Abstract
Data on preparation methods for 3'-modified oxythymidines are summarized and systematized. A synthesis tree is presented permitting a selection of rational schemes for thymidine derivatives preparation, in particular those that can be potential anti-HIV/AIDS drugs.
Similar content being viewed by others
REFERENCES
ABC of AIDS, Adler, M., Ed., New York: Americain College of Physicians, 1988.
Kraevskii, A.A., Bibilashvili, R.Sh., Kukhanova, M.K., and Raifeld, Yu.E., Molek. Biol., 1988, vol. 22, no. 11, pp. 1289-1302.
Newmark, P., Nature, 1987, vol. 327, p. 458.
De Clercq, E., J. Med. Chem., 1986, vol. 29, no. 9, pp. 1591-1598.
Gopinath, L., Chemistry in Britain, 1997, no. 7, pp. 38-41.
Ostrovskii, V.A. and Malin, A.A., Russkii Zhurnal VICh/CPID i Rodstvennye Problemy, 1998, vol. 2, no. 1, pp. 61-67.
Krayevsky, A.A. and Watanabe, K.A., Modified Nucleosides as Anti-Aids Drugs: Current Status and Perspectives, Moscow: Bioinform, 1993.
Esikov, K.A., Ostrovskii, V.A., Zubarev, V.Yu., and Malin, A.A., Russkii Zhurnal VICh/SPID i Rodstvennye Problemy, 1999, vol. 3, no. 1, pp. 22-27.
Mitsua, H., Weinhold, K.J., Furnan, P.A., Buckheit, R.W., and Bolognesi, D.P., Virology, 1987, vol. 157, no. 2, pp. 3873396.
Brown, D.Z., Barnes, D.M., and Calvert, C.Ch., J. Nutr., 1987, vol. 117, pp. 2106-2108.
De Clercq, E., Chem. Scripta, 1986, vol. 26, pp. 41-47.
Herdewijn, P., Dideoxynucleoside Analogues as Inhibitors of the Replications of Human Immunodeficiency Virus (HIV), Leuven: University Press, 1989.
Kraevskii, A.A., Molek. Biol., 1994, vol. 28, no. 6, pp. 1245-1257.
Korneeva, M.N., Nosik, D.N., Kruglov, N.V., Galegov, G.A., and Bibilashvili, R.Sh., Molek. Biol., 1989, vol. 23, no. 6, pp. 1716-1724.
Gallo, R., V Mire Nauki, 1987, no. 3, pp. 27-37.
Periugaud, C., Gosselin, G., and Imbach, J.-L., Nucleosides & Nucleotides, 1992, vol. 11, no. 2-4, pp. 903-945.
Chidzhavadze, Z.G., Bibilashvili, R.Sh., Rozovskaya, T.A., Atrazhaev, A.M., Kukhanova, M.K., Papchikhin, A.V., and Kraevskii, A.A., Molek. Biol., 1989, vol. 23, no. 6, pp. 1716-1724.
Preobrazhenskaya, M.N., Bioorg. Khim., 1989, vol. 15, no. 11, pp. 1445-1461.
Atkinson, M.R., Deutsher, M.P., Kornberg, A., Russell, A.F., and Moffatt, J.G., Biochemistry, 1969, vol. 8, no. 12, pp. 4897-4904.
Sanger, F., Nicklen, S., and Coulson, A., Proc. Natl. Acad. Sci., 1977, vol. 74, no. 12, pp. 5463-5467.
Fischer, E.E., Roeder, J., Ber., 1901, vol. 34, no. 3, pp. 3751-3763.
Obol,nikova, E.A., Volkova, O.I., Davydova, L.P., and Samokhvalova, G.I., USSR Inventor,s Certificate, 197598, 1966; Byull. Izobret., 1967, no. 13.
Wheller, H. and McFarland, D., Am. Chem. J., 1910, vol. 43, pp. 19321.
German Patent 222591, 1983. Chem. Abstr., 1986, vol. 104, 109671m.
Guben-Veil, Metody organicheskoi khimii. Metody analiza (Methods of Organic Chemistry. Methods of Analysis), Moscow: Goskhimizdat, 1963.
