Auranthine

Auranthine is an antimicrobial chemical compound isolated from a nephrotoxic strain[1] of Penicillium fungus, Penicillium aurantiogriseum.[2]

Auranthine
Names
IUPAC name
6,7,7a,8-Tetrahydroquinazolino[3’,2’:1,6]pyrido[2,3-b] [1,4]benzodiazepine-9,16-dione
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C19H14N4O2/c24-18-11-5-1-3-7-13(11)21-17-15(22-18)9-10-16-20-14-8-4-2-6-12(14)19(25)23(16)17/h1-8,15H,9-10H2,(H,22,24)
    Key: QSYOIPMDADNFRO-UHFFFAOYSA-N
  • InChI=1/C19H14N4O2/c24-18-11-5-1-3-7-13(11)21-17-15(22-18)9-10-16-20-14-8-4-2-6-12(14)19(25)23(16)17/h1-8,15H,9-10H2,(H,22,24)
    Key: QSYOIPMDADNFRO-UHFFFAOYAR
  • C1CC2=NC3=CC=CC=C3C(=O)N2C4=NC5=CC=CC=C5C(=O)NC41
Properties
C19H14N4O2
Molar mass 330.347 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

A total synthesis of auranthine has been reported.[3]

References
  1. MacGeorge, K. M; Mantle, P. G (1990). "Nephrotoxicity of Penicillium aurantiogriseum and P. Commune from an endemic nephropathy area of Yugoslavia". Mycopathologia. 112 (3): 139–45. doi:10.1007/bf00436643. PMID 2089255. S2CID 28572592.
  2. Yeulet, Stephanie E; Mantle, Peter G; Bilton, John N; Rzepa, Henry S; Sheppard, Richard N (1986). "Auranthine, a new benzodiazepinone metabolite of Penicillium aurantiogriseum". Journal of the Chemical Society, Perkin Transactions 1: 1891. doi:10.1039/P19860001891.
  3. Kshirsagar, Umesh A; Puranik, Vedavati G; Argade, Narshinha P (2010). "Total Synthesis of Proposed Auranthine". The Journal of Organic Chemistry. 75 (8): 2702–2705. doi:10.1021/jo100400z. PMID 20302381.
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