DRD3/MSCI molecular genotypes and abnormal involuntary movements in first psychotic episode of patients followed-up one year

Abstract

Nucleophilic substitution reactions of an allyl alcohol system in the 2′-deoxy-2′-methylidene pyrimidine nucleosides with various nucleophiles were investigated. The allyl alcohol system reacted with softer nucleophiles such as azide, thiophenoxide, and iodo anion through an SN2′ manner to afford 2′-substituted-methyl-2′,3′-didehydro-2′,3′-dideoxy nucleosides, but with hard oxygen-nucleophiles such as benzoyloxy and phenoxide through an SN2 manner to afford 2′-deoxy-2′-methylidene-3′-substituted nucleosides with inversion at the 3′-position. Based on this characteristic reactivity, 2′,3′-didehydro-2′,3′-dideoxy-2′-phenylselenomethyl pyrimidine nucleosides 16b and 16c were synthesized. These nucleosides were converted into 3′-amino-2′,3′-dideoxy-2′-methylidene pyrimidine nucleosides 3b and 3c via oxidative [2,3]-sigmatropic rearrangement of the allylic selenides as a key step. The cytosine derivative 3a was also prepared from the corresponding uracil derivative.