6325-58-2

Basic information

• Product Name: [(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid
• CAS NO: 6325-58-2
• Molecular Formula: C₁₃H₁₀O₄S
• Molecular Weight: 262.2811
• Mol File: 6325-58-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 464.8°C at 760 mmHg
• Flash Point: 234.9°C
• Density: 1.44g/cm³
• Vapor Pressure: 1.93E-09mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: [(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid(6325-58-2)
• EPA Substance Registry System: [(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid(6325-58-2)

Safety Data

• Hazardous Substances Data: 6325-58-2(Hazardous Substances Data)

Usage

Description

[(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid is a thioester derivative of naphthalene, characterized by a naphthalene ring with a sulfur atom attached, a methyl group, two carbonyl groups, and an acetic acid moiety. This unique structure and composition endow the compound with potential applications in organic synthesis and medicinal chemistry.

Uses

Used in Organic Synthesis:
[(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid is used as a building block for the synthesis of various organic compounds due to its versatile chemical structure and functional groups.
Used in Medicinal Chemistry:
[(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid is used as a starting material for the development of new pharmaceutical agents, leveraging its unique structure and properties to potentially create novel therapeutics.
Used in Pharmaceutical Development:
In the pharmaceutical industry, [(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid is used as a precursor for the synthesis of new drug candidates, aiming to explore its potential in treating various diseases and conditions.
Further research and exploration of the chemical reactivity and biological activity of [(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid may reveal additional applications in different industries, such as materials science or environmental chemistry.

Upstream product

• 58-27-5 menadione 
• 856197-80-3 2,6,7-tribromo-3-methyl-5,6,7,8-tetrahydro-naphthalene-1,4-diol 
• 859997-89-0 2-bromo-3-methyl-5,8-dihydro-[1,4]naphthoquinone 
• 3090-46-8 2-methyl-5,8-dihydro-1,4-naphthalenediol 
• 3129-39-3 2-bromo-3-methyl-[1,4]naphthoquinone 
• 68-11-1 mercaptoacetic acid 

Downstream Products

• 58-27-5 menadione 

Relevant articles and documents

Characterization of molecular complexes of 1,4-naphthoquinone derivatives

The structures of sulphur atom tethered quinone containing flexible carboxylic acid (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylsulfanyl)acetic acid (1) and its molecular complex with 4,4′-bipyridine (3) are determined. The compound 1 crystallizes in P-1 (triclinic, a = 7.5378(6) A, b = 7.6413(7) A, c = 10.3101(9) A; α = 89.779 (7)°, β = 81.042 (5)°, γ = 89.101(7)°) and the molecular complex 3 crystallises in P2(1)/n (monoclinic, a = 9.3383(7) A, b = 3.970(3) A, c = 42.130(3) A, β = 91.056(5)°) space groups, respectively. The R 2 2 (8) type hydrogen bonding between dicarboxylic acid groups present in the parent compound 1 is lost on interaction with 4, 4′-bipyridine; in the molecular complex 3 R 2 2 (7) type of O???H-C and O-H???N interactions are present between the pyridine rings and carboxylic acid groups. The molecular complex (4) derived from 3-carboxymethylsulfanyl-1,4- dihydroxynaphthalen-2-yl-sulfanyl) acetic acid (2) with triphenylphosphine oxide in 1:2 ratio, crystallises in C2/c space group have monoclinic, a = 26.0494(13) A, b = 10.5402(5) A, c = 17.1023(8) A, β = 108.719 (5)°). The triphenylphosphine oxide molecules are preferentially held by O-H???O interactions between carboxylic acid and P=O bond.

Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity

CDC25 dual-specificity phosphatases are essential key regulators of eukaryotic cell cycle progression and the CDC25A and B isoforms are over-expressed in different tumors and related cancer cell lines. CDC25s are now considered to be interesting targets in the search for novel anticancer agents. We describe new compounds derived from vitamin K3 that inhibit CDC25B activity with IC50 values in the low micromolar range. These naphthoquinone derivatives also display antiproliferative activity on HeLa cells as expected for CDC25 inhibitors and inhibit cell growth in a clonogenic assay at submicromolar concentrations. They increase inhibitory tyrosine 15 phosphorylation of CDK and induce the cleavage of PARP, a hallmark of apoptosis.