16819-41-3

Upstream product

• 19578-68-8 4-(4-benzyloxyphenyl) iodide 
• 84284-70-8 [4-(benzyloxy)phenyl]acetylene 

Downstream Products

• 220230-79-5 dimethyl 3,4-bis(4-benzyloxyphenyl)-1,2-diazine-2,5-dicarboxylate 
• 220230-84-2 dimethyl 3,4-bis(4-benzyloxyphenyl)-1-<2-(4-methoxyphenyl)-2-oxoethyl>pyrrole-2,5-dicarboxylate 
• 220230-86-4 3,4-bis(4-benzyloxyphenyl)-5-(methoxycarbonyl)-1-<2-(4-methoxyphenyl)-2-oxoethyl>pyrrole-2-carboxylic acid 
• 220230-88-6 methyl 3,4-bis(4-benzyloxyphenyl)-1-<2-(4-methoxyphenyl)-2-oxoethyl>pyrrole-2-carboxylate 
• 220230-90-0 3,4-bis-(4-benzyloxy-phenyl)-1-[2-(4-methoxy-phenyl)-2-oxo-ethyl]-1H-pyrrole-2-carboxylic acid 
• 220230-93-3 1H-7,8-bis(4-benzyloxyphenyl)-3-(methoxyphenyl)pyrrolo<2,1-c><1,4>-oxazin-1-one 
• 220230-81-9 dimethyl 3,4-bis(4-(benzyloxy)phenyl)-1H-pyrrole-2,5-dicarboxylate 
• 144398-24-3 3,7,8-tris(4-hydroxyphenyl)-1H-pyrrolo[2,1-c][1,4]oxazin-1-one 

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.