14963-97-4

Usage

Uses

3-Methoxyphthalic Acid has metallo-β-lactamase inhibitory activity.

InChI:InChI=1/C9H8O5/c1-14-6-4-2-3-5(8(10)11)7(6)9(12)13/h2-4H,1H3,(H,10,11)(H,12,13)

Upstream product

• 2944-49-2 2,3-dimethylanisole 
• 32136-52-0 dimethyl 3-methoxyphthalate 
• 17802-94-7 (2-carboxy-3-methoxy-phenyl)-glyoxylic acid 
• 601-97-8 3-hydroxyphthalic acid 
• 77-78-1 dimethyl sulfate 
• 19056-23-6 3-methoxybenzene-1,2-dicarbonitrile 
• 4792-33-0 4-methoxyphthalide 
• 1008-19-1 5-methoxy-1,2,3,4-tetrahydro-naphthalene 
• 72049-14-0 1-Hydroxy-3-(hydroxymethyl)-8-methoxy-9,10-anthraquinone 
• 30839-37-3 3,8-Dimethoxy-[1,2]naphthochinon 
• 4938-06-1 7-Methoxy-3-methylphthalide 
• 3588-80-5 5-methoxynaphthalen-1-ol 
• 10075-63-5 1,5-dimethoxynaphthalene 
• 139583-90-7 2-methoxy-6-methylbenzamide 

Downstream Products

• 601-97-8 3-hydroxyphthalic acid 
• 90047-52-2 3-methoxy-o-xylene-α,α'-diol 
• 932745-87-4 diethyl 2-(benzyloxycarbonylamino)-4-methoxyindane-2-phosphonate 
• 71785-96-1 2,3-bisbromomethylanisole 
• 53015-08-0 2-formyl-6-methoxy-benzoic acid 
• 60407-04-7 2-formyl-3-methoxy-benzoic acid 
• 60314-07-0 2-methoxy-6-methoxycarbonylbenzoic acid 
• 71013-35-9 1,8-dimethoxy-3-methyl-9,10-anthraquinone 
• 481-74-3 Chrysophanol 
• 21794-55-8 (+)-Daunomycinone 
• 37418-88-5 3-hydroxyphthalic anhydride 
• 41709-83-5 4-methoxy-isoindole-1,3-dione 
• 400781-21-7 (+/-)-3-(4-methoxybenzyl)-7-methoxyphthalide 

Relevant academic research and scientific papers

Methylation and Hydroxylation Studies on Aloe-emodin

The chemistry of aloe-emodin (3) has been explored with a view toward its use as a synthon for the regiospecific synthesis of adriamycin and analogues of it.Routes for satisfactory large-scale monomethyl ether formation at C8 (4) and regiospecific introduction of a phenolic oxygen function at C4 (21) are described.Interesting side reactions were encountered, including an apparent peri O to O acyl wandering reaction during methylation and a reductive debromination reaction during displacement of an aryl bromide by methanolic methoxide.

Impact of N-Alkylamino Substituents on Serotonin Receptor (5-HTR) Affinity and Phosphodiesterase 10A (PDE10A) Inhibition of Isoindole-1,3-dione Derivatives

In this study, a series of compounds derived from 4-methoxy-1H-isoindole-1,3(2H)-dione, potential ligands of phosphodiesterase 10A and serotonin receptors, were investigated as potential antipsychotics. A library of 4-methoxy-1H-isoindole-1,3(2H)-dione derivatives with various amine moieties was synthesized and examined for their phosphodiesterase 10A (PDE10A)-inhibiting properties and their 5-HT1A and 5-HT7 receptor affinities. Based on in vitro studies, the most potent compound, 18 (2-[4-(1H-benzimidazol-2-yl)butyl]-4-methoxy-1H-isoindole-1,3(2H)-dione), was selected and its safety in vitro was evaluated. In order to explain the binding mode of compound 18 in the active site of the PDE10A enzyme and describe the molecular interactions responsible for its inhibition, computer-aided docking studies were performed. The potential antipsychotic properties of compound 18 in a behavioral model of schizophrenia were also investigated.

