6307-22-8

Basic information

• Product Name: 2-chloro-3-(phenethylamino)naphthalene-1,4-dione
• Synonyms: 2-chloro-3-(phenethylamino)naphthalene-1,4-dione
• CAS NO: 6307-22-8
• Molecular Formula: C₁₈H₁₄ClNO₂
• Molecular Weight: 311.76
• Mol File: 6307-22-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 454.3°C at 760 mmHg
• Flash Point: 228.6°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 1.92E-08mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 2-chloro-3-(phenethylamino)naphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-3-(phenethylamino)naphthalene-1,4-dione(6307-22-8)
• EPA Substance Registry System: 2-chloro-3-(phenethylamino)naphthalene-1,4-dione(6307-22-8)

Safety Data

• Hazardous Substances Data: 6307-22-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H14ClNO2/c19-15-16(20-11-10-12-6-2-1-3-7-12)18(22)14-9-5-4-8-13(14)17(15)21/h1-9,20H,10-11H2

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 64-04-0 phenethylamine 

Relevant articles and documents

Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber's Hereditary Optic Neuropathy (LHON)

Leber's hereditary optic neuropathy (LHON) is a rare genetic mitochondrial disease and the primary cause of chronic visual impairment for at least 1 in 10 ?000 individuals in the U.K. Treatment options remain limited, with only a few drug candidates and therapeutic approaches, either approved or in development. Recently, idebenone has been investigated as drug therapy in the treatment of LHON, although evidence for the efficacy of idebenone is limited in the literature. NAD(P)H:quinone oxidoreductase 1 (NQO1) and mitochondrial complex III were identified as the major enzymes involved in idebenone activity. Based on this mode of action, computer-aided techniques and structure-activity relationship (SAR) optimization studies led to the discovery of a series naphthoquinone-related small molecules, with comparable adenosine 5′-triphosphate (ATP) rescue activity to idebenone. Among these, three compounds showed activity in the nanomolar range and one, 2-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-3-(methylthio)naphthalene-1,3-dione (1), demonstrated significantly higher potency ex vivo, and significantly lower cytotoxicity, than idebenone.

Dichloro-naphthoquinone as a non-classical inhibitor of the mycobacterial carbonic anhydrase Rv3588c

The soluble mycobacterial carbonic anhydrases Rv3588c and Rv1284 belong to a different class of carbonic anhydrases than those found in humans, making them attractive drug targets by using the inherent differences in the folds of the different classes. By screening a natural product library, we identified naphthoquinone derivatives as a novel non-classical inhibitor scaffold of mycobacterial carbonic anhydrases that lack the sulfonamide/sulfamate group and thus did not affect human carbonic anhydrase II.