Anti-bacterial stilbene derivatives and methods of use
AssigneeYale University
InventorsJason CRAWFORD, Tyler GODDARD, Hyun Bong PARK, Jaymin PATEL
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Abstract
Provided herein are novel antibacterial compounds of Formula I. The compounds can be made through enzymatic oxidative dimerization in the presence of a suitable organism and one or more metal salts. Pathogenic bacteria exposed to the compound of Formula I do not develop resistance to these compounds even after prolonged exposure. Also provided herein are methods of treating bacterial infections, and method of killing or disinfecting bacteria.
Claims41
A compound of Formula I, or a salt, solvate, tautomer, enantiomer, or geometric isomer thereof:
- wherein:
- at each occurrence R1, R2, R3, R4, R5, A1, A2, A3, A4, A5, A1′, A2′, A3′, A4′, and A5′ is independently selected from hydrogen, F, Cl, Br, I, OR, OC(O)N(R)2, CN, NO, NO2, ONO2, azido, CF3, OCF3, R, methylenedioxy, ethylenedioxy, N(R)2, SR, SOR, SO2R, SO2N(R)2, SO3R, C(O)R, C(O)C(O)R, C(O)CH2C(O)R, C(S)R, C(O)OR, OC(O)R, C(O)N(R)2, OC(O)N(R)2, C(S)N(R)2, (CH2)0-2N(R)C(O)R, (CH2)0-2N(R)N(R)2, N(R)N(R)C(O)R, N(R)N(R)C(O)OR, N(R)N(R)CON(R)2, N(R)SO2R, N(R)SO2N(R)2, N(R)C(O)OR, N(R)C(O)R, N(R)C(S)R, N(R)C(O)N(R)2, N(R)C(S)N(R)2, N(COR)COR, N(OR)R, C(═NH)N(R)2, C(O)N(OR)R, and C(═NOR)R;
- at each occurrence R6 is independently selected from hydrogen, CF3, R, methylenedioxy, ethylenedioxy, C(O)R, C(O)C(O)R, C(O)CH2C(O)R, C(S)R, C(O)OR, OC(O)R, C(O)N(R)2, OC(O)N(R)2, C(S)N(R)2, (CH2)1-2N(R)C(O)R, (CH2)1-2N(R)N(R)2, C(═NH)N(R)2, C(O)N(OR)R, and C(═NOR)R;
- and
- at each occurrence R is independently hydrogen, (C1-C100)hydrocarbyl, alkyl, acyl, cycloalkyl, aryl, aralkyl, heterocyclyl, heteroaryl, or heteroarylalkyl.
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A method of making a compound of Formula Ia, the method comprising:
- contacting a compound of Formula IV, or a salt, solvate, tautomer, enantiomer, or geometric isomer thereof:
- with a medium comprising an organism and at least one metal salt, to yield a compound of Formula Ia, or a salt, solvate, tautomer, enantiomer, or geometric isomer thereof:
- wherein:
- at each occurrence R2, R3, A1, A2, A3, A4, and A5, is independently selected from hydrogen, F, Cl, Br, I, OR, OC(O)N(R)2, CN, NO, NO2, ONO2, azido, CF3, OCF3, R, methylenedioxy, ethylenedioxy, N(R)2, SR, SOR, SO2R, SO2N(R)2, SO3R, C(O)R, C(O)C(O)R, C(O)CH2C(O)R, C(S)R, C(O)OR, OC(O)R, C(O)N(R)2, OC(O)N(R)2, C(S)N(R)2, (CH2)0-2N(R)C(O)R, (CH2)0-2N(R)N(R)2, N(R)N(R)C(O)R, N(R)N(R)C(O)OR, N(R)N(R)CON(R)2, N(R)SO2R, N(R)SO2N(R)2, N(R)C(O)OR, N(R)C(O)R, N(R)C(S)R, N(R)C(O)N(R)2, N(R)C(S)N(R)2, N(COR)COR, N(OR)R, C(═NH)N(R)2, C(O)N(OR)R, and C(═NOR)R;
- and
- at each occurrence R is independently hydrogen, (C1-C100)hydrocarbyl, alkyl, acyl, cycloalkyl, aryl, aralkyl, heterocyclyl, heteroaryl, or heteroarylalkyl.
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Dependencies are inferred from the claim text.