Synthesis of novel substituted pyrimidine derivatives bearing a sulfamide group and their in vitro cancer growth inhibition activity.

作者: Carole-Anne Lefebvre , Elsa Forcellini , Sophie Boutin , Marie-France Côté , René C.-Gaudreault

DOI: 10.1016/J.BMCL.2016.11.052

关键词:

摘要: The synthesis of two series novel substituted pyrimidine derivatives bearing a sulfamide group have been described and their in vitro cancer growth inhibition activities evaluated against three human tumour cell lines (HT-29, M21, MCF7). In general, activity has enhanced by the introduction bulky substituent on aromatic ring with best compound having GI50<6μM for all lines. MCF7 selective compounds were four additional invasive breast ductal carcinoma (MDA-MB-231, MDA-MB-468, SKBR3, T47D) T47D line cases except one, suggesting potential antiestrogen activity.

参考文章(20)
Massaba Keita, Mathilde Vandamme, Olivier Mahé, Jean-François Paquin, Synthesis of isocyanides through dehydration of formamides using XtalFluor-E Tetrahedron Letters. ,vol. 56, pp. 461- 464 ,(2015) , 10.1016/J.TETLET.2014.11.128
Bianca Malo-Forest, Grégory Landelle, Jessye-Ann Roy, Jacques Lacroix, René C. Gaudreault, Jean-François Paquin, Synthesis and growth inhibition activity of fluorinated derivatives of tamoxifen. Bioorganic & Medicinal Chemistry Letters. ,vol. 23, pp. 1712- 1715 ,(2013) , 10.1016/J.BMCL.2013.01.057
Francis X. Tavares, Joyce A. Boucheron, Scott H. Dickerson, Robert J. Griffin, Frank Preugschat, Stephen A. Thomson, Tony Y. Wang, Hui-Qiang Zhou, N-Phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amines as potent and selective inhibitors of glycogen synthase kinase 3 with good cellular efficacy. Journal of Medicinal Chemistry. ,vol. 47, pp. 4716- 4730 ,(2004) , 10.1021/JM040063I
Snahel D. Patel, Wendy M. Habeski, Alan C. Cheng, Elisa de la Cruz, Christine Loh, Natasha M. Kablaoui, Quinazolin-4-piperidin-4-methyl sulfamide PC-1 inhibitors: alleviating hERG interactions through structure based design. Bioorganic & Medicinal Chemistry Letters. ,vol. 19, pp. 3339- 3343 ,(2009) , 10.1016/J.BMCL.2009.04.006
Allen B Reitz, Garry R Smith, Michael H Parker, The role of sulfamide derivatives in medicinal chemistry: a patent review (2006-2008). Expert Opinion on Therapeutic Patents. ,vol. 19, pp. 1449- 1453 ,(2009) , 10.1517/13543770903185920
Marco Radi, Silvia Schenone, Maurizio Botta, Recent highlights in the synthesis of highly functionalized pyrimidines. Organic and Biomolecular Chemistry. ,vol. 7, pp. 2841- 2847 ,(2009) , 10.1039/B906445A
Adam R. Renslo, Andy Atuegbu, Prudencio Herradura, Priyadarshini Jaishankar, Mingzhe Ji, Karen L. Leach, Michael D. Huband, Michael R. Dermyer, Luping Wu, J.V.N. Vara Prasad, Mikhail F. Gordeev, A distal methyl substituent attenuates mitochondrial protein synthesis inhibition in oxazolidinone antibacterials Bioorganic & Medicinal Chemistry Letters. ,vol. 17, pp. 5036- 5040 ,(2007) , 10.1016/J.BMCL.2007.07.022
Zhi-Hui Peng, Michel Journet, Guy Humphrey, A highly regioselective amination of 6-aryl-2,4-dichloropyrimidine. Organic Letters. ,vol. 8, pp. 395- 398 ,(2006) , 10.1021/OL052578P
Jean-Yves Winum, Loic Toupet, Véronique Barragan, Georges Dewynter, Jean-Louis Montero, N-(tert-Butoxycarbonyl)-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl] Azanide: A New Sulfamoylating Agent. Structure and Reactivity toward Amines Organic Letters. ,vol. 3, pp. 2241- 2243 ,(2001) , 10.1021/OL0161312
Dengfeng Dou, Kok-Chuan Tiew, Guijia He, Sivakoteswara Rao Mandadapu, Sridhar Aravapalli, Kevin R. Alliston, Yunjeong Kim, Kyeong-Ok Chang, William C. Groutas, Potent inhibition of Norwalk virus by cyclic sulfamide derivatives. Bioorganic & Medicinal Chemistry. ,vol. 19, pp. 5975- 5983 ,(2011) , 10.1016/J.BMC.2011.08.054