Compounds with antimicrobial activity

A compound of Formula 1:

• or a pharmaceutically acceptable salt, solvate, or tautomer thereof, wherein
• A represents a moiety selected from the group consisting of:
• m is a whole number selected from 1-5;
• n is a whole number selected from 1-4;
• p is a whole number selected from 1-4;
• q is a whole number selected from 2-5;
• X1 is —S—, —O—, —C(R)2—, or —N(R)—;
• X2 is —S—, —O—, —C(R)2—, —N(R)—, —C(O)—, —C(S)—, —C(O)C(R)2—*, —C(R)2C(O)—*, —N═CH—*, —(CR2)q—, —CH═N—*, —(R)C═C(R)—*, —C≡C—*, —NRC(R)2—*, —CR2N(R)—*, —OC(R)2—*, —C(R)2—O—*, —SC(R)2—*, —C(R)2S—*, —N(R)C(O)—*, —C(O)N(R)—*, —CR(OH)C(R)2—*, —CR2CR(OH)—*, —S(O)C(R)2—*, —S(O)2C(R)2—*, —C(R)2S(O)—*, —C(R)2S(O)2—*, —S(O)CR(OH)—*, —S(O)2CR(OH)—*, —CR(OH)S(O)—*, —CR(OH)S(O)2—*, —S(O)N(R)—*, —S(O)2N(R)—*, —N(R)S(O)—*, —NRS(O)2—*, —S(O)NR(OH)—*, —S(O)2NR(OH)—*, —NR(OH)S(O)—*, or —NR(OH)S(O)2—*, wherein * indicates the position of a covalent bond with the moiety:
• X3 is hydrogen or —OR;
• X4 is —O—, —N(OR4)—, or —N(R4)—;
• R for each instance is independently selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or aralkyl;
• or two instances of R together with the atom they are covalently bonded form a 3-6 membered cycloalkyl and heterocyloalkyl;
• R1 for each instance is independently selected from the group consisting of hydrogen, halide, nitrile, nitro, azido, —OR, —SR, —N(R)2, —C(O)R, —C(O)OR, —OC(O)R, —N(R)C(O)R, —C(O)N(R)2, —N(R)C(O)OR, —OC(O)N(R)—, —OC(O)OR, —N(R)C(O)N(R)2, —S(O)2R, —S(O)2N(R)2, —N(R)S(O)2R, perhaloalkoxyl, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and aralkyl;
• R2 for each instance is independently selected from the group consisting of hydrogen, halide, nitrile, nitro, azido, —OR, —SR, —N(R)2, —C(O)R, —C(O)OR, —OC(O)R, —N(R)C(O)R, —C(O)N(R)2, —N(R)C(O)OR, —OC(O)N(R)—, —OC(O)OR, —N(R)C(O)—N(R)2, —S(O)2R, —S(O)2N(R)2, —N(R)S(O)2R, perhaloalkoxyl, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and aralkyl;
• R3 for each instance is independently selected from the group consisting of hydrogen, halide, nitrile, nitro, azido, —OR, —SR, —N(R)2, —C(O)R, —C(O)OR, —OC(O)R, —N(R)C(O)R, —C(O)N(R)2, —N(R)C(O)OR, —OC(O)N(R)—, —OC(O)OR, —N(R)C(O)N(R)2, —S(O)2R, —S(O)2N(R)2, —N(R)S(O)2R, perhaloalkoxyl, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and aralkyl;
• and
• R4 is selected from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, or —(CR2)tY, wherein t is 1-10 and Y is halide, nitrile, nitro, azido, —OR, —SR, —N(R)2, —C(O)R, —C(O)OR, —OC(O)R, —N(R)C(O)R, —C(O)N(R)2, —N(R)C(O)OR, —OC(O)N(R)—, —OC(O)OR, —N(R)C(O)N(R)2, —S(O)2R, —S(O)2N(R)2, —N(R)S(O)2R, perhaloalkoxyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and aralkyl,
• with the proviso that the compound of Formula 1 does not have the structure: