Purmorphamine

Purmorphamine
Identifiers

IUPAC name 9-cyclohexyl-N-(4-morpholinophenyl)-2-(naphthalen-1-yloxy)-9H-purin-6-amine
CAS Number	483367-10-8^N
PubChem (CID)	5284329
ChemSpider	4447411
Chemical and physical data
Formula	C₃₁H₃₂N₆O₂
Molar mass	520.62 g/mol
3D model (Jmol)	Interactive image
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 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.^[1]^[2]^[3]^[4]^[5]^[6]

References

↑ Wu, X.; Ding, S.; Ding, Q.; Gray, N. S.; Schultz, P. G. (2002). "A small molecule with osteogenesis-inducing activity in multipotent mesenchymal progenitor cells". Journal of the American Chemical Society. 124 (49): 14520–14521. doi:10.1021/ja0283908. PMID 12465946.
↑ Wu, X.; Walker, J.; Zhang, J.; Ding, S.; Schultz, P. G. (2004). "Purmorphamine Induces Osteogenesis by Activation of the Hedgehog Signaling Pathway". Chemistry & Biology. 11 (9): 1229–1238. doi:10.1016/j.chembiol.2004.06.010. PMID 15380183.
↑ Sinha, S.; Chen, J. K. (2005). "Purmorphamine activates the Hedgehog pathway by targeting Smoothened". Nature Chemical Biology. 2 (1): 29–30. doi:10.1038/nchembio753. PMID 16408088.
↑ Lee, S. J.; Lee, H. K.; Cho, S. Y.; Choi, J. K.; Shin, H. K.; Kwak, E. J.; Cho, M. R.; Kim, H. R.; Kim, S. R.; Kim, Y. M.; Park, K. J.; Choi, J. K. (2008). "Identification of osteogenic purmorphamine derivatives". Molecules and cells. 26 (4): 380–386. PMID 18695357.
↑ Stanton, B. Z.; Peng, L. F. (2010). "Small-molecule modulators of the Sonic Hedgehog signaling pathway". Molecular BioSystems. 6 (1): 44–54. doi:10.1039/b910196a. PMID 20024066.
↑ Aravamudhan, A.; Ramos, D. M.; Nip, J.; Subramanian, A.; James, R.; Harmon, M. D.; Yu, X.; Kumbar, S. G. (2013). "Osteoinductive small molecules: Growth factor alternatives for bone tissue engineering". Current pharmaceutical design. 19 (19): 3420–3428. doi:10.2174/1381612811319190008. PMID 23432678.

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