119736-15-1

Upstream product

• 1968-51-0 2-Hydroxymethyl-3-hydroxy-pyran-4(1H)-one 
• 100-39-0 benzyl bromide 
• 61049-69-2 3-O-benzylmaltol 
• 496-63-9 3-hydroxy-pyran-4-one 
• 50-00-0 formaldehyd 
• 100-44-7 benzyl chloride 
• 28787-36-2 2-methyl-4-oxo-4H-pyran-3-yl acetate 
• 118-71-8 Maltol 
• 98-00-0 (2-furyl)methyl alcohol 

Downstream Products

• 500371-01-7 3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde 
• 119736-16-2 3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Purification and characterization of molybdenum-containing aldehyde dehydrogenase that oxidizes benzyl maltol derivative from Pseudomonas nitroreducens SB32154

Maltol derivatives are used in a variety of fields due to their metal-chelating abilities. In the previous study, it was found that cytochrome P450 monooxygenase, P450nov, which has the ability to effectively convert the 2-methyl group in a maltol derivative, transformed 3-benzyloxy-2-methyl-4-pyrone (BMAL) to 2-(hydroxymethyl)-3-(phenylmethoxy)-4H-pyran-4-one (BMAL-OH) and slightly to 3-benzyloxy-4-oxo-4 H-pyran-2-carboxaldehyde (BMAL-CHO). We isolated Pseudomonas nitroreducens SB32154 with the ability to convert BMAL-CHO to BMAL-COOH from soil. The enzyme responsible for aldehyde oxidation, a BMAL-CHO dehydrogenase, was purified from P. nitroreducens SB32154 and characterized. The purified BMAL-CHO dehydrogenase was found to be a xanthine oxidase family enzyme with unique structure of heterodimer composed of 75 and 15 kDa subunits containing a molybdenum cofactor and [Fe-S] clusters, respectively. The enzyme showed broad substrate specificity toward benzaldehyde derivatives. Furthermore, one-pot conversion of BMAL to BMAL-COOH via BMAL-CHO by the combination of the BMAL-CHO dehydrogenase with P450nov was achieved.

Method for preparing 2-hydroxymethyl-3-alkoxy-4H-pyran-4-one by one-pot process

The invention relates to a method for preparing 2-hydroxymethyl-3-alkoxy-4H-pyran-4-one by a one-pot process. The method is characterized by comprising the following steps: (1) dissolving pyromeconicacid with the concentration of 0.1-5 mol/L in a solvent, adding an alkali, controlling the molar ratio of pyromeconic acid to the alkali to be 1:(0.5-5), adding a formaldehyde aqueous solution with the weight percentage content of 20-50%, controlling the molar ratio of formaldehyde to pyromeconic acid to be (1-3):1, and reacting for 1-24 hours at the temperature of 0-100 DEG C; and (2) directly adding an alkylation reagent into step (1), controlling the molar ratio of the alkylation reagent to pyromeconic acid to be (1-3):1, and reacting at 10-100 DEG C for 1-24 hours. The method has the following advantages: on the basis of ensuring the reaction yield and the product quality, the separation of an intermediate is omitted, the operation steps are reduced, and the production period is shortened; and consumption of solvents and acid-base materials is reduced, and production cost is saved.

Synthesis method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

The invention discloses a synthesis method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid. The synthesis method takes furfuryl alcohol as a starting raw material and four-step reaction including rearrangement, addition, hydroxyl protection and oxidization is carried out; the total mol yield of a synthesis route is greater than 32 percent; the synthesis method has the characteristics of relatively moderate reaction conditions and the like, and the yield and purity of the 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid are remarkably improved; meanwhile, the synthesis method has the advantagesof detailed technological operation steps, specific parameters, controllable conditions and stable technology, and can realize industrial large-batch production.

Preparation method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

The invention relates to a novel synthesis route of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid. 3-hydroxy-2-methyl-4H-pyran-4-one used as a raw material undergoes acetyl protection, a brominationreaction, benzyl protection and oxidation reaction to synthesize a dolutegravir intermediate in four steps at a high yield. The above preparation method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid has the advantages of high yield, low cost, environmental protection, easiness operation, and suitableness for realizing industrialization.

ANTIVIRAL AGENT

The present invention provides an integrase inhibitor. The inventors have have found the following compound of formula (I) possessing an integrase inhibitory activity. (wherein, R C and R D taken together with the neighboring carbon atoms form a ring which may be a condensed ring, Y is hydroxy, mercapto or amino; Z is O, S or NH ; R A is a group shown by (wherein, C ring is N-containing aromatic heterocycle) or the like)

Orally active iron (III) chelators

A novel 3-hydroxypyridin-4-one compound of formula I is provided wherein R is hydrogen or a group that is removed by metabolism in vivo to provide the free hydroxy compound, R1 is an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by a hydroxy group or a carboxylic acid ester, sulpho acid ester or a C1-6 alkoxy, C6-aryloxy or C7-10aralkoxy ether thereof, R3 is selected from hydrogen and C1-6alkyl; and R4 is selected from hydrogen, C1-6alkyl and a group as described for R2; characterised in that R2 is selected from groups —CONH—R5??(i) —CH2NHCO—R5??(ii) —SO2NH—R5??(iii) —CH2NHSO2—R5??(iv) —CR6R6OR7??(v) —CONHCOR5??(viii) ?wherein R5 is selected from hydrogen and optionally hydroxy, alkoxy, or aralkoxy substituted C1-13 alkyl, aryl and C71-13 aralkyl, R6 is independently selected from hydrogen, C1-13 alkyl, aryl and C7-13 aralkyl, and R7 is selected from hydrogen, C1-13 alkyl, aryl and C7-13 aralkyl or a pharmaceutically acceptable salt of any such compound with the proviso that when R7 is hydrogen, R6 is not selected from aryl and with the proviso that the compound is not 1-ethyl-2-(1′-hydroxyethyl)-3-hydroxypyridin-4-one.

Orally active iron (III) chelators

A compound of formula I wherein R is hydrogen or a group that is removed by metabolism in vivo to provide the free hydroxy compound, R1is an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by a hydroxy group or a carboxylic acid ester, sulpho acid ester or a C1-6alkoxy, C6-aryloxy or C7-10aralkoxy ether thereof, and R3is selected from hydrogen and C1-6alkyl; characterized in that R2is selected from groups (i) —CONH—R5(ii)—CR6R6OR7(iii) —CONHCOR5and (iv) —CON(CnH2n+1)2 R4is selected from hydrogen, C1-6alkyl and a group as described for R2; R5is selected from hydrogen and optionally hydroxy, alkoxy, aryloxy or aralkoxy substituted C1-13alkyl, aryl and C7-13alkyl R6is independently selected from hydrogen and C1-13alkyl, R7is selected from hydrogen, C1-13alkyl, aryl and C7-13aralkyl or a pharmaceutically acceptable salt of any such compound and CnH2n+1is C1-6alkyl with the proviso that the compound is not one of 1-ethyl-2-(1′-hydroxyethyl)-3-hydroxypyridin-4-one and 1-methyl-2-hydroxymethyl-3-hydroxypyridoin-4-one.