SCOPUS 정보 검색 플랫폼

Volumn 1, Issue 1, 2010, Pages 79-83

Synthesis and biological activity of new pyridone diaryl ether non-nucleoside inhibitors of HIV-1 reverse transcriptase

(20) Kennedy Smith, Joshua J a Arora, Nidhi a Billedeau, J Roland a Fretland, Jennifer a Hang, Julie Q a Heilek, Gabrielle M a Harris, Seth F a Hirschfeld, Donald a Javanbakht, Hassan a Li, Yu a Liang, Weiling a Roetz, Ralf a Smith, Mark a Su, Guoping a Suh, Judy M a Villaseñor, Armando G a Wu, Jeffrey a Yasuda, Dennis a Klumpp, Klaus a Sweeney, Zachary K a

a Roche Palo Alto ^* (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; PYRIDONE DIARYL ETHER NONNUCLEOSIDE INHIBITOR; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ANTIVIRAL RESISTANCE; ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS; NONHUMAN; PRIORITY JOURNAL; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 79952524156 PISSN: 20402503 EISSN: 20402511 Source Type: Journal
DOI: 10.1039/c0md00009d Document Type: Article

Times cited : (28)

References (25)

1
- 36749088862
- C. Flexner Nat. Rev. Drug Discovery 2007 6 959
- (2007) Nat. Rev. Drug Discovery , vol.6 , pp. 959
- Flexner, C.¹

2
- 36048981531
- F. Maggiolo M. Airoldi H. D. Kleinloog A. Callegaro V. Ravasio C. Arici E. Bombana F. Suter HIV Clin. Trials 2007 8 282
- (2007) HIV Clin. Trials , vol.8 , pp. 282
- Maggiolo, F.¹ Airoldi, M.² Kleinloog, H.D.³ Callegaro, A.⁴ Ravasio, V.⁵ Arici, C.⁶ Bombana, E.⁷ Suter, F.⁸

3
- 34247877844
- S. M. Vrouenraets F. W. Wit J. van Tongeren J. M. Lange Expert Opin. Pharmacother. 2007 8 851
- (2007) Expert Opin. Pharmacother. , vol.8 , pp. 851
- Vrouenraets, S.M.¹ Wit, F.W.² Van Tongeren, J.³ Lange, J.M.⁴

4
- 48349089312
- D. Ripamonti F. Maggiolo Curr. Opin. Invest. Drugs 2008 9 899
- (2008) Curr. Opin. Invest. Drugs , vol.9 , pp. 899
- Ripamonti, D.¹ Maggiolo, F.²

5
- 46749104685
- Z. K. Sweeney K. Klumpp Curr. Opin. Drug Discovery Develop. 2008 11 458
- (2008) Curr. Opin. Drug Discovery Develop. , vol.11 , pp. 458
- Sweeney, Z.K.¹ Klumpp, K.²

6
- 57349096037
- Z. K. Sweeney S. F. Harris N. Arora H. Javanbakht Y. Li J. Fretland J. P. Davidson J. R. Billedeau S. K. Gleason D. Hirschfeld J. J. Kennedy-Smith T. Mirzadegan R. Roetz M. Smith S. Sperry J. Suh J. Wu S. Tsing A. G. Villasenor A. Paul G. Su G. Heilek J. Q. Hang A. S. Zhou J. A. Jernelius F.-J. Zhang K. Klumpp J. Med. Chem. 2008 51 7449
- (2008) J. Med. Chem. , vol.51 , pp. 7449
- Sweeney, Z.K.¹ Harris, S.F.² Arora, N.³ Javanbakht, H.⁴ Li, Y.⁵ Fretland, J.⁶ Davidson, J.P.⁷ Billedeau, J.R.⁸ Gleason, S.K.⁹ Hirschfeld, D.¹⁰ Kennedy-Smith, J.J.¹¹ Mirzadegan, T.¹² Roetz, R.¹³ Smith, M.¹⁴ Sperry, S.¹⁵ Suh, J.¹⁶ Wu, J.¹⁷ Tsing, S.¹⁸ Villasenor, A.G.¹⁹ Paul, A.²⁰ more..

7
- 47749136565
- Z. K. Sweeney S. Acharya A. Briggs J. P. Dunn T. R. Elworthy J. Fretland A. M. Giannetti G. Heilek Y. Li A. C. Kaiser M. Martin Y. D. Saito M. Smith J. M. Suh S. Swallow J. Wu J. Q. Hang A. S. Zhou K. Klumpp Bioorg. Med. Chem. Lett. 2008 18 4348
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 4348
- Sweeney, Z.K.¹ Acharya, S.² Briggs, A.³ Dunn, J.P.⁴ Elworthy, T.R.⁵ Fretland, J.⁶ Giannetti, A.M.⁷ Heilek, G.⁸ Li, Y.⁹ Kaiser, A.C.¹⁰ Martin, M.¹¹ Saito, Y.D.¹² Smith, M.¹³ Suh, J.M.¹⁴ Swallow, S.¹⁵ Wu, J.¹⁶ Hang, J.Q.¹⁷ Zhou, A.S.¹⁸ Klumpp, K.¹⁹

