98192-72-4

Upstream product

• 565-61-7 3-methyl-pentan-2-one 
• 105-58-8 Diethyl carbonate 
• 196937-20-9 3-Hydroxy-4-methyl-hexanoic acid ethyl ester 
• 5856-79-1 iso-butyl chloroformate 
• 96-17-3 2-Methylbutyraldehyde 
• 623-73-4 diazoacetic acid ethyl ester 
• 116-53-0 2-Methylbutanoic acid 
• 1071-46-1 hydrogen ethyl malonate 
• 6148-64-7 ethyl potassium malonate 

Downstream Products

• 16117-33-2 ferruol A(mammea D/BB) 
• 121660-16-0 [2-sec-butyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-methanol 
• 121660-42-2 2-sec-butyl-4-(4-fluoro-phenyl)-quinoline-3-carbaldehyde 
• 102322-83-8 (E)-5-methyl-2-hepten-4-one 

Relevant academic research and scientific papers

First total synthesis of (±)-hyperolactone A

The first total synthesis of (±)-hyperolactone A, isolated from Hypericum chinense L., is accomplished from 3-furoic acid and 2-methylbutanal.

Scalable preparation of enantioenriched (S)-5-methylhept-2-en-4-one. Synthesis and aroma properties of achiral analogues thereof

(S)-5-Methylhept-2-en-4-one is a key flavour compound in hazelnuts. We have performed its chiral-pool-based chemoenzymatic synthesis with 39% overall yield (73% ee). The four-step aldol-based sequence avoids the use of highly reactive and/or toxic reagents, does not require anhydrous conditions and uses only distillation as the purification method. Thus, such methodology represents a green and scalable alternative to only two stereoselective approaches towards this natural product known so far. In addition, we have designed and prepared a set of new (di)enones as achiral synthetic analogues of the title compound. The results of their sensory analyses clearly show that relatively minor structural changes of the natural molecule significantly alter its olfactory properties. Thus, simple (poly)methylation completely changes the original hazelnut aroma of (S)-5-methylhept-2-en-4-one and shifts the odour of its analogues to eucalyptus, menthol, camphor, and sweet aroma.

SUBSTITUTED THIAZOLO-PYRIDINE COMPOUNDS AS MALT1 INHIBITORS

Disclosed are compounds of the general formula (I), wherein R1-R3 are as defined herein, for use as MALT1 inhibitors in the treatment of autoimmune and inflammatory diseases or disorders. Methods of synthesizing the compounds are also disclosed. Also disc

NOVEL PYRAZOLO PYRIMIDINE DERIVATIVES AND THEIR USE AS MALT1 INHIBITORS

The present invention describes new pyrazolo-pyrimidine derivatives of formula (I) or a pharmaceutically acceptable salt thereof; (I) wherein, R1 is halogen, cyano, or C1-C3alkyl optionally substituted by halogen; R2 is C1-C6alkyl optionally substituted one or more times by C1-C6alkyl, C2-C6alkenyl, hydroxyl, N,N-di-C1-C6alkyl amino, N-mono-C1-C6alkyl amino, O-Rg, Rg, phenyl, or by C1-C6alkoxy wherein said alkoxy again may optionally be substituted by C1-C6alkoxy, N,N-di-C1-C6alkyl amino, Rg or phenyl; C3-C6cycloalkyl optionally substituted by C1-C6alkyl, N,N-di-C1-C6alkyl amino or C1-C6alkoxy-C1-C6alkyl, and/or two of said optional substituents together with the atoms to which they are bound may form an annulated or spirocyclic 4 - 6 membered saturated heterocyclic ring comprising 1 - 2 O atoms; phenyl optionally substituted by C1-C6alkoxy; a 5 - 6 membered heteroaryl ring having 1 to 3 heteroatoms selected from N and O said ring being optionally substituted by C1-C6alkyl which may be optionally substituted by amino or hydroxy; Rg; or N,N-di-C1-C6alkyl amino carbonyl; and R is phenyl independently substituted two or more times by Ra, 2-pyridyl independently substituted one or more times by Rb, 3-pyridyl independently substituted one or more times by Rc, or 4-pyridyl independently substituted one or more times by Rd; which are generally interacting with MALT1 proteolytic and/or autoproteolytic activity, and in particular which may inhibit said activity. The present invention further describes the synthesis of said new pyrazolo-pyrimidine derivatives, their use as a medicament, especially by interacting with MALT1 proteolytic and/or autoproteolytic activity.

