601520-76-7

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 62500-88-3 2-(5-ethyl-1H-indol-3-yl)ethylamine 
• 589-16-2 4-aminoethylbenzene 
• 54840-34-5 (4-ethylphenyl)hydrazine 
• 136281-75-9 (5-ethyl-1H-indol-3-yl)acetonitrile 
• 107-08-4 1-iodo-propane 

Downstream Products

• 1073542-94-5 C₂₃H₃₀N₂O 

Relevant academic research and scientific papers

Antioxydant activity of β-carboline derivatives in the LDL oxidation model

A series of β-carboline compounds were synthesized, starting from compound GWC22, their antioxidant activity was determined by inhibition of lipid peroxidation. The oxidation of LDL was induced in the presence of CuSO 4 or 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH). The protective actions of these compounds against the cytotoxicity were evaluated with lactate dehydrogenase (LDH) activity in bovine aortic endothelial cells (BAECs) and cellular vitality by measuring mitochondrial activity in the presence of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide). Most of compounds showed an higher antioxidant activity than GWC22 derivative (R = 1.6 for 5 μM CuSO4). The best antioxidant activities are phenolic and benzyloxy derivatives with ratio R = 1.9 to 2.8 for 1 μM CuSO4. These substances have protective actions and increase significantly the cell viability.

A mild and efficient route to 2-benzyl tryptamine derivatives via ring-opening of β-carbolines

We described a mild and easy method, in two steps, by which various benzyl groups were introduced in the C-2 position of tryptamine. The first step consisted on the synthesis of β-carbolines, starting from tryptamine derivatives, by a Pictet-Spengler reaction. Ring-opening of the β-carbolines, by hydrogenation, led to the desired 2-substituted benzyl tryptamine indole products. A supplementary step of alkylation could be realized to give N-alkyl-2-substituted benzyl tryptamine. During these reactions, nitrogen atoms require no step of protection.

Antioxidant activity of pinoline analogues in the LDL oxidation model

Recently it has been shown that pinoline (6-methoxy-1,2,3,4-tetrahydro-β-carboline) is as potent as melatonin in the inhibition of lipid peroxidation. We have synthesized some 1-aryl-1,2,3,4-tetrahydro-β-carbolines and investigated their ability to prevent LDL copper-induced peroxidation in comparison with melatonin and pinoline. In this model, we found that the introduction of a phenyl group in position 1 of the β-carboline skeleton resulted in more active compounds. The presence ofa methoxy group in position 6 of the β-carboline skeleton had a beneficial influence on this activity, whereas replacement of this methoxy by an ethyl side chain increased the antioxidant potency. On the other hand, substitution of the 1-phenyl substituent with a methoxy group did not affect the activity. Finally, compounds bearing a propyl group on position 2 of the β-carboline skeleton are the most active. Taken together these results confirm the role of lipophilicity in the ability to inhibit LDL oxidation.