Roberts, N., Vesser, A., J. Am. Chem. Soc., 1952, vol. 74, no. 3, pp. 668-669.
Farkas, J., Kaplan, L., and Fox, J., J. Org. Chem., 1964, vol. 29, no. 6, pp. 1469-1471.
Lukevits, E.Ya. and Zabolotskaya, A.E., Silil,nyi metod sinteza nukleozidov (Silyl Method of Nucleosides Synthesis), Riga: Zinatne, 1985.
Berezovskii, V.M., Khimiya vitaminov, Moscow: Pishch. Prom., 1973.
Jones, S.S., Reese, C.B., and Ubasawa, A.A., Synthesis, 1982, no. 4, pp. 259-260.
Zinchenko, A.I., Bokut,, C.B., Barai, V.N., Kvasnyuk, E.I., and Mikhailopulo, I.A., Dokl. Akad. Nauk BSSR, 1989, vol. 33, no. 3, pp. 73-76.
Recondo, E. and Rinderknecht, H., Helv. Chim. Acta, 1959, vol. 42, no. 4, pp. 1171-1173.
Zinchenko, A.I., Bokut,, S.B., Barai, V.N., and Mikhailopulo, I.A., Dokl. Akad. Nauk BSSR, 1989, vol. 33, no. 4, pp. 373-375.
Hoffer, M., Chem. Ber., 1960, vol. 93, no. 12, pp. 2777-2781.
Kochetkov, N.K., Bochkov, A.F., and Dmitriev, B.A., Khimiya uglevodov (Hydrocarbons Chemistry), Moscow: Khimiya, 1967.
Jomasy, J., Acta Chim. Acad. Sci. Hung., 1971, vol. 70, no. 3, pp. 263-266.
Holy, A., Coll. Czech. Chem. Commun., 1972, vol. 37, no. 12, pp. 4072-4074.
Schinazi, R., Chen, M., and Prussof, W., J. Med. Chem., 1979, vol. 22, no. 10, pp. 1273-1277.
Marumoto, R. and Honjo, M., Chem. Pharm. Bull., 1974, vol. 22, no. 1, pp. 128-134.
Mikhailov, C.N., Padyukova, N.Sh., and Panov, K.I., Khim. Geterotsikl. Soed., 1989, no. 2, pp. 246-248.
Drawar, P., Hein, L., and Beranek, J., Coll. Czech. Chem. Commun., 1976, vol. 41, no. 7, pp. 2110-2123.
Sowa, T. and Tsunoda, K., Bull. Chem. Soc. Jpn., 1975, vol. 48, no. 2, pp. 505-507.
Zashchitnye gruppy v organicheskoi khimii (Protection Groups in Organic Chemistry), McOmi, J., Ed., Moscow: Mir, 1976, p. 392.
Hanessan, S., Liak, T., and Vonasse, B., Synthesis, 1981, no. 5, pp. 396-398.
Koster, H. and Sinha, N., Tetrahedron Lett., 1982, vol. 23, pp. 2641-2644.
Charabala, R., Uhlmann, E., Beiter, A., and Pflieder, W., Synthesis, 1984, no. 11, pp. 965-968.
Nelson, J., Leonard, N., and Neelima, S., Tetrahedron Lett., 1995, vol. 36, pp. 7833-7836.
Leikauf, E., Barnekow, F., Koster, H., Tetrahedron, 1995, vol. 51, pp. 3793-3802.
Glinski, R., Ash, A., Stevens, C., Sporn, M., and Lazarus, H., J. Org. Chem., 1971, vol. 36, no. 2, pp. 245-253.
Hampton, A., Patel, A.D., Chawla, R., Kappler, F., and Hai, T., J. Med. Chem., 1982, vol. 25, no. 4, pp. 644-649.
Garcia-Alles, L. and Cotor, V., Tetrahedron, 1995, vol. 51, no. 1, pp. 307-316.
Verheyden, J.P. and Moffatt, J., J. Org. Chem., 1970, vol. 35, no. 9, pp. 2868-2877.
Bergstrem, D., Romo, E., and Shum, P., Nucleosides & Nucleotides, 1987, vol. 6, no. 12, pp. 53-63.
