Solid-phase total synthesis of cherimolacyclopeptide e and discovery of more potent analogues by alanine screening

Journal of Natural Products

Volumn 75, Issue 11, 2012, Pages 1882-1887

  Shaheen, Farzana ^a   Rizvi, Tania S ^a   Musharraf, Syed G ^a   Ganesan, A ^b   Xiao, Kai ^c   Townsend, Jared B ^c   Lam, Kit S ^c   Choudhary, M Iqbal ^a,d  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; CHERIMOLACYCLOPEPTIDE E; CYTOTOXIC AGENT; GLYCINE; HEXAPEPTIDE; SULFONAMIDE; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

ANNONA CHERIMOLA; ARTICLE; BIOLOGICAL ACTIVITY; BREAST CANCER; CANCER CELL CULTURE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CYTOTOXICITY; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL LINE; NASOPHARYNX CARCINOMA; SCREENING; SOLID PHASE SYNTHESIS;

EID: 84870231166     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np300266e     Document Type: Article

References (25)

1. Calzadaa, F.; Yépez-Muliaa, L.; Aguilar, A. J. Ethnopharmacol. 2006, 108, 367-370
2. Castillo-Juáreza, I.; Gonzáleza, V.; Jaime-Aguilara, H.; Martíneza, G.; Linares, E.; Byeb, R.; Romero, I. J. Ethnopharmacol. 2009, 122, 402-405
3. Wělě, A.; Zhang, Y.; Caux, C.; Brouard, J.-P.; Dubost, L.; Guette, C.; Pousset, J.-L.; Bodo, B. J. Chem. Soc., Perkin Trans. 1 2002, 2712-2718
4. Wélé, A.; Ndoye, I.; Zhang, Y.; Brouard, J. P.; Pousset, J. L.; Bodo, B. Phytochemistry 2005, 66, 1154-1157
5. Wélé, A.; Zhang, Y.; Ndoye, I.; Brouard, J. P.; Pousset, J. L.; Bodo, B. J. Nat. Prod. 2004, 67, 1577-1579
6. Wélé, A.; Zhang, Y.; Ndoye, I.; Brouard, J. P.; Pousset, J. L.; Bodo, B. Phytochemistry 2005, 66, 693-696
7. Wélé, A.; Zhang, Y.; Brouard, J-. P.; Pousset, J. L.; Bodo, B. Phytochemistry 2005, 66, 2376-2380
8. Wélé, A.; Zhang, Y.; Dubost, L.; Pousset, J. L.; Bodo, B. Nigerian J. Nat. Prod. Med. 2005, 9, 68-72
9. Dahiya, R. J. Chil. Chem. Soc. 2007, 52, 1224-1229
10. Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1996, 118, 3055-3056
11. Yang, L.; Morriello, G. Tetrahedron Lett. 1999, 40, 8197-8200
12. Heidler, P.; Link, A. Bioorg. Med. Chem. 2005, 13, 585-599
13. Ganesan, A. In Linker Strategies in Solid-phase Organic Synthesis; Scott, P., Ed.; Wiley: New York, 2009; pp 135-149.
14. Lebreton, S.; Pateek, M. In Linker Strategies in Solid-phase Organic Synthesis; Scott, P., Ed.; Wiley: New York, 2009; pp 195-219.
15. White, J. C.; Yudin, A. K. Nat. Chem. 2011, 3, 509-524
16. Bourel-Bonnet, L.; Rao, K. V.; Hamann, M. T.; Ganesan, A. J. Med. Chem. 2005, 48, 1330-1335
17. Ali, L.; Musharraf, S. G.; Shaheen, F. J. Nat. Prod. 2008, 71, 1059-1062
18. Siemion, I. Z.; Wieland, T.; Pook, K. H. Angew. Chem., Int., Ed. Engl. 1975, 14, 702-703
19. Auvin-Guette, C.; Baraguey, C.; Blond, A.; Xavier, H. S.; Pousset, J. L.; Bodo, B. Tetrahedron 1999, 55, 11495-11510
20. Tabudravu, J.; Morris, L. A.; Kettenes-van den Bosch, J. J.; Jaspars, M. Tetrahedron Lett. 2001, 42, 9273-9276
21. Morrison, K. L.; Weiss, G. A. Curr. Opin. Chem. Biol. 2001, 5, 302-307
22. Napolitano, A.; Rodriquez, M.; Bruno, I.; Marzocco, S.; Autore, G.; Riccio, R.; Gomez-Paloma, L. Tetrahedron 2003, 59, 10203-10211
23. Napolitano, A.; Bruno, I.; Riccio, R.; Gomez-Paloma, L. Tetrahedron 2005, 61, 6808-6815
24. Pettit, G. R.; Toki, B. E.; Xu, J.-P.; Brune, D. C. J. Nat. Prod. 2000, 63, 22-28
25. Fairweather, K. A.; Sayyadi, N.; Roussakis, C.; Jolliffe, K. A. Tetrahedron 2010, 66, 935-939