Coumarin Derivatives Containing Sulfonamide and Dithioacetal Moieties: Design, Synthesis, Antiviral Activity, and Mechanism

Abstract

Cucumber mosaic virus (CMV) is currently a known plant virus with the most hosts, broadest distribution, and economic hazard. To develop new antiviral drugs against this serious virus, a new range of coumarin derivatives containing sulfonamide and dithioacetal structures were designed and synthesized, and their anti-CMV activities were detected by the half-leaf dead spot method. The results of the biological activity assay showed that most of the compounds exhibited outstanding anti-CMV activity. Especially, compound C23 displayed the optimal in vivo anti-CMV activity, with an EC 50 value of 128 μg/mL, which was remarkably better than that of COS (781 μg/mL) and ningnanmycin (436 μg/mL). Excitingly, we found that compound C23 could be a promising plant activator that significantly increased defense-related enzyme activities and the tobacco chlorophyll content. Furthermore, compound C23 enhanced defense responses against viral infection by inducing the abscisic acid (ABA) pathway in tobacco. This work established a basis for multifunction pesticide discovery involving mechanism of action study and structure optimization.

Trifluoromethylpyridine piperazine derivatives: synthesis and anti‐plant virus activity

“…Previous studies have revealed that aliphatic derivatives do not possess the same anti‐CMV viral activity as aromatic and heterocyclic rings, and aliphatic derivatives showed poor anti‐CMV activity 22 . We also found that the anti‐CMV activities were higher when R was benzene ring derivatives.…”

“…Previous studies have revealed that aliphatic derivatives do not possess the same anti-CMV viral activity as aromatic and heterocyclic rings, and aliphatic derivatives showed poor anti-CMV activity. 22 We also found that the anti-CMV activities were higher when R was benzene ring derivatives. Furthermore, benzene ring derivatives without substituent are not as effective as those containing substituent, particularly those with electron-absorbing groups, which have been found to have the best anti-CMV activity.…”

Inactivating Activities and Mechanism of Imidazo[1,2-c]pyrimidin-5(6H)-one Nucleoside Derivatives Incorporating a Sulfonamide Scaffold

“…Imidazo­[1,2- c ]­pyrimidin-5­(6 H )-one has a wide range of antiviral activities such as hepatitis B virus (HBV) and cytomegalovirus (CMV). , Other studies had shown that 2-, 3-, 6-, 7-, and 8-substituted imidazo­[1,2- c ]­pyrimidin-5­(6 H )-one could inhibit cyclin-dependent kinase 2 (CDK2); structure–activity relationships indicated that the smaller the 8-position substituent, the higher the activity, while the larger the substituent, the lower the activity. − Further studies revealed that nucleosides with imidazo­[1,2- c ]­pyrimidin-5­(6 H )-one exhibited good activities against HBV and human immunodeficiency virus (HIV). ,, The sulfonamide scaffold plays an important role in the development of antibacterial, insecticidal, , herbicidal, and antiviral, − and it can be considered as “molecular chimera”, which is found to form hydrogen bonds as well as interact with unipolar environments within proteins.…”

Development of Sustainable Insecticide Candidates for Protecting Pollinators: Insight into the Bioactivities, Selective Mechanism of Action and QSAR of Natural Coumarin Derivatives against Aphids

“…Coumarins, potential alternatives for chemical insecticides, are widely distributed in Compositae, Apiaceae, and Leguminosae, among others. , Even more intriguing, it displayed broad-spectrum bioactivities, including antiviral, antibacterial, anticancer, and especially potent insecticidal effects. Conversely, some coumarin analogues naturally, such as scoparone and scopoletin, displayed no toxicity toward the pollinators.…”