Keywords
3-arylidene-1-pyrroline
antitumor activity
proline phosphoryl analogs
Pudovik reaction
α-amino phosphonic acids
Abstract
The Pudovik reactions of 3-arylidene-1-pyrrolinium tri fluoroacetates with hydrophosphoryl compounds in benzene at room temperature for 30 min afford phosphoryl containing proline analogs. The in vitro cytotoxicity studies indicate that the obtained compounds selectively inhibit HuTu 80 tumor cells growth and the activity of some of them is comparable to that of reference 5-fluorouracil.
Funders
Ministry of Education and Science of the Russian Federation
Ministry of Education and Science of the Republic of Kazakhstan
AP23487716
References
1.
Moonen K., Laureyn I., Stevens C.V.
Chemical Reviews,
2004
2.
Lejczak B., Kafarski P.
Topics in Heterocyclic Chemistry,
2009
3.
Van der Veken P., Soroka A., Brandt I., Chen Y., Maes M., Lambeir A., Chen X., Haemers A., Scharpé S., Augustyns K., De Meester I.
Journal of Medicinal Chemistry,
2007
4.
Belyaev A., Zhang X., Augustyns K., Lambeir A., De Meester I., Vedernikova I., Scharpé S., Haemers A.
Journal of Medicinal Chemistry,
1999
5.
Gilmore B.F., Lynas J.F., Scott C.J., McGoohan C., Martin L., Walker B.
Biochemical and Biophysical Research Communications,
2006
6.
Sabidó E., Tarragó T., Niessen S., Cravatt B.F., Giralt E.
ChemBioChem,
2009
7.
Monbaliu J., Tinant B., Marchand-Brynaert J.
Journal of Organic Chemistry,
2010
8.
Davis F.A., Lee S.H., Xu H.
Journal of Organic Chemistry,
2004
9.
Beck J., Gharbi S., Herteg-Fernea A., Vercheval L., Bebrone C., Lassaux P., Zervosen A., Marchand-Brynaert J.
European Journal of Organic Chemistry,
2008
10.
Matziari M., Bauer K., Dive V., Yiotakis A.
Journal of Organic Chemistry,
2008
11.
Odinets I.L., Artyushin O.I., Lyssenko K.A., Shevchenko N.E., Nenajdenko V.G., Röschenthaler G.
Journal of Fluorine Chemistry,
2009
12.
Haak E., Bytschkov I., Doye S.
European Journal of Organic Chemistry,
2002
13.
Development of Potent and Selective Phosphinic Peptide Inhibitors of Angiotensin-Converting Enzyme 2
Mores A., Matziari M., Beau F., Cuniasse P., Yiotakis A., Dive V.
Journal of Medicinal Chemistry,
2008
14.
Gravel E., Poupon E., Hocquemiller R.
Tetrahedron,
2006
15.
De Kimpe N., Stevens C.
Journal of Organic Chemistry,
1993
16.
Smolobochkin A.V., Gazizov A.S., Melyashova A.S., Voronina J.K., Strelnik A.G., Vatsadze S.Z., Burilov A.R., Pudovik M.A., Fedorova O.A., Sinyashin O.G.
RSC Advances,
2017