220230-81-9

Basic information

• Product Name: dimethyl 3,4-bis(4-(benzyloxy)phenyl)-1H-pyrrole-2,5-dicarboxylate
• Synonyms: dimethyl 3,4-bis(4-(benzyloxy)phenyl)-1H-pyrrole-2,5-dicarboxylate
• CAS NO: 220230-81-9
• Molecular Weight: 547.607
• Mol File: 220230-81-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: dimethyl 3,4-bis(4-(benzyloxy)phenyl)-1H-pyrrole-2,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 3,4-bis(4-(benzyloxy)phenyl)-1H-pyrrole-2,5-dicarboxylate(220230-81-9)
• EPA Substance Registry System: dimethyl 3,4-bis(4-(benzyloxy)phenyl)-1H-pyrrole-2,5-dicarboxylate(220230-81-9)

Safety Data

• Hazardous Substances Data: 220230-81-9(Hazardous Substances Data)

Upstream product

• 57177-83-0 O-benzyltyrosine methyl ester 
• 74649-85-7 3-(4-(benzyloxy)phenyl)-2-diazapropionic acid methyl ester 
• 84284-70-8 [4-(benzyloxy)phenyl]acetylene 
• 19578-68-8 4-(4-benzyloxyphenyl) iodide 
• 16819-41-3 1,2-bis(4-benzyloxyphenyl)acetylene 
• 2166-14-5 1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester 
• 220230-79-5 dimethyl 3,4-bis(4-benzyloxyphenyl)-1,2-diazine-2,5-dicarboxylate 

Downstream Products

• 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 
• 144398-24-3 3,7,8-tris(4-hydroxyphenyl)-1H-pyrrolo[2,1-c][1,4]oxazin-1-one 
• 220230-84-2 dimethyl 3,4-bis(4-benzyloxyphenyl)-1-<2-(4-methoxyphenyl)-2-oxoethyl>pyrrole-2,5-dicarboxylate 

Relevant articles and documents

Cu/Mn Co-oxidized cyclization for the synthesis of highly substituted pyrrole derivatives from amino acid esters: A strategy for the biomimetic syntheses of lycogarubin c and chromopyrrolic acid

An effective and concise approach to synthesis of tetrasubstituted pyrroles from readily available amino acid esters by the promotion of Cu(OAc) 2 in conjunction with Mn(OAc)3 has been developed. This reaction proceeds through multiple dehydrogenations, deamination, and oxidative cyclization. This oxidized system tolerates substrates bearing various electron-donating or electron-withdrawing groups. With this methodology, several key intermediates of natural products have been effectively prepared, and the total syntheses of lycogarubin C and chromopyrrolic acid have been completed in high efficiency.

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.