Dihydroquinine
Names
IUPAC name
(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Other names
(8α,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.578 Edit this at Wikidata
UNII
  • 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/s1 checkY
    Key: LJOQGZACKSYWCH-WZBLMQSHSA-N checkY
  • 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/s1
    Key: LJOQGZACKSYWCH-WZBLMQSHBC
  • O[C@@H](C1N2CCC(C(CC)C2)C1)C3=CC=NC4=CC=C(OC)C=C43
  • O(c4cc1c(nccc1[C@@H](O)[C@H]2N3CC[C@@H](C2)[C@@H](CC)C3)cc4)C
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

  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.
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