59147-84-1

Usage

Uses

Used in Pharmaceutical Industry:
2-[(2-Hydroxyethyl)thio]-3-methyl-1,4-naphthoquinone is used as an approach to anti-cancer therapy for its potent inhibitory effect on the Cdc25A protein, which plays a crucial role in the regulation of the cell cycle. By inhibiting Cdc25A, 2-[(2-Hydroxyethyl)thio]-3-methyl-1,4-naphthoquinone can potentially disrupt the cell division process in cancer cells, leading to their growth arrest and eventual death. This makes it a promising candidate for the development of novel anti-cancer drugs and therapies.

Upstream product

• 58-27-5 menadione 
• 60-24-2 2-hydroxyethanethiol 
• 15448-59-6 2,3-epoxy-2-methyl-2,3-dihydro-1,4-naphthoquinone 

Relevant academic research and scientific papers

SYNTHESIS OF SULFUR-CONTAINING ANALOGS OF THE K GROUP VITAMINS BY AN ELECTROCHEMICAL METHOD

An efficient electrochemical method is proposed for obtaining structural analogues of the K group vitamins (3-alkylthio and 3-arylthio ethers of 2-methyl-1,4-naphthoquninone). Keywords: 2-methyl-1,4-naphthoquinone, vitamin K1, mercaptans, electrochemical synthesis.

Discovery of the First Vitamin K Analogue as a Potential Treatment of Pharmacoresistant Seizures

Despite the availability of more than 25 antiseizure drugs on the market, approximately 30% of patients with epilepsy still suffer from seizures. Thus, the epilepsy therapy market has a great need for a breakthrough drug that will aid pharmacoresistant patients. In our previous study, we discovered a vitamin K analogue, 2h, which displayed modest antiseizure activity in zebrafish and mouse seizure models. However, there are limitations to this compound due to its pharmacokinetic profile. In this study, we develop a new series of vitamin K analogues by modifying the structure of 2h. Among these, compound 3d shows full protection in a rodent pharmacoresistant seizure model with limited rotarod motor toxicity and favorable pharmacokinetic properties. Furthermore, the brain/plasma concentration ratio of 3d indicates its excellent permeability into the brain. The resulting data shows that 3d can be further developed as a potential antiseizure drug in the clinic.

Oxidative radical coupling of hydroquinones and thiols using chromic acid: One-pot synthesis of quinonyl alkyl/aryl thioethers

An efficient, simple and practical protocol for one-pot sequential oxidative radical C-H/S-H cross-coupling of thiols with hydroquinones (HQs) and oxidation leading to the formation of quinonyl alkyl/aryl thioethers using H2CrO4was developed. This cross-coupling of thiyl and aryl radicals offers mono thioethers in good to moderate yield and works well with a wide variety of thiols. Similarly, this method works well for coupling of 2-amino thiophenol and HQs to form phenothiazine-3-ones5a-c. C-S bond formationviathioether synthesis was observed using a chromium reagent for the first time. Theoretical studies on the pharmacokinetic properties of compounds5a-crevealed that due to drug-like properties, compound5bstrongly binds with Alzheimer's disease (AD) associated AChE target sites.

NAPHTHAQUINONE METHYLTRANSFERASE INHIBITORS AND USES THEREOF

Provided herein are compounds of (I), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, and prodrugs thereof. Also provided are pharmaceutical compositions and methods involving the inventive compounds for the treatment of proliferative diseases (e.g., cancer (e.g., leukemia, breast cancer, melanoma, metastatic cancer) and diseases associated with inappropriate SET8 activity. Also provided are methods for inhibiting SET8 and methods for labelling SET8.

Anticancer activity and SAR studies of substituted 1,4-naphthoquinones

In this paper, we report the structure-activity relationship studies of substituted 1,4-naphthoquinones for its anticancer properties. 1,4-Naphthoquinone, Juglone, Menadione, Plumbagin and LLL12.1 were used as lead molecules to design PD compounds. Most o

Site-specific binding of quinones to proteins through thiol addition and addition-elimination reactions

Ubiquinone-0, menaquinone-0, and 2,3,5-trimethyl-1,4-benzoquinone were site-specifically bound to free cysteine of proteins (yeast iso-1 cytochrome c as a model protein) through thioether bond formation. Model thioether quinone conjugates showed unexpecte

Synthesis and anticancer evaluation of vitamin K3 analogues

Novel vitamin K3 analogues were synthesized and evaluated for their anticancer activity. Compound 6, 9, 10, 11, 14, and (±)15 demonstrated a strong inhibitory activity against the tumor cells of A-549, Hep G2, MCF7, MES-SA, MES-SA/Dx5, MKN45, S

Thioalkyl derivatives of vitamin K3 and vitamin K3 oxide inhibit growth of Hep3B and HepG2 cells

A new hypothesis regarding the effect of vitamin K3 on hepatoma cell growth is presented. In brief, exploration of cell growth activity has been identified with the action of p34(cdc2) kinase and its associated protein tyrosine phosphatase. After exploring a series of substituted derivatives of vitamin K and vitamin K3 oxide, we suggest a mechanism involving alkylation at the active-site cysteine for the inhibition of the protein tyrosine phosphatase which controls the activity of the p34(cdc2) kinase.

Synthesis and spectral properties of porphyrinquinone derivatives based on deuteroporphyrin IX

A series of diquinone derivatives of deuteroporphyrin IX, having different bond lengths between the chromophores, have been prepared. Deuteroporphyrin IX was condensed with modified hydroxyl-containing quinones by the mixed anhydride method. PMR spectrosc