Abstract A series of N-1 or C-2 phenylalkyl substituted tryptophans and C-1 phenylalkyl substituted 3, 4-dihydro-β-carbolines were prepared from the apropriate aniline, 1b or 1e, or tryptophan, 8 or 11, by ring closure methods. None of the compounds prepared were more potent than 5-bromotryptophan (11) as inhibitors of sickle cell hemoglobin gelation.