936-12-9

Usage

Chemical Properties

White to orange-red crystalline powder

InChI:InChI=1/C8H11NO2/c1-3-11-8(10)7-4-5-9-6(7)2/h4-5,9H,3H2,1-2H3

Upstream product

• 1117-96-0 Diazoethan 
• 37102-48-0 2-methyl-1H-pyrrole-3-carboxylic acid 
• 623-33-6 glycine ethyl ester hydrochloride 
• 24442-57-7 1,2-dibromoethyl acetate 
• 141-97-9 ethyl acetoacetate 
• 136814-21-6 ethyl N-[2-hydroxyethyl]-β-aminocrotonate 
• 623-46-1 1,2-dichloro-2-ethoxyethane 
• 108-05-4 vinyl acetate 
• 74469-98-0 1-Acetyl-2-methyl-1H-pyrrol-3-carbonsaeure-ethylester 
• 75-05-8 acetonitrile 
• 107-20-0 2-chloroethanal 
• 1135793-19-9 ethyl 3-[(2,2-diethoxyethyl)amino]but-2-enoate 
• 86214-88-2 1-Acetyl-4,5-dihydro-2-methyl-1H-pyrrol-3-carbonsaeure-ethylester 
• 626-34-6 ethyl aminocrotonate 

Downstream Products

• 101112-93-0 2-methyl-5-phenylcarbamoyl-pyrrole-3-carboxylic acid ethyl ester 
• 876490-64-1 5-acetyl-2-methyl-pyrrole-3-carboxylic acid ethyl ester 
• 57061-48-0 ethyl 5-formyl-2-methyl-1H-pyrrole-3-carboxylate 
• 102655-02-7 2,2'-dimethyl-5,5'-phenylmethanediyl-bis-pyrrole-3-carboxylic acid diethyl ester 
• 636-41-9 2-methyl-1H-pyrrole 
• 37102-48-0 2-methyl-1H-pyrrole-3-carboxylic acid 
• 91238-26-5 Benzyl 4',5-dimethyl-3'-<2-(ethoxycarbonyl)ethyl>-4-(ethoxycarbonyl)dipyrrylmethane-5'-carboxylate 
• 80326-73-4 1-phenyl-2-methyl-pyrrol-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

The synthesis of pyrroles and oxazoles based on gold α-imino carbene complexes

Cationic gold complexes of α-oximimino carbenes have been identified to react with weak nucleophiles including enol ethers and nitriles. These findings allowed us to develop the highly efficient synthesis of pyrroles and oxazoles.

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.

PYRROLO CARBOXAMIDES AS MODULATORS OF ORPHAN NUCLEAR RECEPTOR RAR-RELATED ORPHAN RECEPTOR-GAMMA (ROR?, NR1F3) ACTIVITY AND FOR THE TREATMENT OF CHRONIC INFLAMMATORY AND AUTOIMMUNE DISEASES

The invention provides modulators for the orphan nuclear receptor ROR? and methods for treating ROR? mediated diseases by administrating these novel ROR? modulators to a human or a mammal in need thereof. Specifically, the present invention provides pyrrolo carboxamide compounds of Formula (1) and the enantiomers, diastereomers, N-oxides, tautomers, solvates and pharmaceutically acceptable salts thereof.

Regioselective synthesis of functionalized pyrroles via gold(I)-catalyzed [3+2] cycloaddition of stabilized vinyl diazo derivatives and nitriles

The reaction of nitriles with alkenyldiazo compounds in the presence of gold catalysts provides functionalized pyrrole derivatives in moderate to high yields. This formal [3+2] cyclization reaction takes place with complete regioselectivity. The observed regiochemical outcome suggests the attack of the nitrile to the terminal position of the alkenylgold carbenoid (vinylogous reactivity). A broad range of nitriles (including those bearing functional groups) is compatible with this cyclization reaction. Copyright

Synthesis and biological evaluation of 3-substituted-indolin-2-one derivatives containing chloropyrrole moieties

Eighteen novel 3-substituted-indolin-2-ones containing chloropyrroles were synthesized and their biological activities were evaluated. The presence of a chlorine atom on the pyrrole ring was crucial to reduce cardiotoxicity. The presence of a 2-(ethylamino) ethylcarbamoyl group as a substituent at the C-4' position of the pyrrole enhanced the antitumor activities notably. IC 50 values as low as 0.32, 0.67, 1.19 and 1.22 μM were achieved against non-small cell lung cancer (A549), oral epithelial (KB), melanoma (K111) and large cell lung cancer cell lines (NCI-H460), respectively.

Novel synthesis of [13C4,15N]1H-pyrrole-2, 3,5-tricarboxylic acid: An important biomarker for melatonin metabolism

1H-pyrrole-2,3,5-tricarboxylic acid is a breakdown product of melatonin. A labeled version of this compound would serve as a key biomarker for drug candidates which track this substance to monitor their effectiveness (e.g. hyperpigmentation drugs). A Hantzsch synthesis using readily available starting materials was used to generate [13C4,15N]1H- pyrrole-2,3,5-tricarboxylic acid in six steps (12% overall yield). Copyright

Discovery of potent, selective sulfonylfuran urea endothelial lipase inhibitors

Endothelial lipase (EL) activity has been implicated in HDL catabolism, vascular inflammation, and atherogenesis, and inhibitors are therefore expected to be useful for the treatment of cardiovascular disease. Sulfonylfuran urea 1 was identified in a high-throughput screening campaign as a potent and non-selective EL inhibitor. A lead optimization effort was undertaken to improve potency and selectivity, and modifications leading to improved LPL selectivity were identified. Radiolabeling studies were undertaken to establish the mechanism of action for these inhibitors, which were ultimately demonstrated to be irreversible inhibitors.

Synthesis of 3-Acylpyrroles, 3-(Alkoxycarbonyl)pyrroles, 1,5,6,7-Tetrahydro-4H-indol-4-ones and 3-Benzoylpyridines Based on Staudinger-Aza-Wittig Reactions of 1,3-Dicarbonyl Compounds with 2- and 3-Azido-1,1-dialkoxy- alkanes

The Staudinger-aza-Wittig reaction of 1,3-dicarbonyl compounds with 2-azido-1,1-diethoxyethane and subsequent cy- clization allowed an efficient synthesis of a variety of pyrroles, 1,5,6,7-tetrahydro-4H-indol-4-ones, and of a pyridine. Georg Thieme Verlag

INHIBITORS OF THE HIV INTEGRASE ENZYME

The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as modulators or inhibitors of the human immunodeficiency virus (“HIV”) integrase enzyme.

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.