Design, synthesis and biological activities of echinopsine derivatives containing acylhydrazone moiety

• Published in: Scientific reports 2022-02, Vol.12 (1), p.2935-2935, Article 2935
• Main Authors: Cui, Peipei, Cai, Mingjiang, Meng, Yanan, Yang, Yan, Song, Hongjian, Liu, Yuxiu, Wang, Qingmin
• Format: Article
• Language: English
• Subjects: 639/638/309; 639/638/403; 639/638/549; Animals; Antifungal Agents; Antiviral Agents; Ascomycota - drug effects; Bioassays; Biological activity; Design; Drug Design - methods; Granulovirus - drug effects; Humanities and Social Sciences; Hydrazones - chemistry; Inactivation; Insecticides; multidisciplinary; Natural products; Quinolones - chemical synthesis; Quinolones - chemistry; Quinolones - pharmacology; Ribavirin; Science; Science (multidisciplinary); Spodoptera - drug effects; Tobacco; Tobacco Mosaic Virus - drug effects; Viruses
• ISSN: 2045-2322; 2045-2322
• DOI: 10.1038/s41598-022-06775-7

Based on the broad-spectrum biological activities of echinopsine and acylhydrazones, a series of echinopsine derivatives containing acylhydrazone moieties have been designed, synthesized and their biological activities were evaluated for the first time. The bioassay results indicated that most of the compounds showed moderate to good antiviral activities against tobacco mosaic virus (TMV), among which echinopsine ( I ) (inactivation activity, 49.5 ± 4.4%; curative activity, 46.1 ± 1.5%; protection activity, 42.6 ± 2.3%) and its derivatives 1 (inactivation activity, 44.9 ± 4.6%; curative activity, 39.8 ± 2.6%; protection activity, 47.3 ± 4.3%), 3 (inactivation activity, 47.9 ± 0.9%; curative activity, 43.7 ± 3.1%; protection activity, 44.6 ± 3.3%), 7 (inactivation activity, 46.2 ± 1.6%; curative activity, 45.0 ± 3.7%; protection activity, 41.7 ± 0.9%) showed higher anti-TMV activity in vivo at 500 mg/L than commercial ribavirin (inactivation activity, 38.9 ± 1.4%; curative activity, 39.2 ± 1.8%; protection activity, 36.4 ± 3.4%). Some compounds exhibited insecticidal activities against Plutella xylostella , Mythimna separate and Spodoptera frugiperda. Especially, compounds 7 and 27 displayed excellent insecticidal activities against Plutella xylostell (mortality 67 ± 6% and 53 ± 6%) even at 0.1 mg/L. Additionally, most echinopsine derivatives exhibited high fungicidal activities against Physalospora piricola and Sclerotinia sclerotiorum .