Dihydroquinine

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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.578
EC Number
  • 208-334-0
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/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
SMILES
  • 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
Chemical formula
 C20H26N2O2
Molar mass 326.440 g·mol−1
Melting point 173–175 °C
Hazards
GHS labelling:[1]
Pictograms
 GHS07: Exclamation mark
Signal word
 Warning
Hazard statements
 H302, H312, H332
Precautionary statements
 P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

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. PMID 35646733.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.