Inhibitors of HIV-1 attachment. Part 8: The effect of C7-heteroaryl substitution on the potency, and in vitro and in vivo profiles of indole-based inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 1, 2013, Pages 203-208

  Yeung, Kap Sun ^a   Qiu, Zhilei ^a   Yin, Zhiwei ^a   Trehan, Ashok ^a   Fang, Haiquan ^a   Pearce, Bradley ^a   Yang, Zheng ^a   Zadjura, Lisa ^a   D'Arienzo, Celia J ^a   Riccardi, Keith ^a   Shi, Pei Yong ^a   Spicer, Timothy P ^a   Gong, Yi Fei ^a   Browning, Marc R ^a   Hansel, Steven ^a   Santone, Kenneth ^a   Barker, Jonathan ^b   Coulter, Thomas ^b   Lin, Ping Fang ^a   Meanwell, Nicholas A ^a   Kadow, John F ^a   more..

^a BRISTOL MYERS SQUIBB   (United States)

^b EVOTEC UK LTD   (United Kingdom)

Author keywords

Heterocycles; HIV 1 attachment inhibitors; Indole glyoxamide; Ligand efficiency; Lipophilic ligand efficiency

Indexed keywords

1,2,4 OXADIAZOLE DERIVATIVE; 4 FLUOROINDOLE; 7 HETEROARYL INDOLE DERIVATIVE; AMINOOXADIAZOLE; ANTIVIRUS AGENT; HIV 1 ATTACHMENT INHIBITOR; INDOLE DERIVATIVE; LIGAND; MANNITOL; METHYLOXADIAZOLE; METHYLTRIAZOLE; METOPROLOL; OXADIAZOLE DERIVATIVE; TETRAZOLE DERIVATIVE; TRIAZOLE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CELL ASSAY; CELL STRAIN CACO 2; CONTROLLED STUDY; CYTOTOXICITY; DRUG CLEARANCE; DRUG HALF LIFE; DRUG POTENCY; DRUG STABILITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; IN VIVO STUDY; LIGAND BINDING; LIPOPHILICITY; MEMBRANE PERMEABILITY; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; VIRUS ATTACHMENT;

ADMINISTRATION, ORAL; ANIMALS; ANTI-HIV AGENTS; CACO-2 CELLS; CELL MEMBRANE PERMEABILITY; HALF-LIFE; HIV-1; HUMANS; INDOLES; MICROSOMES, LIVER; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS ATTACHMENT;

HUMAN IMMUNODEFICIENCY VIRUS 1; RATTUS;

EID: 84870994257     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.10.117     Document Type: Article

References (28)

