CAS 95233-18-4 | Atovaquone

Application:

    A hydroxynaphthoquinone antiprotozoal agent, used for the treatment and prevention of Pneumocystis jirovecii pneumonia (PCP) in immunocompromised patients (e.g., HIV/AIDS patients), and for the treatment of toxoplasmosis and babesiosis.

    Inhibits the mitochondrial electron transport chain (complex III, cytochrome bc1 complex) in protozoa, disrupting ATP production and selectively killing the parasite without significant effect on human mitochondria.

 

Intermediates

1. 2-Chloro-3-(4-chlorophenyl)-1,4-naphthoquinone  CAS: 36982-84-0

Role: naphthoquinone intermediate, formed via Friedel-Crafts acylation and chlorination, serving as the aromatic backbone for atovaquone.

2. 2-Chloro-3-(4-chlorophenyl)-4-hydroxy-1-naphthoic acid

Role: Intermediate in the hydroxylation and ring closure step, leading to the formation of the 2-hydroxy-1,4-naphthoquinone moiety.

3. 4-(4-Chlorophenyl)-2-hydroxy-1,4-naphthoquinone  CAS: 6854-26-8

Role:  precursor to atovaquone, formed by decarboxylation and oxidation of the naphthoic acid intermediate, providing the 2-hydroxy-3-aryl-naphthoquinone core structure.

4. 2-trans-(4-tert-Butylcyclohexyl)-3-hydroxy-1,4-naphthoquinone

Role: last step intermediate before atovaquone, where the 4-tert-butylcyclohexyl group is introduced via nucleophilic addition to the 3-position of the naphthoquinone ring, followed by isomerization to the trans configuration.

5. 4-tert-Butylcyclohexanone   CAS: 98-53-3

Role: A starting material for the aliphatic side chain, providing the trans-4-tert-butylcyclohexyl moiety via Grignard or organolithium addition to the naphthoquinone core.

6.  2-Hydroxy-1,4-naphthoquinone (Lawsone)   CAS: 83-72-7

 

Synonyms:

95233-18-4

cis-Atovaquone

Atavaquone

94015-53-9

137732-39-9

Mepron (antipneumocystic)

3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione

2-(trans-4-(p-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone

 

 

Properties	Safety Information	Statements
Melting point:216-2190C Boiling point:535.0±50.0 °C Density 1.349±0.06 g/cm3 solubility DMSO: >10mg/mL pka5.01±0.10	Symbol(GHS) GHS07 Signal word Warning	Hazard statements H413 Precautionary statements P501-P273 Hazard Codes N

 

 

 

 

 

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