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Volumn 53, Issue , 2012, Pages 229-234

Chiral resolution, absolute configuration assignment and biological activity of racemic diarylpyrimidine CH(OH)-DAPY as potent nonnucleoside HIV-1 reverse transcriptase inhibitors

(9) Gu, Shuang Xi a Li, Zhi Ming a Ma, Xiao Dong a Yang, Shi Qiong a He, Qiu Qin a Chen, Fen Er a De Clercq, Erik b Balzarini, Jan b Pannecouque, Christophe b

a FUDAN UNIVERSITY (China)

b REGA INSTITUTE FOR MEDICAL RESEARCH (Belgium)

Author keywords

Absolute configuration; Chiral resolution; Diarylpyrimidines; HIV 1; Molecular docking; NNRTIs

Indexed keywords

4 [[4 [(2 CHLOROPHENYL)(HYDROXY)METHYL]PYRIMIDIN 2 YL]AMINO]BENZONITRILE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CHIRALITY; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DOSE RESPONSE; DRUG POTENCY; ENANTIOMER; HUMAN IMMUNODEFICIENCY VIRUS 1; MOLECULAR DOCKING; NONHUMAN; SUPERCRITICAL FLUID CHROMATOGRAPHY; WILD TYPE;

HIV REVERSE TRANSCRIPTASE; HIV-1; HIV-2; MODELS, MOLECULAR; PROTEIN CONFORMATION; PYRIMIDINES; REVERSE TRANSCRIPTASE INHIBITORS; STEREOISOMERISM;

EID: 84861632263 PISSN: 02235234 EISSN: 17683254 Source Type: Journal
DOI: 10.1016/j.ejmech.2012.04.004 Document Type: Article

Times cited : (28)

References (42)

1
- 0026713228
- R. Crossley Tetrahedron 48 1992 8155 8178
- (1992) Tetrahedron , vol.48 , pp. 8155-8178
- Crossley, R.¹

2
- 80053928122
- W.J. Lu, V. Ferlito, C. Xu, D.A. Flockhart, and S. Caccamese Chirality 23 2011 891 896
- (2011) Chirality , vol.23 , pp. 891-896
- Lu, W.J.¹ Ferlito, V.² Xu, C.³ Flockhart, D.A.⁴ Caccamese, S.⁵

3
- 80053903882
- G. Cannazza, U. Battisti, M.M. Carrozzo, L. Brasili, D. Braghiroli, and C. Parenti Chirality 2011 851 859
- (2011) Chirality , pp. 851-859
- Cannazza, G.¹ Battisti, U.² Carrozzo, M.M.³ Brasili, L.⁴ Braghiroli, D.⁵ Parenti, C.⁶

4
- 58149133507
- S.G. Sarafianos, B. Marchand, K. Das, D.M. Himmel, M.A. Parniak, S.H. Hughes, and E. Arnold J. Mol. Biol. 385 2009 693 713
- (2009) J. Mol. Biol. , vol.385 , pp. 693-713
- Sarafianos, S.G.¹ Marchand, B.² Das, K.³ Himmel, D.M.⁴ Parniak, M.A.⁵ Hughes, S.H.⁶ Arnold, E.⁷

5
- 0030586090
- Y. Hsiou, J. Ding, K. Das, A.D. Clark, S.H. Hughes, and E. Arnold Structure 4 1996 853 860
- (1996) Structure , vol.4 , pp. 853-860
- Hsiou, Y.¹ Ding, J.² Das, K.³ Clark, A.D.⁴ Hughes, S.H.⁵ Arnold, E.⁶

6
- 70349395798
- P. Zhan, X. Liu, and Z. Li Curr. Med. Chem. 16 2009 2876 2889
- (2009) Curr. Med. Chem. , vol.16 , pp. 2876-2889
- Zhan, P.¹ Liu, X.² Li, Z.³

7
- 0032544154
- Z.Q. Xu, R.W. Buckheit, T.L. Stup, M.T. Flavin, A. Khilevich, J.D. Rizzo, L. Lin, and D.E. Zembower Bioorg. Med. Chem. Lett. 8 1998 2179 2184
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2179-2184
- Xu, Z.Q.¹ Buckheit, R.W.² Stup, T.L.³ Flavin, M.T.⁴ Khilevich, A.⁵ Rizzo, J.D.⁶ Lin, L.⁷ Zembower, D.E.⁸

8
- 3042836102
- T. Venkatachalam, C. Mao, and F. Uckun Bioorg. Med. Chem. 12 2004 4275 4284
- (2004) Bioorg. Med. Chem. , vol.12 , pp. 4275-4284
- Venkatachalam, T.¹ Mao, C.² Uckun, F.³

