1885-13-8

Usage

Uses

Used in Dye and Pigment Production:
4-Methoxyphthalic acid is utilized as a key intermediate in the production of dyes and pigments, contributing to the development of vibrant and stable colorants for various applications.
Used in Pharmaceutical Synthesis:
As a building block in pharmaceutical synthesis, 4-Methoxyphthalic acid is employed for the creation of various medicinal compounds, enhancing the therapeutic potential of new and existing drugs.
Used in Polymer and Resin Manufacturing:
4-Methoxyphthalic acid serves as a crucial component in the manufacturing of polymers and resins, improving the properties and performance of these materials in diverse industries.
Used in Antimicrobial Applications:
Leveraging its potential antimicrobial properties, 4-Methoxyphthalic acid is used as an agent to inhibit the growth of microorganisms, making it valuable in the development of products for hygiene and sanitation.
Used in Antioxidant Formulations:
4-Methoxyphthalic acid is employed as an antioxidant in various formulations, protecting materials and products from oxidative damage and extending their shelf life and durability.
Used in Industrial and Consumer Product Development:
Due to its low toxicity and general safety, 4-Methoxyphthalic acid is incorporated into the development of a wide array of industrial and consumer products, enhancing their performance and safety profiles.

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

Upstream product

• 4685-47-6 3,4-dimethylanisole 
• 5111-69-3 5-methoxyindane 
• 57-62-5 Chlortetracycline 
• 22895-19-8 dimethyl 4-methoxyphtalate 
• 3168-59-0 5-methoxy-o-toluic acid 
• 1730-48-9 6-methoxy-1,2,3,4-tetrahydronaphthalene 
• 610-35-5 4-hydroxyphthalic acid 
• 77-78-1 dimethyl sulfate 
• 1596-15-2 (S)-Cyclohexyl-4-methoxy-2-methyl-benzene 
• 91061-91-5 2-Acetoxy-5-methoxy-2-methyl-cyclohexadien-(3,5)-on-⁽¹⁾ 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 42923-77-3 6-methoxy-1,2,3,4-tetrahydro-isoquinoline 
• 13623-25-1 6-methoxy-2,3-dihydro-1H-inden-1-one 
• 5111-70-6 5-methoxy-1-indanone 

Downstream Products

• 28281-76-7 5-methoxyisobenzofuran-1,3-dione 
• 610-35-5 4-hydroxyphthalic acid 
• 98589-66-3 4-methoxy-3-nitro-phthalic acid 
• 408339-12-8 4-methoxy-5-nitro-phthalic acid 
• 201287-73-2 4-methoxy-3-nitro-phthalic acid monomethyl ester 
• 856806-20-7 4-methoxy-5-nitro-phthalic acid dimethyl ester 
• 50727-04-3 4-methoxyphthalimide 
• 36132-95-3 (2-hydroxymethyl-5-methoxy-phenyl)-methanol 
• 22246-66-8 6-methoxy-2,3-dihydro-isoindol-1-one 
• 1089667-07-1 5-methoxy-2-(4-nitrophenyl)isoindol-1,3-dione 
• 1310530-55-2 5-{1-tert-butyl-2-[5-methoxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-1H-benzimidazol-5-yl}pyrimidin-2-ylamine 
• 1035797-89-7 2-chlorocarbonyl-5-methoxybenzoic acid methyl ester 
• 1310532-03-6 5-methoxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid methyl ester 
• 1310532-04-7 [5-methoxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanol 

Relevant academic research and scientific papers

Synthesis and blocking activities of isoindolinone- and isobenzofuranone-containing phenoxylalkylamines as potent α1- adrenoceptor antagonists

This paper describes the synthesis and blocking activities of twelve new isoindolinone- and isobenzofura-none-containing phenoxylalkylamines as potent α1-Adrenoceptor antagonists. These compounds were synthesized in moderate to good yields starting from 3,4-dimethylphenol, and characterized with 1H-NMR, MS, IR and elemental analysis. Their blocking activities toward α1-Adrenoceptors were evaluated on isolated rat anococcygeus muscles. The results indicated that these compounds were very strong in blocking α1-Adrenoceptors, and most of them exhibited activities that were comparable to that of known potent α1- Adrenoceptor antagonist 1-(2,6-dimethylphenoxy)-2-(3,4- dimethoxyphenylethylamino)propane hydrochloride (DDPH).

