An antimicrobial agent
A technology of compounds and general formulas, applied in the field of novel thioamides
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Embodiment 1
[0091] N,N-Didecyl-S-(2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranosyl)thioamide 3 (n=8):
[0092] Didecylamine (8-10 fold excess compared to thioacetate 2) was dissolved in a 1:1 dry DMF / THF mixture (typically 60 mL) and incubated under N 2 Heat to 40°C under atmosphere. To this solution was added one portion of 1-S-acetyl-2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranose 2 (0.5 mmol) and propyl bromide Diethyl diacid (1-2 mmol, 2-4 equiv) was dissolved in a 1:1 dry DMF / THF mixture solution (4 mL). The reaction was stirred overnight at room temperature. The next morning all volatile compounds were carefully removed under high vacuum with gentle heating (to about 50°C). The resulting amorphous solid residue was dissolved in boiling ethyl acetate and cooled to room temperature to crystallize excess amine. The solid was filtered off and the solvent was removed from the mother liquor under reduced pressure. The resulting orange residue was purified by flash chromatograph...
Embodiment 2
[0097] N,N-Dioctyl-S-(2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranosyl)thioamide 3 (n=6)
[0098] Dissolve 1-S-acetyl-2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranose 2 (780 mg, 1.19 mmol) in dry THF (25 mL) middle. Then diethyl bromomalonate (305 μl, 1.79 mmol, 1.5 molar equivalents) was added, and the mixture was heated under N 2 Stir at room temperature for 10 minutes. Dioctylamine (1.44 mL, 4.76 mmol, 4 molar equivalents) was then added and the reaction was stirred at room temperature under argon for 70 hours. Volatile compounds were then removed under reduced pressure. The residue was then diluted in ethyl acetate (100 mL) and washed twice with saturated NaCl (2×100 mL), washed with Na 2 SO 4 Dry, filter, and remove solvent under reduced pressure. The residue was chromatographed (hexane-ethyl acetate 16:1, then hexane-ethyl acetate 6:1. TLC; R f 0.57, hexane-ethyl acetate 4:1) to give N,N-dioctyl-S-(2,3,5,6-tetra-O-benzoyl-1-thio-β -D-galactofuranosyl)thioami...
Embodiment 3
[0102] N,N-Dihexyl-S-(2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranosyl)thioamide 3 (n=4)
[0103] 1-S-Acetyl-2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranose 2 (193 mg, 0.3 mmol) was dissolved in dry DMF (3 mL) . Then dry THF (3 mL), diethyl bromomalonate (453 μl, 9 molar equivalents) were added, and the mixture was stirred at room temperature for 10 minutes. Dihexylamine (1.0 mL, approximately 15 molar excess) was then added, and the reaction was 2 Stir at room temperature for 40 hours. Volatile compounds were then removed by heating at 35°C for 24 hours under reduced pressure. The waxy residue was then diluted in ethyl acetate (100 mL) and excess amine hydrobromide crystallized out and filtered from solution. The ethyl acetate solution was washed twice with brine (2×100 mL), Na 2 SO 4 Dry, filter, and remove solvent under reduced pressure. The residue was chromatographed twice (silica gel, #1 hexane-ethyl acetate 8:1; #2 hexane-ethyl acetate 16:1, TLC; R f 0.54...
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