Lactams
Lactams of formulae (I) and (II) and their use in the treatment of microbial infections and microbial contamination of surfaces, particularly infections and surface contaminations characterized by biofilm formation. Compounds of formula (I) and (II) substituted with acrylate or methacrylate groups and their attachment to surfaces or polymers to inhibit microbial contamination are also provided.
1. A compound of formula I:
wherein:
R 2 is selected from the group consisting of heterocyclyl, heteroaryl, aryl and arylalkyl;
R 3 is selected from the group consisting of hydrogen, hydroxy, alkyl, cycloalkyl, alkoxy, oxoalkyl, alkenyl, heterocyclyl, heteroaryl, cycloalkyl, aryl, arylalkyl, and —C(O)CR 6 ═CH 2 ;
R 6 is selected from the group consisting of hydrogen or methyl.
2. A compound selected from the group consisting of
5-methylene-4-phenyl-dihydro-pyrrol-2-one;
1-methyl-5-methylene-4-phenyl-dihydro-pyrrol-2-one;
5-methylene-1,4-diphenyl-dihydro-pyrrol-2-one;
4-(4′-bromophenyl)-5-methylene-2-dihydro-pyrrol-2-one;
4-benzyl-5-methylene-dihydro-pyrrol-2-one;
4-(4′-methoxyphenyl)-5-methylene-dihydro-pyrrol-2-one;
5-methylene-4-(4′-fluorophenyl)-dihydro-pyrrol-2-one;
5-methylene-4-(4′-trifluoromethylphenyl)-dihydro-pyrrol-2-one;
5-methylene-4-(3′-trifluoromethylphenyl)-dihydro-pyrrol-2-one;
5-methylene-4-(2′-fluorophenyl)-dihydro-pyrrol-2-one; and
5-methylene-4-(3′-fluorophenyl)-dihydro-pyrrol-2-one.
3. A method of treating a microbial infection caused by an organism selected from the group consisting of S. epidermis, P. aeruginosa and E. coli in a subject, the method comprising administering a compound according to claim 1 to the subject.
4. A method of treating a microbial infection caused by an organism selected from the group consisting of S. epidermis, P. aeruginosa and E. coli in a subject, the method comprising administering a compound according to claim 2 to the subject.
5. A method according to claim 3 wherein the infection is a bacterial infection.
6. A method according to claim 3 wherein the infection is characterised by biofilm formation.
7. A method of inhibiting microbial contamination of a surface by an organism selected from the group consisting of S. epidermis, P. aeruginosa and E. coli , the method comprising administering a compound according to claim 1 to the surface.
8. A formulation comprising a compound according to claim 1 and a carrier.
9. A formulation comprising a compound according to claim 2 and a carrier.
10. A compound according to claim 1 wherein R 3 is —C(O)CR 6 ═CH 2 .
11. A compound according to claim 10 when used to form an oligomer or polymer.
12. A compound according to claim 11 wherein the oligomer or polymer is formed by polymerisation of a terminal vinyl group of the compound.
13. A polymer or oligomer formed by oligomerising or polymerising a compound accordingly to claim 10 directly or with one or more other monomers.
14. A compound according to claim 10 wherein a terminal vinyl group of the compound is reacted with a functional group.
15. A compound according to claim 10 when attached to a surface.
16. A compound according to claim 15 wherein the compound is attached to the surface by reaction of a terminal vinyl group of the compound with a functional group.
17. A surface comprising one or more compounds according to claim 10 attached to the surface.
18. A surface comprising the polymer or oligomer according to claim 13 attached to the surface.
19. A compound of formula II:
wherein
R 3 is selected from the group consisting of hydrogen, hydroxy, alkyl, cycloalkyl, alkoxy, oxoalkyl, alkenyl, heterocyclyl, heteroaryl, aryl, arylalkyl, and —C(O)CR 6 ═CH 2 ;
R 6 is selected from the group consisting of hydrogen and methyl;
R 7 is —C(O)CR 6 ═CH 2 ;
and R 2 is selected from the group consisting of heterocyclyl, heteroaryl, aryl and arylalkyl.
20. A method of treating a microbial infection caused by an organism selected from the grup consisting of S. epidermis, P. aeruginosa and E. coli in a subject, the method comprising administering a compound according to claim 19 to the subject.
21. A method according to claim 20 wherein the infection is a bacterial infection.
22. A method according to claim 20 wherein the infection is characterised by biofilm formation.
23. A method of inhibiting microbial contamination of a surface by an organism selected from the group consisting of S. epidermis. P. aeruginosa and E. coli , the method comprising administering a compound according to claim 19 to the surface.
24. A formulation comprising a compound according to claim 19 and a carrier.
25. A compound according to claim 19 wherein at least one of R 3 and R 7 is selected from —C(O)CR 6 ═CH 2 .
26. A compound according to claim 25 wherein each of R 3 and R 7 is selected from —C(O)CR 6 ═CH 2 .
27. A compound according to claim 25 when used to form an oligomer or polymer.
28. A compound according to claim 27 wherein the oligomer or polymer is formed by polymerisation of a terminal vinyl group of the compound.
29. A polymer or oligomer formed by oligomerising or polymerising a compound accordingly to claim 25 directly or with one or more other monomers.
30. A compound according to claim 25 wherein a terminal vinyl group of the compound is reacted with a functional group.
31. A compound according to claim 25 when attached to a surface.
32. A compound according to claim 30 wherein the compound is attached to the surface by reaction of a terminal vinyl group of the compound with a functional group.
33. A surface comprising one or more compounds according to claim 25 attached to the surface.
34. A surface comprising the polymer or oligomer according to claim 29 attached to the surface.