Development of Purines-containing Butenolides and a Tetrahydroimidazobenzodiazepinone Analog as Anticancer and Anti-HIV Agents. Silicon-Promoted Norrish Type II Cleavage by a β-Stablization Effect.

• Main Authors: Nai-Wen Mei, 梅乃文
• Other Authors: Jih -Ru Hwu
• Format: Others
• Language: en_US
• Published: 2000
• Online Access: http://ndltd.ncl.edu.tw/handle/99369057305652406380

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.