1438393-75-9

Upstream product

• 57778-93-5 1H-indol-3-amine hydrochloride 
• 1438393-65-7 diethyl 5H-pyrimido[5,4-b]indole-2,4-dicarboxylate 
• 1438393-71-5 ethyl 4-(hydroxymethyl)-5H-pyrimido[5,4-b]indole-2-carboxylate 
• 1438393-72-6 2-(ethoxycarbonyl)-5H-pyrimido[5,4-b]indole-4-carboxylic acid 
• 1438393-73-7 ethyl 4-(4-methoxybenzoyl)-5H-pyrimido[5,4-b]indole-2-carboxylate 
• 1438393-74-8 (4-methoxyphenyl)(5H-pyrimido[5,4-b]indol-4-yl)methanone 
• 1438393-76-0 5H-pyrimido-[5,4-b]indole-4-carboxylic acid 
• 771-50-6 1H-indole-3-carboxylic acid 
• 1199215-71-8 tert-butyl 1H-indol-3-ylcarbamate 

Relevant academic research and scientific papers

Design and Synthesis of Aza-β-Carboline Analogs and their Antibacterial Evaluation

Bacterial drug resistance has become a growing problem worldwide due to the excessive use of antibiotics in recent decades. Two small focused libraries of 5H-pyrimido[5,4-b]indole-4-carboxamides and 5H-pyrimido-[5,4-b]indole-4-ketones were designed as eudistomin Y3 and 1-acetyl-β-carboline (1-ABC) analogs and prepared via application of Inverse Electron-Demand Diels-Alder (IEDDA) reaction of 1,3,5-triazines and 3-aminoindoles. Compounds 2a and 2b were discovered to have activity against Mycobacterium bovis BCG with Minimum Inhibitory Concentration (MICs) values of 25 and 50 μg/mL respectively while compound 2e was against all three strains of Candida albicans tested with MIC values of 50 μg/mL. Moreover, compound 2e demonstrated synergistic antibacterial activity with fluconazol, which suggested that future drug candidates from this class of compounds could be used in combination with existing drugs to treat C. albicans infections.

Total synthesis of 4-azaeudistomin Y1 and analogues by inverse-electron demand diels-alder reactions of 3-aminoindoles with 1,3,5-triazines

A new inverse-electron-demand Diels-Alder (IDA) reaction of 3-aminoindoles as dienophiles was developed for the efficient preparation of 4-aza-β-carbolines in high yields. Because N1-unprotected 3-aminoindoles show poor thermal stability, a one-pot protocol was developed that combines the removal of tert-butoxycarbonyl protecting groups with the IDA reaction. This protocol, using tert-butyl 1H-indol-3-ylcarbamates as reactants, gave the corresponding IDA products in excellent yields. The new IDA methodology was used in a total synthesis of 4-azaeudistomin Y1, which was obtained in 57% overall yield in four steps. Moreover, the chemistry is suitable for the rapid preparation, through either Friedel-Crafts acylation or amide-formation reactions, of analogues that are useful for exploring structure-activity relationships at the C1-position. Georg Thieme Verlag Stuttgart · New York.