Синтез гетероциклических аналогов подофиллотоксина
Диссертация
Разработан новый удобный общий подход к синтезу разнообразных потенциально биологически активных гетероциклических аналогов подофиллотоксина. В качестве исходных веществ использованы доступные альдегиды, амины, циклические дикетоны, малононитрил. В последнее время в синтетической органической химии большое внимание уделяется получению аналогов известных природных соединений. Автор выражает… Читать ещё >
Список литературы
- Ugi I., Heck S. The multicomponent reactions and their libraries for natural and preparative chemistry. // Comb. Chem. High Throughput Screening 2001.4. P. 1−34.
- Bishop J.F., Lowenthal R.M., Jushua D., Matthews J.P., Todd D., Cobcroft R., et al. Etoposide in acute nonlymphocytic leukemia. // Australian Leukemia Study Group. Blood 1990. 75. P. 27−32.
- Rivera G., Bowman W.P., Murphy S.B., Dahl G.V., Aur R.J., Kalwinsky D.K., et al. VM-26 with prednisone for treatment of refractory acute lymphocytic leukemia. //Med. Pediatr. Oncol. 1982. 10. P. 439−445.
- Bosl G.J., Geller N.L., Bajorin, D.A. randomized trial of etoposide + cisplatin versus vinblastine + bleomycin + cisplatin + cyclophosphamide + dactinomycin in patients with good prognosis germ tumors. // J. Clin. Oncol. 1988. 6. P. 1231−1236.
- Jonson D.H. Management of small cell lung cancer: current state of the art.// Chest. 1999. 116 (Suppl.3). P. 525−530.
- Sparano J.A., Wearne P.H., Leaf A., Dutcher J.P. Infusional cyclophospamide, doxorubicin, and etoposide for a schedule-dependent effect favoring infusional administration of chemotherapy. // J. Clin. Oncol. 1993. 11. P. 1071−1079.
- Salles G., Shipp M.A., Coiffer B. Chemotherapy of non-Hodgkin aggressive lymhpomas. // Sem. Oncol. 1994. 31. P. 46−54.
- Kaplan I.W. Condylomata acuminate. // New Orleans Med Surg J. 1942. 94. P. 388−395.
- Podwyssotzki V. On the active constituent of podophillin. // Pharm. J. Trans.1881. 12. P. 217−218.
- Podwyssotzki V. On the active constituent of podophillin. // Am. J. Pharm.1882. 12. P. 102−115.
- Borshe W., Niemann J. Podophyllin. Justus Liebigs // Ann. Chem. 1932. 494. P. 126−142.
- Schecker A.W., Hartwell J.L. Component of podophyllin. XX. The absolute configuration of podophyllotoxin and related lignans. // J. Org. Chem. 1985. 21. P. 381−382.
- Gensler W.J., Gatsonis C.D. Synthesis of podophyllotoxin. // J. Am. Chem. Soc. 1962. 84. P. 1748−1749.
- Gensler W.J., Gatsonis C.D. Synthesis of podophyllotoxin. // J. Am. Chem. Soc. 1966. 31. P. 4004−4008.
- Sackett D.L. Podophyllotoxin, steganacin and combretastatin: natural products that bind at the site of tubulin. // Pharmacol. Ther. 1993. 59. P. 163 228.
- Youngjae Y. Podophyllotoxin derivatives: current synthetic Approaches for
- New Anticancer Agents. // Cur. Pharm. Des. 2005. 11. P. 1695−1717. 23. Stahelin H., von Warburg A. From podophyllotoxin glycoside to etoposide.// Prog. Drug. Res. 1989. 33. P. 169−267. j
- Leteurtre F., Madalengoitia J., Orr A., Guzi T.J., Lehnert E., Macdonald T., et al. Rational design and molecular effects of a new topoisomerase II inhibitor, azatoxin. // Canser Res. 1992. 52. P. 4478−4483.
- Utsugi N., Shibata J., Sugimoto Y., Aoyagi K., Werzba K., Kobunai T., et al. Antitumor activity of novel podophyllotoxin. derivative (TOP-53) against lung cancer and lung metastatic cancer. // Cancer Res. 1996. 56. P. 28 092 814.
