8-Aminoquinoline

8-Aminoquinoline is the 8-amino derivative of quinoline. Often abbreviated AQ, it is a pale yellow solid. It is structurally analogous to 8-hydroxyquinoline.[2]

8-Aminoquinoline
Names
Preferred IUPAC name
Quinolin-8-amine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.008.572
PubChem CID
UNII
InChI
  • InChI=1S/C9H8N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,10H2 Y
    Key: WREVVZMUNPAPOV-UHFFFAOYSA-N Y
SMILES
  • Nc1cccc2cccnc12
Properties
Chemical formula
 C9H8N2
Molar mass 144.177 g·mol−1
Appearance pale yellow solid
Density 1.337 g/cm3[1]
Melting point 65 °C (149 °F; 338 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Drug derivatives

The derivatives primaquine, tafenoquine and pamaquine have been tested for anti-malaria activity.[3][4] Primaquine is still used routinely worldwide as part of the treatment of Plasmodium vivax and Plasmodium ovale malaria. Tafenoquine was approved for medical use in Australia and in the United States in 2018.[5][6]

Directing group

The amine functional group is amenable to formation of amides, and thus can serve as a directing group in organic synthesis.[7][8]

Preparation

The original synthesis of AQ involved nitration of quinoline to give a mixture of the 5- and 8-nitroderivatives, which were separated by distillation and sublimation. Reduction of the 8-nitro isomer with tin powder in the presence of hydrochloric acid gave the amines.[9] AQ can also be produced by amination of 8-chloroquinoline.

References
  1. Van Meervelt, L.; Goethals, M.; Leroux, N.; Zeegers-Huyskens, Th. (1997). "X-ray and vibrational studies of 8-aminoquinoline. Evidence for a three-center hydrogen bond". Journal of Physical Organic Chemistry. 10 (9): 680–686. doi:10.1002/(SICI)1099-1395(199709)10:9<680::AID-POC902>3.0.CO;2-Y.
  2. Rej, Supriya; Ano, Yusuke; Chatani, Naoto (2020). "Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds". Chemical Reviews. 120 (3): 1788–1887. doi:10.1021/acs.chemrev.9b00495. PMID 31904219. S2CID 209895281.
  3. Nqoro, Xhamla; Tobeka, Naki; Aderibigbe, Blessing (2017). "Quinoline-Based Hybrid Compounds with Antimalarial Activity". Molecules. 22 (12): 2268. doi:10.3390/molecules22122268. PMC 6149725. PMID 29257067.
  4. Sweeney AW; Blackburn CRB; KH Rieckmann (1 August 2004). "Short report: The activity of pamaquine, an 8-aminoquinoline drug, against sporozoite-induced infections of Plasmodium vivax (New Guinea strains)". Am J Trop Med Hyg. 71 (2): 187–189. doi:10.4269/ajtmh.2004.71.2.0700187. PMID 15306708.
  5. Haston JC, Hwang J, Tan KR (November 2019). "Guidance for Using Tafenoquine for Prevention and Antirelapse Therapy for Malaria — United States, 2019" (PDF). MMWR. Morbidity and Mortality Weekly Report. 68 (46): 1062–1068. doi:10.15585/mmwr.mm6846a4. PMC 6871897. PMID 31751320.
  6. Hounkpatin, Aurore B; Kreidenweiss, Andrea; Held, Jana (March 2019). "Clinical utility of tafenoquine in the prevention of relapse of Plasmodium vivax malaria: a review on the mode of action and emerging trial data". Infection and Drug Resistance. 12: 553–570. doi:10.2147/IDR.S151031. PMC 6411314. PMID 30881061.
  7. Daugulis, Olafs; Roane, James; Tran, Ly Dieu (2015). "Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon–Hydrogen Bonds". Accounts of Chemical Research. 48 (4): 1053–1064. doi:10.1021/ar5004626. PMC 4406856. PMID 25756616.
  8. Corbet, Matthieu; De Campo, Floryan (2013). "8-Aminoquinoline: A Powerful Directing Group in Metal-Catalyzed Direct Functionalization of C-H Bonds". Angewandte Chemie International Edition. 52 (38): 9896–9898. doi:10.1002/anie.201303556. PMID 23939922.
  9. Kaufmann, Adolf; Zeller, Otto (1917). "Über Nitro‐amino‐chinoline". Berichte der Deutschen Chemischen Gesellschaft. 50 (2): 1626–1630. doi:10.1002/cber.19170500264.
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