Non-Lactone Carbocyclic and Heterocyclic Antagonists and Agonists of Bacterial Quorum Sensing

A compound of formula I:

• A-[Z]n-L1-[Y]q-W-[V]m-L2-HG
• or a pharmaceutically acceptable salt or ester thereof
• where:
• W is —NH— or
• Y is —CO—, —CO—CH2—CO—, —NH—CO—, —CO—CH2—C(Y1)-, or —SO2—,
• where Y1 is —OH, —SH, —NH2 or —F;
• q is 1 or 0 to indicate the presence or absence, respectively of Y;
• L1 and L2 independently are —[CH2]p1— and —[CH2]p2—, where p1 and p2, independently, are 0 or integers ranging from 1-10 and one or more of the carbons of L1 or L2 can be substituted with one or two non-hydrogen substituents;
• V is
• where RN is an alkyl group having 1-3 carbon atoms;
• m is 1 or 0 to indicate the presence or absence of the V group;
• Z is —CO—, —O—CO—, —CO—O—, —NH—CO—, —CO—NH—, —NH—CO—NH—, —O—, —S—, or —NH2—;
• n is 1 or 0 to indicate the presence or absence of the Z group;
• A is an aryl or heteroaryl group having one or two 5- or 6-member rings with up to 1-3 heteroatoms in a ring, a C5-C8 cycloalkyl group, a C5-C8 cycloalkenyl group, a heterocyclic group having one or two 5- to 8-member rings with 1-3 heteroatoms in a ring, each of which groups are optionally substituted;
• and
• HG is a head group selected from a heteroaryl group having one or two 5- or 6-member rings with up to 1-3 heteroatoms in a ring;
• a C5-C8 cycloalkyl group;
• a C5-C8 cycloalkenyl group;
• a heterocyclic group having one or two 5- to 8-member rings with 1-3 heteroatoms in a ring;
• an alkyl group having 1-3 carbon atoms substituted with two aryl or heteroaryl groups;
• a cyclic lactam, thiolactone or ketone group having a 4- to 8-member ring, or an ester group RE—CO—CO—, where RE is an optionally substituted alkyl group having 1-6 carbon atoms, all of which groups are optionally substituted;
• wherein optional substitution is substitution with one or more non-hydrogen substituents selected from the group consisting of halogen, nitro, hydroxyl, nitrile, azide, —R, —OR, —COOR, —OCOR, —COR, —OCOOR, —CON(R)2, —OCON(R)2, —N(R)2, —SR, —SO2R, —SOR, and —SO2N(R)2;
• wherein each R is independently selected from the group consisting of hydrogen, an amine group, a substituted or unsubstituted unbranched C1-C12 acyclic aliphatic group, a substituted or unsubstituted branched C1-C12 acyclic aliphatic group, a substituted or unsubstituted C3-C8 cycloalkyl group, a substituted or unsubstituted C3-C8 cycloalkenyl group, a fluorinated C1-C12 alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a protecting group;
• additionally, two R groups of the same substituent optionally form a 4 to 8-member ring.