METHOD FOR SYNTHESIS OF LOBARIC ACID AND ANALOG THEREOF

The present invention can synthesize lobaric acid and four analogues thereof, which are five phenolic lichen metabolites isolated from an extract of the Antarctic lichen Stereocaulon alpinum and selectively inhibit PTP1B, by a simple, economic and efficient chemical synthesis method.

NOVEL BROMINATED FURANONE DERIVATIVE, METHOD FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a novel brominated furanone derivative, a method for preparing the same, and a pharmaceutical composition containing the same as an active ingredient, wherein the novel brominated furanone derivative or a pharmaceutically acceptable 5 salt thereof according to the present invention exhibits a quorum sensing inhibitory activity of bacteria and also can effectively inhibit the formation of biofilm of bacteria, and thus can be used as a pharmaceutical composition containing the same as an active ingredient, thereby having an effect of being useful, 10 for example, for periodontal diseases such as gingivitis and periodontitis, oral diseases, and the like.

Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen Stereocaulon alpinum

The first total syntheses of the natural products lobaric acid (1) and its derivatives isolated from the Antarctic lichen Stereocaulon alpinum are reported in this study. Lobarin (3), with a pseudodepsidone structure, was synthesized first in 11 steps by utilizing an Ullmann aryl ether coupling reaction, and lobaric acid was synthesized in an additional three steps by a seven-membered lactonization reaction. Various derivatives were also obtained from the prepared lobaric acid, and the synthetic compounds exhibited significant PTP1B inhibitory activities.

Synthesis, biological evaluation and molecular modeling studies of phthalazin-1(2: H)-one derivatives as novel cholinesterase inhibitors

A new series of donepezil analogues based on the phthalazin-1(2H)-one scaffold was designed and synthesized with the aim of exploring its potential as human ChEIs. Biological results revealed that the structural modifications proposed significantly affected ChE inhibitory potency as well as selectivity for AChE/BuChE. Compound 1d showed promising in vitro inhibition of both enzymes in the μM range. However, most target compounds were significantly more active against AChE than BuChE, specifically 1f, 1h and 1j, with IC50 values in the low micromolar or submicromolar range, the most active compounds in the series. Docking simulations suggested that the most active compounds can recognize the donepezil binding site using a similar interactions network. These results allowed us to rationalize the observed structure-activity relationships. Moreover, the predicted physicochemical and ADME properties were also comparable to those of donepezil.

Divergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor–Acceptor Cyclopropanes

Efficient methods for the convergent synthesis of (poly)cyclic scaffolds are urgently needed in synthetic and medicinal chemistry. Herein, we describe new annulation reactions of thioalkynes with phthalimide-substituted donor–acceptor cyclopropanes, which gave access to highly substituted cyclopentenes and polycyclic ring systems. With silyl-thioalkynes, the Lewis acid catalyzed [3+2] annulation reaction with donor–acceptor cyclopropanes took place to afford 1-thio-cyclopenten-3-amines. On the other hand, an unprecedented polycyclic compound was formed with alkyl-thioalkynes through a reaction pathway directly involving the phthalimide group. The two transformations proceeded in good yields and tolerated a large variety of functional groups.

Dynamic kinetic asymmetric [3 + 2] annulation reactions of aminocyclopropanes

We report the first example of a dynamic kinetic asymmetric [3 + 2] annulation reaction of aminocyclopropanes with both enol ethers and aldehydes. Using a Cu catalyst and a commercially available bisoxazoline ligand, cyclopentyl- and tetrahydrofurylamines were obtained in 69-99% yield and up to a 98:2 enantiomeric ratio using the same reaction conditions. The method gives access to important enantio-enriched nitrogen building blocks for the synthesis of bioactive compounds.

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.

Discovery of (2,4-Dihydroxy-5-isopropylphenyl)-[5-(4-methylpiperazin-1- ylmethyl)-1,3-dihydroisoindol-2-yl]methanone (AT13387), a novel inhibitor of the molecular chaperone Hsp90 by fragment based drug design

Inhibitors of the molecular chaperone heat shock protein 90 (Hsp90) are currently generating significant interest in clinical development as potential treatments for cancer. In a preceding publication (DOI: 10.1021/jm100059d) we describe Astex's approach to screening fragments against Hsp90 and the subsequent optimization of two hits into leads with inhibitory activities in the low nanomolar range. This paper describes the structure guided optimization of the 2,4-dihydroxybenzamide lead molecule 1 and details some of the drug discovery strategies employed in the identification of AT13387 (35), which has progressed through preclinical development and is currently being tested in man.

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.