Calvo-Mateo, A., Camarasa, M.-J., Diaz-Ortiz, A., de las Heras, F., and Balzarini, J., Tetrahedron, 1988, vol. 44, pp. 4895-4899.
Camarasa, M.-J., Diaz-Ortiz, A., Calvo-Mateo, A., de las Heras, F., Balzarini, J., and de Clercq, E., J. Med. Chem., 1989, vol. 32, no. 8, pp. 1732-1738.
Serafinovski, P. and Barnes, C., Tetrahedron, 1996, vol. 52, no. 23, pp. 7929-7938.
Fox, J. and Miller, N., J. Org. Chem., 1963, vol. 28, no. 4, pp. 936-941.
Fox, J., Pure Appl. Chem., 1969, vol. 18, no. 1, pp. 223-255.
Horwitz, J., Chua, J., and Urbanski, J., J. Org. Chem., 1962, vol. 27, no. 1-2, pp. 3300-3310.
Fox, J., Codingto, J., Yung, N., Kaplan, L., and Lampen, J., J. Am. Chem. Soc., 1958, vol. 80, no. 19, pp. 5155-5160.
Horwitz, J., Chua, J., and Noel, M., J. Org. Chem., 1964, vol. 29, no. 7, pp. 2078.
Horwitz, J., Chua, J., da Rooge, M., Noel, M., and Klundt, I., J. Org. Chem., 1966, vol. 31, no. 1, pp. 205-209.
Chu, C., Schinazi, R., Ahn, M., Ullas, G., and Zi Gu, J. Med. Chem., 1989, vol. 32, no. 3, pp. 612-617.
Mansuri, M., Wos, J., Martin, J., Nucleosides & Nucleotides, 1989, vol. 8, no. 8, pp. 1461-1471.
Kumar, P. and Weibe, L., Nucleosides & Nucleotides, 1992, vol. 11, no. 2-4, pp. 401-416.
Parkes, K., Taylor, K., Tetrahedron Lett., 1988, vol. 29, no. 24, pp. 2995-2996.
Bankston, D. and Almond, M., J. Heterocyclic Chem., 1992, vol. 29, no. 6, pp. 1405-1407.
Kofoed, T., Rusmussen, P.B., Valentin-Hansen, P., and Pedersen, E.B., Acta. Chem. Scand., 1997, vol. 51, no. 3, pp. 318-324.
Petersen, G. and Wengel, J., Tetrahedron, 1995, vol. 51, no. 7, pp. 2145-2154.
Sterzycki, R., Mansuri, M., and Brankovan, V., Nucleosides & Nucleotides, 1989, vol. 8, no. 5-6, pp. 1115-1120.
Beconarn, S., Czernecki, S., and Valery, J.-M., Tetrahedron Lett., 1995, vol. 36, no. 6, pp. 873-877.
Horwitz, J., Chua, J., Urbanski, J., and Noel, M., J. Org. Chem., 1963, vol. 28, pp. 942-944.
Huang, J., J. Heterocyclic Chem., 1995, vol. 32, no. 2, pp. 691-696.
Lin, T. and Prusoff, W., J. Med. Chem., 1978, vol. 21, no. 1, pp. 109-112.
Maillard, M., Farai, A., Frappier, F., Flarent, J.-C., Grierson, D., and Monneret, C., Tetrahedron Lett., 1989, vol. 30, no. 15, pp. 1955-1958.
Karl, R., Lemmen, P., and Ugi, I., Synthesis, 1989, no. 9, pp. 718-719.
Hiebl, J., Zbiral, E., Balzarini, J., and de Clercq, E., J. Med. Chem., 1991, vol. 34, no. 4, pp. 1426-1430.
Hirota, K., Hosono, H., Kitade, Y., Maki, Y., Chu, C., Schimati, R., Nakane, M., and Ono, K., Chem. Pharm. Bull., 1990, vol. 38, no. 9, pp. 2597-2601.
Habich, D., Barth, W., and Rosner, M., Heterocycles, 1989, vol. 29, no. 11, pp. 2083-2086.
Habich, D., Synthesis, 1992, no. 4, pp. 358-360.
Miller, N. and Fox, J., J. Org. Chem., 1964, vol. 29, no. 7, pp. 1772-1776.
