Abstract
A new efficient method for the synthesis of 1,4-dihydroxy-2-naphthylmethyl-and 1,4-dioxo-2(1H,4H)-2-naphthylmethyl-phosphonium salts by reactions of 2-methyl-1,4-naphtho-quinone with appropriate P–H-phosphonium trifluoroacetates has been suggested. The reactions were carried out under mild conditions and provided high yields of target compounds. Representative reaction products have been found to possess moderate antimicrobial and antitumor activity.
References
1.
Millard M., Pathania D., Shabaik Y., Taheri L., Deng J., Neamati N.
PLoS ONE,
2010
2.
Costantini P.
Journal of the National Cancer Institute,
2000
3.
Lopez J., Tait S.W.
British Journal of Cancer,
2015
4.
Leanza L., Zoratti M., Gulbins E., Szabo I.
Oncogene,
2014
5.
Grinius L.L., Jasaitis A.A., Kadziauskas Y.P., Liberman E.A., Skulachev V.P., Topali V.P., Tsofina L.M., Vladimirova M.A.
Biochimica et Biophysica Acta - Bioenergetics,
1970
6.
Zielonka J., Joseph J., Sikora A., Hardy M., Ouari O., Vasquez-Vivar J., Cheng G., Lopez M., Kalyanaraman B.
Chemical Reviews,
2017
7.
Murphy M.P.
Biochimica et Biophysica Acta - Bioenergetics,
2008
8.
Finichiu P.G., James A.M., Larsen L., Smith R.A., Murphy M.P.
Journal of Bioenergetics and Biomembranes,
2012
9.
10.1016/j.mencom.2019.07.027_bib0045
Chen
Mitochondria: The Anti-cancer Target for the Third Millennium,
2014
10.
Modica-Napolitano J.S., Aprille J.R.
Advanced Drug Delivery Reviews,
2001
11.
Mironov V.F., Karaseva A.N., Nizamov I.S., Kedrov I.S., Konovalov A.I.
Russian Journal of Organic Chemistry,
2004
12.
Khasiyatullina N.R., Vazykhova A.M., Voronina Y.K., Mironov V.F.
Russian Journal of General Chemistry,
2017
13.
Khasiyatullina N.R., Vazykhova A.M., Mironov V.F., Krivolapov D.B., Voronina Y.K., Voloshina A.D., Kulik N.V., Strobykina A.S.
Mendeleev Communications,
2017
14.
Tolstikova L.L., Bel’skikh A.V., Shainyan B.A.
Russian Journal of General Chemistry,
2011
15.
Burns J.A., Butler J.C., Moran J., Whitesides G.M.
Journal of Organic Chemistry,
1991
16.
17.
Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard – Fifth Edition. Approved Standard M7-A5, NCCLS, Wayne, PA, 2000.
18.
Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium-Forming Filamentous Fungi. Proposed Standard M38-P, NCCLS, Wayne, PA, 1998.
19.
Semenov V.E., Mikhailov A.S., Voloshina A.D., Kulik N.V., Nikitashina A.D., Zobov V.V., Kharlamov S.V., Latypov S.K., Reznik V.S.
European Journal of Medicinal Chemistry,
2011
20.
10.1016/j.mencom.2019.07.027_bib0095
Pashirova
2015
21.
Voloshina A.D., Semenov V.E., Strobykina A.S., Kulik N.V., Krylova E.S., Zobov V.V., Reznik V.S.
Russian Journal of Bioorganic Chemistry,
2017