Isolation, purification, and structure elucidation of the antiproliferative compound coibamide A
View Patent ↗Novel antiproliferative compounds, compositions comprising the same, and methods of use thereof are disclosed.
1. An isolated compound of formula I or a pharmaceutically acceptable salt thereof,
wherein:
R 1 =Me or H;
R 2 =Me or H;
R 3 =L/D N,N-dimethylvaline, L/D valine, L/D leucine, L/D isoleucine, or L/D allo-isoleucine;
R 4 =O, NH, S, or NMe;
R 5 =L/D 2-hydroxyisovaleric acid, L/D valine, L/D leucine, L/D isoleucine, or L/D allo-isoleucine;
R 6 =H or Me;
R 7 =L/D serine or L/D O-methylserine;
R 8 =H or Me;
R 9 =L/D leucine, L/D valine, L/D isoleucine, or L/D allo-isoleucine;
R 10 =Me or H;
R 11 =H, Me, CH 3 CH 2 —, or CH 3 CH 2 CH 2 —;
R 12 =O, N, or S;
R 13 =L/D alanine;
R 14 =H or Me;
R 15 =L/D tyrosine, L/D O-methyl tyrosine, or L/D phenylalanine;
R 16 =H or Me;
R 17 =L/D leucine, L/D valine, L/D isoleucine, or L/D allo-isoleucine;
R 18 =H or Me;
R 19 =L/D alanine;
R 20 =H or Me;
R 21 =L/D isoleucine, L/D allo-isoleucine, L/D leucine, or L/D valine;
R 22 =H or Me;
R 23 =L/D serine or L/D O-methyl-serine; and
R 24 =H or Me,
wherein R 3 , R 5 , R 7 , R 9 , R 13 , R 15 , R 17 , R 19 , R 21 , and R 23 are the amino acid side chains of the listed amino acids.
2. The compound of claim 1 , wherein the compound is:
3. A composition comprising at least one compound of claim 1 and at least one pharmaceutically acceptable carrier.
4. The composition of claim 3 , further comprising at least one chemotherapeutic agent.