Quinoline-indole antimicrobial agents, uses and compositions related thereto

A compound represented by general formula 2:

• wherein
• R, Ra, R3, R1 , and R2′, for each occurrence, independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R4, and R5, for each occurrence, independently represent halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• T represents a covalent linker;
• the B-ring of the 2-quinolinyl moiety may be unsubstituted, or substituted between one and four times inclusive by R4;
• the B-ring of the 3-indolyl moiety is substituted with between one and four instances of R5;
• R80 represents an aryl, a cycloalkyl, a cycloalkenyl, a heterocycle, or a polycycle;
• and
• m is an integer in the range 0 to 8 inclusive.

A compound represented by the following general formula:

• wherein
• R3, R5, R6, R7, R8, R21, R22, R1′, R2′, R4′, R5′, R6′, and R7′, for each occurrence, independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• at least one member of the group consisting of R4′, R5′, R6′, and R7′ is not hydrogen,
• R80 represents an aryl, a cycloalkyl, a cycloalkenyl, a heterocycle, or a polycycle;
• and
• m is an integer in the range 0 to 8 inclusive.

The compound represented by general formula 3:

• wherein
• R3, R1′, and R2′, for each occurrence, independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R4, for each occurrence, independently represent halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, for each occurrence, independently represents halogen, alkyl, alkenyl, alkynyl, hydroxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• the B-ring of the 2-quinolinyl moiety may be unsubstituted, or substituted between one and four times inclusive by R4;
• the B-ring of the 3-indolyl moiety is substituted with between one and four instances of R5;
• R80 represents an aryl, a cycloalkyl, a cycloalkenyl, a heterocycle , or a polycycle;
• and
• m is an integer in the range 0 to 8 inclusive.

The compound represented by the following general structure:

• wherein
• R2′ and R3 independently for each occurrence represent H, C1-C6 alkyl, or aryl;
• R5, R6, R7, and R8 independently for each occurrence represent H, C1-C6 alkyl, 1-alkenyl, 1-alkynyl, aryl, —C(O)N(R)2, halogenated C1-C6 alkyl, or halogen;
• R represents, independently for each occurrence, hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R1′ represents H, alkyl, aryl, Me, or p-toluenesulfonyl;
• R4′, R5′, R6′ and R7′ independently for each occurrence represent H, C1-C6 alkyl halogenated C1-C6 alkyl, halogen, —C(O)NR2, —CN, —NO2, —OH, —O2Caryl, or —O2Calkyl;
• and
• at least one member of the group consisting of R4′, R5 ′, R6′, and R7′ is not hydrogen.

The compound represented by general formula 4:

• wherein
• R20 represents H, Me, lower alkyl, halogen, —C(Z)N(R)2, —S(Z)2N(R)2, or —P(Z)2N(R)2, wherein Z independently for each occurrence represents (R)2, O, S, or NR;
• R, R3, R1′, and R2′, for each occurrence, independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R4, for each occurrence, independently represent halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, for each occurrence, independently represents halogen, alkyl, alkenyl, alkynyl, hydroxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)n—R80;
• the B-ring of the 2-quinolinyl moiety may be unsubstituted, or substituted between one and four times inclusive by R4;
• the B-ring of the 3-indolyl moiety is substituted with between one and four instances of R5;
• R80 represents an aryl, a cycloalkyl, a cycloalkenyl, a heterocycle, or a polycycle;
• n is an integer in the range 1 to 8 inclusive;
• and
• m is an integer in the range 0 to 8 inclusive.

The compound represented by the following general formula:

• wherein
• R3, R4, R1′, R2′, and R60 for each occurrence, independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, and R7, for each occurrence, independently represent halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• the B-ring of the 2-quinolinyl moiety may be unsubstituted beyond the alkynyl group or substituted between one and three times inclusive by R5;
• the B-ring of the 3-indolyl moiety may be unsubstituted or substituted between one and four times inclusive by R7;
• R80 represents an aryl, a cycloalkyl, a cycloalkenyl, a heterocycle , or a polycycle;
• and
• m is an integer in the range 0 to 8 inclusive.

