220448-44-2

Upstream product

• 1816-92-8 Methyl azidoacetate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 637-81-0 ethyl-2-azidoacetate 
• 124-41-4 sodium methylate 

Downstream Products

• 1158503-82-2 C₁₀H₈BrNO₂ 
• 167479-13-2 4-bromo-1H-indole-2-carboxylic acid methyl ester 
• 1362861-11-7 methyl 3-(2,5-dimethoxyphenyl)-4-(4-methoxyphenyl)-1H-indole-2-carboxylate 
• 1362861-10-6 methyl 3-(2-methoxyphenyl)-4-(4-methoxyphenyl)-1H-indole-2-carboxylate 
• 1362861-03-7 methyl 3-iodo-4-(4-methoxyphenyl)-1H-indole-2-carboxylate 
• 1362861-01-5 methyl 4-(4-methoxyphenyl)-1H-indole-2-carboxylate 
• 1362861-29-7 2-hydroxy-11-(4-hydroxyphenyl)chromeno[3,4-b]indole-6(7H)-one 
• 1362861-28-6 11-(4-hydroxyphenyl)chromeno[3,4-b]indole-6(7H)-one 

Relevant academic research and scientific papers

Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry

Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chemistry, allowing formation of peptide adducts which can be subsequently labeled with fluorine tags.

Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: A novel DYRK1A inhibitor class

A library of substituted chromeno[3,4-b]indoles was developed as Lamellarin isosters. Synthesis was achieved from indoles after a four-step pathway sequence involving C-3 iodination, a Suzuki cross-coupling reaction, and a one pot deprotection/lactonisation step. Twenty final compounds were tested in order to determine their activity against topoisomerase I and kinases, the two major biological activities of Lamellarins. One newly synthesized derivative exhibited a strong topoisomerase activity comparable to reference compounds such as campthotecin and Lamellarin with only a weak kinase inhibition. Two other lead compounds were identified as new nanomolar DYRK1A inhibitors and several other drugs affected the kinases in the sub-micromolar range. These results will enable us to use the chromeno[3,4-b]indole as a pharmacophore to develop potent treatments for neurological or oncological disorders in which DYRK1A is fully involved.