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Purmorphamine

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Chemical compound Pharmaceutical compound
Purmorphamine
Identifiers
IUPAC name
  • 9-cyclohexyl-N-(4-morpholinophenyl)-2-(naphthalen-1-yloxy)-9H-purin-6-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC31H32N6O2
Molar mass520.637 g·mol
3D model (JSmol)
SMILES
  • C1(N(C2CCCCC2)C=N3)=C3C(NC4=CC=C(N5CCOCC5)C=C4)=NC(OC6=CC=CC7=C6C=CC=C7)=N1
InChI
  • InChI=1S/C31H32N6O2/c1-2-9-25(10-3-1)37-21-32-28-29(33-23-13-15-24(16-14-23)36-17-19-38-20-18-36)34-31(35-30(28)37)39-27-12-6-8-22-7-4-5-11-26(22)27/h4-8,11-16,21,25H,1-3,9-10,17-20H2,(H,33,34,35)
  • Key:FYBHCRQFSFYWPY-UHFFFAOYSA-N

Purmorphamine was the first small-molecule agonist developed for the protein Smoothened, a key part of the hedgehog signaling pathway, which is involved in bone growth, cardiovascular regeneration and brain development as well as having a number of other functions in the body. Purmorphamine has been shown to induce osteogenesis in bone tissue as well as influencing growth and differentiation of neurons in the brain.

References

  1. Wu X, Ding S, Ding Q, Gray NS, Schultz PG (December 2002). "A small molecule with osteogenesis-inducing activity in multipotent mesenchymal progenitor cells". Journal of the American Chemical Society. 124 (49): 14520–1. doi:10.1021/ja0283908. PMID 12465946.
  2. Wu X, Walker J, Zhang J, Ding S, Schultz PG (September 2004). "Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway". Chemistry & Biology. 11 (9): 1229–38. doi:10.1016/j.chembiol.2004.06.010. PMID 15380183.
  3. Sinha S, Chen JK (January 2006). "Purmorphamine activates the Hedgehog pathway by targeting Smoothened". Nature Chemical Biology. 2 (1): 29–30. doi:10.1038/nchembio753. PMID 16408088. S2CID 29035911.
  4. Lee SJ, Lee HK, Cho SY, Choi JK, Shin HK, Kwak EJ, et al. (October 2008). "Identification of osteogenic purmorphamine derivatives". Molecules and Cells. 26 (4): 380–6. PMID 18695357.
  5. Stanton BZ, Peng LF (January 2010). "Small-molecule modulators of the Sonic Hedgehog signaling pathway". Molecular BioSystems. 6 (1): 44–54. doi:10.1039/b910196a. PMID 20024066.
  6. Aravamudhan A, Ramos DM, Nip J, Subramanian A, James R, Harmon MD, et al. (2013). "Osteoinductive small molecules: growth factor alternatives for bone tissue engineering". Current Pharmaceutical Design. 19 (19): 3420–8. doi:10.2174/1381612811319190008. PMID 23432678.
  7. Sharma S, Kaur A, Sharma S (April 2018). "Preconditioning potential of purmorphamine: a hedgehog activator against ischaemic reperfusion injury in ovariectomised rat heart". Perfusion. 33 (3): 209–218. doi:10.1177/0267659117732401. PMID 29065787. S2CID 3978923.
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