Inhibitors of HIV-1 attachment. Part 9: An assessment of oral prodrug approaches to improve the plasma exposure of a tetrazole-containing derivative

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 1, 2013, Pages 209-212

  Yeung, Kap Sun ^a   Qiu, Zhilei ^a   Yang, Zheng ^a   Zadjura, Lisa ^a   D'Arienzo, Celia J ^a   Browning, Marc R ^a   Hansel, Steven ^a   Huang, Xiaohua Stella ^a   Eggers, Betsy J ^a   Riccardi, Keith ^a   Lin, Ping Fang ^a   Meanwell, Nicholas A ^a   Kadow, John F ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Antivirals; HIV 1 attachment inhibitors; Indole glyoxamide; Produrgs; Tetrazole

Indexed keywords

7 (2H TETRAZOL 5 YL) 1H INDOLE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; N ACETOXY METHYL DERIVATIVE; PRODRUG; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIVIRAL THERAPY; ARTICLE; CYTOTOXICITY; DRUG ABSORPTION; DRUG BLOOD LEVEL; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; LIVER MICROSOME; NONHUMAN; RAT;

ADMINISTRATION, ORAL; ANIMALS; ANTI-HIV AGENTS; HALF-LIFE; HIV-1; HUMANS; PRODRUGS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAZOLES; VIRUS ATTACHMENT;

HUMAN IMMUNODEFICIENCY VIRUS 1; RATTUS;

EID: 84870994672     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.10.125     Document Type: Article

References (30)

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, H.-G.H. Wang, and P.-F. Lin Curr. Opin. Invest. Drugs 7 2006 721
6. 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
7. H.-T. Ho, L. 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
8. 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
9. 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
10. 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
11. 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
12. 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
13. 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.M. Grasela J. Med. Chem. 55 2012 2048
14. 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. 2012 22 accepted for publication
15. Part 8: K.-S. Yeung, Z. Qiu, Z. Yin, A. Trehan, H. Fang, B. Pearce, Z. Yang, L. Zadjura, C.J. D'Arienzo, K. Riccardi, P.-Y. Shi, T.P. Spicer, Y.-F. Gong, M.R. Browning, S. Hansel, K. Santone, J. Barker, T. Coulter, P.-F. Lin, N.A. Meanwell, and J.F. Kadow Bioorg. Med. Chem. Lett. 2012 22 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. 241st ACS National Meeting & Exposition, Anaheim, CA, United States. Mar 27-31, 2011, MEDI-29.
20. R.J. Herr Bioorg. Med. Chem. 10 2002 3379
21. K. Beaumont, R. Webster, I. Gardner, and K. Dack Curr. Drug Metab. 4 2003 461
22. A search of SciFinder using 'tetrazole and prodrug' as the query only provided the articles cited below as Refs. 15,16,17a.b,18,19. The concpet has not been captured in reviews on prodrugs e.g. J. Rautio, H. Kumpulainen, T. Heimbach, R. Oliyai, D. Oh, T. Järvinen, and J. Savolainen Nat. Rev. Drug Discovery 7 2008 255
23. J. Alexander, M.L. Renyer, and G.S. Rork Pharm. Sci. 86 1994 893
24. K. Kubo, Y. Kohara, Y. Yoshimura, Y. Inada, Y. Shibouta, Y. Furukawa, T. Kato, K. Nishikawa, and T. Naka J. Med. Chem. 36 1993 2343 A methyltetrazole derivative reported in this paper did not provide an improvement in either oral bioavailability or the effect on decreasing the AII-induced pressor response in rats compared to the parent tetrazole
25. D.E. Ryono, J. Lloyd, M.A. Poss, J.E. Bird, J. Buote, S. Chong, T. Dejneka, K.E.J. Dickinson, Z. Gu, P. Mathers, S. Moreland, R.A. Morrison, E.W. Petrillo, J.R. Powell, T. Schaeffer, E.R. Spitzmiller, and R.E. White Bioorg. Med. Chem. Lett. 4 1994 201
26. M.T. Obermeier, S. Chong, S.A. Dando, A.M. Marino, D.E. Ryono, A. Starrett-Arroyo, G.C. DiDonato, B.M. Warrack, R.E. White, and R.A. Morrison J. Pharm. Sci. 85 1996 828
27. The cellular activity of a tetrazole-containing protein kinase C inhibitor in human neutrophils was achieved by its pivaloyloxymethyl analog, which was designed as a prodrug to improve cell penetration. However, the corresponding methyltetrazole analog was inactive under the same assay conditions: J.M. Heerding, J.W. Lampe, J.W. Darges, and M.L. Stamper Bioorg. Med. Chem. Lett. 5 1995 1839
28. N-cyanoethyl-protected tetrazole derivatives were speculated to release the parent tetrazoles by a base-catalyzed β-elimination in an assay against a resistant strain of malaria: C. Biot, H. Bauer, R.H. Schirmer, and E. Davioud-Charvet J. Med. Chem. 47 2004 5972
29. S.D. Kuduk, R.K. Chang, R.M. DiPardo, C.N. Di Marco, K.L. Murphy, R.W. Ransom, D.R. Reiss, C. Tang, T. Prueksaritanont, D.J. Pettibone, and M.G. Bock Bioorg. Med. Chem. Lett. 18 2008 5107
30. K.M. Huttunen, N. Mähönen, H. Raunio, and J. Rautio Curr. Med. Chem. 15 2008 2346