911301-33-2

Upstream product

• 20583-78-2 ethyl (E)-3,4-dimethoxycinnamate 
• 637-81-0 ethyl-2-azidoacetate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 88210-96-2 5,6-dimethoxyindole-2-carboxylic acid 
• 16382-18-6 5,6-dimethoxy-1H-indole-2-carboxylic acid ethyl ester 
• 1380411-91-5 ethyl 4-(3,4-dimethoxyphenyl)-1-methyl-2-phenyl-1H-imidazole-5-carboxylate 
• 1345509-65-0 ethyl 4-(3,4-dimethoxyphenyl)-1,2-diphenyl-1H-imidazole-5-carboxylate 
• 128217-61-8 ethyl 2-(N-(tert-butoxycarbonyl)amino)-3-(3,4-dimethoxyphenyl)propanoate 
• 148806-54-6 3-(3,4-dimethoxyphenyl)alanine ethyl ester 

Relevant academic research and scientific papers

Structural influence of indole C5-N-substitutents on the cytotoxicity of seco-duocarmycin analogs

A series of racemic indole C5-substituted seco-cyclopropylindoline compounds (2,3 and 5-7) were prepared by coupling 1-(tert-butyloxycarbonyl)-3- (chlorocarbonyl)indoline (seg-A) with 5,6,7-trimethoxy-, 5,6-dimethoxy-, 5-amino-, 5-methylsulfonylamino- and 5-(N,N-dimethylaminosulfonylamino) indole-2-carboxylic acid as seg-B in the presence of 1-ethyl-3-(3- dimethylaminopropyl) carbodiimide. The synthetic compounds (2,3 and 5-7) were tested for cytotoxic activity against human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using the MTT assay.

Synthesis of phenylalanine analogs

A straight forward synthesis of phenylalanine analogs is described. Cerium ammonium nitrate (CAN) mediated addition of azide to cinnamicester, followed by reaction with sodium acetate aff orded the α-azidocinnamate in moderate yield. Hydrogenation of α-azidocinnamate, followed by BOC, CBZ or Fmoc protection gave phenylalanine analogs. A new approach for synthesizing racemic p-boronophenylalanine analog was also explored.