Figure 1

Synthesis of 1-substituted carbazolyl-1, 2, 3, 4-tetrahydro-β-carboline and carbazolyl-3, 4-dihydro-β-carboline derivatives. (A) Chemical structures of all 12 β-carboline derivatives. 1: 1-(9′-methyl-3′-carbazole)-1, 2, 3, 4-tetrahydro-β-carboline; 2: 1-(9′-ethyl-3′-carbazole)-1, 2, 3, 4-tetrahydro-β-carboline; 3: 1-(9′-propyl-3′-carbazole)-1, 2, 3, 4-tetrahydro-β-carboline; 4: 1-(9′-isopropyl-3′-carbazole)-1, 2, 3, 4-tetrahydro-β-carboline; 5: 1-(9′-[1″-methyl]propyl-3′-carbazolyl)-1, 2, 3, 4-tetrahydro-β-carboline; 6: 1-(9′-[1″-ethyl]propyl-3′-carbazole)-1, 2, 3, 4-tetrahydro-β-carboline; 7: 1-(9′-methyl-3′-carbazole)-3, 4-dihydro-β-carboline; 8: 1-(9′-ethyl-3′-carbazole)-3, 4-dihydro-β-carboline; 9: 1-(9′-propyl-3′-carbazole)-3, 4-dihydro-β-carboline; 10: 1-(9′-isopropyl-3′-carbazole)-3, 4-dihydro-β-carboline; 11: 1-(9′[1″-methyl]propyl-3′-carbazole)-3, 4-dihydro-β-carboline; 12: 1-(9′-[1″-ethyl]propyl-3′-carbazole)-3, 4-dihydro-β-carboline. The core structure of manzamine A is highlighted in red. (B) Preparation scheme of compounds 1–12.