The compound represented by the following general structure:

• wherein
• Z independently for each occurrence represents (R)2, O, S, or NR;
• R5, R7, and R8 independently for each occurrence represent H, Me, C1-C6 alkyl, heteroalkyl, 1-alkenyl, 1-alkynyl, aryl, heteroaryl, —OR, —OCF3, —OCR2OR, —CR2OR, —CO2R, halogenated C1-C6 alkyl, or halogen;
• R represents, independently for each occurrence, hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R6 is selected from the group comprising NHR, N(R)2, 1-piperidyl, 1-piperazinyl, 1-pyrrolidinyl, 2-phenylethylamino, 4-morpholinyl, and 4-phenylmethyl-1-piperidyl;
• R1′ represents H, alkyl, aryl, p-toluenesulfonyl, —(CH2)nN(Phth), or —(CH2)nN(R)2;
• wherein n is an integer in the range 1 to 6 inclusive;
• R2′ and R3 independently for each occurrence represent H, Me, C1-C6 alkyl, or aryl;
• R4′, R5′, R6′ and R7′ independently for each occurrence represent H, C1-C6 alkyl, halogenated C1-C6 alkyl, halogen, —C(O)NR2, —CN, —NO2, —OH, —OR, —O2Caryl, or —O2Calkyl;
• and
• R21 and R22 independently for each occurrence represent H, alkyl, heteroalkyl, aryl, heteroaryl, —(CH2)m—R80, or —(CH2)nN(R1′)2, wherein n is an integer in the range 1 to 6 inclusive, ortho-, meta-, or para-CH2C6H4CH2N(R1 ′)2, ortho-, meta-, or para-C6H4CH2N(R1′)2, ortho-, meta-, or para-CH2C6H4O(R1′), ortho-, meta-, or para-CH2C6H4OMe, ortho-, meta-, or para-CH2C6H4OH, (2-benzimidazolyl)CH2—, 2-, 3-, or 4-(R1′)Ophenyl, 2-, 3-, or 4-methoxyphenyl, 2-, 3-, or 4-hydroxyphenyl, or 2-, 3-, or 4-((R1′)2NCH2)cyclohexylmethyl, or 2-, 3-, or 4-((R1 ′)2N)cyclohexylmethyl;
• or N(R21)R22 taken together represent a heterocycle comprising from 4 to 8 members inclusive.

The compound represented by the following general structure:

• wherein
• Z independently for each occurrence represents (R)2, O, S, or NR;
• R represents, independently for each occurrence, hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, R7, and R8 independently for each occurrence represent H, Me, C1-C6 alkyl, heteroalkyl, 1-alkenyl, 1-alkynyl, aryl, heteroaryl, —OR, —OCF3, —OCR2OR, —CR2OR, —CO2R, halogenated C1-C6 alkyl, or halogen;
• R6 is selected from the group comprising NHR, N(R)2, 1-piperidyl, 1-piperazinyl, 1-pyrrolidinyl, 2-phenylethylamino, 4-morpholinyl, and 4-phenylmethyl-1-piperidyl;
• R1′ represents H, alkyl, aryl, p-toluenesulfonyl, —(CH2)nN(Phth), or —(CH2)nN(R)2;
• wherein n is an integer in the range 1 to 6 inclusive;
• R2′ and R3 independently for each occurrence represent H, Me, C1-C6 alkyl, or aryl;
• R4′, R5′, R6′ and R7′ independently for each occurrence represent H, C1-C6 alkyl, halogenated C1-C6 alkyl, halogen, —C(O)NR2, —CN, —NO2, —OH, —OR, —O2Caryl, or —O2Calkyl;
• and
• m and n are integers independently selected from the range 1 to 4 inclusive.