Lin, T., Brubaker, W., Wang, Zi., Park, S., and Prussoff, W., J. Med. Chem., 1986, vol. 29, pp. 862-865.
Wigerinck, P., van Aerschot, A., and Kerremans, L., Nucleosides & Nucleotides, 1991, vol. 10, no. 1-3, pp. 583-584.
Pannecouque, C., Busson, R., Balzarini, J., Claes, P., and de Clercq, E., Tetrahedron, 1995, vol. 51, no. 18, pp. 5369-5380.
Converso, A., Siciliano, C., and Sindona, G., Targets in Heterocyclic Systems. Chemistry and Properties, 1998, vol. 2, Attanasi, O.A. and Spinelli, D., Eds., Ital. Soc. Chem., pp. 17-57.
Van Aerschot, A., Balzarini, J., Pauwels, J., Kerremans, Z., de Clercq, E., and Herdewijn, P., Nucleosides & Nucleotides, 1989, vol. 8, no. 5-6, pp. 1121-1122.
Van Aerschot, A., Herdewijn, P., and Balzarini, J., J. Med. Chem., 1989, vol. 32, no. 8, pp. 1743-1749.
Huss, S., de las Heras, F., and Camarasa, M., Tetrahedron, 1991, vol. 47, no. 9, pp. 1727-1736.
Yuzhakov, A.A., Chidzhavadze, Z.G., Bibilashvili, R.Sh., Kraevskii, A.A., Galegov, G.A., Korneeva, M.N., Nosik, D.N., and Kilesso, T.Yu., Bioorg. Khim., 1991, vol. 17, no. 4, pp. 504-510.
Joshi, B. and Reese, C., Tetrahedron Lett., 1992, vol. 33, no. 17, pp. 2371-2374.
Malin, A.A. and Ostrovskii, V.A., Yas'ko, M.V., and Kraevskii, A.A., Zh. Org. Khim., 1995, vol. 31, no. 4, pp. 628-629.
Ostrovskii, V., Studentsov, E., Poplavskii, V., Ivanova, N., Gurskaya, G., Zavodnik, V., Jasko, M., Semizarov, D., and Krayevsky, A., Nucleosides & Nucleotides, 1995, vol. 14, no. 6, pp. 1289-1300.
Ostrovskii, V.A., Ctudentsov, E.P., Poplavskii, V.C., Ivanova, N.V., Gurskaya, G.V., Zavodnik, V.E., Yas'ko, M.V., and Cemizarov, D., Bioorg. Khim., 1995, vol. 21, no. 1, pp. 49-54.
Ostrovskii, V.A., Ivanova, N.V., Malin, A.A., Shcherbinin, M.B., Poplavskii, V.C., and Studentsov, E.P., Zh. Org. Khim., 1993, vol. 29, no. 11, pp. 2333-2334.
Filichev, V.V., Malin, A.A., Yas'ko, M.V., Shcherbinin, M.B., and Ostrovskii, V.A., Zh. Org. Khim., 1998, vol. 34, no. 3, pp. 177-180.
Russian Patent 2124020, 1993; Byull. Izobr., 1998, no. 36.
Kofman, T.P., Manuilova, V.I., Pevzner, M.C., and Timofeeva, T.N., Khim. Geterotsikl. Soed., 1975, no. 5, pp. 705-707.
Kofman, T.P., Vasil'eva, I.V., and Pevzner, M.C., Khim. Geterotsikl. Soed., 1976, no. 9, pp. 1281-1285.
Kofman, T.P., Manuilova, V.I., and Pevzner, M.C., Khim. Geterotsikl. Soed., 1977, no. 10, p. 1407.
Malinovskii, M.C., Okisi olefinov i ikh proizvodnye (Oxides of Olefins and Their Derivatives ), Moscow: Goskhimizdat, 1961.
Mete, A., Hobbs, J., Scopes, D., and Newton, R., Tetrahedron Lett., 1985, vol. 26, no. 1, pp. 97-100.
Bazin, M. and Chattopadhyaya, J., Chem. Scr., 1986, vol. 26, pp. 13-15.
Matsuda, A., Satoh, M., Nakoshina, H., Yamamoto, N., and Ueda, T., Heterocycles, 1988, vol. 27, no. 11, pp. 2545-2548.
