216581-47-4

Basic information

• Product Name: 6-methyl-4-oxo-3-phenylmethoxypyran-2-carboxylic acid
• Synonyms: 6-methyl-4-oxo-3-phenylmethoxypyran-2-carboxylic acid
• CAS NO: 216581-47-4
• Molecular Formula: C₁₄H₁₂O₅
• Molecular Weight: 260.24208
• Mol File: 216581-47-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-methyl-4-oxo-3-phenylmethoxypyran-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methyl-4-oxo-3-phenylmethoxypyran-2-carboxylic acid(216581-47-4)
• EPA Substance Registry System: 6-methyl-4-oxo-3-phenylmethoxypyran-2-carboxylic acid(216581-47-4)

Safety Data

• Hazardous Substances Data: 216581-47-4(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
6-methyl-4-oxo-3-phenylmethoxypyran-2-carboxylic acid is used as a potential active pharmaceutical ingredient for the development of new drugs. Its unique structure may confer specific biological activities that can be harnessed for therapeutic purposes.
Used in Drug Development:
In the pharmaceutical industry, 6-methyl-4-oxo-3-phenylmethoxypyran-2-carboxylic acid is used as a lead compound for the design and synthesis of novel therapeutic agents. Its complex structure provides a foundation for further chemical modifications to optimize pharmacological properties, such as potency, selectivity, and bioavailability.
Used in Organic Chemistry Research:
6-methyl-4-oxo-3-phenylmethoxypyran-2-carboxylic acid serves as an interesting subject for research in organic chemistry, where its synthesis, structural elucidation, and reactivity can provide insights into the development of new synthetic methods and the exploration of novel chemical space.
While the specific applications and properties of 6-methyl-4-oxo-3-phenylmethoxypyran-2-carboxylic acid are not yet fully understood, its unique structure and potential for biological activity make it a valuable target for further investigation in various scientific and industrial fields.

Upstream product

• 216581-46-3 2-formyl-3-benzyloxy-6-methyl-pyran-4(1H)-one 
• 644-46-2 allomaltol 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 7559-81-1 chlorokojic acid 
• 22639-17-4 2-hydroxymethyl-3-hydroxy-6-methyl-pyran-4(1H)-one 
• 216581-77-0 2-Hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one 
• 7758-19-2 sodium chlorite 
• 5329-14-6 aminosulfonic acid 

Downstream Products

• 216581-49-6 N-(3-benzyloxy-6-methyl-pyran-4(1H)-one-2-carbonyl)-1,3-thiazolidine-2-thione 
• 868368-26-7 AM-2 
• 932024-46-9 3-benzyloxy-6-methylpyran-4(1H)-one-2-carboxy-N-(4-methoxybenzylamide) 
• 868368-24-5 3-benzyloxy-6-methylpyran-4(1H)-one-2-carboxy-N-(4-iodobenzylamide) 
• 870102-32-2 3-benzyloxy-6-methylpyran-4(1H)-one-2-carboxy-N-(4-phenylbenzylamide) 
• 932024-45-8 3-benzyloxy-6-methylpyran-4(1H)-one-2-carboxy-N-[2-(4-biphenyl)ethylamide] 
• 932025-43-9 3-benzyloxy-6-methylpyran-4(1H)-one-2-carboxy-N-(4,4-cyanophenylbenzylamide) 
• 932025-51-9 3-benzyloxy-6-methylpyran-4(1H)-one-2-carboxy-N-(4,4-biphenylbenzylamide) 
• 887774-72-3 3-benzyloxy-1-cyclopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid 
• 444103-11-1 3-(benzyloxy)-N,N-diethyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide 
• 216581-60-1 1,6-dimethyl-3-benzyloxy-pyridin-4(1H)-one-2-carboxy-(N-methyl)-amide 
• 922159-35-1 C₂₁H₁₈FNO₄ 
• 922159-37-3 C₁₄H₁₂FNO₄ 
• 1064077-28-6 3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 

Relevant articles and documents

Synthesis, molecular modelling and biological studies of 3-hydroxy-pyrane-4-one and 3-hydroxy-pyridine-4-one derivatives as HIV-1 integrase inhibitors

Background: Despite the progress in the discovery of antiretroviral compounds for treating HIV-1 infection by targeting HIV integrase (IN), a promising and well-known drug target against HIV-1, there is a growing need to increase the armamentarium against

Structure-Activity Relationships in Metal-Binding Pharmacophores for Influenza Endonuclease

Metalloenzymes represent an important target space for drug discovery. A limitation to the early development of metalloenzyme inhibitors has been the lack of established structure-activity relationships (SARs) for molecules that bind the metal ion cofactor(s) of a metalloenzyme. Herein, we employed a bioinorganic perspective to develop an SAR for inhibition of the metalloenzyme influenza RNA polymerase PAN endonuclease. The identified trends highlight the importance of the electronics of the metal-binding pharmacophore (MBP), in addition to MBP sterics, for achieving improved inhibition and selectivity. By optimization of the MBPs for PAN endonuclease, a class of highly active and selective fragments was developed that displays IC50 values 50 values of ～10 nM, illustrating the utility of a metal-centric development campaign in generating highly active and selective metalloenzyme inhibitors.

MULTIDENTATE PYRONE-DERIVED CHELATORS FOR MEDICINAL IMAGING AND CHELATION

Provided herein are chelating agents and metal chelates that are useful in diagnostic and therapeutic applications. The uses of metal chelates provided herein include their use as contrast agents in medical imaging modalities, such as magnetic resonance imaging (MRI).

ANTIVIRAL COMPOUNDS

The invention is related to phosphorus substituted anti-viral inhibitory compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

ZINC-BINDING GROUPS FOR METALLOPROTEIN INHIBITORS

The present invention relates to metalloprotein inhibitors comprising: a. an organic backbone molecule (Pep) and at least one zinc binding group (ZBG) covalently attached thereto; or b. at least one ZBG substituted by a side chain that comprises one or more amido and/or amino moieties, wherein the ZBG is of formula (I): wherein the wavy line represents a Pep molecule or a side chain that is an R3 or an R4 group which comprises one or more amido and/or amino moieties, and wherein X is O or S and each R1, R2, R3, and R4 is individually hydrogen or an organic radical. The metalloprotein inhibitors are useful for preventing or treating a pathological disease, condition, or symptom that is associated with pathological metalloprotein activity and/or that is alleviated by inhibition of said activity.

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.

Synthesis of 2-amido-3-hydroxypyridin-4(1H)-ones: Novel iron chelators with enhanced pFe3+ values

The synthesis of a range of 2-amido-3-hydroxypyridin-4-ones as bidentate iron(III) chelators with potential for oral administration is described. The pKa values of the ligands together with the stability constants of their iron(III) complexes have been determined. Results indicate that the introduction of an amido substituent at the 2-position leads to an appreciable enhancement of the pFe3+ values. The ability of these novel 3-hydroxypyridin-4-ones to facilitate the iron excretion in bile was investigated using a 59Fe-ferritin loaded rat model. The optimal effect was observed with the N-methyl amido derivative 15b, which has an associated pFe3+ value of 21.7, more than two orders of magnitude higher than that of deferiprone (1,2-dimethyl-3-hydroxypyridin-4-one) 1a (pFe3+=19.4). Dose response studies suggest that chelators with high pFe3+ values scavenge iron more effectively at lower doses when compared with simple dialkyl substituted hydroxypyridinones. Copyright