Pyrroloterpenes and use of the same as antimicrobial and anticancer agents

A compound having the structure of Formula (I) and acid-addition salts and pro-drug esters thereof:

• wherein R1, R2, and R3 are separately selected from the group consisting of a hydrogen atom, halogen atom, mono-substituted, poly-substituted and unsubstituted variants of the following residues:
• saturated C1-C24 alkyl, unsaturated C2-C24 alkenyl or C2-C24 alkynyl, acyl, acyloxy, alkyloxycarbonyloxy, aryloxycarbonyloxy, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, aryl, heteroaryl, arylalkoxy carbonyl, alkoxy carbonylacyl, amino, aminocarbonyl, aminocarboyloxy, nitro, azido, phenyl, hydroxy, alkylthio, arylthio, oxysulfonyl, carboxy, cyano, and halogenated alkyl including polyhalogenated alkyl;
• wherein (R4)n is a multiple-unit chain and R4 for each unit is separately selected and has the structure of Formula (IA):
• and is optionally functionalized with hydroxy, oxo, epoxy, ether, cyclic ether, and carbonyl groups and wherein R4 for the first unit is attached to the structure of Formula (I) via either attachment point 1 or 2 and R4 for each additional unit is attached to the previous unit via either attachment point 1 or 2;
• wherein n is an integer greater than 2;
• wherein a bond represented by a dashed and solid line is either a carbon-carbon single bond or a carbon-carbon double bond;
• and
• any bond represented by a dashed and solid line that is a carbon-carbon double bond has a configuration selected from the group consisting of cis and trans.

A compound having the structure of Formula (II) and acid-addition salts and pro-drug esters thereof:

• wherein R1, R2, and R3 are separately selected from the group consisting of a hydrogen atom, halogen atom, mono-substituted, poly-substituted or unsubstituted variants of the following residues:
• saturated C1-C24 alkyl, unsaturated C2-C24 alkenyl and C2-C24 alkynyl, acyl, acyloxy, alkyloxycarbonyloxy, aryloxycarbonyloxy, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, aryl, heteroaryl, arylalkoxy carbonyl, alkoxy carbonylacyl, amino, aminocarbonyl, aminocarboyloxy, nitro, azido, phenyl, hydroxy, alkylthio, arylthio, oxysulfonyl, carboxy, cyano, and halogenated alkyl including polyhalogenated alkyl;
• R4, R5, and R6 are separately selected from the group consisting of a hydrogen atom, halogen atom, methyl, hydroxy, oxo, ether, and carboxy groups or are separately absent;
• wherein each repeated unit n is optionally functionalized with methyl, hydroxy, oxo, epoxy, ether, cyclic ether, and carboxy groups;
• wherein n is an integer greater than 0;
• wherein a bond represented by a dashed and solid line is either a carbon-carbon single bond or a carbon-carbon double bond;
• and
• any bond represented by a dashed and solid line that is a carbon-carbon double bond has a configuration selected from the group consisting of cis and trans.

A compound having the structure of Formula (III) and acid-addition salts and pro-drug esters thereof:

• wherein R1, R2, and R3 are separately selected from the group consisting of a hydrogen atom, halogen atom, mono-substituted, poly-substituted and unsubstituted variants of the following residues:
• saturated C1-C24 alkyl, unsaturated C2-C24 alkenyl or C2-C24 alkynyl, acyl, acyloxy, alkyloxycarbonyloxy, aryloxycarbonyloxy, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, aryl, heteroaryl, arylalkoxy carbonyl, alkoxy carbonylacyl, amino, aminocarbonyl, aminocarboyloxy, nitro, azido, phenyl, hydroxy, alkylthio, arylthio, oxysulfonyl, carboxy, cyano, and halogenated alkyl including polyhalogenated alkyl;
• and
• wherein R4 is a seven carbon alkyl or alkenyl optionally functionalized with methyl, hydroxy, oxo, epoxy, ether, cyclic ether, and carboxy groups.