4042-30-2

Basic information

• Product Name: parvaquone
• Synonyms: parvaquone;2-Cyclohexyl-3-hydroxy-1,4-naphthalenedione;2-Cyclohexyl-3-hydroxy-1,4-naphthoquinone;3-cyclohexyl-4-hydroxy-1,2-naphthoquinone;3-cyclohexyl-4-hydroxy-naphthalene-1,2-dione;3-cyclohexyl-4-hydroxynaphthalene-1,2-dione;2-Hydroxy-3-cyclohexyl-1,4-naphthoquinone;Parvexon
• CAS NO: 4042-30-2
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.29644
• EINECS: 223-734-5
• Mol File: 4042-30-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 135-136°
• Boiling Point: 429.9°Cat760mmHg
• Flash Point: 227.9°C
• Appearance: /
• Density: 1.310
• Vapor Pressure: 3.73E-08mmHg at 25°C
• Refractive Index: 1.636
• PKA: 5.10±0.10(Predicted)
• CAS DataBase Reference: parvaquone(CAS DataBase Reference)
• NIST Chemistry Reference: parvaquone(4042-30-2)
• EPA Substance Registry System: parvaquone(4042-30-2)

Safety Data

• Hazardous Substances Data: 4042-30-2(Hazardous Substances Data)

Usage

General Description

Parvaquone is a hydroxynaphthoquinone-related compound that is widely used as an antiprotozoal medication. It's primarily used in veterinary medicine, particularly for treating cattle with theileriosis, a disease caused by protozoan parasites. This chemical works by interfering with the cellular respiration of the parasites, affecting their ability to produce energy. Due to its hydrophobic nature, it readily penetrates tissue and cells, enhancing its effectiveness. Despite its widespread use, it is generally not recommended for long-term use due to potential side effects such as skin irritation or harm to aquatic life. Although resistance to parvaquone has been reported, it remains one of the leading treatments for theileriosis.

InChI:InChI=1/C16H16O3/c17-14-11-8-4-5-9-12(11)15(18)16(19)13(14)10-6-2-1-3-7-10/h4-5,8-10,17H,1-3,6-7H2

Upstream product

• 41245-70-9 1a-cyclohexyl-1a,7a-dihydronaphth<2,3b>oxirene-2,7-dione 
• 2043-61-0 cyclohexanecarbaldehyde 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 4904-55-6 cyclohexanecarbonyl peroxide 
• 4441-56-9 cyclohexylboronic acid 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 98-89-5 Cyclohexanecarboxylic acid 
• 110-82-7 cyclohexane 
• 110-83-8 cyclohexene 
• 571-60-8 1,4-Dihydroxynaphthalene 
• 130-15-4 [1,4]naphthoquinone 
• 1539-59-9 4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester 
• 6498-34-6 cyclohexylhydrazine 
• 85-44-9 phthalic anhydride 

Downstream Products

• 502486-24-0 3-cyclohexyl-[1,2]naphthoquinone 
• 1402666-24-3 2-(3-bromopropoxy)-3-cyclohexylnaphthalene-1,4-dione 
• 1402666-22-1 2-((6-bromohexyl)oxy)-3-cyclohexylnaphthalene-1,4-dione 
• 1402665-95-5 3-[(3-(cyclohexyl)-1,4-dioxonaphthalen-2-yl)oxy]propyltriphenylphosphonium bromide 
• 1402665-93-3 6-[(3-(cyclohexyl)-1,4-dioxonaphthalen-2-yl)oxy]hexyltriphenylphosphonium bromide 

Relevant articles and documents

A new combination of cyclohexylhydrazine and IBX for oxidative generation of cyclohexyl free radical and related synthesis of parvaquone

The present paper demonstrates a single-step and straightforward synthesis of parvaquone through intermediacy of cyclohexyl radical generated from novel combination of cyclohexylhydrazine and o-iodoxybenzoic acid and subsequently trapped by 2-hydroxy-1,4-naphthoquinone. Formation of cyclohexyl free radical using this new combination was reaffirmed by cyclohexylation of readily available 2-amino-1,4-naphthoquinone.

Tridentate 3-Substituted Naphthoquinone Ruthenium Arene Complexes: Synthesis, Characterization, Aqueous Behavior, and Theoretical and Biological Studies

A series of nine RuII arene complexes bearing tridentate naphthoquinone-based N,O,O-ligands was synthesized and characterized. Aqueous stability and their hydrolysis mechanism were investigated via UV/vis photometry, HPLC-MS, and density functional theory calculations. Substituents with a positive inductive effect improved their stability at physiological pH (7.4) intensely, whereas substituents such as halogens accelerated hydrolysis and formation of dimeric pyrazolate and hydroxido bridged dimers. The observed cytotoxic profile is unusual, as complexes exhibited much higher cytotoxicity in SW480 colon cancer cells than in the broadly chemo- (incl. platinum-) sensitive CH1/PA-1 teratocarcinoma cells. This activity pattern as well as reduced or slightly enhanced ROS generation and the lack of DNA interactions indicate a mode of action different from established or previously investigated classes of metallodrugs.

Visible-light-mediated photoredox minisci C-H alkylation with alkyl boronic acids using molecular oxygen as an oxidant

Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation reactions of heteroarenes with alkyl boronic acids using molecular oxygen as the sole oxidant. This mild protocol uses an inexpensive, green oxidant; permits efficient functionalization of various N-heteroarenes with a broad range of primary and secondary alkyl boronic acids; and is scalable to the gram level. We demonstrated the practicality and sustainability of the protocol by preparing or functionalizing several pharmaceuticals and natural products.