Svansson, L., Kvarnstrom, I., Classon, B., and Samuelson, B., J. Org. Chem., 1991, vol. 56, no. 9, pp. 2993-2997.
Pudlo, J. and Townsend, L., Nucleosides & Nucleosides, 1992, vol. 11, no. 2-4, pp. 279-293.
Pudlo, J., Cao, X., Swaminathan, S., and Mattencci, M., Tetrahedron Lett., 1994, vol. 35, no. 50, pp. 9315-9319.
Mikhailopulo, I., Synthesis, 1993, no. 7, pp. 700-705.
Sujino, K. and Suginura, H., Chem. Commun., 1994, no. 22, pp. 2541-2544.
Huryn, D., Okabe, M., Chem. Rev., 1992, vol. 92, no. 8, pp. 1745-1768.
Greengrass, C., Hoople, D., Street, S., Hamilton, F., Marriot, M., Bordner, J., Dalgleish, A., Mitsua, H., and Broder, S., J. Med. Chem., 1989, vol. 32, no. 3, pp. 618-622.
Fedorov, I., Kazmina, E., Novicov, N., Gurskaya, G., Bochkarev, A., Jasko, M., Victorova, L., Kukhanova, M., Balzarini, J., de Clercq, E., and Krayevsky, A., J. Med. Chem., 1992, vol. 35, pp. 4567-4576.
Hammelschimdt, F., Ohler, E., Polster, J., Zbiral, E., Balzarini, J., and de Clercq, E., Lieb. Ann., 1995, no. 3, pp. 5593565.
Hossain, N., Blaton, N., Peeters, O., Rozenski, J., and Herdewijn, P., Tetrahedron, 1996, vol. 52, no. 15, pp. 5563-5578.
Hammelschimdt, F., Ohler, E., Polster, J., Zbiral, E., Balzarini, J., and de Clercq, E., Lieb. Ann., 1995, no. 3, pp. 565-571.
Sujino, K., Yoshida, T., and Suginura, H., Tetrahedron Lett., 1996, vol. 37, pp. 6133-6136.
Tornieporth—Oetting, I. and Klapotke, T., Angew. Chem. Int. Ed., 1995, vol. 34, pp. 511-515.
Nishino, S., Yamamoto, H., Nagane, Y., Ishido, Y., Nucleosides & Nucleotides, 1986, vol. 5, no. 2, pp. 159-168.
Zaitseva, V.E., Dyatkina, N.B., and Kraevskii, A.A., Bioorg. Khim., 1984, vol. 10, no. 5, pp. 670-680.
Davis, L., Nucleosides & Nucleotides., 1985, vol. 4, no. 3, pp. 395-400.
Kochetkov, N.K., Organicheskaya khimiya nukleinovykh kislot (Organic Chemistry of Nucleic Acids), Moscow: Khimiya, 1970.
Colla, L., Herdewijn, P., de Clercq, E., Balzarini, and J., Vanderhaegene, H., Eur. J. Med. Chem., 1985, vol. 20, no. 4, pp. 295-301.
French Patent 2626001, 1988; Chem. Abstr., 1990, vol. 112, 56586u.
Becouarn, S., Czernecki, S., and Valery, J.-M., Nucleosides & Nucleotides, 1995, vol. 16, no. 6, pp. 1227-1232.
German Patent 3705794, 1987; Chem. Abstr., 1988, vol. 109, 211404s.
Glinski, R., Sami, Khan, M., Kalamas, R., and Sporn, M., J. Org. Chem., 1973, vol. 38, no. 25, pp. 4299-4305.
Kowollick, G., Gaertner, K., and Langen, P., Tetrahedron Lett., 1969, vol. 10, pp. 3863-3865.
Janazawa, M. and Eckstein, F., J. Org. Chem., 1978, vol. 43, no. 15, pp. 3044-3048.
Zaitseva, G.V., Vaaks, E.V., and Pashennik, V.I., Zh. Org. Khim., 1988, vol. 24, no. 12, pp. 2629-2630.
Aggei-Aye, K., van, Shijia, H., Hebber, A., and Baker, D., Nucleosides & Nucleotides, 1989, vol. 8, no. 3, pp. 327-337.
