78265-13-1

Usage

Uses

Used in Pharmaceutical Industry:
1 4-DIMETHOXY-2-NAPHTHOIC ACID 97 is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications.
Used in Chemical Industry:
1 4-DIMETHOXY-2-NAPHTHOIC ACID 97 is used as a key component in the production of dyes, pigments, and other organic compounds, playing a vital role in the creation of a wide range of chemical products.
Used in Medicinal Chemistry and Drug Development:
1 4-DIMETHOXY-2-NAPHTHOIC ACID 97 is used as a potential anti-inflammatory and antioxidant agent, providing valuable properties for the research and development of novel therapeutic agents in the field of medicinal chemistry.

InChI:InChI=1/C13H12O4/c1-16-11-7-10(13(14)15)12(17-2)9-6-4-3-5-8(9)11/h3-7H,1-2H3,(H,14,15)

Upstream product

• 127536-35-0 1,4-dimethoxynaphthalene-2-carboxylic acid methyl ester 
• 124-38-9 carbon dioxide 
• 10075-62-4 1,4-dimethoxynaphthalene 
• 75965-83-2 1,4-dimethoxynaphthalene-2-carbaldehyde 
• 481-85-6 2-methyl-1,4-naphthohydroquinone 
• 58-27-5 menadione 
• 53772-19-3 1,4-dimethoxy-2-methylnaphthalene 
• 31519-22-9 1,4-dihydroxy-2-naphthoic acid 
• 77-78-1 dimethyl sulfate 
• 64648-81-3 2-bromo-1,4-dimethoxynaphthalene 

Downstream Products

• 208338-13-0 1,4-Dimethoxy-naphthalene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester 
• 208647-40-9 (1'R,2'S,5'R)-(-)-menthyl 1,4-dimethoxy-2-naphthoate 
• 208335-56-2 2-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-[1,4]naphthoquinone 
• 208338-08-3 (R)-4-Benzyl-3-(1,4-dimethoxy-naphthalene-2-carbonyl)-oxazolidin-2-one 
• 208337-85-3 1,4-Dioxo-1,4-dihydro-naphthalene-2-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester 
• 686347-86-4 13-hydroxy-13-phenyl-spiro[indeno[2,1-f]naphtho[1,2-b]pyran-3,9'-thioxanthene] 
• 867019-38-3 2-(1'-phenyl-4'-methoxynaphth-2'-yl)-4,4-dimethyl-4,5-dihydrooxazole 
• 78250-40-5 4-Methoxy-1-phenyl-2-naphthoic acid 

Relevant academic research and scientific papers

1,4-BIS (SUBSTITUTED OXY)-2-NAPHTHOIC ACID COMPOUND AND APPLICATION THEREOF

PROBLEM TO BE SOLVED: To provide a photopolymerization sensitizer hardly generating blooming or migration. SOLUTION: There is provided a photopolymerization sensitizer containing a 1,4-bis(substituted oxy)-2-naphthoic acid compound represented by the formula (1), where R1 and R2 are each independently a C1 to 8 alkyl group or a silyl group having C1 to 8 alkyl group, R3 is H or an aryl group, X is H or a C1 to 8 alkyl group and a plurality of alkyl groups in the silyl group are each independent. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Oxadiazole-substituted naphtho[2,3-b]thiophene-4,9-diones as potent inhibitors of keratinocyte hyperproliferation. Structure?activity relationships of the tricyclic quinone skeleton and the oxadiazole substituent

Novel analogues of oxadiazole-substituted naphtho[2,3-b]thiophene-4,9-diones were synthesized in which the tricyclic quinone skeleton was systematically replaced with simpler moieties, such as structures with fewer rings and open-chain forms, while the oxadiazole ring was maintained. In addition, variants of the original 1,2,4-oxadiazole ring were explored. Overall, the complete three-ring quinone was essential for potent suppression of human keratinocyte hyperproliferation, whereas analogous anthraquinones were inactive. Also, the oxadiazole ring per se was not sufficient to elicit activity. However, rearrangement of the heteroatom positions in the oxadiazole ring resulted in highly potent inhibitors with compound 24b being the most potent analogue of this series showing an IC50 in the nanomolar range. Furthermore, experiments in isolated enzymatic assays as well as in the keratinocyte-based hyperproliferation assay did not support a major role of redox cycling in the mode of action of the compounds.

