89827-54-3

Upstream product

• 15741-79-4 N-benzyl tryptamine 
• 922-67-8 propynoic acid methyl ester 
• 61-54-1 tryptamine 
• 100-52-7 benzaldehyde 
• 16979-93-4 N-benzylidene-2-(1H-indol-3-yl)ethylamine 

Downstream Products

• 140406-29-7 2-benzyl-1-carbomethoxymethyl-9-methyl-1,2,3,4-tetrahydro-β-carboline 
• 256407-56-4 tert-butyl 1-(2-methoxy-2-oxoethyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate 
• 1027091-17-3 9-Benzenesulfonyl-1-(2-methanesulfonyloxy-1-methoxycarbonyl-but-3-enyl)-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester 
• 157024-91-4 methyl 2-(9-benzenesulfonyl-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-β-carbolin-1-yl)-3-hydroxy-4-pentenoate 
• 157024-90-3 methyl 9-benzenesulfonyl-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-β-carboline-1-acetate 
• 157024-97-0 methyl 13-benzenesulfonyl-3,4,7,8,13,13b-hexahydro<1', 2'>oxazepino<2',3':1,2>pyrido<3,4-b>indole-1-carboxylate 
• 157024-89-0 methyl 9-benzenesulfonyl-1,2,3,4-tetrahydro-β-carboline-1-acetate 
• 920515-43-1 [2-(2-ethyl-allyl)-9-(toluene-4-sulfonyl)-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl]-acetic acid methyl ester 
• 920515-41-9 3-ethyl-12-(toluene-4-sulfonyl)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine-2,3-diol 
• 920515-42-0 3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-3,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-2-one 
• 920515-44-2 1-allyl-2-(2-ethyl-allyl)-9-(toluene-4-sulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline 

Relevant academic research and scientific papers

Design and synthesis of Pictet-Spengler condensation products that exhibit oncogenic-RAS synthetic lethality and induce non-apoptotic cell death

A series of Pictet-Spengler condensation derivatives (tetrahydro-β- carbolines) was designed, synthesized and evaluated for lethality against a panel of seven cancer cell lines. Seven compounds (2a, 13, 20, 21, 27, 29 and 34) showed lethality in at least five cell lines. Among these, compound 27 showed a unique selectivity towards oncogenic-RAS expressing BJ-TERT/LT/ST/RASV12 tumor cells, compared to non-transformed BJ-TERT cells. Further investigation revealed that 27 induces cell death without activation of caspases. This represents a useful new probe of non-apoptotic cell death and oncogenic-RAS synthetic lethality.

A ring closing metathesis approach to the indole alkaloid mitralactonine

An efficient utilisation of RCM leading to a convenient synthesis of a pentacyclic indole alkaloid is described.

Synthesis of ajmalicine derivatives using Wittig-Horner and Knoevenagel reactions

2-(2,3,4,9-Tetrahydro-1H-β-carbolin-1-yl)acetaldehyde, synthesized from tryptamine in five steps, is easily homologated by Wittig-Horner or Knoevenagel reactions to substituted acrylates. These highly reactive compounds are key intermediates in the synthesis of analogs of the natural indol alkaloid ajmalicine.