352015-85-1

Basic information

• Product Name: (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• Synonyms: (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• CAS NO: 352015-85-1
• Molecular Weight: 458.514
• Mol File: 352015-85-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(352015-85-1)
• EPA Substance Registry System: (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(352015-85-1)

Safety Data

• Hazardous Substances Data: 352015-85-1(Hazardous Substances Data)

Upstream product

• 4299-70-1 L-tryptophan methyl ester 
• 6527-32-8 4-(benzyloxy)-3,5-dimethoxybenzaldehyde 
• 352015-84-0 methyl (3S,1R)-1-[3,5-dimethoxy-4-(phenylmethoxy)phenyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate 

Downstream Products

• 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 
• 352016-03-6 (S)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-3-hydroxy-propionic acid methyl ester 
• 352016-02-5 (R)-2-{[(1R,3S)-1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carbonyl]-amino}-3-hydroxy-propionic acid methyl ester 

Relevant articles and documents

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.