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Volumn 46, Issue 7, 1998, Pages 1135-1139

Syntheses of taxuspine C derivatives as functional inhibitors of P- glycoprotein, an ATP-associated cell-membrane transporter

Author keywords

Functional inhibitor; P glycoprotein; Photochemical transannular reaction; Taxinine; Taxuspine C

Indexed keywords

TAXUSPINE C; UNCLASSIFIED DRUG; VINCRISTINE;

EID: 0031851582     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1135     Document Type: Article
Times cited : (20)

References (42)
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    • c) from Taxus wallichiana: Zhang J.-Z., Fang Q.-C., Liang X.-T., He C.-H., Chin. Chem. Lett., 5, 497-500 (1994); Zhang J.-Z., Fang Q.-C., Liang X.-T., He C.-H., Kong M., He W.-Y., Jin X.-L., Phytochemistry, 40, 881-884 (1995); Chattopadhyay S. K., Kulshrestha M. K., Saha G. C., Sharma R. P., Kumar S., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 35B, 508-509 (1996); Banerjee S., Upadhyay N., Kukreja A. K., Ahuja P. S., Kumar S., Saha G. C., Sharma R. P., Chattopadhyay S. K., Planta Med., 62, 333-335 (1996);
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    • d) from Taxus baccata: Guo Y., Diallo B., Jaziri M., Vanhaelen-Fastre R., Vanhealen M., Ottinger R., J. Nat. Prod., 58, 1906-1912 (1995); Breeden S. W., Jordan A. M., Lawrence N. J., McGown A. T., Planta Med., 62, 94-95 (1996); Rojatkar S. R., Sinha B., Sawaikar D. D., Sonawane K. B., Pawar S. S., Panse G. T., Ravindranathan T., Nagasampagi B. A., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 36B, 114-117 (1997).
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    • From Taxus wallichiana: Ref. 5c
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    • a) From Taxus mairei: Liang J., Min Z., Niwa M., Huaxue Xuebao, 46, 1053-1054 (1988); Yang S.-J., Fang J.-M., Cheng Y.-S., Phytochemistry, 43, 839-842 (1996); Shen Y.-C., Tai H.-R., Hsieh P.-W., Chen C.-Y., Chin. Pharm. J. (Taipei), 48, 207-217 (1996);
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    • a) From Taxus mairei: Liang J., Min Z., Niwa M., Huaxue Xuebao, 46, 1053-1054 (1988); Yang S.-J., Fang J.-M., Cheng Y.-S., Phytochemistry, 43, 839-842 (1996); Shen Y.-C., Tai H.-R., Hsieh P.-W., Chen C.-Y., Chin. Pharm. J. (Taipei), 48, 207-217 (1996);
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    • from Austrotaxus spicata: Ref. 5a
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    • from Taxus cuspidata: Ref. 5b
    • d) from Taxus cuspidata: Ref. 5b;
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    • e) from Taxus wallichiana: Ref. 5c; Chattopadhyay S. K., Saha G. C., Kulshrestha M., Sharma R. P., Kumar S., Indian J. Chem., Sect. B: Org. Chem. Ind. Med. Chem., 35B, 175-177 (1996); Singh B., Gujral R. K., Sood R. P., Duddeck H., Planta Med., 63, 191-192 (1997);
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    • from Taxus baccata: Ref. 5d
    • f) from Taxus baccata: Ref. 5d; Rojatkar S. R., Sinha B., Sawaikar D. D., Sonawane K. B., Pause G. T., Ravindranathan T., Nagasampagi B. A., Indian J. Chem., Sect. B. Org. Chem. Ind. Med. Chem., 35B, 752-753 (1996).
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    • note
    • 5b)
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    • Photolysis of Taxol®, possessing a fused oxetane ring in the molecule, has been documented to give the corresponding pentacyclic derivative constructed by photochemical transannulation between the C-3 and C-11 positions in a similar manner to that of taxinine (2a) leading to taxuspine C (3a). The mechanism for this reaction, however, has been proposed to involve a triplet excitation of the C-9 carbonyl group and subsequent oxa-di-π-methane rearrangement, in which the initial steps differ from that of the transannular reaction of the taxoid 2a. cf. Chen S.-H., Farina V., Huang S., Gao Q., Golik J., Doyle T. W., Tetrahedron, 50, 8633-8650 (1994).
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    • Chen, S.-H.1    Farina, V.2    Huang, S.3    Gao, Q.4    Golik, J.5    Doyle, T.W.6
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  • 39
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    • 3H]vincristine and 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid with or without the taxoids and verapamil, according to the known method (cf., Tsuruo T., Iida H., Tsukagoshi S., Sakurai Y., Cancer Res., 41, 1967-1972 (1981)). Radioactivity of the supernatant fluid obtained after centrifugation of the mixture was counted in a liquid scintillation system for the biological evaluation.
    • (1981) Cancer Res. , vol.41 , pp. 1967-1972
    • Tsuruo, T.1    Iida, H.2    Tsukagoshi, S.3    Sakurai, Y.4


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