8
- 47749109429
- Z. K. Sweeney J. Dunn Y. Li G. Heilek P. Dunten T. R. Elworthy X. Han S. F. Harris D. R. Hirschfeld J. H. Hogg W. Huber A. C. Kaiser D. J. Kertesz W. Kim T. Mirzadegan M. G. Roepel Y. D. Saito T. M. P. C. Silva S. Swallow J. L. Tracy A. Villasenor H. Vora A. S. Zhou K. Klumpp Bioorg. Med. Chem. Lett. 2008 18 4352
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 4352
- Sweeney, Z.K.¹ Dunn, J.² Li, Y.³ Heilek, G.⁴ Dunten, P.⁵ Elworthy, T.R.⁶ Han, X.⁷ Harris, S.F.⁸ Hirschfeld, D.R.⁹ Hogg, J.H.¹⁰ Huber, W.¹¹ Kaiser, A.C.¹² Kertesz, D.J.¹³ Kim, W.¹⁴ Mirzadegan, T.¹⁵ Roepel, M.G.¹⁶ Saito, Y.D.¹⁷ Silva, T.M.P.C.¹⁸ Swallow, S.¹⁹ Tracy, J.L.²⁰ more..

9
- 58549120191
- Ab initio calculations on a model system confirmed that fluorination increased the electropositive character of the relevant aromatic hydrogen atom
- Z. K. Sweeney J. J. Kennedy-Smith J. Wu N. Arora J. R. Billedeau J. P. Davidson J. Fretland J. Q. Hang G. M. Heilek S. Harris D. Hirschfeld P. Inbar H. Javanbakht J. A. Jernelius Q. Jin Y. Li W. Liang R. Roetz K. Sarma M. Smith D. Stefanidis G. Su J. M. Suh A. G. Villasenor M. Welch F.-J. Zhang K. Klumpp ChemMedChem 2009 4 88
- (2009) ChemMedChem , vol.4 , pp. 88
- Sweeney, Z.K.¹ Kennedy-Smith, J.J.² Wu, J.³ Arora, N.⁴ Billedeau, J.R.⁵ Davidson, J.P.⁶ Fretland, J.⁷ Hang, J.Q.⁸ Heilek, G.M.⁹ Harris, S.¹⁰ Hirschfeld, D.¹¹ Inbar, P.¹² Javanbakht, H.¹³ Jernelius, J.A.¹⁴ Jin, Q.¹⁵ Li, Y.¹⁶ Liang, W.¹⁷ Roetz, R.¹⁸ Sarma, K.¹⁹ Smith, M.²⁰ more..

10
- 34250327170
- A. Beyer L. Lawtrakul P. Pungpo P. Wolschann Curr. Comput.-Aided Drug Des. 2007 3 87
- (2007) Curr. Comput.-Aided Drug Des. , vol.3 , pp. 87
- Beyer, A.¹ Lawtrakul, L.² Pungpo, P.³ Wolschann, P.⁴

11
- 46749128681
- J. L. Medina-Franco K. Martinez-Mayorga C. Juarez-Gordiano R. Castillo ChemMedChem 2007 2 1141
- (2007) ChemMedChem , vol.2 , pp. 1141
- Medina-Franco, J.L.¹ Martinez-Mayorga, K.² Juarez-Gordiano, C.³ Castillo, R.⁴

12
- 72249123164
- J. Guillemont A. Benjahad S. Oumouch L. Decrane P. Palandjian D. Vernier L. Queguiner K. Andries M.-P. de Bethune K. Hertogs D. S. Grierson C. H. Nguyen J. Med. Chem. 2009 52 7473
- (2009) J. Med. Chem. , vol.52 , pp. 7473
- Guillemont, J.¹ Benjahad, A.² Oumouch, S.³ Decrane, L.⁴ Palandjian, P.⁵ Vernier, D.⁶ Queguiner, L.⁷ Andries, K.⁸ De Bethune, M.-P.⁹ Hertogs, K.¹⁰ Grierson, D.S.¹¹ Nguyen, C.H.¹²

13
- 28144445329
- D. Himmel K. Das A. D. Clark S. H. Hughes A. Benjahad S. Oumouch J. Guillemont S. Coupa A. Poncelet I. Csoka C. Meyer K. Andries C. H. Nguyen D. S. Grierson E. Arnold J. Med. Chem. 2005 48 7582
- (2005) J. Med. Chem. , vol.48 , pp. 7582
- Himmel, D.¹ Das, K.² Clark, A.D.³ Hughes, S.H.⁴ Benjahad, A.⁵ Oumouch, S.⁶ Guillemont, J.⁷ Coupa, S.⁸ Poncelet, A.⁹ Csoka, I.¹⁰ Meyer, C.¹¹ Andries, K.¹² Nguyen, C.H.¹³ Grierson, D.S.¹⁴ Arnold, E.¹⁵

