170238-96-7

Upstream product

• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 170238-94-5 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 5720-07-0 4-methoxyphenylboronic acid 
• 41564-67-4 (E)-1,3-bis(4-methoxyphenyl)-2-propene-1-one 
• 74-88-4 methyl iodide 
• 1337927-65-7 (E)-4,4'-(1-nitroethene-1,2-diyl)bis(4-methoxybenzene) 
• 59019-40-8 1-[(1Z)-2-bromo-2-nitroethenyl]-4-methoxybenzene 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 170238-95-6 4,5-bis(4-methoxyphenyl)isoxazole 
• 55097-58-0 [3-(4-methoxyphenyl)oxiran-2-yl]-(4-methoxyphenyl)methanone 
• 284663-53-2 N,N-dimethyl 2-methoxycarbonyl-3,4-bis(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide 
• 284663-33-8 N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-iodo-1H-pyrrole-1-sulfonamide 
• 6443-74-9 p-methoxy-α-p-methoxyphenylcinnamonitrile 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 170238-97-8 1H-3,7,8-tris(4-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 

Relevant academic research and scientific papers

Lamellarin O, a pyrrole alkaloid from an Australian marine sponge, Ianthella sp., reverses BCRP mediated drug resistance in cancer cells

ATP binding cassette (ABC) transporters, such as P-gp, BCRP and MRP1, can increase efflux of clinical chemotherapeutic agents and lead to multi-drug resistance (MDR) in cancer cells. While the discovery and development of clinically useful inhibitors has proved elusive to date, this molecular target nevertheless remains a promising strategy for addressing and potentially overcoming MDR. In a search for new classes of inhibitor, we used fluorescent accumulation and efflux assays supported by cell flow cytometry and MDR reversal assays, against a panel of sensitive and MDR human cancer cell lines, to evaluate the marine sponge co-metabolites 1-12 as inhibitors of P-gp, BCRP or MRP1 initiated MDR. These studies identified and characterized lamellarin O (11) as a selective inhibitor of BCRP mediated drug efflux. A structure-activity relationship analysis inclusive of the natural products 1-12 and the synthetic analogues 13-19, supported by in silico docking studies, revealed key structural requirements for the lamellarin O (11) BCRP inhibitory pharmacophore.

Synthesis of lamellarin R, lukianol A, lamellarin O and their analogues

Three lamellarin alkaloids type III (lamellarin R, lukianol A and lamellarin O) were synthesized using the Barton-Zard reaction as a key step to construct the central pyrrole core. Some of their corresponding 4-benzoyl and 5-phenyl substituted pyrrole ana

A Paal-Knorr approach to 3,4-diaryl-substituted pyrroles: Facile synthesis of lamellarins O and Q

A very simple, yet efficient synthetic methodology, to obtain 3,4-diaryl-substituted pyrroles is described. The approach is based on the Knoevenagel condensation between arylacetonitriles and substituted aromatic aldehydes, followed by conjugate addition of cyanide to afford succinonitriles in excellent yields. The products thus obtained were subjected to DIBAL-H reduction, followed by cyclization under acidic conditions to produce the corresponding pyrroles in good overall yields. The utility of this protocol is exemplified by the synthesis of the marine alkaloids lamellarins O and Q.

Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles: A formal total synthesis of lukianol A

A combined use of α-lithiation and nucleophilic substitutions of N,N- dimethyl 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamide 8c led to several 2-substituted 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamides. Utilizing the β-effect of a trimethylsilyl group, a highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles 23 and 34 was accomplished. The marine natural product lukianol A (3) was prepared utilizing this strategy.