869304-55-2

Upstream product

• 73-22-3 L-Tryptophan 
• 100-83-4 meta-hydroxybenzaldehyde 
• 869304-05-2 (1S,3S)-1-(3-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid 
• 3173-56-6 benzyl isothiocyanate 
• 869304-52-9 (5S,11aS)-2-benzyl-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione 
• 4299-70-1 L-tryptophan methyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 33696-06-9 3-benzoyloxybenzaldehyde 
• 1223077-66-4 (1R,3S)-methyl 1-(3-(benzoyloxy)phenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 
• 100-46-9 benzylamine 
• 1223077-74-4 (5R,11aS)-2-benzyl-5-(3-benzoyloxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione 
• 153-94-6 D-tryptophan 
• 869304-06-3 (1R,3R)-1-(3-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid 
• 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 

Relevant academic research and scientific papers

A general strategy for the highly stereoselective synthesis of HR22C16-like mitotic kinesin Eg5 inhibitors from both l- and d-tryptophans

An efficient and general strategy for the highly stereoselective synthesis of HR22C16-like mitotic kinesin Eg5 inhibitors 1 from both l- and d-tryptophan methyl ester hydrohalides is described. (1R,3S)-trans-1,3-Disubstituted 1,2,3,4-tetrahydro-β-carbolines (1R,3S)-trans-2 could be obtained in high yields and with high stereoselectivities from the Pictet-Spengler reaction of l-tryptophan methyl ester hydrohalide with some 3-acyloxyl benzaldehydes via a CIAT (crystal induced asymmetric transformation) process, whereas (1R,3R)-cis-1,3-disubstituted 1,2,3,4-tetrahydro-β-carbolines (1R,3R)-cis-2 could also be obtained in high yields and with high stereoselectivities from a Pictet-Spengler reaction of d-tryptophan methyl ester hydrohalide with some other 3-acyloxyl benzaldehydes via a CIAT process. Both compounds (1R,3S)-trans-2 and (1R,3R)-cis-2 were efficiently converted into HR22C16-like mitotic kinesin Eg5 inhibitors 1 by the same one-pot procedure through tandem reactions. A total of eighteen target compounds 1 were obtained from six intermediate compounds 2 in 87-95% yields.

The first highly stereoselective approach to the mitotic kinesin Eg5 inhibitor HR22C16 and its analogues

A general method for the synthesis of the mitotic kinesin Eg5 inhibitor HR22C16 1 and its analogues based on protecting group (PG)-modulated highly diastereoselective Pictet-Spengler reaction of l-tryptophan methyl ester hydrochloride with meta-(RO)-benzaldehyde is described. By using the enantiomerically pure (1R,3S)-1,3-disubstituted tetrahydro-β-carboline trans-4c as a common chiral synthon, HR22C16 1 and its analogues 2 and 3 were synthesized in 90.1%, 90.2%, and 86.5% overall yields, respectively.

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