865619-25-6

Upstream product

• 67-56-1 methanol 
• 35737-15-6 Fmoc-Trp-OH 
• 446-52-6 2-Fluorobenzaldehyde 
• 4299-70-1 L-tryptophan methyl ester 
• 73-22-3 L-Tryptophan 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 

Downstream Products

• 223690-89-9 1-(2-fluoro-phenyl)-9H-β-carboline-3-carboxylic acid methyl ester 
• 865619-31-4 1-(2-fluoro-phenyl)-2-(2-nitro-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of fused tetrahydro-β-carbolinequinoxalinones in 1-n-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide ([bdmim][Tf2N]) and 1-n-butyl-2,3-dimethylimidazolium perfluorobutylsulfonate ([bdmim][PFBuSO3]) ionic liquids

Starting from tryptophan methyl ester, a three-step synthesis of fused tetrahydro-β-carbolinequinoxalinones in two new ionic liquids, [bdmim][Tf2N] and [bdmim][PFBuSO3], was described. Both ionic liquids can be readily prepared from commercially available starting materials in high yields. Unlike the commonly used [PF6]-based ionic liquids that evidently undergo slow hydrolysis of the PF6 anion with the concomitant release of HF, ionic liquids of [bdmim][Tf2N] and [bdmim][PFBuSO3] are not only chemically stable but also apparently inert to hydrolysis and therefore organic reactions carried out in both ionic liquids proceed smoothly with good yields. The overall isolated yields for this three-step synthesis of tetrahydro-β-carbolinequinoxalinones were 34-55%. To the best of our knowledge, the preparation of fused tetrahydro-β- carbolinequinoxalinones was unprecedented.

Synthesis and evaluation of novel hybrids β-carboline-4-thiazolidinones as potential antitumor and antiviral agents

A series of novel hybrids β-carboline-4-thiazolidinones were synthesized and evaluated for their in vitro antitumor activity against human cancer cell lines and for antiviral activity towards Herpes simplex virus type-1 (HSV-1). From the N′-(2-ylidene-4-thiazolidinone)-β-carboline-3-carbohydrazide series (9–11), compounds 9c and 11d were the most active, showing growth inhibition 50% (GI50) values less than 5 μM for all cell lines tested. Compound 9c, bearing the 4-dimethylaminophenyl group at C-1 of β-carboline was selected for further investigation concerning cell death and cell cycle profile, focusing on the human renal adenocarcinoma cell line 786-0. Treatments with 25 μM of compound 9c induced cell death after 15 h of treatment, characterized by phosphatidylserine exposure and loss of membrane integrity. Moreover, treatment with 12.5 μM promoted a sub-G1 arrest, which indicates cell death. Derivatives of the N-(2-substituted-aryl-4-thiazolidinone)-β-carboline-3-carboxamide series (18–23) showed a potent activity and high selectivity for glioma (U251) and ovarian (OVCAR-3) cancer cell lines. Also, some β-carboline-4-thiazolidinone hybrids showed potent antiviral activity against Herpes simplex virus type-1. The N-(2-substituted-aryl-4-thiazolidinone)-carboxamide moiety in 18, 19 and 22 confer a potent anti-HSV-1 activity for these derivatives, which presented EC50values of 0.80, 2.15 and 2.02 μM, respectively. The assay results showed that the nature of 4-thiazolidinone moiety and of the substituent attached at the 3- and 1- position of β-carboline nucleus influenced the antitumor and antiviral activities.

Parallel synthesis of 1,2,3,4-tetrahydro-β-carbolines using microwave irradiation

Novel soluble polymer supported synthesis of 1,2,3,4-tetrahydro-β-carboline derivatives in the microwave oven is reported. Commercially available Fmoc-protected tryptophan was directly anchored to MeO-PEG-OH via an ester linkage in the presence of DCC and DMAP. One pot cyclocondensation of polymer-bound tryptophan with a variety of aldehydes and ketones has been carried out under microwave irradiation to provide immobilized 1,2,3,4-tetra-hydro-β-carboline derivatives. The desired products were then liberated from the soluble matrix in good yield and good purity.