Synthesis and antiviral activity of novel a-aminophosphonates containing 6-fluorobenzothiazole moiety

GRAPHICAL ABSTRACT

ABSTRACT

A series of novel a-aminophosphonates containing 6-fluorobenzothiazole moiety derivatives were synthesized by one-pot reaction under microwave irradiation and their structures were characterized by IR, ¹H, ¹³C, and ³¹P NMR and element analysis data. Antiviral assays showed that some compounds possess good curative and protective activities against tobacco mosaic virus (TMV) in vivo at 500 µg/mL In particular, compounds diethyl [(6-fluorobenzo[d]thiazol-2-ylamino)(phenyl)methyl]phosphonate (4b), diethyl [(6-methoxybenzo[d]thiazol-2-ylamino)(thiophen-2-yl)methyl]phosphonate (4j) and diphenyl [(6-fluorobenzo[d]thiazol-2-ylamino)(4-methoxyphenyl)methyl]phosphonate (4q) exhibited remarkable antiviral activities than Ribavirin against TMV and PVY. Compound diphenyl [(6-fluorobenzo[d]thiazol-2-ylamino)(4-methoxyphenyl)methyl]phosphonate (4q) showed similar curative and protective activity against potato virus Y (PVY) to Dufulin.

KEYWORDS:

• a-Aminophosphonates derivatives
• 6-fluorobenzothiazole moiety
• microwave chemistry
• multicomponent reaction
• antiviral activity

Funding

The authors gratefully acknowledge the National Natural Science Foundation of China (Nos. 21362004, 21562013) and Subsidy Project for Outstanding Key Laboratory of Guizhou Province in China (20154004) and Collaborative Innovation Center for Natural Products and Biological Drugs of Yunnan for supporting the project.