Geiparvarinis acoumarinderivative found in the leaves of the Australian Willow (Geijera parviflora).[1]It is amonoamine oxidase inhibitor.[2]

Geiparvarin
Names
Preferred IUPAC name
7-{[(2E)-3-(5,5-Dimethyl-4-oxo-4,5-dihydrofuran-2-yl)but-2-en-1-yl]oxy}-2H-1-benzopyran-2-one
Identifiers
3D model (JSmol)
ChemSpider
MeSH Geiparvarin
UNII
  • InChI=1S/C19H18O5/c1-12(15-11-17(20)19(2,3)24-15)8-9-22-14-6-4-13-5-7-18(21)23-16(13)10-14/h4-8,10-11H,9H2,1-3H3/b12-8+☒N
    Key: OUTLLBZGJYDUQE-XYOKQWHBSA-N☒N
  • InChI=1/C19H18O5/c1-12(15-11-17(20)19(2,3)24-15)8-9-22-14-6-4-13-5-7-18(21)23-16(13)10-14/h4-8,10-11H,9H2,1-3H3/b12-8+
    Key: OUTLLBZGJYDUQE-XYOKQWHBBW
  • CC(=CCOC1=CC2=C(C=C1)C=CC(=O)O2)C3=CC(=O)C(O3)(C)C
  • O=C/3Oc2c(ccc(OC/C=C(/C=1OC(C(=O)C=1)(C)C)C)c2)\C=C\3
Properties
C19H18O5
Molar mass 326.343 g/mol
Density 1.242 g/mL
Boiling point 533 °C (991 °F; 806 K)
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Severalanaloguesof geiparvarin have been studied for antitumor properties.[3][4][5]

References

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  1. ^Lahey FN, Macleod JK (September 1967). "The coumarins ofGeijera parvifloraLindl ".Aust J Chem.20(9): 1943–55.doi:10.1071/CH9671943.
  2. ^Carotti A, Carrieri A, Chimichi S, et al. (December 2002). "Natural and synthetic geiparvarins are strong and selective MAO-B inhibitors. Synthesis and SAR studies".Bioorg. Med. Chem. Lett.12(24): 3551–3555.doi:10.1016/S0960-894X(02)00798-9.PMID12443774.
  3. ^Baraldi PG, Guarneri M, Manfredini S, Simoni D, Balzarini J, De Clercq E (February 1989). "Synthesis and cytostatic activity of geiparvarin analogues".J Med Chem.32(2): 284–288.doi:10.1021/jm00122a002.PMID2913291.
  4. ^Valenti P, Rampa A, Recanatini M, et al. (September 1997). "Synthesis, cytotoxicity and SAR of simple geiparvarin analogues".Anticancer Drug Des.12(6): 443–51.PMID9311554.
  5. ^Viola G, Vedaldi D, dall'Acqua F, et al. (September 2004). "Synthesis, cytotoxicity, and apoptosis induction in human tumor cells by geiparvarin analogues".Chemistry & Biodiversity.1(9): 1265–1280.doi:10.1002/cbdv.200490089.PMID17191904.S2CID22355393.