219783-09-2

Upstream product

• 61404-52-2 3-(3,4,5-trimethoxyphenyl)pyruvic acid 
• 55-81-2 4-Methoxyphenethylamine 
• 220230-99-9 dimethyl 4,5-bis(3,4,5-trimethoxyphenyl)-1,2-diazine-3,6-dicarboxylate 
• 220231-01-6 3,4-bis-(3,4,5-trimethoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester 
• 220230-97-7 3,3',4,4',5,5'-hexamethoxydiphenylacetylene 
• 143287-98-3 3,4,5-trimethoxyphenyl trifluoromethanesulfonate 
• 53560-33-1 3,4,5-trimethoxyphenylacetylene 
• 220231-03-8 dimethyl 3,4-bis(3,4,5-trimethoxyphenyl)-1-<2-(4-methoxyphenyl)ethyl>pyrrole-2,5-dicarboxylate 

Downstream Products

• 220231-07-2 3,4-bis(3,4,5-trimethoxyphenyl)-1-<2-(4-methoxyphenyl)ethyl>pyrrole-2,5-biscarboxamide 
• 219783-10-5 1-[2-(4-methoxy-phenyl)-ethyl]-3,4-bis-(3,4,5-trimethoxy-phenyl)-1H-pyrrole-2,5-dicarboxylic acid diamide 
• 220231-09-4 E,Z-3,4-bis(3,4,5-trimethoxyphenyl)-1-<2-(4-methoxyphenyl)ethyl>pyrrole-2,5-biscarboxamide 
• 220231-11-8 Z,Z-3,4-bis(3,4,5-trimethoxyphenyl)-1-<2-(4-methoxyphenyl)ethyl>pyrrole-2,5-biscarboxamide 

Relevant academic research and scientific papers

Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels - Alder reactions

Concise, efficient total syntheses of ningalin A (1), lamellarin O (2), lukianol A (3), and permethyl storniamide A (5) are detailed on the basis of a common heterocyclic azadiene Diels-Alder strategy (1,2,4,5-tetrazine → 1,2-diazine → pyrrole) ideally suited for construction of the densely functionalized pyrrole cores found in the three classes of marine natural products. Examination of the natural products and a number of synthetic intermediates revealed that some including lamellarin O (2) and lukianol A (3) exhibit modest cytotoxic activity against both wild-type and multidrug- resistant tumor cell lines. Fundamentally more important, a new class of agents including permethyl storniamide A (5) and its precursor 30, which lack inherent cytotoxic activity, are disclosed which 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.

A concise synthesis of storniamide a nonamethyl ether [1]

(E,E)-Storniamide A nonamethyl ether is obtained from 3-(3,4,5- trimethoxyphenyl)-pyruvic acid and 2-(4-hydroxyphenyl)ethylamine in three steps with an overall yield of 19%.