Yamamoto, I., Sekine, M., and Hata, T., J. Chem. Soc., Perkin Trans. I, 1980, no. 1, pp. 306-310.
Pan, D.-C., Weng, Z.-Y., and Chen, Z.-H., J. Heterocyclic Chem., 1990, vol. 27, no. 2, pp. 1569-1574.
Fleet, G., Jong, S., and Derome, A., Tetrahedron, 1988, vol. 44, no. 2, pp. 625-636.
Ozols, A., Azhaev, A., Dyatkina, N., and Krayevsky, A., Synthesis, 1980, no. 7, pp. 557-559.
Bibilashvili, R.Sh., Chidzhavadze, Z.G., and Kraevskii, A.A., Biopolimery i kletka (Biopolymers and Cell), 1985, vol. 1, no. 6, pp. 293-307.
Dyatkina, N.B., Kraevskii, A.A., and Azhaev, A.V., Bioorg. Khim., 1986, vol. 12, no. 8, pp. 1048-1053.
Chu, Chung, K., Beach, J., Ullas, G., and Kosugi, V., Tetrahedron Lett., 1988, vol. 29, no. 42, pp. 5349-5352.
Benhaddon, R., Czernecki, S., Valery, J.-M., and Bellosta, V., Bull. Soc. Chim., 1991, vol. 127, no. 1, pp. 108-111.
Chen. Y., Bauman, J., and Chu. C., Nucleosides & Nucleotides, 1992, vol. 11, no. 2-4, pp. 693-705.
Wengel, J., Lau, J., Pedersen, E., and Nielsen, C., J. Org. Chem., 1991, vol. 56, no. 11, pp. 3591-3594.
Andres, J., Bohm, S., Moliner, V., Silla, E., and Tunon, I., J. Phys. Chem., 1994, vol. 98, no. 28, pp. 6955-6960.
Perlman, M. and Watanabe, K., Nucleosides & Nucleotides, 1987, vol. 6, no. 3, pp. 621-630.
Holy, A., Nucleosides & Nucleotides, 1987, vol. 6, no. 3, pp. 147-155.
Puech, F., Gosselin, G., Balzarini, J., de Clercq, E., Imbach, J.-L., J. Med. Chem., 1988, vol. 31, no. 10, pp. 1897-1907.
De Clercq, E., Biochem. Pharmacol., 1991, vol. 42, no. 5, pp. 963-972.
Van Aerschot, A., Everaert, D., Balzarini, J., Augustyns, K., Jie, L., Janssen, G., Peeters, O., Blaton, N., and de Ranter, J., J. Med. Chem., 1990, vol. 33, no. 6, pp. 2481-2486.
Krayevsky, A., Tarussova, N., Zhu, Q.-Y., Vidal, P., Chou, T.-C., Baron, P., Polsky, B., Jiang, X.-J., Matulic-Adamic, J., Rosenberg, I., and Watanabe, K., Nucleosides & Nucleotides, 1992, vol. 11, no. 2-4, pp. 177-196.
Gosselin, G., Perigaud, C., Lefebure, I., Pompon, A., Aubertin, A.-M., Kirn, A., Szabo, T., Stavinsky, J., and Imbach, J.-L., Antiviral Res., 1993, vol. 22, no. 2-3, pp. 143-153.
Jasko, M., Shipitsin, A., Shirokova, E., Krayev-sky, A., Polsky, B., MacLow, C., Ostrander, M., and O'Hara, B., Nucleosides & Nucleotides, 1993, vol. 12, no. 8, pp. 879-890.
Mansuri, M.M., Starrett, J.E., Ghazzouli, I., Hitchcock, M.J.M., Sterzycky, R.Z., Brankovan, V., and Lin, T.-S., August, E.M., Prusoff, W.H., Sommadossi, J.-P., and Martin, J.C., J. Med. Chem., 1989, vol. 32, no. 2, pp. 4613466.
Mansuri, M.M., Starrett, J.E., Wos, J.A., Tortolani, D.R., Brodfuehrer, P.R., Howell, H.G., and Martin, J.C., J. Org. Chem., 1989, vol. 54, pp. 4780-4785.
Joshi, B.V., Rao, T.S., and Reese, C.B., J. Chem. Soc., Perkin Trans. I, 1992, no. 19. P.2537-2544.
