Small-molecule modulators of melanin expression
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 composition comprising a compound according to formula (I)
wherein
R 1 is selected from straight or branched chain C 1 to C 6 hydrocarbon;
R 2 is selected from H, —O—R 3 , —NH—R 3 , and —S—R 3 , where R 3 is selected from H, straight or branched chain C 1 to C 6 hydrocarbon, and alkoxyalkyl;
W is optional and can be a straight or branched chain C 1 to C 6 hydrocarbon, —(CH 2 ) p NH—, or —(CH 2 ) p N(CH 3 )—, where p is an integer from 0 to 3;
X is selected from (CH 2 ) n , O, —(CH 2 ) q NH—, or —(CH 2 ) q N(CH 3 )—, where n is an integer from 0 to 8 and q is an integer from 0 to 3;
Y is selected from (CH 2 ) m —, where m is an integer from 0 to 3; and
Z is selected from
where Q is selected from H and halogen,
and a carrier, wherein the composition is in the form of a sunless tanning lotion.
2. A compound selected from the group of N-(4-fluorophenethyl)-2-ethylquinoline-3-carboxamide and N-(3-fluorophenethyl)-2-ethylquinoline-3-carboxamide.
3. The compound according to claim 2 , wherein the compound is N-(4-fluorophenethyl)-2-ethylquinoline-3-carboxamide.
4. The compound according to claim 2 , wherein the compound is N-(3-fluorophenethyl)-2-ethylquinoline-3-carboxamide.
5. A composition comprising a compound according to claim 2 and a carrier.
6. The composition according to claim 5 , wherein the carrier is selected from the group of lotion, gel, solution, or aerosol.