Design, synthesis and antiviral activity of novel pyridazines.
ABSTRACT A series of pyridazines were prepared and evaluated for their anti-HIV activity. The new synthetic route involving a novel rearrangement reaction provided a practical method for the preparation of 5-hydroxypyridazines. The primary bioassay results indicated that most of the pyridazines possess anti-HIV activity. It ought to been mentioned that the rearranged compounds 35 and 39 exhibited relatively higher HIV inhibitory effect. Most of the synthesized compounds were also found to possess good anti-TMV activity, of which compound 9 showed similar in vivo anti-TMV activity to commercial plant virucide Ribavirin. This work provides a new and efficient approach to evolve novel multi-functional antiviral agents by rational integration and optimization of previously reported antiviral agents.
- [Show abstract] [Hide abstract]
ABSTRACT: A biologically inspired organocatalytic one-pot synthesis of highly functionalized pyridazines, which are ubiquitous structural units in a number of biologically active compounds, has been developed by starting from readily available diazo compounds and Morita-Baylis-Hillman (MBH) carbonates. Under mild reaction conditions, this synthetic route tolerated significant substrate variation to deliver a broad range of substituted products, including CF3 -substituted pyridazines derivatives. Moreover, the introduction of trifluoromethyl groups into the ring of pyridazine could be completed conveniently from 2,2,2-trifluorodiazoethane.Chemistry 02/2014; · 5.93 Impact Factor