Corrigendum to "Inhibitors of HIV-1 attachment. Part 4: A study of the effect of piperazine substitution patterns on antiviral potency in the context of indole-based derivatives" [Bioorg. Med. Chem. Lett. 19 (2009) 5140] (DOI:10.1016/j.bmcl.2009.07.076);Inhibitors of HIV-1 attachment. Part 4: A study of the effect of piperazine substitution patterns on antiviral potency in the context of indole-based derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 17, 2009, Pages 5140-5145

  Wang, Tao ^a   Kadow, John F ^a   Zhang, Zhongxing ^a   Yin, Zhiwei ^a   Gao, Qi ^a   Wu, Dedong ^a   Parker, Dawn DiGiugno ^a   Yang, Zheng ^a   Zadjura, Lisa ^a   Robinson, Brett A ^a   Gong, Yi Fei ^a   Blair, Wade S ^a   Shi, Pei Yong ^a   Yamanaka, Gregory ^a   Lin, Pin Fang ^a   Meanwell, Nicholas A ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

gp120; HIV; HIV attachment; Piperazine

Indexed keywords

4 FLUORO 1 (4 BENZOYLPIPERAZIN 1 YL) 2 (1H INDOL 3 YL)ETHANE 1,2 DIONE DERIVATIVE; 4 METHOXY 1 (4 BENZOYLPIPERAZIN 1 YL) 2 (1H INDOL 3 YL)ETHANE 1,2 DIONE DERIVATIVE; ANTIVIRUS AGENT; BENZAMIDE; CD4 ANTIGEN; CELL RECEPTOR; FUNCTIONAL GROUP; GLYCOPROTEIN GP 120; INDOL GLYOXAMIDE; INDOLE DERIVATIVE; PIPERAZINE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BINDING SITE; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; HOST CELL; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; VIRUS ATTACHMENT; VIRUS INHIBITION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

ANTI-HIV AGENTS; CELL LINE; HIV ENVELOPE PROTEIN GP120; HIV-1; HUMANS; INDOLES; PIPERAZINES; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS ATTACHMENT;

EID: 68349141359     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.01.022     Document Type: Erratum

References (37)

