266674-75-3

Upstream product

• 4302-52-7 4-ethynylveratrole 
• 266674-73-1 dimethyl 4-(4,5-dimethoxy-2-(methoxymethoxy)phenyl)-5-(3,4-dimethoxyphenyl)-1,2-diazine-3,6-dicarboxylate 
• 266674-80-0 2-(3,4-dimethoxy-phenylethynyl)-4,5-dimethoxy-phenol 
• 266674-71-9 2-[(3,4-dimethoxyphenyl)ethynyl]-4,5-dimethoxybenzaldehyde 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 570402-54-9 dimethyl 1-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-bis(trifluoromethanesulfonyloxy)pyrrole-2,5-dicarboxylate 
• 570402-52-7 dimethyl 3,4-dihydroxy-1-[2-(3,4-dimethoxyphenyl)ethyl]pyrrole-2,5-dicarboxylate 
• 570402-50-5 dimethyl N-[2-(3,4-dimethoxyphenyl)ethyl]iminodiacetate 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 2859-78-1 4-Bromoveratrole 
• 570402-63-0 4,5-dimethoxy-2-(methoxymethoxy)phenylboronic acid 
• 570402-62-9 3-(3,4-dimethoxy-phenyl)-1-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-trifluoromethanesulfonyloxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester 
• 40173-90-8 3,4-dimethoxyphenethyl bromide 

Downstream Products

• 266674-77-5 7,8-dimethoxy-3-(2-(3,4-dimethoxyphenyl)ethyl)-1-(3,4-dimethoxyphenyl)-[1]-benzopyrano[3,4-b]pyrrol-4(3H)-one-2-carboxylic acid 
• 266674-78-6 1-(3,4-dimethoxyphenyl)-3-[2-(3,4-dimethoxyphenyl)ethyl]-7,8-dimethoxy-4-oxo-3H-[1]benzopyrano[3,4-b]pyrrole-4-one 
• 181423-71-2 14-(3,4-dimethoxyphenyl)-2,3,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 266674-76-4 methyl 7,8-dimethoxy-3-(2-(3,4-dimethoxyphenyl)ethyl)-1-(3,4-dimethoxyphenyl)-[1]-benzopyrano[3,4-b]pyrrol-4(3H)-one-2-carboxylate 

Relevant academic research and scientific papers

Short and flexible route to 3,4-diarylpyrrole marine alkaloids: Syntheses of permethyl storniamide A, ningalin B, and lamellarin G trimethyl ether

A highly efficient route to 3,4-diarylpyrrole marine alkaloids has been developed using Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki cross-coupling of the 3,4-dihydroxypyrrole bis-triflate derivatives as key reactions. Based on this approach, formal syntheses of permethyl storniamide A and ningalin B, and a total synthesis of lamellarin G trimethyl ether have been achieved.

Ningalin b analogs employable for reversing multidrug resistance

Anlogs of ningalin B lacking inherent cytotoxic activity may be employed to reverse multi-drug resistant (MDR) phenotype and to resensitize transformed cells, including a human colon cancer cell line (HCT116/VM46), with respect to a variety of cytotoxic agents, e.g., vinblastine and doxorubicin. In many instances, resensitization is achieved at lower doses than the prototypical agent verapamil. Total synthesis of ningalin B and its analogs was achieved using a concise, efficient approach based on a heterocyclic azadiene Diels-Alder strategy (1,2,4,5-tetrazine → 1,2-diazine → pyrrole) ideally suited for construction of the densely functionalized pyrrole core found in the natural product is detailed.

Total synthesis of Ningalin B utilizing a heterocyclic azadiene Diels- Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents

A concise, efficient approach to the total synthesis of ningalin B (1) based on a heterocyclic azadiene Diels-Alder strategy (1,2,4,5-tetrazine → 1,2-diazine → pyrrole) ideally suited for construction of the densely functionalized pyrrole core found in the natural product is detailed. Examination of the natural product and a number of synthetic intermediates revealed that while lacking inherent cytotoxic activity, many reverse the multidrug-resistant (MDR) phenotype, resensitizing a human colon cancer cell line (HCT116/VM46) to vinblastine and doxorubicin at lower doses than the prototypical agent verapamil.