9
- 61449115978
- M. Radi, G. Maga, M. Alongi, L. Angeli, A. Samuele, S. Zanoli, L. Bellucci, A. Tafi, G. Casaluce, G. Giorgi, M. Armand-Ugon, E. Gonzalez, J.A. Esté, M. Baltzinger, G. Bec, P. Dumas, E. Ennifar, and M. Botta J. Med. Chem. 52 2009 840 851
- (2009) J. Med. Chem. , vol.52 , pp. 840-851
- Radi, M.¹ Maga, G.² Alongi, M.³ Angeli, L.⁴ Samuele, A.⁵ Zanoli, S.⁶ Bellucci, L.⁷ Tafi, A.⁸ Casaluce, G.⁹ Giorgi, G.¹⁰ Armand-Ugon, M.¹¹ Gonzalez, E.¹² Esté, J.A.¹³ Baltzinger, M.¹⁴ Bec, G.¹⁵ Dumas, P.¹⁶ Ennifar, E.¹⁷ Botta, M.¹⁸

10
- 33646033414
- K. Krajewski, Y. Zhang, D. Parrish, J. Deschamps, P.P. Roller, and V.K. Pathak Bioorg. Med. Chem. Lett. 16 2006 3034 3038
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 3034-3038
- Krajewski, K.¹ Zhang, Y.² Parrish, D.³ Deschamps, J.⁴ Roller, P.P.⁵ Pathak, V.K.⁶

11
- 36749073433
- E. De Clercq Nat. Rev. Drug. Discov. 6 2007 1001 1018
- (2007) Nat. Rev. Drug. Discov. , vol.6 , pp. 1001-1018
- De Clercq, E.¹

12
- 79251472419
- X. Chen, P. Zhan, D. Li, E. De Clercq, and X. Liu Curr. Med. Chem. 18 2011 359 376
- (2011) Curr. Med. Chem. , vol.18 , pp. 359-376
- Chen, X.¹ Zhan, P.² Li, D.³ De Clercq, E.⁴ Liu, X.⁵

13
- 77249134151
- Y. Mehellou, and E. De Clercq J. Med. Chem. 53 2010 521 538
- (2010) J. Med. Chem. , vol.53 , pp. 521-538
- Mehellou, Y.¹ De Clercq, E.²

14
- 77953089657
- Z.-S. Zeng, Y.-H. Liang, X.-Q. Feng, F.-E. Chen, C. Pannecouque, J. Balzarini, and E. De Clercq ChemMedChem 5 2010 837 840
- (2010) ChemMedChem , vol.5 , pp. 837-840
- Zeng, Z.-S.¹ Liang, Y.-H.² Feng, X.-Q.³ Chen, F.-E.⁴ Pannecouque, C.⁵ Balzarini, J.⁶ De Clercq, E.⁷

15
- 79955455754
- D. Rotili, D. Tarantino, M. Artico, M.B. Nawrozkij, E. Gonzalez-Ortega, B. Clotet, A. Samuele, J.A. Este, G. Maga, and A. Mai J. Med. Chem. 54 2011 3091 3096
- (2011) J. Med. Chem. , vol.54 , pp. 3091-3096
- Rotili, D.¹ Tarantino, D.² Artico, M.³ Nawrozkij, M.B.⁴ Gonzalez-Ortega, E.⁵ Clotet, B.⁶ Samuele, A.⁷ Este, J.A.⁸ Maga, G.⁹ Mai, A.¹⁰

16
- 84860390578
- S.-X. Gu, Q.-Q. He, S.-Q. Yang, X.-D. Ma, F.-E. Chen, E. De Clercq, J. Balzarini, and C. Pannecouque Bioorg. Med. Chem. 19 2011 5117 5124
- (2011) Bioorg. Med. Chem. , vol.19 , pp. 5117-5124
- Gu, S.-X.¹ He, Q.-Q.² Yang, S.-Q.³ Ma, X.-D.⁴ Chen, F.-E.⁵ De Clercq, E.⁶ Balzarini, J.⁷ Pannecouque, C.⁸

17
- 0000103208
- R. Noyori, I. Tomino, and Y. Tanimoto J. Am. Chem. Soc. 101 1979 3129 3131
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 3129-3131
- Noyori, R.¹ Tomino, I.² Tanimoto, Y.³

18
- 0000549143
- R. Noyori Pure Appl. Chem. 53 1981 2315 2322
- (1981) Pure Appl. Chem. , vol.53 , pp. 2315-2322
- Noyori, R.¹

19
- 0342697384
- L. Deloux, and M. Srebnik Chem. Rev. 93 1993 763 784
- (1993) Chem. Rev. , vol.93 , pp. 763-784
- Deloux, L.¹ Srebnik, M.²

20
- 0032541271
- E.J. Corey, and C.J. Helal Angew. Chem. Int. Ed. 37 1998 1986 2012
- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1986-2012
- Corey, E.J.¹ Helal, C.J.²

21
- 34249686052
- N. Berova, L. Di Bari, and G. Pescitelli Chem. Soc. Rev. 36 2007 914 931
- (2007) Chem. Soc. Rev. , vol.36 , pp. 914-931
- Berova, N.¹ Di Bari, L.² Pescitelli, G.³

22
- 21844473750
- L. Di Bari, S. Guillarme, S. Hermitage, D.A. Jay, G. Pescitelli, and A. Whiting Chirality 17 2005 323 331
- (2005) Chirality , vol.17 , pp. 323-331
- Di Bari, L.¹ Guillarme, S.² Hermitage, S.³ Jay, D.A.⁴ Pescitelli, G.⁵ Whiting, A.⁶

