6339-66-8

Upstream product

• 2199-49-7 ethyl 4-methylpyrrole-3-carboxylate 
• 874496-31-8 ethyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate 
• 10544-63-5 ethyl crotonate 
• 6277-13-0 3-ethoxycarbonyl-4-methylpyrrole-2-carboxylic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 74-90-8 hydrogen cyanide 

Downstream Products

• 600-28-2 2,3-dimethyl-1H-pyrrole 
• 1196887-72-5 (Z)-5-((2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-6-oxo-6,7-dihydropyrrolo[2,3-d]pyrimidin-5-ylidene)methyl)-4-methyl-1H-pyrrole-3-carboxylic acid 
• 1355372-19-8 (Z)-2-chloro-N-(2-(ethylamino)ethyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-4-methyl-1H-pyrrole-3-carboxamide 
• 1561964-53-1 ethyl 1-(3-(tert-butyl)-5-(1-methylcyclopropyl)phenyl)-5-formyl-4-methyl-1H-pyrrole-3-carboxylate 
• 1561964-36-0 ethyl 5-formyl-1-(4-methoxybenzyl)-4-methyl-1H-pyrrole-3-carboxylate 
• 1561966-23-1 5-benzoyl-1-(3-(tert-butyl)-5-(1-methylcyclopropyl)phenyl)-4-methyl-1H-pyrrole-3-carboxylic acid 
• 1561966-21-9 ethyl 5-benzoyl-1-(3-(tert-butyl)-5-(1-methylcyclopropyl)phenyl)-4-methyl-1H-pyrrole-3-carboxylate 
• 1561966-17-3 ethyl 5-benzoyl-4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-3-carboxylate 
• 1561966-15-1 ethyl 5-(hydroxy(phenyl)methyl)-4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-3-carboxylate 
• 1561965-42-1 ethyl 2-bromo-1-(4-(N-(tert-butyl)sulfamoyl)-3-(trifluoromethyl)phenyl)-5-(cyclohexylmethyl)-4-methyl-1H-pyrrole-3-carboxylate 
• 1561958-70-0 1-(3-(tert-butyl)-5-(1-methylcyclopropyl)phenyl)-5-(cyclohexyl(methoxy)methyl)-4-methyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrrole-3-carboxamide 
• 1561965-08-9 1-(3-(tert-butyl)-5-(1-methylcyclopropyl)phenyl)-5-(cyclohexyl(methoxy)methyl)-4-methyl-1H-pyrrole-3-carboxylic acid 
• 1561965-02-3 ethyl 1-(3-(tert-butyl)-5-(1-methylcyclopropyl)phenyl)-5-(cyclohexyl(methoxy)methyl)-4-methyl-1H-pyrrole-3-carboxylate 
• 1561964-99-5 ethyl 1-(3-(tert-butyl)-5-(1-methylcyclopropyl)phenyl)-4-methyl-5-(piperidine-1-carbonyl)-1H-pyrrole-3-carboxylate 

Relevant academic research and scientific papers

INHIBITORS OF TYROSINE KINASE

The present disclosure provides compounds and compositions thereof which are useful as inhibitors of tyrosine kinase and which exhibit desirable characteristics for the same. Further disclosed herein are methods of treating cancer using these tyrosine kin

Design, Sustainable Synthesis, and Programmed Reactions of Templated N-Heteroaryl-Fused Vinyl Sultams

A de novo design and synthesis of N-heteroaryl-fused vinyl sultams as templates for programming chemical reactions on vinyl sultam periphery or (hetero)aryl ring is described. The key features include rational designing and sustainable synthesis of the template, customized reactions of vinyl sultams at C=C bond or involving N-S bond cleavage, and reactions on the periphery of the heteroaryl ring for late-stage diversification. The simple, easy access to the template coupled with opportunities for the synthesis of diversely functionalized heterocyles from a single template constitutes a rare study in contemporary organic synthesis.

CARBOXAMIDE OR SULFONAMIDE SUBSTITUTED NITROGEN-CONTAINING 5-MEMBERED HETEROCYCLES AS MODULATORS FOR THE ORPHAN NUCLEAR RECEPTOR ROR GAMMA

The invention provides modulators for the orphan nuclear receptor RORy and methods for treating RORy mediated diseases by administering these novel RORy modulators to a human or a mammal in need thereof. Specifically, the present invention provides carboxamide containing cyclic compounds of Formula (1) to Formula (5) and the enantiomers, diastereomers, tautomers, /V-oxides, solvates and pharmaceutically acceptable salts thereof.

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.

