Analogs incorporating trans-4-hydroxy-L-proline that reverse multidrug resistance better than hapalosin

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 790-791

  Dinh, Tam Q ^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

CYCLOPEPTIDE; DACTINOMYCIN; DAUNORUBICIN; DEPSIPEPTIDE; HAPALOSIN; HAPALOSIN DERIVATIVE; UNCLASSIFIED DRUG; VINBLASTINE;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MULTIDRUG RESISTANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TUMOR CELL;

EID: 0030951560     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962180u     Document Type: Article

References (17)

1. For reviews, see: (a) Simon, S. M.; Schindler, M. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3497. (b) Gottesman, M. M.; Pastan, I. Annual Rev. Biochem. 1993, 62, 385.
2. For reviews, see: (a) Simon, S. M.; Schindler, M. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3497. (b) Gottesman, M. M.; Pastan, I. Annual Rev. Biochem. 1993, 62, 385.
3. Stratmann, K.; Burgoyne, D. L.; Moore, R. E.; Patterson, G. M. L.; Smith, C. D. J. Org. Chem. 1994, 59, 7219.
4. 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. Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467. Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557.
5. 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. Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467. Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557.
6. 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. Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467. Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557.
7. 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. Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467. Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557.
8. Dinh, T. Q.; Du, X.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6606.
9. Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432.
10. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139.
11. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021.
12. Evans, D. A.; Miller, S. J.; Ennis, M. D. J. Org. Chem. 1993, 58, 471.
13. Iversen, T.; Bundle, D. R. J. Chem. Soc., Chem. Commun. 1981, 1240.
14. Hughes, D. L. Org. React. 1992, 42, 335.
15. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
16. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
17. 3 are being conducted.