2048-10-4

Usage

Class

Pyrrole derivatives

Structure

Contains a pyrrole ring with two 4-methoxyphenyl groups attached at positions 3 and 4

Usage

Organic synthesis, pharmaceutical research

Potential pharmacological activities

Anticancer, antimicrobial

Electronic properties

Interesting electronic properties that make it suitable for use in organic electronic materials.

Upstream product

• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 93362-54-0 3,4-dibromo-1--1H-pyrrole 
• 1357168-93-4 3,4-di(4-methoxyphenyl)-1-tosylpyrrole 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 
• 2234-38-0 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid 
• 246868-68-8 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester 
• 29559-26-0 (p-methoxyphenyl)nitromethane 
• 1041424-88-7 3,4-di(4-methoxyphenyl)-1H-pyrrol-2-carboxylic acid 
• 6443-74-9 p-methoxy-α-p-methoxyphenylcinnamonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-47-2 p-methoxybenzylnitrile 
• 343823-36-9 meso-2,3-bis(p-methoxyphenyl)succinonitrile 

Downstream Products

• 1357169-01-7 (C₃HO₂BF₂)(C₄H₂N((C₆H₄)OCH₃)2)2 
• 1357168-98-9 1,3-bis(3,4-di(4-methoxyphenyl)pyrrol-2-yl)-1,3-propanedione 
• 170238-94-5 3,4-bis(4-methoxyphenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 170238-96-7 methyl 3,4-bis(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate 
• 65112-26-7 (3,4-bis(4-methoxyphenyl)-1H-pyrrol-1-yl)(phenyl)methanone 
• 1418216-89-3 3,4-bis[4-(benzyloxy)phenyl]-1H-pyrrole 
• 1261079-21-3 1,3,4-tris(4-methoxyphenyl)-1H-pyrrole 

Relevant academic research and scientific papers

Total synthesis and biological evaluation of 7-hydroxyneolamellarin A as hypoxia-inducible factor-1α inhibitor for cancer therapy

7-Hydroxyneolamellarin A (7-OH-Neo A, 1), a natural marine product derived from sponge Dendrilla nigra, was first synthesized with 10% overall yield under the instruction of convergent synthetic strategy. We found that 7-OH-Neo A could attenuate the accum

Total synthesis and application of natural product of 7-hydroxy novel lamellarin A and analogues of natural product of 7-hydroxy novel lamellarin A

The invention belongs to the technical field of pharmaceutical and chemical engineering, and provides total synthesis and application of a natural product of 7-hydroxy novel lamellarin A and analoguesof the natural product of the 7-hydroxy novel lamellarin A. The invention provides the 7-hydroxy novel lamellarin A natural product and the series of analogues of the 7-hydroxy novel lamellarin A natural product. Tested compounds all have medium to good HIF-1 inhibitory activity, and have no market toxicity under the effective inhibition concentration of HIF-1 of the tested compounds, and it is indicated that the compounds have the potential for treating cancers by inhibiting transcription activating of the HIF-1.

Structure-activity relationships study of neolamellarin A and its analogues as hypoxia inducible factor-1 (HIF-1) inhibitors

The novel marine pyrrole alkaloid neolamellarin A derived from sponge has been shown to inhibit hypoxia-induced HIF-1 activity. In this work, we designed and synthesized neolamellarin A and its series of derivatives by a convergent synthetic strategy. The HIF-1 inhibitory activity and cytotoxicity of these compounds were evaluated in Hela cells by dual-luciferase reporter gene assay and MTT assay, respectively. The results showed that neolamellarin A 1 (IC50 = 10.8 ± 1.0 μM) and derivative 2b (IC50 = 11.9 ± 3.6 μM) had the best HIF-1 inhibitory activity and low cytotoxicity. Our SAR research focused on the effects of key regions aliphatic carbon chain length, aromatic ring substituents and C-7 substituent on biological activity, providing a basis for the subsequent research on the development of novel pyrrole alkaloids as HIF-1 inhibitors and design of small molecule probes for target protein identification.

Synthesis of 3,4-diaryl- and 4-acyl-3-arylpyrroles and study of their antimitotic activity

The Barton–Zard reaction of nitro substituted stilbenes and chalcones with ethyl isocyanoacetate afforded 3,4-diaryl- and 4-acyl-3-arylpyrroles, respectively. 3-Arylpyrrole-2,4- dicarboxylates and 4-arylisoxazoline N-oxides were side reaction products. An

Pyrrole marine alkaloid Neolamellarin A analogs and its preparation method and application

The invention relates to pyrrole ocean alkaloids Neolamellarin A analogues as shown in the formula I and a preparation method and application thereof. Experiments show that, some of the pyrrole ocean alkaloids Neolamellarin A analogues have strong inhibitory effect on tumor cell lines; some of the pyrrole ocean alkaloids Neolamellarin A analogues have very good neuro cell protective effect; and some of the pyrrole ocean alkaloids Neolamellarin A analogues have very strong inhibitory effect on heat shock protein Hsp90.

Rhodium-catalyzed transannulation of 1,2,3-triazoles to polysubstituted pyrroles

Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with vinyl ether has been accomplished for the synthesis of various polysubstituted pyrroles. The present method allows the synthesis of mono-, di-, and trisubstituted pyrroles with appropriate substitutions. Furthermore, the developed methodology was applied in the formal synthesis of neolamellarin A, an antitumor agent.

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.

Charge-based and charge-free molecular assemblies comprising π-extended derivatives of anion-responsive acyclic oligopyrroles

Assemblies comprising anion complexes of π-extended oligopyrrole derivatives and counter cations, as well as those of anion-free receptor molecules, exhibited the formation of mesophases based on columnar structures using electrostatic and π-π interactions. The Royal Society of Chemistry.

Palladium-catalyzed cross-coupling of N-benzenesulfonyl-3,4-dibromopyrrole and its application to the total syntheses of lamellarins O, P, Q, and R

Palladium-catalyzed Suzuki-Miyaura coupling of N-benzenesulfonyl-3,4-dibromopyrrole with a variety of arylboronic acids gave the corresponding 3,4-diarylpyrroles in high yields. The 3,4-differentially arylated pyrroles could also be prepared by stepwise cross-coupling approach. The total syntheses of lamellarins O, P, Q, and R have been achieved by using the cross-coupling and the directed lithiation as key reactions.

Synthesis of 3,4-diarylpyrroles and conversion into dodecaarylporphyrins; a new approach to porphyrins with altered redox potentials

3,4-Diarylpyrroles (1) have been directly prepared in 20-50% yield by the reaction of β-nitrostyrenes with aqueous TiCl3 in 1,4-dioxane. Pyrroles 1 were also prepared via Barton-Zard pyrrole synthesis using the reaction of α-nitrostilbenes with ethyl isocyanoacetate followed by de-ethoxycarbonylation. 3,4-Diarylpyrroles have been converted into dodecaarylporphyrins by reaction with aromatic aldehydes. Various aryl groups are readily introduced at the periphery of porphyrins by this method. Phenyl substitution at any of the positions of pyrroles decreases E1/2ox while E1/2red is almost unchanged. On the other hand, substitution of the 2-thienyl group affects both the HOMO and LUMO energies, and the UV-vis spectra of dodeca-2-thienylporphyrins (4f or 4i) are extremely red-shifted.