Dihydroquinine
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Names | |
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IUPAC name
(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
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Other names
(8α,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.007.578 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C20H26N2O2 | |
Molar mass | 326.440 g·mol−1 |
Melting point | 173–175 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dihydroquinine, also known as hydroquinine[1] or DHQ, is an organic compound and as a cinchona alkaloid closely related to quinine. The specific rotation is −148° in ethanol. A derivative of this molecule is used as chiral ligand in the AD-mix for Sharpless dihydroxylation.
DHQ also inhibits growth of the parasite Toxoplasma gondii by inducing mitochondrial membrane damage, but does not disrupt host mitochondrial membrane potential, as well as reactive oxygen species (ROS) generation.[2]
See also
References
- ^ "Dihydroquinine chemical information". ChemIndustry.com.
- ^ Huffman, Aarin M.; Ayariga, Joseph A.; Napier, Audrey; Robertson, Boakai K.; Abugri, Daniel A. (2022). "Inhibition of Toxoplasma gondii Growth by Dihydroquinine and Its Mechanisms of Action". Frontiers in Cellular and Infection Microbiology. 12. doi:10.3389/fcimb.2022.852889. ISSN 2235-2988. PMC 9131874.
Categories:
- Chemical articles with multiple compound IDs
- Multiple chemicals in an infobox that need indexing
- Articles without EBI source
- Articles without KEGG source
- ECHA InfoCard ID from Wikidata
- Articles containing unverified chemical infoboxes
- Chembox image size set
- Articles with short description
- Short description matches Wikidata
- Secondary alcohols
- Phenol ethers
- Quinoline alkaloids
- Quinuclidine alkaloids