56448-22-7

Usage

Uses

Used in Pharmaceutical Industry:
5-phenyl-1H-pyrrole-3-carbaldehyde is used as an intermediate in the synthesis of various pharmaceutical compounds. One of its notable applications is in the production of Vonoprazan, a competitive potassium acid blocker. Vonoprazan is a proton pump inhibitor (PPI) that helps in reducing the production of stomach acid, providing relief from conditions like gastroesophageal reflux disease (GERD) and peptic ulcers.
As an Impurity:
5-phenyl-1H-pyrrole-3-carbaldehyde is also recognized as an impurity in the synthesis of Vonoprazan. The presence of 5-phenyl-1H-pyrrole-3-carbaldehyde can affect the purity and efficacy of the final product. Therefore, it is essential to monitor and control the levels of 5-phenyl-1H-pyrrole-3-carbaldehyde during the manufacturing process to ensure the quality and safety of Vonoprazan.
While the provided materials do not mention other specific applications of 5-phenyl-1H-pyrrole-3-carbaldehyde, it is worth noting that compounds with similar structures are often explored for their potential use in various fields, such as materials science, agrochemistry, and the development of new drugs. Further research and development could potentially reveal additional applications for 5-phenyl-1H-pyrrole-3-carbaldehyde in different industries.

Upstream product

• 110-00-9 furan 
• 2227-79-4 benzenecarbothioamide 
• 881673-95-6 (5-phenyl-1H-pyrrol-3-yl)methanol 
• 114615-82-6 tetrapropylammonium perruthennate 
• 881676-32-0 5-bromo-1H-pyrrole-3-carboxaldehyde 
• 98-80-6 phenylboronic acid 
• 7126-39-8 pyrrole-3-carboxaldehyde 
• 10341-75-0 (E)-1-phenylethanone oxime 
• 1240491-46-6 ethyl 3-(((E)-(1-phenylethylidene)amino)oxy)acrylate 
• 161958-61-8 ethyl 5-phenyl-1H-pyrrole-3-carboxylate 
• 158692-57-0 Ethyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate 
• 70-11-1 α-bromoacetophenone 
• 22984-74-3 Ethyl 2-cyano-4-oxo-4-phenylbutanoate 

Downstream Products

• 1100364-04-2 C₁₅H₁₇NO₂ 
• 881676-61-5 2-[(4-formyl-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzonitrile 
• 881676-81-9 1-{[4-(methylsulfonyl)phenyl]sulfonyl}-5-phenyl-1H-pyrrole-3-carbaldehyde 
• 881676-87-5 1-[(3-nitrophenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde 
• 881676-58-0 1-(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)-5-phenyl-1H-pyrrole-3-carbaldehyde 
• 881676-67-1 methyl 3-[(4-formyl-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzoate 
• 881676-63-7 4-[(4-formyl-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzonitrile 
• 881681-44-3 5-phenyl-1-(3-thienylsulfonyl)-1H-pyrrole-3-carbaldehyde 
• 881676-90-0 5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde 
• 881676-65-9 methyl 2-[(4-formyl-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzoate 
• 881676-92-2 1-[(6-methoxypyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde 
• 881676-78-4 1-(1-benzothien-2-ylsulfonyl)-5-phenyl-1H-pyrrole-3-carbaldehyde 
• 881676-96-6 1-(2-chloropyridin-3-ylsulfonyl)-5-phenyl-1H-pyrrole-3-carbaldehyde 
• 881676-98-8 1-(2-chloropyrimidin-5-ylsulfonyl)-5-phenyl-1H-pyrrole-3-carbaldehyde 

Relevant academic research and scientific papers

A Practical route to substituted 7-aminoindoles from pyrrole-3-carboxaldehydes

Among privileged structures, indoles occupy a central place in medicinal chemistry and alkaloid research. Here we report a flexible and efficient conversion of pyrrole-3-carboxaldehydes to substituted 7-amino-5-cyanoindoles. Phosphine addition to fumaronitrile proceeds with prototropic rearrangement of the initially formed zwitterion to the thermodynamically favored phosphonium ylide, which is poised for in situ Wittig olefination. The predominantly E-alkene product positions the allylic nitrile for facile intramolecular Hoeben-Hoesch reaction in the presence of BF3·OEt2. Syntheses of 2,5- and 3,5-disubstituted 7-aminoindoles are illustrated. Additionally, dianion alkylation of the allylic nitrile is demonstrated to furnish, after cyclization, 5,6-disubstituted 7-aminoindoles to further exemplify this scalable and high-yielding method.

