ANTI-CANCER AND ANTI-MICROBIAL OXAZOLIDINONES

1 . A compound having the structure of formula I or Ia:

and pharmaceutically acceptable salts or prodrugs thereof, wherein:

R 1 and R 2 are separately selected, wherein one of R 1 and R 2 is a molecular fragment having the structure of formula (II),

Z is selected from the group consisting of O, S, and NR 5 ;

R 6 and R 7 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl;

R 8 and R 9 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; and halogenated alkyl including polyhalogenated alkyl; or are separately absent;

R 10 and R 11 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl; or are separately absent;

and the remaining substituent of R 1 and R 2 is selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; heteroaryl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl;

R 3 is ═O;

R 1′ is selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl; or are separately absent;

R 2′ is selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; heteroaryl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl; or are separately absent;

Y is separately selected from the group consisting of O, S, and NR 5 ;

R 4 and each R 5 are separately selected from the group consisting of hydrogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-6 heteroalkyl, C 2-6 aminoalkyl, C 2-6 haloalkyl, C 1-6 alkoxycarbonyl, and C 2-6 hydroxyalkyl; C 3-8 cycloalkyl; —C(O)—C 5-6 aryl substituted with C 1-3 alkyl or halo; C 5-6 aryl; C 5-6 heteroaryl; C 5-6 cycloalkyl; and C 5-6 heterocycloalkyl, or are separately absent, provided that R 4 is not absent in a compound of formula Ia;

any bond represented by a dashed and solid line represents a bond selected from the group consisting of a single bond and a double bond;

any bond represented by a single dashed line is a single bond or is absent; and

any carbon-carbon double bond has a configuration selected from the group consisting of cis and trans.

2 . The compound of claim 1 , wherein Y is O.

3 . The compound of claim 1 , wherein Z is O.

4 . The compound of claim 1 , wherein R 4 is H.

5 . The compound of claim 1 , wherein R 4 is absent.

6 . The compound of claim 1 , wherein R 8 , R 9 , R 10 , and R 11 are separately hydrogen or absent.

7 . The compound of claim 1 , wherein R 2 is a mono-substituted, poly-substituted, or unsubstituted variant of C 1 -C 24 alkyl.

8 . The compound of claim 1 , wherein R 6 and R 7 are separately mono-substituted, poly-substituted, or unsubstituted variants of C 1 -C 24 alkyl.

9 . A compound having the structure of formula III or IIIa:

and pharmaceutically acceptable salts or prodrugs thereof, wherein:

Y is selected from the group consisting of O, S, and NR 5 ;

R 2 , R 6 , and R 7 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl;

R 2′ is selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl; or is absent;

R 4 and R 5 are separately selected from the group consisting of hydrogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-6 heteroalkyl, C 2-6 aminoalkyl, C 2-6 haloalkyl, C 1-6 alkoxycarbonyl, and C 2-6 hydroxyalkyl; C 3-8 cycloalkyl; —C(O)—C 5-6 aryl substituted with C 1-3 alkyl or halo; C 5-6 aryl; C 5-6 heteroaryl; C 5-6 cycloalkyl; and C 5-6 heterocycloalkyl or are separately absent, provided that R 4 is not absent in a compound of formula IIIa;

R 8 , R 9 , R 10 , and R 11 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl; or are separately absent;

any bond represented by a dashed and solid line represents a bond selected from the group consisting of a single bond and a double bond;

any bond represented by a single dashed line is a single bond or is absent; and

any carbon-carbon double bond has a configuration selected from the group consisting of cis and trans.

10 . The compound of claim 9 , wherein Y is O.

11 . The compound of claim 9 , wherein R 2 is a mono-substituted, poly-substituted, or unsubstituted variant of C 1 -C 24 alkyl.

12 . The compound of claim 9 , wherein R 6 and R 7 are separately mono-substituted, poly-substituted, or unsubstituted variants of straight chain C 1 -C 24 alkyl.

13 . The compound of claim 9 , wherein R 4 is H.

14 . The compound of claim 9 , wherein R 4 is absent.

15 . The compound of claim 9 , wherein R 2 ′ is H.

16 . The compound of claim 9 , wherein R 2 ′ is absent.

17 . The compound of claim 9 , wherein R 8 , R 9 , R 10 , and R 11 are separately hydrogen or absent.

18 . A compound having the structure of formula IV or IVa:

and pharmaceutically acceptable salts or prodrugs thereof, wherein:

R 2 , R 6 , and R 7 are separately selected from the group consisting of mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl;

R 2′ is selected from the group consisting of hydrogen and mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl;

R 4 is selected from the group consisting of hydrogen, straight- or branched-chain C 1-6 alkyl, straight- or branched-chain C 2-6 alkenyl, and straight- or branched-chain C 2-6 alkynyl, or is absent, provided that R 4 is not absent in a compound of formula IVa;

any bond represented by a dashed and solid line represents a bond selected from the group consisting of a single bond and a double bond with the proviso that such bonds in the compound of formula IV may not both be double bonds; and

any carbon-carbon double bond has a configuration selected from the group consisting of cis and trans.