The compound represented by the following general structure:

• wherein
• Z independently for each occurrence represents (R)2, O, S, or NR;
• R represents, independently for each occurrence, hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine, oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5 R, and R, independently for each occurrence represent H, Me, C1-C6 alkyl, heteroalkyl, 1-alkenyl, 1-alkynyl, aryl, heteroaryl, —OR, —OCF3, —OCR2OR, —CR2OR, —Co2R, halogenated C1-C6 alkyl, or halogen;
• R7 is selected from the group comprising NHR, N(R)2, 1-piperidyl, 1-piperazinyl, 1-pyrrolidinyl, 2-phenylethyl amino, 4-morpholinyl, and 4-phenylmethyl-1-piperidyl;
• R1′ represents H, alkyl, aryl, p-toluenesulfonyl, —(CH2)nN(Phth), or —(CH2)nN(R)2 wherein n is an integer in the range 1 to 6 inclusive;
• R2′ and R3 independently for each occurrence represent H, Me, C1-C6 alkyl, or aryl;
• R4′, R5′, R6′ and R7′ independently for each occurrence represent H, C1-C6 alkyl, halogenated C1-C6 alkyl, halogen, —C(O)NR2, —CN, —NO2, —OH, —OR, —O2Caryl, or —O2Calkyl;
• and
• R21 and R22 independently for each occurrence represent H, alkyl, heteroalkyl, aryl, heteroaryl, —(CH2)m—R80, or —(CH2)nN(R1′)2, wherein n is an integer in the range 1 to 6 inclusive, ortho-, meta-, or para-CH2C6H4CH2N(R1′)2, ortho-, meta-, or para-C6H4CH2N(R1 ′)2, ortho-, meta-, or para-CH2C6H4O(R1′), ortho-, meta-, or para-CH2C6H4OMe, ortho-, meta-, or para-CH2C6H4OH, (2-benzimidazolyl)CH2—, 2-, 3-, or 4-(R1′)Ophenyl, 2-, 3-, or 4-methoxyphenyl, 2-, 3-, or 4-hydroxyphenyl, or 2-, 3-, or 4-((R1′)2NCH2)cyclohexylmethyl, or 2-, 3-, or 4-((R1′)2N)cyclohexylmethyl;
• or N(R21)R22 taken together represent a heterocycle comprising from 4 to 8 members inclusive.

The compound represented by the following general formula:

• wherein
• Z independently for each occurrence represents (R)2, O, S, or NR;
• R represents, independently for each occurrence, hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, R6, and R8 independently for each occurrence represent H, Me, C1-C6 alkyl, heteroalkyl, 1-alkenyl, 1-alkynyl, aryl, heteroaryl, —OR, —OCF3, —OCR2OR, —CR2OR, -CO2R, halogenated C1-C6 alkyl, or halogen;
• R7 is selected from the group comprising NHR, N(R)2, 1-piperidyl, 1-piperazinyl, 1-pyrrolidinyl, 2-phenylethylamino, 4-morpholinyl, and 4-phenylmethyl-1-piperidyl;
• R1′ represents H, alkyl, aryl, p-toluenesulfonyl, —(CH2)nN(Phth), or —(CH2)nN(R)2;
• wherein n is an integer in the range 1 to 6 inclusive;
• R2′ and R3 independently for each occurrence represent H, Me, C1-C6 alkyl, or aryl;
• R4′, R5′, R6′ and R7′ independently for each occurrence represent H, C1-C6 alkyl, halogenated C1-C6 alkyl, halogen, —C(O)NR2, —CN, —NO2, —OH, —OR, —O2Caryl, or-O2Calkyl;
• and
• m and n are integers independently selected from the range 1 to 4 inclusive.