Synthetic process of rhein

The invention relates to a synthetic process of rhein. The synthetic process comprises the steps of: adopting 2,3-dimethyl phenol as a raw material, performing methylation and oxidation to obtain 3-methoxy phthalic acid, performing dehydration by using acetic anhydride to obtain acid anhydride, then performing a Friedel-Crafts reaction between the obtained acid anhydride and excess methyl anisoleunder the action of aluminum trichloride to obtain the product, and then conducting cyclization by using sulfuric acid to obtain an intermediate chrysophanol, performing acetylation on the obtained chrysophanol, performing oxidation to obtain diacerein, and finally carrying out deacetylation to synthesize rhein.

Preparation method of 3-hydroxyl phthalic anhydride

The invention belongs to the technical field of organic synthesis and in particular relates to a preparation method of a key medical intermediate, 3-hydroxyl phthalic anhydride. The method comprises the following steps: with a compound I as a raw material, oxidizing the raw material to obtain 3-methoxyl phthalic acid; performing a reaction on 3-methoxyl phthalic acid to generate 3-hydroxyl phthalic acid; and performing dehydration and condensation on 3-hydroxyl phthalic acid to generate 3-hydroxyl phthalic anhydride. 3-hydroxyl phthalic anhydride prepared by the method provided by the invention is high in yield and good in purity. The method is free of special equipment demands, has mild conditions and is safe and environmental-friendly in an industrial process, and the process technology provided by the invention can be industrially performed.

Metallo-β-lactamase inhibitory activity of 3-alkyloxy and 3-amino phthalic acid derivatives and their combination effect with carbapenem

3-Alkyloxy and 3-amino phthalic acid derivatives were found to have metallo-β-lactamase inhibitory activity. Among them, 3-amino phthalic acid derivatives showed both potent activity against metallo-β-lactamase, IMP-1 inhibitory activity and a strong combination effect with biapenem (BIPM), carbapenem antibiotic. In particular, the 4′-hydroxy-piperidine derivative showed strong IMP-1 inhibitory activity and a combination effect with various antibiotics.

Insecticidal Benzenedicarboxamide Derivative

The present invention relates to a novel benzenedicarboxamide derivative and the use thereof as an insecticide having the formula (I) wherein the chemical groups W1 to W9, and R1 to R3 are as defined here-in.

PHARMACEUTICAL COMPOUNDS

The invention provides a compound for use in medicine, the compound being a compound of the formula (VI0) or a salt, solvate, tautomer or N-oxide thereof: wherein the bicyclic group: is selected from the structures C1, C5 and C6: wherein n is 0, 1, 2 or 3; R1 is hydrogen, hydroxy, or O—Rz; R2a is hydroxy, methoxy or O—Rz; provided that at least one of R1 and R2a is O—Rz; Rz is Lp-Rp1; SO3H; a glucuronide residue; a mono-, di- or tripeptide residue; or Lp is a bond, C═O, (C═O)O, (C═O)NRp1 or S(O)xNRp1; x is 1 or 2; Rp1 is hydrogen or a an optionally substituted C1-25 hydrocarbyl group containing 0, 1 or 2 carbocyclic rings and 0, 1, 2, 3, 4, 5 or 6 carbon-carbon multiple bonds, provided that Rp1 is not hydrogen when Lp is a bond, C═O or (C═O)O; and provided also that O—Rz does not contain an O—O moiety; and excluding compounds wherein R1 is hydroxy and R2a is methoxy; Rp2 and Rp3 are the same or different and each is a group Rp1; and R3, R4a, R8 and R10 are defined in the claims. The compounds of formula (VI0) are pro-drugs of parent compounds wherein R1 and/or R2a are hydroxy, wherein the parent compounds have Hsp90 inhibiting activity.

