Small-molecule modulators of melanin expression

Abstract

The present invention relates to small molecule modulators of melanin expression and methods of making the small molecules. Also disclosed are methods of increasing pigmentation in a cell which involve providing compounds of the present invention and contacting a cell with the compounds under conditions effective to induce melanin expression in the cell, thereby increasing pigmentation. The present invention also relates to compositions containing compounds of the present invention and a carrier.

1 . A compound formed by a reaction of a carboxylic acid and an amine, wherein the carboxylic acid is selected from: 
       
         
           
           
               
               
           
         
         and the amine is selected from: 
       
       
         
           
           
               
               
           
         
       
     
     
         2 . The compound according to  claim 1 , wherein the compound is selected from the group of N-(4-fluorophenethyl)-2-ethylquinoline-3-carboxamide; N-(3-fluorophenethyl)-2-ethylquinoline-3-carboxamide; N-((furan-2-yl)methyl)furan-2-carboxamide; N-butylfuran-2-carboxamide; N-(4-fluorophenethyl)furan-2-carboxamide; N-(3-fluorophenethyl)furan-2-carboxamide; (furan-2-yl)(2,2,6,6-tetramethylpiperidin-1-yl)methanone; (2,2,6,6-tetramethylpiperidin-1-yl)(perfluorophenyl)methanone; 2,3,4,5,6-pentafluoro-N-(5-methylisoxazol-3-yl)benzamide; and (benzo [d][1,3]dioxol-5-yl)(4-(4-fluorophenyl)piperazin-1-yl)methanone. 
     
     
         3 . A method of increasing pigmentation in a cell, said method comprising:
 providing a compound according to  claim 1  and   contacting a cell with the compound under conditions effective to induce melanin expression in the cell, thereby increasing pigmentation.   
     
     
         4 . The method according to  claim 3 , wherein the compound is selected from the group of N-(4-fluorophenethyl)-2-ethylquinoline-3-carboxamide; N-(3-fluorophenethyl)-2-ethylquinoline-3-carboxamide; N-((furan-2-yl)methyl)furan-2-carboxamide; N-butylfuran-2-carboxamide; N-(4-fluorophenethyl)furan-2-carboxamide; N-(3-fluorophenethyl)furan-2-carboxamide; (furan-2-yl)(2,2,6,6-tetramethylpiperidin-1-yl)methanone; (2,2,6,6-tetramethylpiperidin-1-yl)(perfluorophenyl)methanone; 2,3,4,5,6-pentafluoro-N-(5-methylisoxazol-3-yl)benzamide; and (benzo[d][1,3]dioxol-5-yl)(4-(4-fluorophenyl)piperazin-1-yl)methanone. 
     
     
         5 . The method according to  claim 3 , wherein the cell is in vitro. 
     
     
         6 . The method according to  claim 3 , wherein the cell is in vivo. 
     
     
         7 . The method according to  claim 6  further comprising:
 administering the compound to a subject under conditions effective to cause the compound to contact the cell. 
 
     
     
         8 . A composition comprising a compound according to  claim 1  and a carrier. 
     
     
         9 . The composition according to  claim 8 , wherein the carrier is selected from the group of lotion, gel, solution, or aerosol. 
     
     
         10 . The composition according to  claim 8  in the form of a sunless tanning lotion. 
     
     
         11 . A method of increasing skin pigmentation, said method comprising:
 applying a composition according to  claim 8  to skin on a subject in a manner and quantity effective to induce melanin production in contacted skin cells, thereby increasing skin pigmentation within a treated area of the skin.   
     
     
         12 . The method according to  claim 11 , wherein the compound is selected from the group of N-(4-fluorophenethyl)-2-ethylquinoline-3-carboxamide; N-(3-fluorophenethyl)-2-ethylquinoline-3-carboxamide; N-((furan-2-yl)methyl)furan-2-carboxamide; N-butylfuran-2-carboxamide; N-(4-fluorophenethyl)furan-2-carboxamide; N-(3-fluorophenethyl)furan-2-carboxamide; (furan-2-yl)(2,2,6,6-tetramethylpiperidin-1-yl)methanone; (2,2,6,6-tetramethylpiperidin-1-yl)(perfluorophenyl)methanone; 2,3,4,5,6-pentafluoro-N-(5-methylisoxazol-3-yl)benzamide; and (benzo [d][1,3]dioxol-5-yl)(4-(4-fluorophenyl)piperazin-1-ylmethanone. 
     
     
         13 .- 20 . (canceled)