| Summary: | 博士 === 國立清華大學 === 化學系 === 89 === In this thesis, we designed novel butenolide derivatives of nucleobases as anticancer agents. We also prepared a tetrahydroimidazobenzodiazepinone analog as anti-HIV agent. Furthermore, silicon-promoted Norrish type II cleavage by a -stabilization effect was investigated.
In part 1 of this thesis, a series of butenolide-containing 6-chloropurine having an active double bond was synthesised to inhibit enzymes crucial to metabolic pathways in cell division. Those compounds exhibited moderate anticancer activity.
In part 2 of this thesis, internal alkylation of N3-position of an adenine acyclonucleoside with its alkyl halide side chain occurred. The resultant tetrahydroimidazobenzodiazepinone analog exhibited antiviral activity in vitro.
In part 3 of this thesis, photolysis of the -silylated and non-silylated bicycloalkanones showed compounds bearing an SIMe3 at position molecule have a higher quantum yields and rate constants. The trimethylsilyl group, being synperiplanar to the -hydrogen, provided greater driving force than the trimethylsilyl group being anticlinalin the cleavage of the C-H bond.
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