Abstract
Reactions of the polyene macrolide antibiotic pimaricin with aromatic aldehydes and hypophosphorous acid are shown to afford pimaricin hydrophosphoryl derivatives. Physicochemical and biological properties of these compounds are explored. Biological studies indicated that the pimaricin hydrophosphoryl derivatives are low toxic agents possessing a high antifungal activity.
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Omura, S. and Tanaka, H., Macrolide Antibiotics: Chemistry, Biology and Practice, Omura, S., Ed., New York: Academic, 1984, p. 351.
Bader, G., Deicke, P., Gedek, B., Gemeihardt, H., Muller, J., Sholer, H., Spitzbart, H., and Wiesner, B., Endomykosen: Schleimhaut-Organ- and Systemmykosen Herausgegeben von Horst Gemeinhardt, Berlin: Gustvtischer, 1989.
Antifungal Drug Therapy (A Complete Guide for the Practitioner), Jacobs, P.H. and Nall, L., Eds., New York: Dekker, 1990.
Recent Progress in Antifungal Chemotherapy, Yamaguchi, H., Kobayashi, G.S., and Takahashi, H., Eds., New York: Dekker, 1992.
Shneider, M.A., in: Uspekhi v oblasti izucheniya i proizvodstva antibiotikov (Advances in Studying and Manufacturing antibiotics), Moscow: 1979, p. 56.
Shneider, M.A., Shtil’bans, E.B., Rachkovskaya, L.A., and Poltorak, V.A., Antibiotiki, 1983, vol. 28, no. 5, p. 352.
Shneider, M.A., Molek. Genet., Mikrobiol. Virusol., 1984, no. 5, p. 41.
Shneider, M.A and Chizhov, N.P., Vopr. Virusol., 1986, vol. 31, no. 1, p. 18.
Ouellette, M., Drummelsmith, J., and Papadopoulou, B., Drug Resist. Updates, 2004, vol. 7, nos. 4–5, p. 257.
Goldsmith, D.R. and Perry, C.M., Drugs, 2004, vol. 64, no. 17, p. 1905.
Golenser, J. and Domb, A., Mini-Review Med. Chem., 2006, vol. 6, no. 2, p. 153.
Vertut-Croquin A., Brajtburg J., and Medoff, G., Cancer Res., 1986, vol. 46, no. 12, p. 6054.
Coune, A., Eur. J. Cancer Clin. Oncol., 1988, vol. 24, no. 2, p. 117.
Feigin, A.M., Med. Hypotheses., 1999, vol. 52, no. 5, p. 383.
Kirkpatrick, C.H., AIDS: Anti-HIV Agents, Therapies and Vaccines (Annals of New York Academy of Sciences), Georgiev, V.S. and McGowan, J.J., Eds., New York, 1990, vol. 616, p. 461.
Vyadro, M.M., Antibiot. Khimioter., 1991, vol. 36, no. 11, p. 45.
Ablordeppey, S.Y., Fan, P., Ablordeppey, J.H., and Mardenborough, L., Curr. Med. Chem., 1999, vol. 6, no. 12, p. 1151.
Hood, S. and Denning, D.W., J. Antimicrob. Chemother., 1996, vol. 37,suppl. B, p. 71.
Gallis, H.A. and Drew, R.H., Rev. Infect. Dis., 1990, vol. 12, no. 2, p. 308.
Georgopapadakou, N.H. and Walsh, T.J., Antimicrob. Agents Chemother., 1996, vol. 40, no. 2, p. 279.
Grillot, R. and Lebeau, B., Antimicrobial Agents, Bryskier, A., Ed., Washington: Publ. Am. Soc. Microbiol., 2005, p. 1260.
Fanos, V. and Cataldi, L., J. Chemother., 2000, vol. 12, no. 6, p. 463.
Deray, G., J. Antimicrob. Chemother., 2002, vol. 49,suppl. S1, p. 37.
Bernardo, J.F., Sabra, R., and Branch, R.A., Clinical Nephrotoxins, De Broe, M.E., Ed., Dordrecht: Kluwer Academic, 2003, p. 199.
Wingard, J.R. and Leather, H., Biol. Blood Marrow Transplant., 2004, vol. 10, p. 73.
Thomas, A.H., Analyst, 1976, vol. 101, no. 1202, p. 321.