Luzzio, F.A. and Menes, M.E., J. Org. Chem., 1994, vol. 59, no. 24, pp. 7267-7272.
Krayevsky, A.A., Molek. Biol., 1992, vol. 26, no. 4, pp. 725-744.
Kraevskii, A.A., Khim.-Farm. Zh., 1992, no. 1, pp. 27-37.
Kukhanova, M.K., Khim.-Farm. Zh., 1992, no. 2, pp. 4-8.
De Clercq, E., Clin. Microb. Rev., 1997, vol. 10, no. 4, pp. 674-693.
Alexander, P. and Holy, A., Coll. Czech. Chem. Commun, 1994, vol. 59, pp. 2127-2165.
De Clercq, E., Coll. Czech. Chem. Commun., 1998, vol. 59, no. 10, pp. 449-479.
Baba, M., Pauwels, R., Balzarini, J., Herdewijn, P., de Clercq, E., Biochem. Biophys. Res. Commun., 1987, vol. 145, no. 3, pp. 1080-1086.
Herdewijn, P., Balzarini, J., Baba, M., Pauwels, R., van Aerschot, A., Jansenn, G., and de Clercq, E., J. Med. Chem., 1988, vol. 31, no. 10, pp. 2040-2048.
Thrane, H., Fensholdt, J., Regner, M., and Wengel, J., Tetrahedron, 1995, vol. 51, pp. 10389-10402.
Mustafin, A.G., Gataulin, R.R., and Spirikhin, L.V., Zh. Org. Khim., 1996, vol. 32, no. 12, pp. 1842-1848.
Wigerinck, P., van Aerschot, A., and Janssen, G., J. Med. Chem., 1990, vol. 33, no. 2, pp. 868-873.
Wigerinck, P., van Aerschot, A., Claes, P., Balzarini, J., de Clercq, E., and Herdewijn, P., J. Heterocyclic Chem., 1989, vol. 26, no. 6, pp. 1635-1642.
Ariza, X., Garces, J., and Vilarrasa, J., Tetrahedron Lett., 1992, vol. 33, no. 28, pp. 4069-4072.
Czernecki, S. and Valery, J.-M., Synthesis, 1991, no. 3, pp. 239-240.
Czernecki, S., Diguarther, L.T., and Valery, J.-M., Nucleoides & Nucleotides, 1993, vol. 12, no. 3-4, pp. 369-380.
Hager, M. and Liotta, D., J. Am. Chem. Soc., 1991, vol. 113, no. 13, pp. 5117-5119.
Minamoto, K., Oishi, M., Kakehi, A., Ohta, N., Matsuda, I., Watanabe, K., Yanagihara, K., Takeuchi, T., and Tanigawa, K., J. Chem. Soc., Perkin Trans. I, 1994, no. 16, pp. 2289-2296.
Okabe, M., Sun, R.-C., Tam, S., Todaro, L., and Coffen, D., J. Org. Chem., 1988, vol. 53, no. 20, pp. 4780-4786.
Eger, K., Kluder, E., Beck, R., and Scholz, U., Pharm. Res., 1993, vol. 10, no. 5, pp. 771-773.
Jorgensen, P., Svedsen, M., Scheuer-Larsen, C., and Wengel, J., Tetrahedron, 1995, vol. 51, no. 7, pp. 2155-2164.
Meier, C., Habel, L., Balzarini, J., and de Clercq, E., Lieb. Ann., 1995, no. 12, pp. 2203-2208.
Hussain, R., Toth, I., and Gibbons, W., Lieb. Ann., 1992, no. 2, pp. 169-171.
Minamoto, K., Hamano, Y., Matsuoka, Y., Watanabe, K., Hirota, T., and Eguchi, S., Nucleosides & Nucleotides, 1992, vol. 11, no. 2-4, pp. 457-471.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Malin, A.A., Ostrovskii, V.A. Synthesis of Thymidine Derivatives as Potential Pharmaceuticals against HIV/AIDS Infection. Russian Journal of Organic Chemistry 37, 759–780 (2001). https://doi.org/10.1023/A:1012441026853
Issue Date:
DOI: https://doi.org/10.1023/A:1012441026853