80055-86-3

Upstream product

• 6921-66-0 4-chloro-2-hydroxy acetophenone 
• 67-64-1 acetone 
• 108-43-0 3-monochlorophenol 
• 541-47-9 3-Methylbutenoic acid 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 142337-53-9 3'-chlorophenyl 3-methylbut-2-enoate 
• 141-79-7 4-methyl-pent-3-en-2-one 

Relevant academic research and scientific papers

Tricyclic 4,4-dimethyl-3,4-dihydrochromeno[3,4-d]imidazole derivatives as microsomal prostaglandin E2 synthase-1 (mPGES-1) inhibitors: SAR and in vivo efficacy in hyperalgesia pain model

A series of substituted tricyclic 4,4-dimethyl-3,4-dihydrochromeno[3,4-d]imidazole derivatives have been synthesized and their mPGES-1 biological activity has been disclosed in detail. Structure-activity relationship (SAR) optimization provided inhibitors with excellent mPGES-1 potency and low to moderate PGE2 release A549 cell potency. Among the mPGES-1 inhibitors studied, 7, 9 and 11l provided excellent selectivity over COX-2 (>200-fold) and >70-fold selectivity for COX-1 except 11l, which exhibited dual mPGES-1/COX-1 activity. Furthermore, the above tested mPGES-1 inhibitors demonstrated good metabolic stability in liver microsomes, high plasma protein binding (PPB) and no significant inhibition observed in clinically relevant CYP isoforms. Besides, selected mPGES-1 tool compounds 9 and 11l provided good in vivo pharmacokinetic profile and oral bioavailability (%F?=?33 and 85). Additionally, the representative mPGES-1 tool compounds 9 and 11l revealed moderate in vivo efficacy in the LPS-induced thermal hyperalgesia guinea pig pain model.

Bismuth(III) triflate catalyzed tandem esterification–Fries–oxa-Michael route to 4-chromanones

An efficient tandem reaction approach is described to prepare 4-chromanones from electron-rich phenols and 3,3-dimethylacrylic acid or trans-crotonic acid in boiling toluene using 20?mol?% bismuth(III) triflate as the catalyst. The reaction is also successful from the corresponding aryl esters of each of these acids under the same conditions. The procedure is convenient to perform, and 25–90% yields of products are realized following chromatography. A range of substrates is included (14 substrates for each acid) to help define the scope of the process. Additional experiments are reported, which confirm that the sequence of events involves (1) esterification, (2) Fries rearrangement and (3) oxa-Michael ring closure.

Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones

A facile photochemical preparation of 5-, 6-, and 7-substituted chroman-4-ones from aryl 3-methyl-2-butenoate esters is described. The two-phase base-catalyzed method relies upon two consecutive processes in one-pot reaction through a photo-Fries rearrangement and a based-catalyzed intramolecular oxa-Michael addition to afford the desired products.

TRICYCLIC COMPOUNDS AS mPGES-1 INHIBITORS

The present invention relates to tricyclic compounds of formula (I) or pharmaceutically acceptable salt thereof as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthama, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases. (I)

TRPV1 ANTAGONISTS

Disclosed herein are compounds of Formula (I), or pharmaceutically acceptable salts, solvates, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and m are defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

TRPV1 ANTAGONISTS

Disclosed herein are compounds of formula (I), or pharmaceutically acceptable salts, solvates, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and m are defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

BENZOPYRAN DERIVATIVES, METHOD OF PRODUCTION AND USE THEREOF

The invention relates to novel benzopyran derivatives of formula (I), to their method of production, to composition comprising the derivatives and use thereof. Formula (I) wherein: R1, R2, R3 and R4 are independ

Synthesen und Umsetzungen von 4-Chromanonen

Zahlreiche Naturstoffe wie die pflanzlichen Insektizide Rotenon und Ageratochromen (Precocen), einige fungitoxische Phytoalexine, Inhaltsstoffe des Haschischs, Vitamin E und Bluetenfarbstoffe enthalten das Chromangeruest.Vor mehreren Jahren fanden wir einen besonders einfachen Zugang zu dieser Heterocyclen-Klasse: Die Kondensation von o-Hydroxyacetophenonen mit aliphatischen Aldehyden und Ketonen in Gegenwart von Pyrrolidin fuehrt in guten Ausbeuten zu 4-Chromanonen.Diese Synthese zeichnet sich durch einen breiten Anwendungsbereich aus; die Tabellen vermitteln einen Eindruck von der Fuelle und Vielfalt der Substituenten.Untypisch verlaeuft die Umsetzung von O-Hydroxyacetophenonen z.B. mit Glyoxylsaeure oder mit α,β-ungesaettigten Ketonen.Die zum groesseren Teil neuen Chromanone koennen unter anderem zur Herstellung von Chromonen, Chromenen und Chromanen sowie zum Aufbau von Tricyclen und hoeheren Ringsystemen verwendet werden.

SYNTHESIS AND REACTIONS OF SOME CHLORO-2,2-DIMETHYLCHROMENS

5-, 6-, 7-, and 8-Chloro-2,2-dimethylchromens have been prepared from the corresponding chlorocumarin and their conversion into the 3,4-dihalogenochroman derivatives is described.The 4-halogen atom is shown to be the more susceptible to hydrolysis by conv