63351-46-2

Basic information

• Product Name: N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2-phenylacetamide
• CAS NO: 63351-46-2
• Molecular Formula: C₁₈H₁₂ClNO₃
• Molecular Weight: 325.7458
• Mol File: 63351-46-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 526.5°C at 760 mmHg
• Flash Point: 272.2°C
• Density: 1.4g/cm³
• Vapor Pressure: 3.57E-11mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2-phenylacetamide(63351-46-2)
• EPA Substance Registry System: N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2-phenylacetamide(63351-46-2)

Safety Data

• Hazardous Substances Data: 63351-46-2(Hazardous Substances Data)

Upstream product

• 2797-51-5 quinoclamine 
• 103-80-0 phenylacetyl chloride 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 103-81-1 Benzeneacetamide 

Downstream Products

• 1610042-67-5 N-(3-(3,5-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide 
• 1610042-73-3 N-(3-(furan-3-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide 

Relevant articles and documents

Structure-activity relationships and colorimetric properties of specific probes for the putative cancer biomarker human arylamine N-acetyltransferase 1

A naphthoquinone inhibitor of human arylamine N-acetyltransferase 1 (hNAT1), a potential cancer biomarker and therapeutic target, has been reported which undergoes a distinctive concomitant color change from red to blue upon binding to the enzyme. Here we describe the use of in silico modeling alongside structure-activity relationship studies to advance the hit compound towards a potential probe to quantify hNAT1 levels in tissues. Derivatives with both a fifty-fold higher potency against hNAT1 and a two-fold greater absorption coefficient compared to the initial hit have been synthesized; these compounds retain specificity for hNAT1 and its murine homologue mNat2 over the isoenzyme hNAT2. A relationship between pKa, inhibitor potency and colorimetric properties has also been uncovered. The high potency of representative examples against hNAT1 in ZR-75-1 cell extracts also paves the way for the development of inhibitors with improved intrinsic sensitivity which could enable detection of hNAT1 in tissue samples and potentially act as tools for elucidating the unknown role hNAT1 plays in ER+ breast cancer; this could in turn lead to a therapeutic use for such inhibitors.

Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of 2-substituted 3-chloro-1,4-naphthoquinone derivatives

A series of 2-substituted 3-chloro-1,4-naphthoquinones was synthesized, and the antiplatelet, antiinflammatory, and antiallergic activities of these compounds were evaluated. The structure-activity relationships in this series were also examined. Most of the 2-alkyl/arylcarboxamido derivatives of 3-chloro-1,4-naphthoquinone showed potent activities with similar trends in each of the activities evaluated.