132292-17-2

Basic information

• Product Name: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid
• Synonyms: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid;6-(4-Methoxyphenyl)-2-naphthoic Acid
• CAS NO: 132292-17-2
• Molecular Formula: C18H14O3
• Molecular Weight: 278.30196
• Mol File: 132292-17-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly, Heated, Sonicated)
• CAS DataBase Reference: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid(132292-17-2)
• EPA Substance Registry System: 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid(132292-17-2)

Safety Data

• Hazardous Substances Data: 132292-17-2(Hazardous Substances Data)

Usage

Description

6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and chemicals. It is characterized by its molecular structure, which includes a naphthalene ring and a methoxyphenyl group, providing it with unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid is used as a reactant for the synthesis of Adapalene (A225000), a retinoid that selectively targets retinoic acid receptor (RAR) subtypes β and γ. Adapalene is widely used in the treatment of acne due to its ability to regulate skin cell turnover, reduce inflammation, and promote the healing of acne lesions.
In the synthesis of Adapalene, 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid plays a crucial role as it forms the backbone of the molecule, allowing for the selective targeting of specific RAR subtypes. This selective action contributes to the effectiveness of Adapalene in treating acne while minimizing potential side effects associated with non-selective retinoids.
Additionally, 6-(4-Methoxyphenyl)-2-naphthalenecarboxylic acid may have potential applications in other industries, such as in the development of new materials or chemicals, due to its unique chemical properties.

Upstream product

• 86471-14-9 ethyl 6-bromo-naphthalene-2-carboxylate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1334137-82-4 ethyl 6-(4-methoxyphenyl)-2-naphthoate 
• 132041-62-4 2-(4-methoxyphenyl)-6-methylnaphthalene 
• 33626-98-1 methyl 6-bromo-2-naphthoate 
• 5773-80-8 6-bromo-2-naphthoic acid 

Downstream Products

• 1334138-60-1 C₅₀H₅₆N₄O₁₀S₂ 
• 1334136-11-6 (11aS)-7-methoxy-8-(3-(2-methoxy-5-(4-(6-(4-methoxyphenyl)-2-naphthoyl)piperazine-1-carbonyl)phenoxy)propoxy)-2,3-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5(11aH)-one 
• 1334137-43-7 C₃₀H₂₈N₂O₅ 
• 1334136-34-3 C₃₃H₃₃BrN₂O₅ 

Relevant articles and documents

Synthesis of aryl-substituted naphthalene-linked pyrrolobenzodiazepine conjugates as potential anticancer agents with apoptosis-inducing ability

A library of new aryl-substituted naphthalene C8-linked pyrrolo[2,1-c][1,4]benzodiazepine (PBD) conjugates with various linker architectures were designed, synthesized, and evaluated for their anticancer activity against a panel of 11 human cancer cell lines. All 32 conjugates show anticancer potential, with some of them exhibiting particularly high activity (0.01-0.19μM). Thermal denaturation studies showed effective DNA binding capacity relative to DC-81. In assays for biological activity relating to cell-cycle distribution, these PBD conjugates induce G0/G1-phase arrest and also cause an increase in the levels of p53 and caspase-9 proteins, followed by apoptotic cell death. One conjugate in particular is the most promising candidate of the series, with the potential to be selected for further studies, either alone or in combination with existing anticancer therapies. Getting into the groove: Pyrrolobenzodiazepine (PBD) conjugates showed an effective ability to bind DNA. They induce G0/G1-phase arrest, enhance the expression levels of p53 and caspase-9, and induce apoptosis. One conjugate stands out as particularly promising; it is a suitable candidate for further study, either alone or in combination with current anticancer therapies.

Naphthalene compounds

A compound represented by the formula: STR1 and a compound represented by the formula: STR2 wherein R is C1 -C3 alkyl or C1 -C3 alkoxy, which is an intermediate for producing the above compound (1) are disclosed.