- Lee C.C., Huang T.S. A novel topoisomerase II poison GL331t preferentialy induces DNA cleavage at (C/G)T sites and can cause telomere DNA damage. II Pharm. Res. 2001. 18. P. 846−851. j
- Huang T.S., Lee C.C., Chao Y., Shu C.H., Chen L.T., Chen L.L., et al. A novel podophyllotoxin-derived compound GL331 is more potent than its congener VP-16 in killing refractory cancer cells. // Pharm. Res. 1999. 16. P. 997−1002.
- Cline S.D., Macdonald T.C., Osheroff N. Azatoxin is mechanistic hybrid of the topoisomerase II-target anticancer drugs etoposide and ellipticine. // Biochemistry. 1997. 36. P. 13 095−13 101.
- Solary E., Leteurte F., Paull K.D., Scudiero D., Hamel E., Pommier Y. Dual inhibition of topoisomerase II and tubuline polymerization by azatoxin, a novel cytotoxic agent. // Biochem. Pharmacol. 1993. 45. P. 2449−2456.
- Yoshida M., Kobunai T., Aoyagi K., Saito H., Utsugi T., Wierzba K., et al. Specific distribution of TOP-53 to the lung and lung-localized tumor is determined by its interaction with phospholipids. // Clin. Canser Res. 2000. 6. P. 4396−43 401.
- Byl J.A., Cline S.D., Utsugi T., Kobunai T., Yamada Y., Osheroff N. DNA topoisomerase II as the target for the anticancer drug TOP-53: mechanistic basis for drug action. // Biochemistry. 2001. 40. P. 712−718.
- Ward R.S. The synthesis of lignans and neolignans. // Chem. Soc. Rev. 1982. 11. P. 75−125.
- Ayres D.C., Loike J.D. Lignans. / Cambridge University Press, 1990. Chapter 3 and 4.
- Gensler W.J., Gatsonis CD. The podophyllotoxin-picropodophyllin equilibrium. //J. Org. Chem. 1966. 31. P. 3224−3227.
- Kende A.S., King M.L., Curran D.P. Total synthesis of (±)-4'-demethyl-4-epipodophyllotoxin by insertion cyclization. // J. Org. Chem. 1981. 46. P. 2826−2828.
- Peterson J.R., Do H.D., Rogers R.D. Anticancer agent development- 61. Applicatio of the heterocyclic annulations-rearrangement strategy in the synthesis of a podophyllotoxin precursor. // Synthesis. 1991. P. 275−277.
- Vayas D.M., Skonezny P.M., Jenkins T.A., Doyle T.W. Total synthesis of (±)-epipodophyllotoxin via A (3+2)-cycloaddinion starege. // Tetrahedron Lett. 1986. 27. P. 3099−3102.
- Koneko T., Wong H. Total synthesis of (±)-podophyllotoxin. // Tetrahedron Lett. 1987. 28. P. 517−520.
- Jones D.W., Tompson A.M. Synthesis of podophyllotoxin. // J. Chem. Soc. Chem. Commun. 1989. P. 1370−1371.
- Macdonald D.I., Durst T.J. A highly stereoselective synthesis of (±)-podophyllotoxin. //J. Org. Chem. 1986. 51. P. 4749−4750.
- Van der Eycken J., de Clercq P., Vandewalle M. Total synthesis of podophyllum lignans: an explaratory stud. // Tetrahedron, 1986- 42: 42 854 295.
- Zeigler F.E., Schwarz J.A. Synthetic studies on lignan lactones aryl pithiane route to (±)-podozhizol and (±)-isopodophyllotoxone and approaches to the stegane skeleton. // J. Org. Chem. 1978. 43. P. 985−991.
- Gonzalez A.G., Perez J.P., Trujillo J.M. Synthesis of two arylnaphtalene lignans. // Tetrahedron. 1978. 34. P. 1011−1013.
- Pelter A., Ward R.S., Pritchard M.C., Kay I.T. A short versatile synthesis of aryltetralin lignans including deoxyisopodophyllotoxin and epi-isopodophyllotoxin. //J. Chem. Soc., Perkin Trans. 1. 1988. P. 1603−1615.
- Pelter A., Ward R.S., Jones M.D., Maddocks P. Asymmetric syntheses of lignans of the dibenzylbutyrolactone, dibenzylbutanediol, aryltetraun and dibenzocyclooctadiene series. // Tetrahedron: Asymmetry. 1992. Vol. 3, Issue 2. P. 239−242