Antiviral compounds and methods
A compound, antiviral technology, applied in the field of compounds and compositions of this method, can solve the problem of no treatment or vaccine, etc.
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Embodiment 1
[0307] Embodiment 1. Synthesis of compounds of the present invention
[0308] As shown in Scheme 1, compounds of the invention can be prepared from the corresponding acid chlorides or methyl esters.
[0309] Both methods are described in detail in the literature.
[0310]
[0311] The following examples show synthetic schemes for some of the compounds of the invention.
Embodiment 2
[0312] Embodiment 2. Synthetic cinnamoyl guanidine from cinnamic acid, cinnamoyl chloride
[0313]
[0314] To a solution of trans-cinnamic acid (1.50 g, 10.12 mmol) in anhydrous benzene (30 mL) containing a drop of N,N-dimethylformamide was added oxalyl chloride (5.14 g, 40.5 mmol), causing the solution to effervesce . After refluxing for 2 hours, the solution was evaporated to dryness under reduced pressure. The resulting solid was dissolved in anhydrous tetrahydrofuran (20 mL) and slowly added to a solution of guanidine hydrochloride in 2M aqueous sodium hydroxide (25 mL). The reaction was stirred at room temperature for 1 hour, then extracted with ethyl acetate (3 x 50 mL). The combined extracts were dried over magnesium sulfate and evaporated to yield an orange oil. The crude product was purified by column chromatography. Elution with 10% to 20% methanol in dichloromethane gave cinnamoylguanidine as a cream solid (0.829 g, 43%).
Embodiment 3
[0316] Synthesis of N-amidino-3-amino-5-phenyl-6-chloro-2-pyrazinecarboxamide
[0317] part 1
[0318]
[0319] To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (0.444 g, 2.0 mmol) in tetrahydrofuran (5 mL) / water (10 mL) / toluene (20 mL) was added phenylboronic acid ( 0.536 g, 4.4 mmol), sodium carbonate (0.699 g, 6.6 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.116 g, 0.10 mmol). The reaction was evacuated and purged several times with nitrogen before being refluxed for 6 hours. The organic layer was separated and the aqueous layer was extracted with toluene (3 x 20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and evaporated under reduced pressure to yield methyl 3-amino-6-chloro-5-phenyl-2-pyrazinecarboxylate as a yellow solid (0.43 g, 82% ).
[0320] part 2
[0321]
[0322] To a solution of sodium (0.040 g, 1.74 mmol) dissolved in methanol (5 mL) was added guanidine hydrochloride (0.258 g, 2.70 mmol)...
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