||(+/-)-7-Hydroxy-1,2,3,4-tetrahydro-3-isoquinoline-4-carboxylic acid methyl ester
||6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid methyl ester hydrochloride; methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate hydrochloride; REF DUPL: (+/-)-7-Hydroxy-1,2,3,4-tetrahydro-3-isoquinoline-4-carboxylic acid methyl ester,
||Data not available, please inquire.
1.Potent 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid-based macrocyclic inhibitors of hepatitis C virus NS3 protease.
Chen KX1, Njoroge FG, Pichardo J, Prongay A, Butkiewicz N, Yao N, Madison V, Girijavallabhan V. J Med Chem. 2006 Jan 26;49(2):567-74.
The NS3 protease of hepatitis C virus (HCV) has emerged as one of the best characterized targets for next-generation HCV therapy. The tetrapeptide 1 and pentapeptide 2 are alpha-ketoamide-type HCV serine protease inhibitors with modest potency. We envisioned that the 1,2,3,4-tetrahydroisoquinoline-3-carboxylamide (Tic) moiety could be cyclized to the P3 capping group. The resulting macrocycle could enhance the binding through its extra contact with the Ala156 methyl group. Macrocyclization could also provide a less peptidic HCV inhibitor. Synthesis started from dipeptide 5, which was obtained via a coupling of two amino acid derivatives. The N-terminal was capped as hept-6-enoylamide to give 6. Hydroboration of the double bond afforded alcohol 7, the precursor to the macrocycle 8. The macrocyclization was achieved under Mitsunobu conditions (PPh(3), ADDP). The macrocyclic acid 9 was then combined with appropriate right-hand fragments 12, 14, or 16, which was prepared from common intermediate 11.