Expanded scope of synthetic bacteriochlorins via improved acid catalysis conditions and diverse dihydrodipyrrin-acetals

(Chemical Equation Presented) Bacteriochlorins are attractive candidates for a wide variety of photochemical studies owing to their strong absorption in the near-infrared spectral region. The prior acid-catalysis conditions [BF 3 · O(Et)2 in CH3CN at room temperature] for self-condensation of a dihydrodipyrrin-acetal (bearing a geminal dimethyl group in the pyrroline ring) typically afforded a mixture of three macrocycles: the expected 5-methoxybacteriochlorin (MeOBC-type), a 5-unsubstituted bacteriochlorin (HBC-type), and a free base B,D-tetradehydrocorrin (TDC-type). Here, a broad survey of >20 acids identified four promising acid catalysis conditions of which TMSOTf/2,6-di-tert-butylpyridine in CH2Cl 2 at room temperature was most attractive owing to formation of the 5-methoxybacteriochlorin as the sole macrocycle regardless of the pyrrolic substituents in the dihydrodipyrrin-acetal (electron-withdrawing, electron-donating, or no substituent). Eleven new dihydrodipyrrin-acetals were prepared following standard routes. Application of the new acid catalysis conditions has afforded diverse bacteriochlorins (e.g., bearing alkyl/ester, aryl/ester, diester, and no substituents) in a few days from commercially available starting materials. Consideration of the synthetic steps and yields for formation of the dihydrodipyrrin-acetal and bacteriochlorin underpins evaluation of synthetic plans for early installation of bacteriochlorin substituents via the dihydrodipyrrin-acetal versus late installation via derivatization of β-bromobacteriochlorins. Treatment of the 5-methoxybacteriochlorins with NBS gave regioselective 15-bromination when no pyrrolic substituents were present or when each pyrrole contained two substituents; on the other hand, the presence of a β-ethoxycarbonyl group caused loss of regioselectivity. The 15 new bacteriochlorins prepared herein exhibit a long-wavelength absorption band in the range 707-759 nm, providing tunable access to the near-infrared region. Taken together, this study expands the scope of available bacteriochlorins for fundamental studies and diverse applications. 2010 American Chemical Society.

4-aryl substituted indolinones

The present invention relates to 4-arylindolinones, as well as pharmaceutical compositions thereof, capable of modulating protein kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation. The present invention also relates to methods for treating protein kinase related disorders.

5-ARALKYSUFONYL-3-(PYRROL-2-YLMETHYLIDENE)-2-INDOLINONE DERIVATIVES AS KINASE INHIBITORS

The present invention relates to certain 5-aralkylsulfonyl-3-(pyrrol-2-yl-methylidene)-2-indolinone derivatives that inhibit kinases, in particular met kinase. Pharmaceutical compositions comprising these compounds, methods of treating diseases mediated by kinases utilizing pharmaceutical compositions comprising these compounds, and methods of preparing them are also disclosed.

Rational design of 4,5-disubstituted-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-ones as a novel class of inhibitors of epidermal growth factor receptor (EGF-R) and Her2(p185(erbB)) tyrosine kinases.

A novel class of 4,5-disubstituted-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-ones has been discovered as potent and selective inhibitors of the EGF-R tyrosine kinase family. These compounds selectively inhibit EGF-R kinase activity at low nanomolar concentration and tyrosine autophosphorylation in cells expressing EGF-R or Her2 (p185(erbB)). Structure-activity relationships (SARs) for this class of compounds are presented.

4-Alkenyl- and 4-alkynyloxindoles

Disclosed are novel 4-alkenyl- and 4-alkynyl oxindoles having the formula and the pharmaceutically acceptable salts thereof, wherein R1, R2, R3, a, b, and X are as defined herein. These compounds inhibit cyclin-dependent kinases (CDKs), in particular CDK2. These compounds and their pharmaceutically acceptable salts, and prodrugs of said compounds, are anti-proliferative agents useful in the treatment or control of cell proliferative disorders, in particular cancer, more particularly, the treatment or control of breast and colon tumors. Also disclosed are pharmaceutical compositions containing the compounds of formula I and II as well as intermediates useful in the preparation of the compounds of formula I and II.

Propentdyopents and Related Compounds. Part 2. The Z E Photoisomerisation of Pyrromethenone Systems

The Z E photoisomerisation of four α-unsubstituted pyrromethenones which are potential precursors of alkanol-propentdyopent adducts is studied using a direct n.m.r. spectroscopic approach in CD3OD-CDCl3.Chemical-shift assignments are made with the help of n.O.e. and decoupling experiments.For the polyalkylpyrromethenones the photostationary state contains ca. 25percent of the E isomer: a system with a β-ethoxycarbonyl group leads to 43percent E isomer at photoequilibrium.The E isomers can be manipulated in solution without appreciable change, but thermodynamic equilibration to the Z isomer (ca. 99percent) occurs on dry silica.A similar photoisomerisation of (4Z,15Z)-bilirubin IIIα in ND3-CD3OD leads to a photoequilibrated mixture containing 16percent of (4E,15Z)-bilirubin IIIα.