Synthetic studies towards the total synthesis of providencin

A synthetic approach to assemble the uncommon furylcyclobutane substructure in providencin has been developed starting from a commercially available cyclobutane precursor. Georg Thieme Verlag Stuttgart.

ARYL PYRIMIDINE DERIVATIVES

The disclosed pyrimidine derivatives, and pharmaceutically acceptable salts and N-oxides thereof, exhibit useful pharmacological properties, in particular use as selective 5HT 2B-antagonists. The invention is also directed to formulations and methods for treatment.

ARYL PYRIMIDINE DERIVATIVES

The aryl pyrimidine derivatives and pharmaceutically acceptable salts and N-oxides thereof, exhibit useful pharmacological properties, including utility as selective 5HT 2B-antagonists.

ARYL PYRIMIDINE DERIVATIVES AND USES THEREOF

The aryl pyrimidine derivatives and pharmaceutically acceptable salts and N-oxides thereof, exhibit useful pharmacological properties, including utility as selective 5HT 2B-antagonists. The 5-HT 2B antagonist is a compound of the formula: STR1 wherein: R. sup.1 is hydrogen, alkyl, lower alkoxy, hydroxyalkyl, cycloalkyl, cycloalkyl lower alkyl, alkenyl, lower thioalkoxy, halo, fluoroalkyl,--NR 6 R. sup.7,--CO 2 R 8,--O(CH 2) n R 9, or lower alkyl optionally substituted with hydroxy, alkoxy, halo, or aryl; in which n is 1, 2, or 3;R 6 and R 7 are hydrogen or lower alkyl; R 8 is hydrogen or lower alkyl; andR 9 is hydrogen, lower alkyl, hydroxy, hydroxy lower alkyl, lower alkenyl, or lower alkoxy;R. sup.2 is hydrogen, lower alkyl, lower alkoxy, halo, or lower fluoroalkyl; R 3 is optionally substituted aryl other than pyridyl, thienyl, or furanyl;R 4 is hydrogen, lower alkyl, cycloalkyl, alkenyl, acyl, amino, amido, aryl,--(CH 2) m NR. sup.10 R 11, or lower alkyl optionally substituted by amino, monosubstituted amino, disubstituted amino, hydroxy, carboxy, aryl, lower alkoxy, amido, alkoxy carbonyl, tetrahydrofuran-2-yl, hydroxyalkoxy, or sulfonamido;in whichR 10 and R. sup.11 are hydrogen or lower alkyl; andR 5 is hydrogen or lower alkyl; provided that: (i) when R 3 is naphthyl, indol-1-yl, or 2,3-dihydroindol-1-yl, and R 2, R 4 and R 5 are all hydrogen, R. sup.1 is not methyl; (ii) when R 3 is phenyl or naphthyl, R 1 is not--NR 6 R 7 ;(iii) when R 3 is phenyl, R 2 is not lower alkoxy, and R 1 and R 2 are not halo;(iv) when R 3 is phenyl and R 1 is H, R 2 is not methyl; and (v) when R 3 is 1,2,3,4-tetrahydroquinolinyl, R 4 and R. sup.5 are hydrogen;or a pharmaceutically acceptable salt or N-oxide thereof.

Synthesis of Mammea Coumarins. Part 1. The Coumarins of the Mammea A, B, and C Series

The naturally-occuring Mammea coumarins of the 4-phenyl-(mammea A), propyl-(mammea B), and 4-pentyl-(mammea C) series have been prepared by Pechmann condensation of an acylphloroglucinol (3-methylbutyryl-, 2-methylbutyryl-, butyryl-, or 2-methylpropionyl-) with the appropriate β-ketoester to give a mixture of 6- and 8-acyl-5,7-dihydroxycoumarins that could be separated.C-Alkylation with 3-methylbut-2-enyl bromide, or 3,7-dimethylocta-2,6-dienyl chloride, in aqueous potassium hydroxide completed the synthesis of the Mammea coumarins having unmodified prenyl or geranyl substituents; oxidative modification of the prenyl group led to the mammea cyclo E and cyclo F coumarins.Some mammea cyclo D (chromeno) coumarins were synthesized by reaction of acylcoumarins with 1,1-dimethoxy-3-methylbutan-3-ol.