Shenin, Yu.D., Belakhov, V.V., Gagarina, A.B., Kasaikina, O.T., and Vainshtein, V.A., Polienovye makrolidnye antibiotiki: inaktivatsiya i sposoby ikh stabilizatsii (Polyene Macrolide Antibiotics: Inactivation and Methods of Stabilization), Review Information, serred ‘Remedies, Economics, Technology, and Perspectives of Producing,” Moscow: VNIISENTI, 1990, no. 12.
Shenin, Yu.D., Belakhov, V.V., Koptelova, T.N., Levina, A.A., and Shchinova, N.E., Antibiot. Khimiot., 1991, vol. 36, no. 8, p. 20.
Lamy-Freund, M.T., Ferreira, V.F. and Schreier, S., J. Antibiot., 1985, vol. 38, no. 6, p. 753.
Belakhov, V.V., Shenin, Yu.D., Nifant’ev, E.E., Kukhareva, T.S., and Soldatova, I.A., Antibiot. Khimioter., 1997, vol. 42, no. 12, p. 6.
Belousova, I.I., Antibiotiki, 1976, vol. 21, no. 7, p. 661.
Kaufman, C.H. and Carver, P.L., Drugs, 1997, vol. 53, no. 4, p. 539.
Bossche, H.V., Dromer, F., Improvisi, I., Lozano-Chiu, M., Rex, J.H., and Sanglard, D., Med. Mycol., 1998, vol. 36, no. 1, p. 119.
Stevens, D.A. and Holmberg, K., Curr. Opin. Anti-Infect. Invest. Drugs, 1999, vol. 1, no. 3, p. 306.
Brik, H., in: Analytical Profiles of Drug Substances, New York: Academic, 1981, vol. 10, p. 513.
Zotchev, S.B., Curr. Med. Chem., 2003, vol. 10, no. 3, p. 221.
Schafner, C.P. and Mechlinski, W., J. Antibiot., 1972, vol. 25, no. 4, p. 259.
Falkowski, L., Stefanska, B., Bylec, E., Golik, J., Kolodziejczyk, P., and Borowski, E., J. Antibiot., 1979, vol. 32, no. 10, p. 1080.
Falkowski, L., Stefanska, B., Zielinski, J., Bylec, E., Golik, J., and Kolodziejczyk, P., Acta Polon. Pharm., 1980, vol. 37, no. 6, p. 631.
Pol. Patent 120 035, Chem. Abstr., 1983, vol. 101, no. 38 277.
Pol. Patent 120 111, Chem. Abstr., 1983, vol. 101, G6 940.
Nirgudkar, A.G., Sastry, M.K., Swami, M.B., and Nanda, R.K., Hind. Antibiot. Bull., 1988, vol. 30, nos. 3–4, p. 66.
Falkowski, L., Zielinski, J., Pawlak, J., Golik, J., Kolodziejczyk, P., Stefanska, B., Bylec, E., and Borowski, E., Acta Polon. Pharm., 1980, vol. 37, no. 5, p. 517.
Stefanska, B., Borowski, E., and Falkowski, L., Acta Polon. Pharm., 1988, vol. 45, no. 1, p. 71.
DE Patent 3 013 631, Chem. Abstr., 1981, vol. 94, p. 121 884.
Swami, M.B., Sastry, M.K., Nirgudkar, A.G., and Nanda, R.K., Hind. Antibiot. Bull., 1983, vol. 25, nos. 3–4, p. 101.
Paquet, V. and Carreira, E.M., Org. Lett., 2006, vol. 8, no. 9, p. 1807.
US Patent 3 957 754, Chem. Abstr., 1976, vol. 85, p. 25 414.
Belg. Patent 877 661, Chem. Abstr., 1980, vol. 93, p. 13 076.
Sulloff, E.C., Marcy, J.E., Hackney, C.R., Sumner, S.S., and Bishop, J.R., J. Food Protect., 2003, vol. 66, no. 8, p. 1499.
Shenin, Yu.D. and Belakhov, V.V., Khimiya polienovykh makrolidnykh antibiotikov (Chemistry of Polyene Macrolide Antibiotics), Review Information, series “Remedies, Economics, Technology, and Perspectives of Production,” Moscow: VNIISENTI, 1989, no. 6.
