Chemistry:Pyrvinium
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Short description: Chemical compound
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| Formula | C26H28N3+ |
| Molar mass | 382.531 g·mol−1 |
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Pyrvinium (Viprynium) is an anthelmintic effective for pinworms.[1] Several forms of pyrvinium have been prepared with variable counter anions, such as halides, tosylate, triflate and pamoate.[2][3] Pyrvinium was identified as a potent Wnt inhibitor, acting through activation of Casein kinase CK1α.[4][5]
Pyrvinium salts can also inhibit the growth of cancer cells.[6] More specifically, the pamoate salt has been shown to have preferential toxicity for various cancer cell lines during glucose starvation.[7]
Synthesis
One synthetic method is based on Skraup synthesis and Paal-Knorr synthesis.[6] More recently, an alternative convergent, synthetic strategy to pyrvinium triflate salts through Friedländer synthesis was reported.[3]
References
- ↑ "Single-dose treatment of oxyuriasis with pyrvinium embonate". British Medical Journal 2 (5319): 1583–5. December 1962. doi:10.1136/bmj.2.5319.1583. PMID 14027194.
- ↑ "Pyrvinium". PubChem. U.S. National Library of Medicine. https://www.ncbi.nlm.nih.gov/pccompound/?term=Pyrvinium.
- ↑ 3.0 3.1 "New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway". Heterocycles 85 (5): 1179–1185. 2012. doi:10.3987/COM-12-12446.
- ↑ "Pyrvinium, a potent small molecule Wnt inhibitor, promotes wound repair and post-MI cardiac remodeling". PLOS ONE 5 (11): e15521. 2010. doi:10.1371/journal.pone.0015521. PMID 21170416. Bibcode: 2010PLoSO...515521S.
- ↑ "Casein Kinase 1α as a Regulator of Wnt-Driven Cancer". International Journal of Molecular Sciences 21 (16): 5940. 2020. doi:10.3390/ijms21165940. PMID 32824859.
- ↑ 6.0 6.1 Macdonald JE, Hysell MK, Yu D, Li H, Wong-Staal F, "Novel Quinolinium Salts and Derivatives", WO patent 2006078754, published 2006-07-27
- ↑ "Antitumor activity of pyrvinium pamoate, 6-(dimethylamino)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-1-methyl-quinolinium pamoate salt, showing preferential cytotoxicity during glucose starvation". Cancer Science 95 (8): 685–90. August 2004. doi:10.1111/j.1349-7006.2004.tb03330.x. PMID 15298733.
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