Reversine

Reversine

Names
IUPAC name N'-cyclohexyl-N-(4-morpholinophenyl)-7H-purine-2,6-diamine
Identifiers
CAS Number	656820-32-5
ChEBI	CHEBI:CHEBI:70723
ChemSpider	182286
Jmol interactive 3D	Image
MeSH	C484369
PubChem	210332
InChI InChI=1S/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27) Key: ZFLJHSQHILSNCM-UHFFFAOYSA-N InChI=1/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27) Key: ZFLJHSQHILSNCM-UHFFFAOYAD
SMILES C1CCC(CC1)NC2=NC(=NC3=C2NC=N3)NC4=CC=C(C=C4)N5CCOCC5
Properties
Chemical formula	C21H27N7O
Molar mass	393.48538
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Reversine, or 2-(4-morpholinoanilino)-6-cyclohexylaminopurine, is a small molecule developed by the group of Peter G. Schultz, used for stem cell dedifferentiation.

It also has the potential to induce selectively cell death of cancer cells.

Reversine is known to act as an antagonist of the adenosine A₃ receptor.

References

• Chen, Shuibing; Zhang, Qisheng; Wu, Xu; Schultz, Peter G.; Ding, Sheng (2004). "Dedifferentiation of Lineage-Committed Cells by a Small Molecule". Journal of the American Chemical Society 126 (2): 410–1. doi:10.1021/ja037390k. PMID 14719906.
• Chen, S.; Takanashi, S.; Zhang, Q.; Xiong, W.; Zhu, S.; Peters, E. C.; Ding, S.; Schultz, P. G. (2007). "Reversine increases the plasticity of lineage-committed mammalian cells". Proceedings of the National Academy of Sciences 104 (25): 10482–7. Bibcode:2007PNAS..10410482C. doi:10.1073/pnas.0704360104. PMC 1965539. PMID 17566101.
• Henry, Celia (January 5, 2004). "Cellular U-Turn". Chemical and Engineering News 82 (1): 9. doi:10.1021/cen-v082n001.p009.
• Piccoli, Marco; Palazzolo, Giacomo; Conforti, Erika; Lamorte, Giuseppe; Papini, Nadia; Creo, Pasquale; Fania, Chiara; Scaringi, Raffaella; Bergante, Sonia; Tringali, Cristina; Roncoroni, Leda; Mazzoleni, Stefania; Doneda, Luisa; Galli, Rossella; Venerando, Bruno; Tettamanti, Guido; Gelfi, Cecilia; Anastasia, Luigi (2012). "The synthetic purine reversine selectively induces cell death of cancer cells". Journal of Cellular Biochemistry 113 (10): 3207–17. doi:10.1002/jcb.24197. PMID 22615034.