PHARMACEUTICAL COMBINATIONS

The invention provides combinations comprising (or consisting essentially of) one or more ancillary compound(s) and a compound of the formula (I): or salts, tautomers, solvates and N-oxides thereof; wherein R1 is hydroxy or hydrogen; R2 is hydroxy; methoxy or hydrogen; provided that at least one of R1 and R2 is hydroxy; R3 is selected from hydrogen; halogen; cyano; optionally substituted C1-5 hydrocarbyl and optionally substituted C1- 5 hydrocarbyloxy; R4 is selected from hydrogen; a group -(O)n-R7 where n is 0 or 1 and R7 is an optionally substituted acyclic C1-5 hydrocarbyl group or a monocyclic carbocyclic or heterocyclic group having 3 to 7 ring members; halogen; cyano; hydroxy; amino; and optionally substituted mono- or di-C1-5 hydrocarbyl-amino; or R3 and R4 together form a monocyclic carbocyclic or heterocyclic ring of 5 to 7 ring members; and NR5R6 forms an optionally substituted bicyclic heterocyclic group having 8 to 12 ring members of which up to 5 ring members are heteroatoms selected from oxygen, nitrogen and sulphur. The combinations have activity as Hsp90 inhibitors.

PHARMACEUTICAL COMBINATIONS

The invention provides combinations comprising (or consisting essentially of) one or more ancillary compound(s) and a compound of the formula (I): or salts, tautomers, solvates and N-oxides thereof; wherein R1 is hydroxy or hydrogen; R2 is hydroxy; methoxy or hydrogen; provided that at least one of R1 and R2 is hydroxy; R3 is selected from hydrogen; halogen; cyano; optionally substituted C1-5 hydrocarbyl and optionally substituted C1-5 hydrocarbyloxy; R4 is selected from hydrogen; a group -(O)n-R7 where n is 0 or 1 and R7 is an optionally substituted acyclic C1-5 hydrocarbyl group or a monocyclic carbocyclic or heterocyclic group having 3 to 7 ring members; halogen; cyano; hydroxy; amino; and optionally substituted mono- or di-C1-5 hydrocarbyl-amino; or R3 and R4 together form a monocyclic carbocyclic or heterocyclic ring of 5 to 7 ring members; and NR5R6 forms an optionally substituted bicyclic heterocyclic group having 8 to 12 ring members of which up to 5 ring members are heteroatoms selected from oxygen, nitrogen and sulphur. The combinations have activity as Hsp90 and/or glycogen synthase kinase-3 and/or cyclin dependent kinase inhibitors.

PHARMACEUTICAL COMBINATIONS

The invention provides combinations comprising (or consisting essentially of) one or more ancillary compound(s) and a compound of the formula (I): or salts, tautomers, solvates and N-oxides thereof; wherein R1 is hydroxy or hydrogen; R2 is hydroxy; methoxy or hydrogen; provided that at least one of R1 and R2 is hydroxy; R3 is selected from hydrogen; halogen; cyano; optionally substituted C1-5 hydrocarbyl and optionally substituted C1-5 hydrocarbyloxy; R4 is selected from hydrogen; a group -(O)n-R7 where n is 0 or 1 and R7 is an optionally substituted acyclic C1-5 hydrocarbyl group or a monocyclic carbocyclic or heterocyclic group having 3 to 7 ring members; halogen; cyano; hydroxy; amino; and optionally substituted mono- or di-C1-5 hydrocarbyl-amino; or R3 and R4 together form a monocyclic carbocyclic or heterocyclic ring of 5 to 7 ring members; and NR5R6 forms an optionally substituted bicyclic heterocyclic group having 8 to 12 ring members of which up to 5 ring members are heteroatoms selected from oxygen, nitrogen and sulphur. The combinations have activity as Hsp90 and/or glycogen synthase kinase-3 and/or cyclin dependent kinase and/or aurora kinase inhibitors.