68963-21-3

Basic information

• Product Name: 8-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione
• Synonyms: 8-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione
• CAS NO: 68963-21-3
• Molecular Weight: 296.346
• Mol File: 68963-21-3.mol

Chemical Properties

• CAS DataBase Reference: 8-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 8-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione(68963-21-3)
• EPA Substance Registry System: 8-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione(68963-21-3)

Safety Data

• Hazardous Substances Data: 68963-21-3(Hazardous Substances Data)

Upstream product

• 103-19-5 di(p-tolyl) disulfide 
• 18855-92-0 3-chlorojuglone 
• 91799-86-9 2,3-dichloro-5-hydroxy-2,3-dihydro-[1,4]naphthoquinone 
• 83-56-7 1,5-dihydroxynaphthalene 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 106-45-6 para-thiocresol 

Downstream Products

• 22333-59-1 7-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 
• 22333-58-0 9-hydroxy-α-lapachone 
• 1309944-31-7 9-hydroxy-2-phenyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione 
• 1309944-32-8 2-(4-bromophenyl)-9-hydroxy-3,4-dihydro-2H-benzo[g] chromene-5,10-dione 
• 1309944-33-9 9-hydroxy-2-p-tolyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione 
• 1309944-34-0 2-(4-chlorophenyl)-9-hydroxy-3,4-dihydro-2H-benzo[g] chromene-5,10-dione 
• 1309944-35-1 2-(4-fluorophenyl)-9-hydroxy-3,4-dihydro-2H-benzo[g] chromene-5,10-dione 
• 1309944-36-2 9-hydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-benzo[g]chromene-5,10-dione 
• 1309944-37-3 9-hydroxy-2-methyl-2-phenyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione 
• 929620-68-8 5-methoxy-3-(p-tolylsulfinyl)-1,4-naphthoquinone 
• 109696-97-1 5-methoxy-3-(p-tolylthio)-1,4-naphthoquinone 

Relevant articles and documents

Synthesis, molecular docking, and biological activity of thioether derived from juglone in preclinical models of chronic myeloid leukemia

In this work, 16 new thio-1,4-naphthoquinones were synthesized, and their antiproliferative effects against tumor cell lines SK-MEL-19, AGP-01, ACP-02, HL-60, K-562, K-562-Lucena-1, FEPS, and non-neoplastic human fibroblast MRC-5, were examined. The compounds were selective active against leukemia cell lines. Based on the screening results for cytotoxic activity, naphthoquinone 11a showed higher cytotoxicity on the chemoresistant leukemia (FEPS) cell line when compared to the chemosensitive (K-562) cell line. Moreover, naphthoquinone 11a presented excellent ADME/T and did not violate Lipinski's rule of five, indicating good oral absorption. Target prediction revealed DNA topoisomerase I (TOP1) as a possible target of 11a. The molecular docking prediction showed an ? 11.94 kcal/mol binding affinity interaction of 11a with TOP1, involving three hydrogen bonds to ARG364, A113, and G11 from the active site of the enzyme. In addition, naphthoquinone 11a significantly suppressed the expression of the TOP1 gene in K-562 and FEPS leukemia cell lines. The naphthoquinone 11a induced significant changes in cell morphology, demonstrating cell and nuclear shrinkage, blebbing formation as well and fragmentation of the cell into apoptotic bodies. Thus, 11a could be a drug that leads to a new set of TOP1 major inhibitors. In summary, the present study showed a cytotoxic effect of 11a against chemoresistant and chemosensitive leukemia cell lines with TOP1 as a possible target.

New naphthoquinone derivatives against glioma cells

This work was aimed to the development of a set of new naphtoquinone derivatives that can act against glioma. The compounds were tested in order to find out their ability to inhibit the growth of glioma cells, and the results of these assays were correlated with electrochemical analysis and NMR-based reoxidation kinetic studies, suggesting that a redox mechanism underlies and may explain the observed biological behavior. In addition to a full description of the synthetic pathways, electrochemistry, NMR and single crystal X-ray diffraction data are provided.

Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines

A synthetic method to obtain α- and β-pyran naphthoquinones 10 and 11 with a hydroxyl substituent on the aromatic ring was developed. Two series of α- and β-pyran naphthoquinones were obtained from the 8-hydroxy-lawsone, and their anticancer properties we

Asymmetric synthesis of rubiginones A2 and C2 and their 11-methoxy regioisomers

Convergent enantioselective syntheses of angucyclinone-type natural products rubiginones A2 (2) and C2 (1) and their 11-methoxy regioisomers 3a and 3b have been achieved by using two domino processes from a common enantiomerically pu

Synthesis and antifungal activity of 2/3-arylthio- and 2,3-bis(arylthio)-5- hydroxy-/5-methoxy-1,4-naphthoquinones

2/3-Arylthio- and 2,3-bis(arylthio)-5-hydroxy-/5-methoxy-1,4- naphthoquinones 5-9 were synthesized and tested for in vitro antifungal activity against Candida species and Aspergillus niger. The synthesized compounds 5-9 generally showed good activities ag