Belakhov, V.V., Levina, A.A., Shenin, Yu.D., Ionin, B.I., Shatik, L.I., Zaitseva, M.B., Grinberg, G.E., Shtil’bans, E.B., and Rachkovskaya, L.A., Antibiot. Khimioter., 1990, vol. 35, no. 8, p. 31.
Belakhov, V.V., Levina, A.A., Shenin, Yu.D., and Ionin, B.I., Khim.-Farm. Zh., 1991, vol. 25, no. 3, p. 86.
Belakhov, V.V., Levina, A.A., Shenin, Yu.D., Ionin, B.I., Grinberg, G.E., Shatik, L.I., Shtil’bans, E.B., and Rachkovskaya, L.A., Khim.-Farm. Zh., 1991, vol. 25, no. 11, p. 45.
Shenin, Yu.D., Belakhov, V.V., and Araviiskii, R.A., Khim.-Farm. Zh., 1993, vol. 27, no. 2, p. 14.
Belakhov, V.V., Shenin, Yu.D., Araviiskii, R.A., and Shtil’bans, E.B., Antibiot. Khimioter., 1996, vol. 41, no. 7/8, p. 4.
Shenin, Yu.D. and Belakhov, V.V., Antibiot. Khimioter., 1997, vol. 42, no. 4, p. 34.
Shenin, Yu.D., Belakhov, V.V., and Araviiskii, R.A., Khim.-Farm. Zh., 1998, vol. 32, no. 2, p. 52.
Shenin, Yu.D. and Belakhov, V.V., Proc. XVI Mendeleev Congress on General and Applied Chemistry, Moscow, 1998, vol. 4, p. 111.
Shenin, Yu.D., Belakhov, V.V., Shatik, L.I., and Araviiskii, R.A., Antibiot. Khimioter., 1998, vol. 43, no. 12, p. 8.
Shenin, Yu.D. and Belakhov, V.V., Trudy mezhdunarodnoi nauchno-prakticheskoi konferentsii, posvyaschennoi 85-letiyu Sankt-Peterburgskoi gosudarstvennoi khimiko-farmatsevticheskoi akademii (Proc. Int. Scientific and Practical Conf. Devoted to 85th Anniversary of St. Peterburg State Chem.-Pharm. Academy), St. Petersburg: SPGKhFA, 2004, p. 151.
Belakhov, V.V. and Shenin, Yu.D., Khim.-Farm. Zh., 2007, vol. 41, no. 6, p. 26.
Belakhov, V.V. and Shenin, Yu.D., Khim.-Farm. Zh., 2007, vol. 41, no. 7, p. 20.
Kabachnik M.I. and Medved’, T.Ya., Dokl. Akad. Nauk SSSR, 1952, vol. 83, no. 3, p. 689.
Fields, E.K., J. Am. Chem. Soc., 1952, vol. 74, p. 1528.
Nifant’ev, E.E., Khimiya gidrofosforil’nykh soedinenii (Chemistry of Hydrophosphoryl Compounds), Moscow: Nauka, 1983.
Cherkasov, R.A. and Galkin, V.I., Usp. Khim., 1998, vol. 67, no. 10, p. 940.
Yudelevich, V.I., Sokolov, L.B., and Ionin, B.I., Usp. Khim., 1980, vol. 49, no. 1, p. 92.
Ionin, B.I., Ershov, B.A., and Kol’tsov, A.M., YaMRspektroskopiya v organicheskoi khimii (NMR Spectroscopy in Organic Chemistry), Leningrad: Khimiya, 1983.
Belakhov, V.V., Yudelevich, V.I., Ionin, B.I., Komarov, E.V., and Petrov, A.A., Zh. Obshch. Khim., 1988, vol. 58, no. 6, p. 1193.
Armarego, W.L.F. and Chai, C., Purification of Laboratory Chemicals, Oxford: Butterworth-Heinemann, 2003.
Barr, F.S., Antibiot. Chemother., 1959, vol. 9, p. 406.
Levinskas, G.J., Ribelin, W.E., and Shaffer, C.B., Toxicol. Applied Pharmacol., 1966, vol. 8, no. 1, p. 97.
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Belakhov, V.V., Shenin, Y.D. & Ionin, B.I. Synthesis of hydrophospohoryl derivatives of the antifungal antibiotic pimaricin by the Kabachnik-Fields reaction. Russ J Gen Chem 78, 305–312 (2008). https://doi.org/10.1134/S1070363208020217
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DOI: https://doi.org/10.1134/S1070363208020217