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

General Description

The chemical compound [(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulfanyl]acetic acid is a thioester derivative of naphthalene. It contains a naphthalene ring with a sulfur atom attached to it, as well as a methyl group and two carbonyl groups. The compound also contains an acetic acid moiety, which is a carboxylic acid. This chemical has potential applications in the fields of organic synthesis and medicinal chemistry due to its unique structure and properties. It could be used as a building block for the synthesis of various organic compounds or as a starting material for the development of new pharmaceutical agents. Further research and exploration of its chemical reactivity and biological activity may reveal its potential in various applications.

Upstream product

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• 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.