14
- 79952504265
- A very recent patent application from Merck published after our work was complete also describes 4-aryloxypyridones: WO2009067166
- A very recent patent application from Merck published after our work was complete also describes 4-aryloxypyridones: T. J. Tucker, R. Tynebor, J. T. Sisko, N. Anthony, R. Gomez and S. M. Jolly, WO2009067166
- Tucker, T.J.¹ Tynebor, R.² Sisko, J.T.³ Anthony, N.⁴ Gomez, R.⁵ Jolly, S.M.⁶

15
- 79952496485
- For a detailed description of the in vitro assays see: WO2008119662 Protein purification and crystallization was performed as described in ref. 6a. Crystallographic data for the cocrystal structure of 2b and HIVRT has been deposited in the PDB
- For a detailed description of the in vitro assays see: Z. K. Sweeney and M. Welch, WO2008119662
- Sweeney, Z.K.¹ Welch, M.²

16
- 0003845223
- Graphics were prepared using Pymol. See: DeLano Scientific, Palo Alto, CA, For the model of 4c in the NNRTI binding pocket see the ESI.
- Graphics were prepared using Pymol. See: W. L. DeLano, The PyMOL Molecular Graphics System, 2002, DeLano Scientific, Palo Alto, CA, www.pymol.org
- (2002) The PyMOL Molecular Graphics System
- Delano, W.L.¹

17
- 0034640387
- -1 in a medium-throughput thermodynamic solubility assay The open NNRTI binding pocket of diaryl ether pyridazinone inhibitors (ref. 6c) was selected for modeling inhibitors presented in this paper. An essential water molecule (captured in the pyridazinone structure) is required to dock the pyridone correctly so that the pyridone CO makes a water-mediated hydrogen bond with K101 backbone NH, while the NH group of the pyridone makes a hydrogen bond with the backbone carbonyl of K101
- J. Ren C. Nichols L. E. Bird T. Fujiwara H. Sugimoto D. I. Stuart D. K. Stammers J. Biol. Chem. 2000 275 14316
- (2000) J. Biol. Chem. , vol.275 , pp. 14316
- Ren, J.¹ Nichols, C.² Bird, L.E.³ Fujiwara, T.⁴ Sugimoto, H.⁵ Stuart, D.I.⁶ Stammers, D.K.⁷

18
- 79952496703
- Lead optimization was guided using models prepared using the molecular mechanics program MOLOC. Ligand molecules were optimized in the protein environment using the MAB forcefield and 500 steps of conjugate gradient optimization. No constraints were placed on the ligand atoms during minimization. See:
- Lead optimization was guided using models prepared using the molecular mechanics program MOLOC. Ligand molecules were optimized in the protein environment using the MAB forcefield and 500 steps of conjugate gradient optimization. No constraints were placed on the ligand atoms during minimization. See:

19
- 0029315603
- P. R. Gerber K. Müller J. Comput.-Aided Mol. Des. 1995 9 251
- (1995) J. Comput.-Aided Mol. Des. , vol.9 , pp. 251
- Gerber, P.R.¹ Müller, K.²

20
- 79952527584
- P. R. Gerber J. Comput.-Aided Mol. Des. 1998 37 12
- (1998) J. Comput.-Aided Mol. Des. , vol.37 , pp. 12
- Gerber, P.R.¹

21
- 9344236011
- Q. Li D. T. Chu A. Claiborne C. S. Cooper C. M. Lee K. Raye K. B. Berst P. Donner W. Wang L. Hasvold A. Fung Z. Ma M. Tufano R. Flamm L. L. Shen J. Baranowski A. Nilius J. Alder J. Meulbroek K. Marsh D. Crowell Y. Hui L. Seif L. M. Melcher J. Plattner J. Med. Chem. 1996 39 3070
- (1996) J. Med. Chem. , vol.39 , pp. 3070
- Li, Q.¹ Chu, D.T.² Claiborne, A.³ Cooper, C.S.⁴ Lee, C.M.⁵ Raye, K.⁶ Berst, K.B.⁷ Donner, P.⁸ Wang, W.⁹ Hasvold, L.¹⁰ Fung, A.¹¹ Ma, Z.¹² Tufano, M.¹³ Flamm, R.¹⁴ Shen, L.L.¹⁵ Baranowski, J.¹⁶ Nilius, A.¹⁷ Alder, J.¹⁸ Meulbroek, J.¹⁹ Marsh, K.²⁰ more..

22
- 17044402190
- M. Schlosser C. Bobbio T. Rausis J. Org. Chem. 2005 70 2494
- (2005) J. Org. Chem. , vol.70 , pp. 2494
- Schlosser, M.¹ Bobbio, C.² Rausis, T.³

23
- 79952508194
- D. Lee and R. A. Stavenger, WO 2005034866
- Lee, D.¹ Stavenger, R.A.²

24
- 84987369442
- C. S. Wang J. Heterocycl. Chem. 1970 7 389
- (1970) J. Heterocycl. Chem. , vol.7 , pp. 389
- Wang, C.S.¹

25
- 0038034652
- C. Morrill R. H. Grubbs J. Org. Chem. 2003 68 6031
- (2003) J. Org. Chem. , vol.68 , pp. 6031
- Morrill, C.¹ Grubbs, R.H.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.