352015-84-0

Upstream product

• 6527-32-8 4-(benzyloxy)-3,5-dimethoxybenzaldehyde 
• 4299-70-1 L-tryptophan methyl ester 

Downstream Products

• 352015-94-2 2-{[1-(4-benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 352015-95-3 2-{[1-(4-benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 352015-96-4 (R)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 352015-97-5 (S)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 352015-90-8 (R)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-3-phenyl-propionic acid methyl ester 
• 352015-91-9 (S)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-3-phenyl-propionic acid methyl ester 
• 352015-92-0 (R)-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-phenyl-acetic acid methyl ester 
• 352015-93-1 (S)-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-phenyl-acetic acid methyl ester 
• 352015-99-7 (S)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-4-methylsulfanyl-butyric acid methyl ester 
• 352015-98-6 (R)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-4-methylsulfanyl-butyric acid methyl ester 
• 352015-87-3 (S)-1-[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-pyrrolidine-2-carboxylic acid methyl ester 
• 352015-86-2 (R)-1-[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-pyrrolidine-2-carboxylic acid methyl ester 
• 352016-07-0 (S)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-4-methyl-pentanoic acid methyl ester 
• 352016-06-9 (R)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-4-methyl-pentanoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of diketopiperazine-based carboline homodimers and in vitro growth inhibition of human carcinomas

Starting from d- or l-tryptophan, we have synthesized and characterized six compounds 2.29-2.31a and b that belong to a class of nitrogen heterocycles: the carboline-based homodimers. Each individual homodimer features a 1,3-trans relationship on each side of the central diketopiperazine core, but differs in absolute stereochemistry and also in substitution on the 4′ and 4″ oxygens (-Bn, -CH3, or -H). The in vitro cytotoxicity of the six compounds was evaluated by measuring the growth inhibition in NCI-H520 and PC-3 human carcinoma cells. Phenol 2.30a inhibited cancer cell growth approximately three times better than its enantiomer 2.30b and possessed a GI50 comparable to the clinically used agent etoposide in both cell lines. We have concluded that both the stereochemistry imparted by l-tryptophan and the presence of hydroxy substituents at the 4′ and 4″ positions are necessary to generate cytotoxic properties in the homodimer class. We are now employing 2.30a as a new lead compound in our efforts to discover improved indole-based cancer chemotherapeutics.

The synthesis of amino-acid functionalized β-carbolines as topoisomerase II inhibitors

The synthesis and biological activity of amino acid functionalized β-carboline derivatives, which are structurally related to azatoxin and the tryprostatins, are reported. These compounds were assayed for their growth inhibition properties in H520 and PC3