Synthesis of 2-bromo-and 2-phenyl-neo-confused porphyrins

Neo-confused porphyrins (neo-CPs), porphyrin isomers with a 1,3-connected pyrrolic subunit, are aromatic structures with a CNNN coordination core. Previously, examples of neo-CPs with fused benzo units or electron-withdrawing ester substituents have been

Proton pump inhibitors

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R 1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R 5 and R 6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

Discovery of a novel pyrrole derivative 1-[5-(2-fluorophenyl)-1-(pyridin-3- ylsulfonyl)-1 H -pyrrol-3-yl]- n -methylmethanamine fumarate (tak-438) as a Potassium-Competitive Acid Blocker (P-CAB)

In our pursuit of developing a novel and potent potassium-competitive acid blocker (P-CAB), we synthesized pyrrole derivatives focusing on compounds with low log"‰D and high ligand-lipophilicity efficiency (LLE) values. Among the compounds synthesized, the compound 13e exhibited potent H +,K+-ATPase inhibitory activity and potent gastric acid secretion inhibitory action in vivo. Its maximum efficacy was more potent and its duration of action was much longer than those of proton pump inhibitors (PPIs). Therefore, compound 13e (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)- 1H-pyrrol-3-yl]-N-methylmethanamine fumarate, TAK-438) was selected as a drug candidate for the treatment of gastroesophageal reflux disease (GERD), peptic ulcer, and other acid-related diseases.

Discovery, synthesis, and biological evaluation of novel pyrrole derivatives as highly selective potassium-competitive acid blockers

To discover a gastric antisecretory agent more potent than existing proton pump inhibitors, novel pyrrole derivatives were synthesized, and their H +,K+-ATPase inhibitory activities and inhibitory action on histamine-stimulated gastric acid secretion in rats were evaluated. Among the compounds synthesized, compound 17a exhibited selective and potent H +,K+-ATPase inhibitory activity through reversible and K+-competitive ionic binding; furthermore, compound 17c exhibited potent inhibitory action on histamine-stimulated gastric acid secretion in rats and Heidenhain pouch dogs.

PROTON PUMP INHIBITORS

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R2, R3 and R4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R5 and R6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

Acid secretion inhibitor

The present invention provides a compound having a superior acid secretion inhibitory effect and showing an antiulcer activity and the like. The present invention provides a compound represented by the formula (I) wherein R1 is a nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle, the nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle optionally has substituent(s), R2 is an optionally substituted C6-14 aryl group, an optionally substituted thienyl group or an optionally substituted pyridyl group, R3 and R4 are each a hydrogen atom, or one of R3 and R4 is a hydrogen atom and the other is an optionally substituted lower alkyl group, an acyl group, a halogen atom, a cyano group or a nitro group, and R5 is an alkyl group or a salt thereof.

PROTON PUMP INHIBITORS

Proton pump inhibitors which have excellent proton pumping activity and which can be converted in vivo into proton pump inhibitors to exhibit antiulcer effect and so on, containing compounds represented by the general formula (I) or salts thereof or prodrugs of the same: (I) wherein X and Y are each independently a free valency or a spacer whose main chain has 1 to 20 carbon atoms; R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; R2, R3 and R4 are each independently hydrogen, an optionally substituted hydrocarbon group, optionally substituted thienyl, optionally substituted benzo[b]thienyl, optionally substituted furyl, optionally substituted pyridyl, optionally substituted pyrazolyl, optionally substituted pyrimidinyl, acyl, halogeno, cyano, or nitro; and R5 and R6 are each independently hydrogen or an optionally substituted hydrocarbon group.

NOVEL ZWITTERIONIC FLUORESCENT DYES FOR LABELING IN PROTEOMIC AND OTHER BIOLOGICAL ANALYSES

The invention relates to compositions and methods useful in the labeling and identification of proteins. The invention provides for highly soluble zwitterionic dye molecules where the dyes and associated side groups are non-titratable and maintain their net zwitterionic character over a broad pH range, e.g. between pH 3 and 12. These dye molecules find utility in a variety of applications, including use in the field of proteomics.