The compound represented by the following general structure:

• wherein
• Z independently for each occurrence represents (R)2, O, S, or NR;
• R represents, independently for each occurrence, hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, R6, and R7 independently for each occurrence represent H, Me, C1-C6 alkyl, heteroalkyl, 1-alkenyl, 1-alkynyl, aryl, heteroaryl, —OR, —OCF3, —OCR2OR, —CR2OR, —CO2R, halogenated C1-C6 alkyl, or halogen;
• R8 is selected from the group comprising NHR, N(R)2, 1-piperidyl, 1-piperazinyl, 1-pyrrolidinyl, 2-phenylethylamino, 4-morpholinyl, and 4-phenylmethyl-1-piperidyl;
• R1′ represents H, alkyl, aryl, p-toluenesulfonyl, —(CH2)nN(Phth), or —(CH2)nN(R)2;
• wherein n is an integer in the range 1 to 6 inclusive;
• R2′ and R3 independently for each occurrence represent H, Me, C1-C6 alkyl, or aryl;
• R4′, R5′, R6′ and R7′ independently for each occurrence represent H, C1-C6 alkyl, halogenated C1-C6 alkyl, halogen, —C(O)NR2, —CN, —NO2, —OH, —OR, —O2Caryl, or-O2Calkyl;
• and
• R21 and R22 independently for each occurrence represent H, alkyl, heteroalkyl, aryl, heteroaryl, —(CH2)m—R80, or —(CH2)nN(R1′)2, wherein n is an integer in the range 1 to 6 inclusive, ortho-, meta-, or para-CH2C6H4CH2N(R1′)2, ortho-, meta-, or para-C6H4CH2N(R1′)2, ortho-, meta-, or para-CH2C6H4O(R1′), ortho-, meta-, orpara-CH2C6H4OMe, ortho-, meta-, or para-CH2C6H4OH, (2-benzimidazolyl)CH2—, 2-, 3-, or 4-(R1′)Ophenyl, 2-, 3-, or 4-methoxyphenyl, 2-, 3-, or 4-hydroxyphenyl, or 2-, 3-, or 4-((R1′)2NCH2)cyclohexylmethyl, or 2-, 3-, or 4-((R1′)2N)cyclohexylmethyl;
• or N(R21 )R22 taken together represent a heterocycle comprising from 4 to 8 members inclusive.

The compound represented by the following general formula:

• wherein
• Z independently for each occurrence represents (R)2, O, S, or NR;
• R represents, independently for each occurrence, hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, R6, and R7 independently for each occurrence represent H, Me, C1-C6 alkyl, heteroalkyl, 1-alkenyl, 1-alkynyl, aryl, heteroaryl, —OR, —OCF3, —OCR2OR, —CR2OR, —CO2R, halogenated C1-C6 alkyl, or halogen;
• R8 is selected from the group comprising NHR, N(R)2, 1-piperidyl, 1-piperazinyl, 1-pyrrolidinyl, 2-phenylethylamino, 4-morpholinyl, and 4-phenylmethyl-1-piperidyl;
• R1′ represents H, alkyl, aryl, p-toluenesulfonyl, —(CH2)nN(Phth), or —(CH2)nN(R)2;
• wherein n is an integer in the range 1 to 6 inclusive;
• R2′ and R3 independently for each occurrence represent H, Me, C1-C6 alkyl, or aryl;
• R4′, R5′, R6′ and R7′ independently for each occurrence represent H, C1-C6 alkyl, halogenated C1-C6 alkyl, halogen, —C(O)NR2, —CN, —NO2, —OH, —OR, —O2Caryl, or —O2Calkyl;
• and
• m and n are integers independently selected from the range 1 to 4 inclusive.

A pharmaceutical preparation comprising, as an active ingredient for inhibition of bacterial cell growth, a compound represented in the general formula 1:

• wherein
• A and B represent fused benzo rings;
• X represents N;
• Y represents NR;
• R, R1, R2, and R3, for each occurrence, independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R4, for each occurrence, independently represent halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, for each occurrence, independently represents halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• A may be unsubstituted or substituted with R4 any number of times up to the limitations imposed by stability and the rules of valence;
• B is substituted with at least one instance of R5, but in no case more than the maximum number of instances of R5 allowed by the limitations imposed by stability and the rules of valence;
• R80 represents an unsubstituted or substituted aryl, a cycloalkyl, a cycloalkenyl, a heterocycle, or a polycycle;
• and
• m is an integer in the range 0 to 8 inclusive.

