Antimicrobial Guanidinium and Thiouronium Functionalized Polymers
An antimicrobial and microbial technology, applied in the direction of drug combination, botanical equipment and methods, biocides, etc., can solve the problems of non-degradable, inactive, narrow biological activity spectrum, etc.
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[0162] Preparation of Cationic Polymers
[0163] Preferably, the cationic polymer as polycarbonate is prepared by organocatalyzed ring-opening polymerization (ROP) of cyclic carbonate monomers bearing side-chain protected guanidinium groups, which for the sake of brevity are It is referred to herein as a "guanidine monomer". ROP produces an initial polymer containing protected guanidine groups. The initial polymer is subsequently deprotected using a protic acid to form a pendant guanidine based antimicrobial cationic polymers. The protic acid may have one or more protons which may be donated to form hydrogen salts of guanidine and / or isothiourea groups. In this case, the negatively charged counterion X' is the conjugate base of the protic acid. Exemplary protic acids include hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, trifluoroacetic acid, methanesulfonic acid, and p-toluenesulfonic acid.
[0164] The ROP reaction mixture comprises guanidine mono...
Embodiment 1
[0407] Example 1: Preparation of Boc protected guanylated alcohol C2G1.
[0408]
[0409]The following procedure is representative. To a solution mixture of ethanolamine (1.37 mL, 22.8 mmol, 2.0 equiv) and N,N-diisopropylethylamine (DIPEA, 6.0 mL, 34.4 mmol, 3.0 equiv) was added in anhydrous dichloromethane (DCM, 20 mL ) in 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (BBocTU, 3.3 g, 11.6 mmol, 1.0 eq) and the mixture was stirred at room temperature overnight. Upon completion of the reaction, a constant flow of nitrogen was bubbled through the reaction mixture for about 1 hour to help purge the gaseous by-product MeSH. After removal of residual solvent in vacuo, the crude product was purified by flash column chromatography using silica gel and a hexane-ethyl acetate solvent system as eluent (gradient elution up to 50% by volume ethyl acetate) to give Boc protected guanylated alcohol C2G1 (3.2 g, 10.4 mmol, 90% yield) as a solid. 1 H-NMR (400 MHz, CDCl 3 , 22°C...
Embodiment 2
[0410] Example 2: Preparation of Boc protected amidinylated alcohol C3G1.
[0411]
[0412] C3G1 was prepared by the procedure of Example 1 using 3-amino-1-propanol. Yield: 87%; 1 H-NMR (400MHz, CDCl 3 , 22°C): δ11.44(s, 1H, NH), 8.47(s, 1H, NH), 3.57(dt, J=12.1, 5.8Hz, 4H, -CH 2 -), 1.72-1.66 (m, 2H, -CH 2 -), 1.48 (d, J = 9.9Hz, 18H, Boc-CH 3 ).
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