Hydroxamic acids and uses thereof

1. A compound of formula I:

wherein R 1 is an alkoxy or O(CH 2 ) p X;

wherein p is an integer from 2 to 3 and X is OH, NH 2 , or CO 2 H;

m is an integer from 0 to 5;

n is an integer from 0 to 5;

each R 2 is independently selected from the group consisting of halogen, hydrogen, alkenyl, hydroxyalkyl, alkoxymethyl, heterocyclyl, hetereocyclylmethyl, amino, amido, hydroxamido, any of which may be optionally substituted with one or more of acyl, alkyl, alkoxy, hydroxyalkyl, or halogen;

each R 3 is independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, carboxy, hydroxymethyl, amido; and

wherein at least one of R 2 and R 3 is not hydrogen.

2. The compound of claim 1 , wherein R 1 is an alkoxy in the R-diastereomeric configuration.

3. The compound of claim 1 , wherein R 1 is an alkoxy in the S-diastereomeric configuration.

4. The compound of claim 1 , wherein R 1 is ethoxy or methoxy.

5. The compound of claim 1 , wherein m=1 and R 3 is 4-chloro.

6. The compound of claim 1 , wherein m is an integer from 0 to 2.

7. The compound of claim 1 , wherein n is an integer from 0 to 4.

8. The compound of claim 1 , wherein each R 2 is a halogen independently selected from the group consisting of fluorine, bromine, and chlorine.

9. The compound of claim 8 , wherein R 2 is a 4-substituted halogen.

10. The compound of claim 1 , wherein the R 2 heterocyclyl or hetereocyclylmethyl group comprises a morpholine, a piperazine, an oxirane, or a piperidine.

11. A compound of formula II:

wherein R 1 is an alkoxy or O(CH 2 ) p X;

wherein p is an integer from 2 to 3 and X is OH, NH 2 , or CO 2 H;

n is an integer from 0 to 5;

X is a halogen;

each R 2 is independently selected from the group consisting of halogen, hydrogen, alkenyl, hydroxyalkyl, alkoxymethyl, heterocyclyl, hetereocyclylmethyl, amino, amido, hydroxamido, any of which may be optionally substituted with one or more of acyl, alkyl, alkoxy, hydroxyalkyl, or halogen; and

R 3 is methyl or hydrogen.

12. The compound of claim 11 , wherein R 1 is methoxy or ethoxy.

13. The compound of claim 11 , wherein at least one R 2 is halogen.

14. The compound of claim 11 , wherein X is chlorine.

15. The compound of claim 11 , wherein x is fluorine.

16. The compound of claim 11 , wherein at least one R 2 is heterocyclyl or hetereocyclylmethyl.

17. The compound of claim 16 , wherein the heterocyclyl or hetereocyclylmethyl group comprises a morpholine, a piperazine, an oxirane, or a piperidine.

18. A compound of formula III:

wherein R 1 is an alkoxy or O(CH 2 ) p X;

wherein p is an integer from 2 to 3 and X is OH, NH 2 , or CO 2 H;

n is an integer from 0 to 5;

each R 2 is independently selected from the group consisting of halogen, hydrogen, alkenyl, hydroxyalkyl, alkoxymethyl, heterocyclyl, hetereocyclylmethyl, amino, amido, hydroxamido, any of which may be optionally substituted with one or more of acyl, alkyl, alkoxy, hydroxyalkyl, or halogen.

19. The compound of claim 11 , wherein at least one R 2 is halogen.

20. The compound of claim 11 , wherein at least one R 2 is hydroxymethyl.

21. The compound of claim 11 , wherein at least on R 2 is heterocyclyl or hetereocyclylmethyl.

22. A pharmaceutical composition comprising a compound according to claim 1 along with a pharmaceutically acceptable carrier.

23. A method of treating botulinum toxicity comprising:

administering to a subject a pharmaceutical composition comprising a compound according to claim 1 .

24. A compound of formula:

selected from the group consisting of:

R 1 =OEt, R 2 =4-F, R 3 =H;

R 1 =OEt, R 2 =4-F, R 3 =3-Br;

R 1 =OMe, R 2 =4-Br, R 3 =4-F;

R 1 =OEt, R 2 =4-F, R 3 =4-Br;

R 1 =OEt, R 2 =4-F, R 3 =4-CH═CH 2 ;

R 1 =OEt, R 2 =4-F, R 3 =Et;

R 1 =OEt, R 2 =4-F, R 3 =4-C(O)—NHMe;

R 1 =OEt, R 2 =4-F, R 3 =4-C(O)—NMe 2 ;

R 1 =OEt, R 2 =4-F, R 3 =4-CH 2 OH;

R 1 =OEt, R 2 =4-F, R 3 =4-CO 2 H;

R 1 =OEt, R 2 =4-F, R 3 =3-(pyridine-4-yl);

R 1 =OEt, R 2 =4-F, R 3 =4-(pyridine-4-yl);

R 1 =OEt, R 2 =4-F, R 3 =4-(pyridine-3-yl); and

R 1 =OEt, R 2 =4-F, R 3 =4-(5-methylpyridine-3-yl).