Antiviral activity of N-phosphorylated amides, thioamides, and their salts
The N-(O,O-dimethylphosphoryl)benzamide (I) was obtained according to [4]; N-(O-methylS-methylphosphoryl)acetamide (acephate) (II) was obtained according to [6], and N-(O,O-diisopropylthiophosphoryl)thiobenzamide (III) (benztriamiph) was obtained according to [7]. The synthesis of N-(O,O-diisopropylthiophosphoryl)thioacetamide (IV), the sodium salt of N-(O,O-dimethylphosphoryl)benzamide (V), and the sodium salt of N-(O,O-diethylphosphoryl)thiobenzamide (VI) is described below.
Synthesis and characterization of N-thiophosphorylated thioureas RC(S)NHP(S)(OiPr)2 (p-(4-imidazol-1-yl)–C6H4NH, p-NC–C6H4NH, (CH2CH–CH2)2N): Unexpected formation of o-HO–C6H4NHC(S)NHP(S)(OiPr)2 from p-NC–C6H4NHC(S)NHP(S)(OiPr)2
Abstract Reaction of p-(4-imidazol-1-yl)–C6H4NH2, p-N C–C6H4NH2 or (CH2 CH–CH2)2NH with O,O′-diisopropylthiophosphoric acid isothiocyanate (iPrO)2P(S)NCS leads to p-(4-imidazol-1-yl)–C6H4NHC(S)NHP(S)(OiPr)2 (HLI), p-N C–C6H4NHC(S)NHP(S)(OiPr)2 (HLII) and (CH2 CH–CH2)2NC(S)NHP(S)(OiPr)2 (HLIII). Recrystallization of HLII from 96% aqueous EtOH solution leads to the formation of o-HO–C6H4NHC(S)NHP(S)(OiPr)2 (HLIV). The structures of HLI–IV were investigated by 1H and 31P{1H} NMR spectroscopy, and microanalysis. The molecular structures of HLI,IV were elucidated by single crystal X-ray diffraction analysis. Single crystal X-ray diffraction studies showed that HLI,IV form both intra- and intermolecular hydrogen bonds, the latter leading to the formation of polymeric chains.
Synthesis of 2,4-dideoxy-.beta.-D-erythro-hexopyranosyl nucleosides
The synthesis of 1-(2,4-dideoxy-β-D-erythro-hexopyranosyl)thymine (12) 1 was accomplished using two different synthetic routes. It was obtained starting either from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose or from tri-O-acetyl-D-glucal. The other modified nucleosides, with either a cytosine, guanine, or adenine moiety, were synthesized using the second reaction scheme. Deoxygenation reactions were accomplished with the (2,4-dichlorophenoxy)thiocarbonyl derivatives generated in situ