1. Pomerantz R.J., and Horn D.L. Nat. Med. 9 (2003) 867
2. Merson M.H. New Eng. J. Med. 354 (2006) 2414
3. De Clercq E. Int. J. Antimicrob. Agents 33 (2009) 307
4. Blair, W. S.; Spicer, T. P. World Patent Application, WO-2001/96610, December 20th, 2001.
5. Blair, W. S.; Deshpande, M.; Fang, H.; Lin, P-F.; Spicer, T. P.; Wallace, O. B.; Wang, H.; Wang, T.; Zhang, Z.; Yeung, K.-S. World Patent Application, WO2000/76521, December 21st, 2000.
6. Lin P.-F., Blair W.S., Wang T., Spicer T.P., Guo Q., Zhou N., Gong Y.-F., Wang H.-W.H., Rose R., Yamanaka G., Robinson B., Li C.-B., Fridell R., Deminie C., Demers G., Yang Z., Zadjura L., Meanwell N.A., and Colonno R.J. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 11013
7. Wang H.-W.H., Williams R.E., and Lin P.-F. Curr. Pharm. Des. 10 (2004) 1785
8. Wang T., Zhang Z., Wallace O.B., Deshpande M., Fang H., Yang Z., Zadjura L.M., Tweedie D.L., Huang S., Zhao F., Ranadive S., Robinson B., Gong Y.-F., Riccardi K., Spicer T.P., Deminie C., Rose R., Wang H.-W.H., Blair W.S., Shi P.-Y., Lin P.-F., Colonno R.J., and Meanwell N.A. J. Med. Chem. 46 (2003) 4236
9. Guo Q., Ho H.-T., Dicker I., Fan L., Zhou N., Friborg J., Wang T., McAuliffe B.V., Wang H.-W.H., Rose R.E., Fang H., Scarnati H.T., Langley D.R., Meanwell N.A., Abraham R., Colonno R.J., and Lin P.-F. J. Virol. 77 (2003) 10528
10. Ho H.-T., Nowicka-Sans B., McAuliffe B., Li C.-B., Yamanaka G., Zhou N., Fang H., Dicker I., Dalterio R., Gong Y.-F., Wang T., Yin Z., Ueda Y., Matiskella J., Kadow J.F., Clapham P., Robinson J., Colonno R., and Lin P.-F. J. Virol. 80 (2006) 4017
11. Si Z., Madani N., Cox J.M., Chruma J.J., Klein J.C., Schön A., Phan N., Wang L., Biorn A.C., Cocklin S., Chaiken I., Freire E., Smith III A.B., and Sodroski J.G. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5036
12. Madani N., Perdigoto A.L., Srinivasan K., Cox J.M., Chruma J.J., LaLonde J., Head M., Smith III A.B., and Sodroski J.G. J. Virol. 78 (2004) 3742
13. Meanwell N.A., Wallace O.B., Fang H., Wang H., Deshpande M., Wang T., Yin Z., Zhang Z., Pearce B.C., James J., Yeung K.-S., Qiu Z., Wright J.J.K., Yang Z., Zadjura L., Tweedie D.L., Yeola S., Zhao F., Ranadive S., Robinson B.A., Gong Y.-F., Wang H.-G.H., Blair W.S., Shi P.-Y., Colonno R.J., and Lin P.-F. Bioorg. Med. Chem. Lett. 19 (2009) 1977
14. Meanwell N.A., Wallace O.B., Wang H., Deshpande M., Pearce B.C., Trehan A., Yeung K.-S., Qiu Z., Wright J.J.K., Robinson B.A., Gong Y.-F., Wang H.-W.G., Blair W.S., Shi P.-Y., and Lin P.-F. Bioorg. Med. Chem. Lett. 19 (2009) 5136
15. Bender J.A., Meanwell N.A., and Wang T. Tetrahedron 58 (2002) 3111
16. Wang T., Zhang Z., and Meanwell N.A. J. Org. Chem. 64 (1999) 7661
17. Zhang Z., Yin Z., Kadow J.F., Meanwell N.A., and Wang T. Org. Lett. 5 (2003) 3399
18. Rossen K., Weissman S.A., Sager J., Reamer R.A., Askin D., Volante R.P., and Reider P.J. Tetrahedron Lett. 36 (1995) 6419
19. Fukushi H., Mabuchi H., Terashita Z.-I., Nishikawa K., and Sugihara H. Chem. Pharm. Bull. 42 (1994) 551
20. Wang T., Zhang Z., and Meanwell N.A. J. Org. Chem. 65 (2000) 4740
21. 3. Full crystallographic data have been deposited to the Cambridge Crystallographic Data Center (reference numbers: CCDC 738923 (6u) and CCDC 738924 (9u)). Copies of the data can be obtained free of charge via the internet at http://www.ccdc.cam.ac.uk.
22. Nasipuri, D. Stereochemistry of Organic Compounds: Principles and Applications. Wiley Eastern Limited: New Delhi, India, 1991.
23. Brameld K.A., Kuhn B., Reuter D.C., and Stahl M. J. Chem. Inf. Model. 48 (2008) 1
24. Bruno I.J., Cole J.C., Edgington P.R., Kessler M., Macrae C.F., McCabe P., Pearson J., and Taylor R. Acta Crystallogr., Sect. B 58 (2002) 389
25. Andrews P.R., Munro S.L.A., Sadek M., and Wong M.G. J. Chem. Soc., Perkin Trans. 2 (1988) 711
26. Johnson F., and Malhotra S.K. J. Am. Chem. Soc. 87 (1965) 5492
27. Johnson F. Chem. Rev. 68 (1968) 375
28. Chevallier F., Beaudet I., Grognec E.L., Toupet L., and Quintard J.-P. Tetrahedron Lett. 45 (2004) 761
29. Lepore U., Gains P., Bombieri G., Gilli G., and Montaudo G. Cryst. Struc. Commun. 6 (1977) 7
30. Okamoto K., Sekido K., Itoh J., Noguchi T., and Hirokawa S. Bull. Chem. Soc. Jpn. 52 (1979) 1896
31. Sakurai T., Nakamaru M., Tsuboyama S., and Tsuboyama K. Acta Crystallogr., Sect. B 33 (1977) 3568
32. Hiramatsu H., Sakurai T., Tsuboyama S., and Tsuboyama K. Acta Crystallogr., Sect. B 34 (1978) 3469
33. Lu R.-J., Tucker J.A., Zinevitch T., Kirichenko O., Konoplev V., Kuznetsova S., Sviridov S., Pickens J., Tandel T., Brahmachary E., Yang Y., Wang J., Freel S., Fisher S., Sullivan A., Zhou J., Stanfield-Oakley S., Greenberg M., Bolognesi D., Bray B., Koszalka B., Jeffs P., Khasanov A., Ma Y.-A., Jeffries C., Liu C., Proskurina T., Zhu T., Chucholowski A., Li R., and Sexton C. J. Med. Chem. 50 (2007) 6535
34. Kong R., Tan J.J., Ma X.H., Chen W.Z., and Wang C.X. Biochim. Biophys. Acta 1764 (2006) 766
35. Teixeira, C.; Serradji, N.; Maurel, F.; Barbault, F. Eur. J. Med. Chem., in press.. doi:10.1016/j.ejmech.2009.03.028.
36. Hanna, G.; Lalezari, J.; Hellinger, J.; Wohl, D.; Masterson, T.; Fiske, W.; Kadow, J. F.; Lin, P-F.; Giordano, M.; Colonno, R. J.; Grasela D. Abstract 141, 11th Conf. Retroviruses Opportunistic Infections, San Francisco, Feb 8-11, 2004.
37. Veazey R.S., Klasse P.J., Schadr S.M., Hu Q., Ketas T.J., Lu M., Marx P.A., Dufour J., Colonno R.J., Shattock R.J., Springer M.S., and Moore J.P. Nature 438 (2005) 99