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Dihydroquinine

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Dihydroquinine
Names
IUPAC name (R)-octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Other names (8α,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.578 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1Key: LJOQGZACKSYWCH-WZBLMQSHSA-N
  • InChI=1/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1Key: LJOQGZACKSYWCH-WZBLMQSHBC
SMILES
  • O(C1N2CCC(C(CC)C2)C1)C3=CC=NC4=CC=C(OC)C=C43
  • O(c4cc1c(nccc1(O)2N3CC(C2)(CC)C3)cc4)C
Properties
Chemical formula C20H26N2O2
Molar mass 326.440 g·mol
Melting point 173–175 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

Dihydroquinine, also known as hydroquinine 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.

See also

References

  1. "Dihydroquinine chemical information". ChemIndustry.com.
  2. 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.
Other drugs for disorders of the musculo-skeletal system (M09)
Quinine and derivatives
Enzymes
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