869304-06-3

Basic information

• Product Name: (1R,3R)-1-(3-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid
• Synonyms: (1R,3R)-1-(3-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid
• CAS NO: 869304-06-3
• Molecular Weight: 308.337
• Mol File: 869304-06-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,3R)-1-(3-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R)-1-(3-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid(869304-06-3)
• EPA Substance Registry System: (1R,3R)-1-(3-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid(869304-06-3)

Safety Data

• Hazardous Substances Data: 869304-06-3(Hazardous Substances Data)

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 73-22-3 L-Tryptophan 
• 153-94-6 D-tryptophan 

Downstream Products

• 869304-23-4 (5R,11aR)-5-(3-hydroxyphenyl)-2-propyl-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione 
• 1186579-61-2 (5R,11aR)-2-(4-benzoic acid ethyl ester)-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione 
• 869304-26-7 (5R,11aR)-2-butyl-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione 
• 869304-19-8 (5R,11aR)-2-ethyl-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione 
• 869304-54-1 (5R,11aR)-2-benzyl-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione 
• 869304-48-3 (5R,11aR)-5-(3-hydroxyphenyl)-2-phenyl-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione 
• 869304-29-0 (5R,11aR)-5-(3-hydroxyphenyl)-2-pentyl-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione 
• 462630-41-7 (5R,11aS)-2-butyl-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione 
• 869304-55-2 (5R,11aS)-2-benzyl-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione 

Relevant articles and documents

Design, synthesis and anticancer evaluation of tetrahydro-β-carboline-hydantoin hybrids

A series of new tetrahydro-β-carboline-hydantoin hybrids have been designed and synthesized based on the structure of the known Eg5 inhibitor HR22C16. These compounds have been evaluated for their anticancer activity against lung (A549), cervical (ME180, HeLa), prostate (PC-3) and breast (MCF-7) cancer cell lines by MTT assay. These hybrids have displayed significant in vitro cytotoxicity in comparison to etoposide against PC-3, A549, and MCF-7 cell lines. The hybrids 3a, 3b, 3c, 3e, 3f, 3g, 4b, 4c, 4e and 4f appear to be more effective against the PC-3 cell line, among which compound 4b displayed the highest cytotoxicity (6.08 ± 0.2, IC50 μM). Based on these results, an attempt was made to rationalize their mechanism of action through cell cycle analysis studies. The flow-cytometric analysis of compound 4b in PC-3 cells indicated a G2/M cell cycle arrest. Molecular docking studies substantiate that these compounds indeed bind to the allosteric site of Eg5 formed from Glu116, Gly117, Glu118, Trp127, Ala133, Ile136, Pro137, Tyr211, Leu214, and Glu215 residues with the most potent compound 4b showing the most favorable interaction.

Synthesis and biological evaluation of new tetrahydro-β-carbolines as inhibitors of the mitotic kinesin Eg5

The mitotic kinesin Eg5 (or KSP) is a crucial player in the development and function of the mitotic spindle. Inhibition of this protein leads to cell cycle arrest and apoptosis without interfering with other microtubule-dependent processes. Therefore, it