521-49-3

Basic information

• Product Name: SL 11010
• CAS NO: 521-49-3
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.2699
• Mol File: 521-49-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 370.9°Cat760mmHg
• Flash Point: 164.5°C
• Density: 1.24g/cm³
• CAS DataBase Reference: SL 11010(CAS DataBase Reference)
• NIST Chemistry Reference: SL 11010(521-49-3)
• EPA Substance Registry System: SL 11010(521-49-3)

Safety Data

• Hazardous Substances Data: 521-49-3(Hazardous Substances Data)

Upstream product

• 870-63-3 prenyl bromide 
• 42164-69-2 Lawsone 2-isopentenyl ether 
• 64469-16-5 2-(1,1-dimethylprop-2-enyl)-3-hydroxy-naphthalene-1.4-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 

Relevant articles and documents

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Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile

In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control β-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H … π interactions with Trp105 and Phe178 residues compared to the control β-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation.

Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

Naphthoquinones are considered privileged structures for anticancer drug molecules. The Heck reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with 1-bromo-3-methyl-2-butene offered easy access to lapachol. Several naturally occurring linear and angular heterocyclic quinoids (α-lapachone, β-lapachone, dunnione, and related analogues) were prepared from lapachol. Furthermore, we demonstrated that the synthetic naphthoquinones inhibit cell proliferation in human leukemia HL-60 cells. In particular, angular-type derivatives were found to possess moderate cytotoxicity and to elevate the levels of intracellular glutathione disulfide (GSSG). Our work highlights the significant potential of naturally occurring angular-series naphthoquinones as antileukemic agents.