Methionine analogs and methods of using same

Abstract

Provided are methionine analogs which may be useful for inhibiting protein synthesis, inhibiting microbial growth and/or treating infectious diseases. In some instances, the analogs exhibit bactericidal, antibacterial, anti-infective, antimicrobial, sporicidal, disinfectant, antifungal and/or antiviral properties. Also provided are methods of treatment and methods of preparation, as well as kits and unit dosages.

1 - 151 . (canceled) 
     
     
         152 . A compound of the formula: 
       
         
           
           
               
               
           
         
         wherein: 
         Y is S or O; 
         R 1  is —(B) w —C; 
         each B and C is independently an unsubstituted or substituted amino acid moiety selected from the group consisting of glycine, alanine, valine, leucine, lysine, methionine, and proline; 
         w is 0, 1, or 2; 
         R 8  is hydrogen, or an optionally substituted moiety selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, heterocycloalkyl, and heterocycloalkyl-alkyl,
 wherein the alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, heterocycloalkyl, and heterocycloalkyl-alkyl, when substituted, has one or more substituents independently selected from the group consisting hydroxyl, nitro, amino, imino, cyano, halo, haloalkyl, thiol, thioalkyl, sulfonyl, thioamido, amidino, oxo, oxamidino, methoxamidino, imidino, guanidino, sulfonamido, carboxyl, formyl, alkyl, cycloalkyl, alkoxy, alkoxy-alkyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, aryl, heteroaryl, arylcarbonyl, aralkylcarbonyl, carbonylamino, heteroarylcarbonyl, heteroaralkyl-carbonyl, alkylthio, aminoalkyl, cyanoalkyl, carbamoyl, and urea; and 
 
         m, n, and p are independently 0, 1, 2, 3, or 4; 
         or a pharmaceutically acceptable salt thereof or solvate of the foregoing. 
       
     
     
         153 . The compound of  claim 152 , wherein Y is S. 
     
     
         154 . The compound of  claim 152 , wherein Y is O. 
     
     
         155 . The compound of  claim 152 , wherein m is 1 or 2. 
     
     
         156 . The compound of  claim 152 , n is 0, 1, or 2. 
     
     
         157 . The compound of  claim 152 , wherein p is 0, 1, or 2. 
     
     
         158 . The compound of  claim 152 , wherein the amino acid moiety is selected from the group consisting of glycine, alanine, lysine, methionine, and proline. 
     
     
         159 . The compound of  claim 158 , wherein the amino acid moiety, when substituted, has one or more substituents independently selected from the group consisting of alkyl, thiol, and sulfonyl. 
     
     
         160 . The compound of  claim 152 , wherein R 1  is linked to the parent structure through an amide bond. 
     
     
         161 . The compound of  claim 152 , wherein w is 0 or 1. 
     
     
         162 . The compound of  claim 152 , wherein Y is S; and w is 0. 
     
     
         163 . The compound of  claim 162 , wherein C is unsubstituted or substituted glycine. 
     
     
         164 . The compound of  claim 152 , wherein Y is S; and w is 1. 
     
     
         165 . The compound of  claim 164 , wherein B is unsubstituted glycine; and C is unsubstituted glycine. 
     
     
         166 . The compound of  claim 152 , wherein R 1  is selected from the group consisting of 
       
         
           
           
               
               
           
         
       
     
     
         167 . The compound of  claim 152 , wherein R 8  hydrogen or unsubstituted or substituted alkyl, wherein when substituted, the alkyl has one or more substituents independently selected from the group consisting of halo and amino. 
     
     
         168 . The compound of  claim 152 , wherein R 8  is unsubstituted alkyl. 
     
     
         169 . The compound of  claim 168 , wherein R 8  is methyl. 
     
     
         170 . A formulation comprising a compound of  claim 152  and a pharmaceutically acceptable carrier. 
     
     
         171 . A method of treating a bacterial infection in an individual, comprising administering to the individual an effective amount of a compound of  claim 152 .