Synthesis, conformational analysis, and evaluation of the multidrug resistance-reversing activity of the triamide and proline analogs of hapalosin

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6773-6783

  Dinh, Tam Q ^a   Du, Xiaohui ^a   Smith, Charles D ^b   Armstrong, Robert W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b FOX CHASE CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; DACTINOMYCIN; DAUNORUBICIN; GLYCOPROTEIN P; HAPALOSIN; HAPALOSIN DERIVATIVE; PROLINE; TRITIUM; UNCLASSIFIED DRUG; VERAPAMIL; VINBLASTINE;

ARTICLE; CANCER CHEMOTHERAPY; CELL STRAIN MCF 7; DRUG ACCUMULATION; DRUG CONFORMATION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MULTIDRUG RESISTANCE; STRUCTURE ACTIVITY RELATION;

EID: 0030761540     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9708396     Document Type: Article

References (44)

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10. For the synthesis of hapalosin, see: (a) Dinh, T. Q.; Armstrong, R. W. J. Org. Chem. 1995, 60, 8118. (b) Ghosh, A. K.; Liu, W.; Xu, Y.; Chen, Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 74. (c) Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467. (d) Dinh, T. Q.; Du, X.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6606. (e) Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557. (f) Okuno, T.; Ohmori, K.; Nishiyama, S.; Yamamura, S.; Nakamura, K.; Houk, K. N.; Okamoto, K. Tetrahedron 1996, 52, 14723. Dinh, T. Q.; Smith, C. D.; Armstrong, R. W. J. Org. Chem. 1997, 62, 790.
11. For the synthesis of hapalosin, see: (a) Dinh, T. Q.; Armstrong, R. W. J. Org. Chem. 1995, 60, 8118. (b) Ghosh, A. K.; Liu, W.; Xu, Y.; Chen, Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 74. (c) Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467. (d) Dinh, T. Q.; Du, X.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6606. (e) Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557. (f) Okuno, T.; Ohmori, K.; Nishiyama, S.; Yamamura, S.; Nakamura, K.; Houk, K. N.; Okamoto, K. Tetrahedron 1996, 52, 14723. Dinh, T. Q.; Smith, C. D.; Armstrong, R. W. J. Org. Chem. 1997, 62, 790.
12. For the synthesis of hapalosin, see: (a) Dinh, T. Q.; Armstrong, R. W. J. Org. Chem. 1995, 60, 8118. (b) Ghosh, A. K.; Liu, W.; Xu, Y.; Chen, Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 74. (c) Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467. (d) Dinh, T. Q.; Du, X.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6606. (e) Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557. (f) Okuno, T.; Ohmori, K.; Nishiyama, S.; Yamamura, S.; Nakamura, K.; Houk, K. N.; Okamoto, K. Tetrahedron 1996, 52, 14723. Dinh, T. Q.; Smith, C. D.; Armstrong, R. W. J. Org. Chem. 1997, 62, 790.
13. For the synthesis of hapalosin, see: (a) Dinh, T. Q.; Armstrong, R. W. J. Org. Chem. 1995, 60, 8118. (b) Ghosh, A. K.; Liu, W.; Xu, Y.; Chen, Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 74. (c) Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467. (d) Dinh, T. Q.; Du, X.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6606. (e) Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557. (f) Okuno, T.; Ohmori, K.; Nishiyama, S.; Yamamura, S.; Nakamura, K.; Houk, K. N.; Okamoto, K. Tetrahedron 1996, 52, 14723. Dinh, T. Q.; Smith, C. D.; Armstrong, R. W. J. Org. Chem. 1997, 62, 790.
14. For the synthesis of hapalosin, see: (a) Dinh, T. Q.; Armstrong, R. W. J. Org. Chem. 1995, 60, 8118. (b) Ghosh, A. K.; Liu, W.; Xu, Y.; Chen, Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 74. (c) Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467. (d) Dinh, T. Q.; Du, X.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6606. (e) Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557. (f) Okuno, T.; Ohmori, K.; Nishiyama, S.; Yamamura, S.; Nakamura, K.; Houk, K. N.; Okamoto, K. Tetrahedron 1996, 52, 14723. Dinh, T. Q.; Smith, C. D.; Armstrong, R. W. J. Org. Chem. 1997, 62, 790.
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