Preparations of anthraquinone and naphthoquinone derivatives and their cytotoxic effects

Chrysophanol and 1,8-di-O-hexylchrysophanol derivatives having nucleic acid bases at position 5 were synthesized. Furthermore, derivatives of menadione substituted at position 11 (type A naphthoquinone derivatives) or methylmenadione substituted at position 7 (type B naphthoquinone derivatives) modified with nucleic acid bases, amines and thiocyano, selenocyano or thioacetyl groups were synthesized. The cytotoxic effects of these derivatives on HCT 116 cells, which poorly express P-glycoprotein (P-gp), and Hep G2 cells, which stably express P-gp, were evaluated by performing 3-(4,5-dimethylthiazol- 2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Results were compared with those obtained using 5-fluorouracil (5-FU), which has been used clinically. Several of these derivatives exhibited markedly higher potent cytotoxic effects not only on HCT cancer cells but also Hep G2 cancer cells as compared with 5-FU.

The effect of a sulphur bridge on the photochromic properties of indeno-fused naphthopyrans

The synthesis of four new 2,2-diphenyl-2H-naphtho[1,2-b]pyrans with a fused indeno group at the f face and a sulphur junction between the 2,2-phenyl groups is described. The photochromic properties in solution of these novel compounds were investigated under continuous irradiation. Compared to known indeno-fused naphthopyrans, these new compounds showed a significant bathochromic shift in the spectra of the open forms, faster ring closure kinetics and an expected decrease in the colourabilities.

Selective oxidation of aromatic aldehydes to arenecarboxylic acids using ebselen-tert-butyl hydroperoxide catalytic system

It has been found that aromatic aldehydes with electron-withdrawing as well as electron-donating substituents are oxidized to arenecarboxylic acids using tert-butyl hydroperoxide in the presence of ebselen (2-phenylbenzisoselenazol-3(2H)-one) as a catalyst. The reaction is highly chemoselective and formation of phenols, being the products of competitive Baeyer-Villiger rearrangement, is marginal. It has been assumed that this rearrangement is inhibited by steric hindrance of the electron-deficient oxygen atom in the transient tetrahedral intermediate.

Selenium(IV) oxide catalyzed oxidation of aldehydes to carboxylic acids with hydrogen peroxide

A convenient method for oxidative transformation of aromatic, heteroaromatic and aliphatic aldehydes into carboxylic acids is presented. It is based on the oxidation of aldehydes in THF using 30% hydrogen peroxide in the presence of 5 molar % of selenium(IV) oxide. The scope and limitation of the method are discussed.

Addition of cyclopentadiene and 2-trimethylsilyloxyfuran to quinones bearing a menthyl ester chiral auxiliary

Addition of cyclopentadiene to 2-carbomethoxy-1,4-benzoquinone 9 afforded Diels-Alder adduct 10 using the Lewis acids ZnCl2 and ZnBr2 whereas the fragmenatation product 11 was the major product when using SnCl4 and TiCl4. Addition of cyclopentadiene to 1,4-benzoquinone 8 bearing a menthyl ester at C-2 afforded Diels-alder adduct 12 in moderate diastereomeric excess using ZnCl2 and ZnBr2 as Lewis acids. Use of TiCl4 and SnCl4 afforded the fragmentation product 13 also in moderate diastereomeric excess. Addition of 2-trimethylsilyloxyfuran to chiral naphthoquinone 4 and benzoquinone 8 afforded furofuran adducts 14 and 15 respectively as a 1:1 mixture of diastereomers.

Asymmetric Diels-Alder addition of cyclopentadiene to chiral naphthoquinones

Diels-Alder reactions of 1,4-naphthoquinones bearing a chiral auxiliary at C-2, with cyclopentadiene under Lewis acid conditions afforded the corresponding Diels-Alder adducts. High levels of diastereomeric excess were obtained using (R)-pantolactone, (S)-N-methyl-2-hydroxysuccinimide and trans- 2-phenylcyclohexanol as auxiliaries. Moderate asymmetric induction was achieved using Oppolzer's camphorsultam and (R)-(+)-4-benzyl-2-oxazolidinone as auxiliaries. X-Ray crystallographic analysis of the pantolactone adduct enabled determination of the stereochemistry of all adducts obtained.

NAPHTHALENE CARBOXAMIDES

Pharmaceutical compounds of the formula: STR1 in which each R 1 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, halogen or nitro, and n is 0, 1, 2 or 3, R 2 is hydrogen, C 1-4 alkyl or C. sub.2-4 alkenyl, R 3 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthi