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Geiparvarin

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Geiparvarin
Names
Preferred IUPAC name 7-{oxy}-2H-1-benzopyran-2-one
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
MeSH Geiparvarin
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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+Key: OUTLLBZGJYDUQE-XYOKQWHBSA-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
SMILES
  • 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
Chemical formula 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 their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Geiparvarin is a coumarin derivative found in the leaves of the Australian Willow (Geijera parviflora). It is a monoamine oxidase inhibitor.

Several analogues of geiparvarin have been studied for antitumor properties.

References

  1. Lahey FN, Macleod JK (September 1967). "The coumarins of Geijera parviflora Lindl". 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. PMID 12443774.
  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. PMID 2913291.
  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. PMID 9311554.
  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. PMID 17191904. S2CID 22355393.


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