Purmorphamine

Purmorphamine
Identifiers
	IUPAC name 9-cyclohexyl-N-(4-morpholinophenyl)-2-(naphthalen-1-yloxy)-9H-purin-6-amine;
CAS Number	483367-10-8 ;
PubChem CID	5284329;
ChemSpider	4447411;
UNII	PB12M2F8KY;
CompTox Dashboard (EPA)	DTXSID20415293 ;
Chemical and physical data
Formula	C31H32N6O2
Molar mass	520.637 g·mol−1
3D model (JSmol)	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, 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.^[1]^[2]^[3]^[4]^[5]^[6] ^[7]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[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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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
UNII	PB12M2F8KY
CompTox Dashboard (EPA)	DTXSID20415293
Chemical and physical data
Formula	C₃₁H₃₂N₆O₂
Molar mass	520.637 g·mol⁻¹
3D model (JSmol)	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