| Revision as of 18:42, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{chembox}} taken from revid 443358631 of page 8-Aminoquinoline for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 03:10, 12 July 2024 edit Pbsouthwood (talk | contribs)Administrators151,180 edits Adding short description: "Antimalarial drug precursor", overriding automatically generated descriptionTag: Shortdesc helper |
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{{Short description|Antimalarial drug precursor}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 443357285 |
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| verifiedrevid = 477226908 |
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| ImageFile = 8-aminoquinoline.png |
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| ImageFile = 8-aminoquinoline.svg |
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| ImageSize =150px |
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| ImageSize = 150px |
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| ImageAlt = |
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| ImageAlt = |
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| IUPACName = Quinolin-8-amine |
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| PIN = Quinolin-8-amine |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10881 |
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| ChemSpiderID = 10881 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WREVVZMUNPAPOV-UHFFFAOYSA-N |
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| StdInChIKey = WREVVZMUNPAPOV-UHFFFAOYSA-N |
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| CASNo =578-66-5 |
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| CASNo = 578-66-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 11359 |
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| PubChem = 11359 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 99932 |
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| ChEMBL = 99932 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = U34EAV21TG |
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| UNII = U34EAV21TG |
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| SMILES = Nc1cccc2cccnc12 }} |
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| SMILES = Nc1cccc2cccnc12 }} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=9 | H=8 | N=2 |
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| C = 9 | H = 8 | N = 2 |
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| Appearance = |
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| Appearance = pale yellow solid |
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| Density = 1.337 g/cm<sup>3</sup><ref>{{cite journal |doi=10.1002/(SICI)1099-1395(199709)10:9<680::AID-POC902>3.0.CO;2-Y|title=X-ray and vibrational studies of 8-aminoquinoline. Evidence for a three-center hydrogen bond |year=1997 |last1=Van Meervelt |first1=L. |last2=Goethals |first2=M. |last3=Leroux |first3=N. |last4=Zeegers-Huyskens |first4=Th. |journal=Journal of Physical Organic Chemistry |volume=10 |issue=9 |pages=680–686 }}</ref> |
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| Density = |
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| MeltingPt = |
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| MeltingPtC = 65 |
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}} |
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| Section3 = {{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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}} |
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}} |
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{{See also| 4-Aminoquinoline}} |
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'''8-Aminoquinoline''' is the 8-amino derivative of ]. Often abbreviated AQ, it is a pale yellow solid. It is structurally analogous to ].<ref>{{cite journal |doi=10.1021/acs.chemrev.9b00495|title=Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds |year=2020 |last1=Rej |first1=Supriya |last2=Ano |first2=Yusuke |last3=Chatani |first3=Naoto |journal=Chemical Reviews |volume=120 |issue=3 |pages=1788–1887 |pmid=31904219 |s2cid=209895281 }}</ref> |
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==Drug derivatives== |
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The derivatives ], ] and ] have been tested for anti-] activity.<ref>{{cite journal|doi=10.3390/molecules22122268|pmid=29257067|pmc=6149725|title=Quinoline-Based Hybrid Compounds with Antimalarial Activity|journal=Molecules|volume=22|issue=12|pages=2268|year=2017|last1=Nqoro|first1=Xhamla|last2=Tobeka|first2=Naki|last3=Aderibigbe|first3=Blessing|doi-access=free }} |
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</ref><ref>{{cite journal | title=Short report: The activity of pamaquine, an 8-aminoquinoline drug, against sporozoite-induced infections of ''Plasmodium vivax'' (New Guinea strains) | author=Sweeney AW | author2=Blackburn CRB | author3=KH Rieckmann | journal=Am J Trop Med Hyg | volume=71 | issue=2 | date=1 August 2004| pages=187–189 | doi=10.4269/ajtmh.2004.71.2.0700187 | url=http://www.ajtmh.org/cgi/content/full/71/2/187 | pmid=15306708 | doi-access=free }}</ref> Primaquine is still used routinely worldwide as part of the treatment of '']'' and '']'' malaria, although how it prevents malarial recurrences is not, at present, clear.<ref>{{cite journal |last1=Markus |first1=MB |title=Putative contribution of 8-aminoquinolines to preventing recrudescence of malaria |journal=Tropical Medicine and Infectious Disease |date=2023 |volume=8 |issue=5 |page=278 |doi=10.3390/tropicalmed8050278 |pmid=37235326|pmc=10223033 |doi-access=free }}</ref> Tafenoquine was approved for medical use in Australia and in the United States in 2018.<ref name=Jul2019>{{cite journal |vauthors=Haston JC, Hwang J, Tan KR |title=Guidance for Using Tafenoquine for Prevention and Antirelapse Therapy for Malaria — United States, 2019 |journal=MMWR. Morbidity and Mortality Weekly Report |date=November 2019 |volume=68 |issue=46 |pages=1062–1068 |doi=10.15585/mmwr.mm6846a4 |pmid=31751320 |pmc=6871897 |url=https://www.cdc.gov/mmwr/volumes/68/wr/pdfs/mm6846a4-H.pdf }}</ref><ref name=Hou2019>{{cite journal |last1=Hounkpatin |first1=Aurore B |last2=Kreidenweiss |first2=Andrea |last3=Held |first3=Jana |title=Clinical utility of tafenoquine in the prevention of relapse of <em>Plasmodium vivax</em> malaria: a review on the mode of action and emerging trial data |journal=Infection and Drug Resistance |date=March 2019 |volume=12 |pages=553–570 |doi=10.2147/IDR.S151031|pmid=30881061 |pmc=6411314 |doi-access=free }}</ref> |
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<gallery> |
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Image:Primaquine.svg|] |
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Image:Pamaquine.svg|] |
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Image:Tafenoquine.svg|] |
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</gallery> |
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==Directing group== |
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The ] functional group is amenable to formation of ]s, and thus can serve as a ] in ].<ref>{{cite journal|doi=10.1021/ar5004626|pmid=25756616|pmc=4406856|title=Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon–Hydrogen Bonds|journal=Accounts of Chemical Research|volume=48|issue=4|pages=1053–1064|year=2015|last1=Daugulis|first1=Olafs|last2=Roane|first2=James|last3=Tran|first3=Ly Dieu}}</ref><ref>{{cite journal|doi=10.1002/anie.201303556|pmid=23939922|title=8-Aminoquinoline: A Powerful Directing Group in Metal-Catalyzed Direct Functionalization of C-H Bonds|journal=Angewandte Chemie International Edition|volume=52|issue=38|pages=9896–9898|year=2013|last1=Corbet|first1=Matthieu|last2=De Campo|first2=Floryan}}</ref> |
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==Preparation== |
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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.<ref>{{cite journal |doi=10.1002/cber.19170500264 |title=Über Nitro-amino-chinoline |year=1917 |last1=Kaufmann |first1=Adolf |last2=Zeller |first2=Otto |journal=Berichte der Deutschen Chemischen Gesellschaft |volume=50 |issue=2 |pages=1626–1630 |url=https://zenodo.org/record/2004918 }}</ref> AQ can also be produced by amination of 8-chloroquinoline. |
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==References== |
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{{Reflist}} |
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{{Antimalarials}} |
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{{DEFAULTSORT:Aminoquinoline, 8-}} |
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] |
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] |