A preparation for topical application to a cutaneous or mucosal tissue, comprising, as an active ingredient for inhibition of bacterial cell growth on the tissue, a compound represented in the general formula 1:

• wherein
• A and B represent fused benzo rings;
• X represents N;
• Y represents NR;
• R, R1, R2, and R3, for each occurrence, independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R4, for each occurrence, independently represent halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, for each occurrence, independently represents halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, sulfhydryl alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• A may be unsubstituted or substituted with R4 any number of times up to the limitations imposed by stability and the rules of valence;
• B is substituted with at least one instance of R5, but in no case more than the maximum number of instances of R5 allowed by the limitations imposed by stability and the rules of valence,
• R80 represents an unsubstituted or substituted aryl, a cycloalkyl, a cycloalkenyl, a heterocycle, or a polycycle;
• and
• m is an integer in the range 0 to 8 inclusive.

A method for inhibiting bacterial cell growth comprising contacting bacteria with a compound represented in the general formula 1:

• wherein
• A and B represent fused benzo rings;
• X represents N;
• Y represents NR;
• R, R1, R2, and R3, for each occurrence, independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R4, for each occurrence, independently represent halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, for each occurrence, independently represents halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2m—R80;
• A may be unsubstituted or substituted with R4 any number of times up to the limitations imposed by stability and the rules of valence;
• B is substituted with at least one instance of R5, but in no case more than the maximum number of instances of R5 allowed by the limitations imposed by stability an the rules of valence;
• R80 represents an unsubstituted or substituted aryl, a cycloalkyl, a cycloalkenyl, a heterocycle , or a polycycle;
• and
• m is an integer in the range 0 to 8 inclusive.

A method for treating or preventing bacterial infection in an animal, or an external tissue surface thereof, comprising administering a pharmaceutical preparation of a compound represented in the general formula 1:

• wherein
• A and B represent fused benzo rings;
• X represents N;
• Y represents NR;
• R, R1, R2, and R3, for each occurrence, independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R4, for each occurrence, independently represent halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, for each occurrence, independently represents halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl silyloxy, amino, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• A may be unsubstituted or substituted with R4 any number of times up to the limitations imposed by stability and the rules of valence;
• B is substituted with at least one instance of R5, but in no case more than the maximum number of instances of R5 allowed by the limitations imposed by stability and the rules of valence:
• R80 represents an unsubstituted or substituted aryl, a cycloalkyl, a cycloalkenyl, a heterocycle, or a polycycle;
• and
• m is an integer in the range 0 to 8 inclusive.

A method for promoting weight gain in a livestock, comprising administering to the livestock a compound represented in the general formula 1:

• wherein
• A and B represent fused benzo rings;
• X represents N;
• Y represents NR;
• R, R1, R2, and R3, for each occurrence, independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R4, for each occurrence, independently represent halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, nitro, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m—R80;
• R5, for each occurrence, independently represents halogen, alkyl, alkenyl, alkynyl, hydroxyl, alkoxyl, silyloxy, amino, sulfhydryl, alkylthio, imine, amide, phosphoryl, phosphonate, phosphine, carbonyl, carboxyl, carboxamide, anhydride, silyl, thioalkyl, alkylsulfonyl, arylsulfonyl, selenoalkyl, ketone, aldehyde, ester, heteroalkyl, nitrile, guanidine, amidine, acetal, ketal, amine oxide, aryl, heteroaryl, azide, aziridine, carbamate, epoxide, hydroxamic acid, imide, oxime, sulfonamide, thioamide, thiocarbamate, urea, thiourea, or —(CH2)m-R80;
• A may be unsubstituted or substituted with R4 any number of times up to the limitations imposed by stability and the rules of valence;
• B is substituted with at least one instance of R5, but in no case more than the maximum number of instances of R5 allowed by the limitations imposed by stability and the rules of valence;
• R80 represents an unsubstituted or substituted aryl, a cycloalkyl, a cycloalkenyl, a heterocycle, or a polycycle;
• and
• m is an integer in the range 0 to 8 inclusive.