1. E. De Clercq Int. J. Antimicrob. Agents 33 2009 307
2. B. Taiwo, C. Hicks, and J. Eron J. Antimicrob. Chemother. 65 2010 1100
3. Y. Mehellou, and E. De Clercq J. Med. Chem. 53 2010 521
4. R.W. Doms, and D. Trono Genes Dev. 14 2000 2677
5. J.F. Kadow, D.R. Langley, N.A. Meanwell, P. Pracitto, M.A. Walker, and K.-S. Yeung M.D. Wendt, Topics in Medicinal Chemistry: Protein-Protein Interactions Vol. 8 2012 Springer Berlin, Heidelberg 105
6. J.F. Kadow, H.-G.H. Wang, and P.-F. Lin Curr. Opin. Invest. Drugs 7 2006 721
7. P.-F. Lin, W. Blair, T. Wang, T. Spicer, Q. Guo, N. Zhou, Y.-F. Gong, H.-G.H. Wang, R. Rose, G. Yamanaka, B. Robinson, C.-B. Li, R. Fridell, C. Deminie, G. Demers, Z. Zhang, L. Zadjura, N. Meanwell, and R. Colonno Proc. Natl. Acad. Sci. U.S.A. 100 2003 11013
8. H.-T. Ho, Li Fan, B. Nowicka-Sans, B. McAuliffe, C.-B. Li, G. Yamanaka, N. Zhou, H. Fang, I. Dicker, R. Delterio, Y.-F. Gong, T. Wang, Z. Yin, Y. Ueda, J. Matiskella, J. Kadow, P. Clapham, J. Robinson, R. Colonno, and P.-F. Lin J. Virol. 80 2006 4017
9. Part 1: T. Wang, Z. Zhang, O.B. Wallace, M. Deshpande, H. Fang, Z. Yang, L.M. Zadjura, D.L. Tweedie, S. Huang, F. Zhao, S. Ranadive, B.S. Robinson, Y.-F. Gong, K. Ricarrdi, T.P. Spicer, C. Deminie, R. Rose, H.-G.H. Wang, W.S. Blair, P.-Y. Shi, P.-F. Lin, R.J. Colonno, and N.A. Meanwell J. Med. Chem. 46 2003 4236
10. Part 2: N.A. Meanwell, O.B. Wallace, H. Fang, H. Wang, M. Deshpande, T. Wang, Z. Yin, Z. Zhang, B.C. Pearce, J. James, K.-S. Yeung, Z. Qiu, J.J.K. Wright, Z. Yang, L. Zadjura, D.L. Tweedie, S. Yeola, F. Zhao, S. Ranadive, B.A. Robinson, Y.-F. Gong, H.-G.H. Wang, W.S. Blair, P.-Y. Shi, R.J. Colonno, and P.-F. Lin Bioorg. Med. Chem. Lett. 19 2009 1977
11. Part 3: N.A. Meanwell, O.B. Wallace, H. Wang, M. Deshpande, B.C. Pearce, A. Trehan, K.-S. Yeung, Z. Qiu, J.J.K. Wright, B.A. Robinson, Y.-F. Gong, H.-G.H. Wang, W.S. Blair, P.-Y. Shi, and P.-F. Lin Bioorg. Med. Chem. Lett. 19 2009 5136
12. Part 4: T. Wang, J.F. Kadow, Z. Zhang, Z. Yin, Q. Gao, D. Wu, D. Digiugno Parker, Z. Yang, L. Zadjura, B.A. Robinson, Y.-F. Gong, W.S. Blair, P.-Y. Shi, G. Yamanaka, P.-F. Lin, and N.A. Meanwell Bioorg. Med. Chem. Lett. 19 2009 5140
13. Part 5: T. Wang, Z. Yin, Z. Zhang, J.A. Bender, Z. Yang, G. Johnson, Z. Yang, L.M. Zadjura, C.J. D'Arienzo, D.D. Parker, C. Gesenberg, G.A. Yamanaka, Y.-F. Gong, H.-T. Ho, H. Fang, N. Zhou, B.V. McAuliffe, B.J. Eggers, L. Fan, B. Nowicka-Sans, I.B. Dicker, Q. Gao, R.J. Colonno, P.-F. Lin, N.A. Meanwell, and J.F. Kadow J. Med. Chem. 52 2009 7778
14. Part 6: J.F. Kadow, Y. Ueda, N.A. Meanwell, T.P. Connolly, T. Wang, C.-P. Chen, K.-S. Yeung, J. Zhu, J.A. Bender, Z. Yang, D. Parker, P.-F. Lin, R.J. Colonno, M. Mathew, D. Morgan, M. Zheng, C. Chien, and D. Grasela J. Med. Chem. 55 2012 2048
15. Part 7: K.-S. Yeung, Z. Qiu, Q. Xue, H. Fang, Z. Yang, L. Zadjura, C.J. D'Arienzo, B.J. Eggers, K. Riccardi, P.-Y. Shi, Y.-F. Gong, M.R. Browning, Q. Gao, S. Hansel, K. Santone, P.-F. Lin, N.A. Meanwell, and J.F. Kadow Bioorg. Med. Chem. Lett. 22 2012 accepted for publication
16. G.J. Hanna, J. Lalezari, J.A. Hellinger, D.A. Wohl, R. Nettles, A. Persson, M. Krystal, P. Lin, R. Colonno, and D.M. Grasela Antimicrob. Agents Chemother. 55 2011 722
17. Nettles, R.; Schurmann, D.; Zhu, L.; Stonier, M.; Huang, S.-P.; Chien, C.; Krystal, M.; Wind-Rotolo, M.; Bertz, R.; Grasela, D. Abstract 49, 18th Conference Retroviruses Opportunistic Infections, Boston, MA, Feb 27-Mar 2, 2011.
18. R. Nettles, D. Schürmann, L. Zhu, M. Stonier, S.-P. Huang, I. Chang, C. Chien, M. Krystal, M. Wind-Rotolo, N. Ray, G.J. Hanna, R. Bertz, and D.M. Grasela J. Infect. Dis. 206 2012 1002
19. Kadow, J. F.; Ueda, Y.; Connolly, T. P.; Wang, T.; Chen, C. P.; Yeung, K.-S.; Bender, J.; Yang, Z.; Zhu, J.; Matiskella, J.; Regueiro-Ren, A.; Yin, Z.; Zhang, Z.; Farkas, M.; Yang, X.; Wong, H.; Smith, D.; Raghaven, K. S.; Pendri, Y.; Staab, A.; Soundararajan, N.; Meanwell, N.; Zheng, M.; Parker, D. D.; Adams, S.; Ho, H.-T.; Yamanaka, G.; Nowicka-Sans, B.; Eggers, B.; McAuliffe, B.; Fang, H.; Fan, L.; Zhou, N.; Gong, Y.-F.; Colonno, R. J.; Lin, P.-F.; Brown, J.; Grasela, D. M.; Chen, C.; Nettles, R. E. 241th ACS National Meeting & Exposition, Anaheim, CA, United States, Mar 27-31, 2011; MEDI-29.
20. A.L. Hopkins, C.R. Groom, and A. Alex Drug Discovery Today 9 2004 430
21. J.A. Wells, and C.L. McClendon Nature 450 2007 1001
22. P.D. Leeson, and B. Springthorpe Nat. Rev. Drug Disc. 6 2007 881
23. G.M. Keserü, and G.M. Makara Nat. Rev. Drug Disc. 8 2009 203
24. C. Laurence, K.A. Brameld, J. Graton, J.-Y. Le Questel, and E. Renault J. Med. Chem. 52 2009 4073
25. D.K. Dalvie, A.S. Kalgutkar, S.C. Khojasteh-Bakht, R.S. Obach, and J.P. O'Donnell Chem. Res. Toxicol. 15 2002 269
26. J. Boström, A. Hogner, A. Llinàs, E. Wellner, and A.T. Plowright J. Med. Chem. 55 2012 1817
27. K. Goldberg, S. Groombridge, J. Hudson, A.G. Leach, P.A. MacFaul, A. Pickup, R. Poultney, J.S. Scott, P.H. Svensson, and J. Sweeney Med. Chem. Commun. 3 2012 600
28. For experimental procedures and analytical data of the compounds described in this paper, see: Wallace, O. B.; Wang, T.; Yeung, K.-S.; Pearce, B. C.; Meanwell, N. A.; Qiu, Z.; Fang, H.; Xue, Q. M.; Yin Z. U.S. Patent 6,573,262, 2003.