吡维铵

吡维铵
臨床資料
AHFS/Drugs.com	Micromedex详细消费者药物信息
ATC碼	P02CX01 (WHO) ;
识别信息
	IUPAC命名法 2-[(E)-2-(2,5-Dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-amine; ;
CAS号	7187-62-4
PubChem CID	5281035;
ChemSpider	21125;
UNII	6B9991FLU3;
ChEBI	CHEBI:8687;
ChEMBL	ChEMBL1201303;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID4023545 ;
ECHA InfoCard	100.020.543
化学信息
化学式	C26H28N3+
摩尔质量	382.53 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES CC1=CC(=C(N1C2=CC=CC=C2)C)/C=C/C3=[N+](C4=C(C=C3)C=C(C=C4)N(C)C)C;
	InChI InChI=1S/C26H28N3/c1-19-17-21(20(2)29(19)24-9-7-6-8-10-24)11-13-23-14-12-22-18-25(27(3)4)15-16-26(22)28(23)5/h6-18H,1-5H3/q+1; Key:QMHSXPLYMTVAMK-UHFFFAOYSA-N;

吡维铵（英语：Pyrvinium）是一种对蛲虫有效的驱虫药。^[1]吡维铵已几种方式存在，例如吡维氯铵、对甲苯磺酸吡维铵、三氟甲磺酸吡维铵和双羟萘酸吡维铵（或叫帕莫酸吡维铵及恩波酸吡维铵）。^[2]^[3]吡维铵被鉴定为一种有效的Wnt抑制剂，通过激活酪蛋白激酶CK1α发挥作用。^[4]^[5]

吡维铵盐还可以抑制癌细胞的生长。^[6]更具体地说，双羟萘酸盐已被证明在葡萄糖饥饿期间对各种癌细胞系具有优先毒性。^[7]

合成

其中一种合成方法基于斯克劳普合成和帕尔-克诺尔合成。^[6]最近，报道了通过弗里德兰德喹啉合成替代三氟甲磺酸吡维铵的收敛合成策略。^[3]

参考资料

^ Desai AS. Single-dose treatment of oxyuriasis with pyrvinium embonate. British Medical Journal. December 1962, 2 (5319): 1583–5. PMC 1926864  . PMID 14027194. doi:10.1136/bmj.2.5319.1583.
^ Pyrvinium. PubChem. U.S. National Library of Medicine. [2023-02-06]. （原始内容存档于2016-04-02）.
^ ^3.0 ^3.1 Mao Y, Lin N, Tian W, Huang Z. New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway. Heterocycles. 2012, 85 (5): 1179–1185. doi:10.3987/COM-12-12446.
^ Saraswati S, Alfaro MP, Thorne CA, Atkinson J, Lee E, Young PP. Pyrvinium, a potent small molecule Wnt inhibitor, promotes wound repair and post-MI cardiac remodeling. PLOS ONE. 2010, 5 (11): e15521. Bibcode:2010PLoSO...515521S. PMC 2993965  . PMID 21170416. doi:10.1371/journal.pone.0015521  .
^ Shen C, Nayak A, Melendez RA, Robbins DJ. Casein Kinase 1α as a Regulator of Wnt-Driven Cancer. International Journal of Molecular Sciences. 2020, 21 (16): 5940. PMC 7460588  . PMID 32824859. doi:10.3390/ijms21165940  .
^ ^6.0 ^6.1 WO 2006078754,Macdonald JE, Hysell MK, Yu D, Li H, Wong-Staal F,「Novel Quinolinium Salts and Derivatives」,发表于2006-07-27
^ Esumi H, Lu J, Kurashima Y, Hanaoka T. 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. August 2004, 95 (8): 685–90. PMID 15298733. doi:10.1111/j.1349-7006.2004.tb03330.x  .

[1] Desai AS. Single-dose treatment of oxyuriasis with pyrvinium embonate. British Medical Journal. December 1962, 2 (5319): 1583–5. PMC 1926864  . PMID 14027194. doi:10.1136/bmj.2.5319.1583.

[2] Pyrvinium. PubChem. U.S. National Library of Medicine. [2023-02-06]. （原始内容存档于2016-04-02）.

[Heterocycles-3] 3.0 ^3.1 Mao Y, Lin N, Tian W, Huang Z. New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway. Heterocycles. 2012, 85 (5): 1179–1185. doi:10.3987/COM-12-12446.

[4] Saraswati S, Alfaro MP, Thorne CA, Atkinson J, Lee E, Young PP. Pyrvinium, a potent small molecule Wnt inhibitor, promotes wound repair and post-MI cardiac remodeling. PLOS ONE. 2010, 5 (11): e15521. Bibcode:2010PLoSO...515521S. PMC 2993965  . PMID 21170416. doi:10.1371/journal.pone.0015521  .

[5] Shen C, Nayak A, Melendez RA, Robbins DJ. Casein Kinase 1α as a Regulator of Wnt-Driven Cancer. International Journal of Molecular Sciences. 2020, 21 (16): 5940. PMC 7460588  . PMID 32824859. doi:10.3390/ijms21165940  .

[Macdonald-6] 6.0 ^6.1 WO 2006078754,Macdonald JE, Hysell MK, Yu D, Li H, Wong-Staal F,「Novel Quinolinium Salts and Derivatives」,发表于2006-07-27

[7] Esumi H, Lu J, Kurashima Y, Hanaoka T. 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. August 2004, 95 (8): 685–90. PMID 15298733. doi:10.1111/j.1349-7006.2004.tb03330.x  .

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