19 . A compound having the structure of formula V or Va:

and pharmaceutically acceptable salts or prodrugs thereof, wherein:

Y is selected from the group consisting of O and NR 5 ;

Z is selected from the group consisting of O, S, and NR 5 ;

R 2 , R 7 , and R 6 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl;

R 2′ is selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl; or is absent;

R 4 and each R 5 are separately selected from the group consisting of hydrogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-6 heteroalkyl, C 2-6 aminoalkyl, C 2-6 haloalkyl, C 1-6 alkoxycarbonyl, and C 2-6 hydroxyalkyl; C 3-8 cycloalkyl; —C(O)—C 5-6 aryl substituted with C 1-3 alkyl or halo; C 5-6 aryl; C 5-6 heteroaryl; C 5-6 cycloalkyl; and C 5-6 heterocycloalkyl or are separately absent, provided that R 4 is not absent in a compound of formula Va;

R 8 and R 9 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; and halogenated alkyl including polyhalogenated alkyl; or are separately absent;

R 10 and R 11 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl; or are separately absent;

R 6 and R 8 are optionally bound together to form an optionally substituted ring;

any bond represented by a dashed and solid line represents a bond selected from the group consisting of a single bond and a double bond;

any bond represented by a single dashed line is a single bond or is absent; and

any carbon-carbon double bond has a configuration selected from the group consisting of cis and trans.

20 . The compound of claim 19 , having the structure:

21 . A compound having the structure of formula V or Va:

and pharmaceutically acceptable salts or prodrugs thereof, wherein:

Y is selected from the group consisting of O, S, and NR 5 ;

Z is selected from the group consisting of O, S, and NR 5 ;

R 2 , R 6 , and R 7 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl;

R 2′ is selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl; or is absent;

R 4 and each R 5 are separately selected from the group consisting of hydrogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-6 heteroalkyl, C 2-6 aminoalkyl, C 2-6 haloalkyl, C 1-6 alkoxycarbonyl, and C 2-6 hydroxyalkyl; C 3-8 cycloalkyl; —C(O)—C 5-6 aryl substituted with C 1-3 alkyl or halo; C 5-6 aryl; C 5-6 heteroaryl; C 5-6 cycloalkyl; and C 5-6 heterocycloalkyl or are separately absent, provided that R 4 is not absent in a compound of formula Va;

R 8 and R 9 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; and halogenated alkyl including polyhalogenated alkyl; or are separately absent;

R 10 and R 11 are separately selected from the group consisting of hydrogen; halogen; mono-substituted, poly-substituted or unsubstituted, straight or branched chain variants of the following residues: C 1 -C 24 alkyl, C 2 -C 24 alkenyl, or C 2 -C 24 alkynyl; acyl; acyloxy; alkyloxycarbonyloxy; aryloxycarbonyloxy; cycloalkyl; cycloalkenyl; alkoxy; cycloalkoxy; aryl; heteroaryl; heterocycloalkyl; ester; arylalkoxy carbonyl; alkoxy carbonylacyl; amino; aminocarbonyl; amide; aminocarbonyloxy; nitro; azido; phenyl; hydroxy; alkylthio; arylthio; oxysulfonyl; carboxy; cyano; and halogenated alkyl including polyhalogenated alkyl; or are separately absent;

R 6 and R 8 are optionally bound together to form an optionally substituted ring, provided that if R 6 and R 8 together form an aryl, then at least one of R 2 , R 4 , and R 11 is not hydrogen;

any bond represented by a dashed and solid line represents a bond selected from the group consisting of a single bond and a double bond;

any bond represented by a single dashed line is a single bond or is absent; and

any carbon-carbon double bond has a configuration selected from the group consisting of cis and trans.

22 . The compound of claim 21 , having the structure:

23 . A pharmaceutical composition, comprising a compound of claim 1 and a physiologically acceptable surface active agent, carrier, diluent, excipient, smoothing agent, suspension agent, film forming substance, or coating assistant, or a combination thereof.

24 . A pharmaceutical composition, comprising a compound of claim 9 and a physiologically acceptable surface active agent, carrier, diluent, excipient, smoothing agent, suspension agent, film forming substance, or coating assistant, or a combination thereof.

25 . A pharmaceutical composition, comprising a compound of claim 18 and a physiologically acceptable surface active agent, carrier, diluent, excipient, smoothing agent, suspension agent, film forming substance, or coating assistant, or a combination thereof.

26 . A pharmaceutical composition, comprising a compound of claim 19 and a physiologically acceptable surface active agent, carrier, diluent, excipient, smoothing agent, suspension agent, film forming substance, or coating assistant, or a combination thereof.

27 . A pharmaceutical composition, comprising a compound of claim 21 and a physiologically acceptable surface active agent, carrier, diluent, excipient, smoothing agent, suspension agent, film forming substance, or coating assistant, or a combination thereof.

28 . A pharmaceutical composition, comprising a compound having the structure of formula VI, VII, VIII, or IX:

and a physiologically acceptable surface active agent, carrier, diluent, excipient, smoothing agent, suspension agent, film forming substance, or coating assistant, or a combination thereof.