, and as an enzyme inhibitor against monoamine oxidase . Recent studies have also demonstrated that 2 H -chromene-3-carbohydrazide derivatives have potential as HIV-1 integrase inhibitor and isopulegol-derived octahydro-2 H -chromenes possess anti-influenza activity …”