Abstract
Chikungunya virus (CHIKV) is a re-emerging disease caused by an alphavirus of the Togaviridae family. Since its first description in 1952, the disease has spread worldwide, affecting populations in both tropical and temperate countries. To date, there is no licensed vaccine or specific pharmacological treatment. Therefore, there is an increasing urgency in developing new antiviral drugs capable of specifically inhibiting viral replication. In the present work, we report the synthesis and antiviral activity evaluation of nineteen naphthoquinone derivatives, containing a sulfonamide or sulfonate group. Cell viability assays indicated a low toxic potential for all tested compounds and inhibitory assays against CHIKV identified five compounds with potent activity. The compounds were also evaluated for their virucidal potential, and the results demonstrated that compound 11a exhibited a virucidal effect higher than 70% in the treatment with 20 µM. Furthermore, in silico studies were performed to predict the antiviral drug targets.
Highlights
Quinones constitute a class of natural products with wide distribution in nature and are structurally characterized by two conjugated carbonyl groups in sixmembered unsaturated rings.[1]
The amino-naphthoquinones (7a-7d) used as starting material for the preparation of sulfonamide-based naphthoquinones derivatives were prepared according to the reported methodology.[42,43]
The desired sulfonamide derivatives (8a-8e, 9a-9e, and 10a-10d) were obtained in one step by choosing the appropriate amino-naphthoquinones (7a-7c) with various aryl sulfonyl chlorides catalyzed by DMAP in pyridine
Summary
Quinones constitute a class of natural products with wide distribution in nature and are structurally characterized by two conjugated carbonyl groups in sixmembered unsaturated rings.[1] Naphthoquinone presents an aromatic ring fused to the quinonoid nucleus, and this chemical characteristic is identified as responsible for its redox potential.[2] Naphthoquinones are considered privileged structures in Medicinal Chemistry and have been extensively studied as synthetic platforms due to their broad range of biological properties, such as anticancer, antibacterial, anti-inflammatory, antiviral, and others.[3,4,5,6,7,8,9]. Chikungunya virus (CHIKV) is a mosquito-transmitted alphavirus of the Togaviridae family that causes a febrile. Synthesis and Anti-Chikungunya Virus (CHIKV) Activity of Novel 1,4-Naphthoquinone Sulfonamide J.
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