220231-03-8

Basic information

• Product Name: 1H-Pyrrole-2,5-dicarboxylic acid, 1-[2-(4-methoxyphenyl)ethyl]-3,4-bis(3,4,5-trimethoxyphenyl)-, dimethyl ester
• CAS NO: 220231-03-8
• Molecular Formula: C35H39NO11
• Molecular Weight: 649.695
• Mol File: 220231-03-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole-2,5-dicarboxylic acid, 1-[2-(4-methoxyphenyl)ethyl]-3,4-bis(3,4,5-trimethoxyphenyl)-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-2,5-dicarboxylic acid, 1-[2-(4-methoxyphenyl)ethyl]-3,4-bis(3,4,5-trimethoxyphenyl)-, dimethyl ester(220231-03-8)
• EPA Substance Registry System: 1H-Pyrrole-2,5-dicarboxylic acid, 1-[2-(4-methoxyphenyl)ethyl]-3,4-bis(3,4,5-trimethoxyphenyl)-, dimethyl ester(220231-03-8)

Safety Data

• Hazardous Substances Data: 220231-03-8(Hazardous Substances Data)

Upstream product

• 182163-96-8 3,4,5-trimethoxyphenylboronic Acid 
• 570402-53-8 1-[2-(4-methoxy-phenyl)-ethyl]-3,4-bis-trifluoromethanesulfonyloxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester 
• 25245-29-8 5-iodo-1,2,3-trimethoxybenzene 
• 55-81-2 4-Methoxyphenethylamine 
• 53560-33-1 3,4,5-trimethoxyphenylacetylene 
• 220230-99-9 dimethyl 4,5-bis(3,4,5-trimethoxyphenyl)-1,2-diazine-3,6-dicarboxylate 
• 570402-51-6 3,4-dihydroxy-1-[2-(4-methoxy-phenyl)-ethyl]-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester 
• 570402-49-2 {methoxycarbonylmethyl-[2-(4-methoxy-phenyl)-ethyl]-amino}-acetic acid methyl ester 
• 14425-64-0 4-methoxyphenethyl bromide 
• 220231-01-6 3,4-bis-(3,4,5-trimethoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester 
• 473401-83-1 3,4-dibromo-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 

Downstream Products

• 220231-07-2 3,4-bis(3,4,5-trimethoxyphenyl)-1-<2-(4-methoxyphenyl)ethyl>pyrrole-2,5-biscarboxamide 
• 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 
• 219783-09-2 3,4-bis(3,4,5-trimethoxyphenyl)-1-<2-(4-methoxyphenyl)ethyl>pyrrole-2,5-dicarboxylic acid 

Relevant articles and documents

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.

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.