23
- 34247242120
- P.L. Polavarapu Chem. Rec. 7 2007 125 136
- (2007) Chem. Rec. , vol.7 , pp. 125-136
- Polavarapu, P.L.¹

24
- 80053892263
- S. Abbate, F. Lebon, G. Longhi, M. Passarello, and V.T. Liveri Chirality 23 2011 910 915
- (2011) Chirality , vol.23 , pp. 910-915
- Abbate, S.¹ Lebon, F.² Longhi, G.³ Passarello, M.⁴ Liveri, V.T.⁵

25
- 0034090652
- F. Furche, R. Ahlrichs, C. Wachsmann, E. Weber, A. Sobanski, F. Vögtle, and S. Grimme J. Am. Chem. Soc. 122 2000 1717 1724
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 1717-1724
- Furche, F.¹ Ahlrichs, R.² Wachsmann, C.³ Weber, E.⁴ Sobanski, A.⁵ Vögtle, F.⁶ Grimme, S.⁷

26
- 65549158808
- S. Abbate, L.F. Burgi, E. Castiglioni, F. Lebon, G. Longhi, E. Toscano, and S. Caccamese Chirality 21 2009 436 441
- (2009) Chirality , vol.21 , pp. 436-441
- Abbate, S.¹ Burgi, L.F.² Castiglioni, E.³ Lebon, F.⁴ Longhi, G.⁵ Toscano, E.⁶ Caccamese, S.⁷

27
- 67650314382
- H.S. Rzepa Org. Lett. 11 2009 3088 3091
- (2009) Org. Lett. , vol.11 , pp. 3088-3091
- Rzepa, H.S.¹

28
- 67749135571
- S. Graule, M. Rudolph, N. Vanthuyne, J. Autschbach, C. Roussel, J. Crassous, and R. Réau J. Am. Chem. Soc. 131 2009 3183 3185
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 3183-3185
- Graule, S.¹ Rudolph, M.² Vanthuyne, N.³ Autschbach, J.⁴ Roussel, C.⁵ Crassous, J.⁶ Réau, R.⁷

29
- 0023687234
- R. Pauwels, J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter, and E. De Clercq J. Virol. Methods 20 1988 309 321
- (1988) J. Virol. Methods , vol.20 , pp. 309-321
- Pauwels, R.¹ Balzarini, J.² Baba, M.³ Snoeck, R.⁴ Schols, D.⁵ Herdewijn, P.⁶ Desmyter, J.⁷ De Clercq, E.⁸

30
- 40749129190
- C. Pannecouque, D. Daelemans, and E. De Clercq Nat. Protocols 3 2008 427 434
- (2008) Nat. Protocols , vol.3 , pp. 427-434
- Pannecouque, C.¹ Daelemans, D.² De Clercq, E.³

31
- 17944374798
- D.W. Ludovici, B.L. De Corte, M.J. Kukla, H. Ye, C.Y. Ho, M.A. Lichtenstein, R.W. Kavash, K. Andries, M.-P. de Béthune, H. Azijn, R. Pauwels, P. Lewi, J. Heeres, L.M.H. Koymans, M.R. de Jonge, K.J.A. Van Aken, F.F.D. Daeyaert, K. Das, E. Arnold, and P.A.J. Janssen Bioorg. Med. Chem. Lett. 11 2001 2235 2239
- (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2235-2239
- Ludovici, D.W.¹ De Corte, B.L.² Kukla, M.J.³ Ye, H.⁴ Ho, C.Y.⁵ Lichtenstein, M.A.⁶ Kavash, R.W.⁷ Andries, K.⁸ De Béthune, M.-P.⁹ Azijn, H.¹⁰ Pauwels, R.¹¹ Lewi, P.¹² Heeres, J.¹³ Koymans, L.M.H.¹⁴ De Jonge, M.R.¹⁵ Van Aken, K.J.A.¹⁶ Daeyaert, F.F.D.¹⁷ Das, K.¹⁸ Arnold, E.¹⁹ Janssen, P.A.J.²⁰ more..

32
- 2342620790
- K. Das, A.D. Clark, P.J. Lewi, J. Heeres, M.R. de Jonge, L.M.H. Koymans, H.M. Vinkers, F. Daeyaert, D.W. Ludovici, M.J. Kukla, B. De Corte, R.W. Kavash, C.Y. Ho, H. Ye, M.A. Lichtenstein, K. Andries, R. Pauwels, M.-P. de Béthune, P.L. Boyer, P. Clark, S.H. Hughes, P.A.J. Janssen, and E. Arnold J. Med. Chem. 47 2004 2550 2560
- (2004) J. Med. Chem. , vol.47 , pp. 2550-2560
- Das, K.¹ Clark, A.D.² Lewi, P.J.³ Heeres, J.⁴ De Jonge, M.R.⁵ Koymans, L.M.H.⁶ Vinkers, H.M.⁷ Daeyaert, F.⁸ Ludovici, D.W.⁹ Kukla, M.J.¹⁰ De Corte, B.¹¹ Kavash, R.W.¹² Ho, C.Y.¹³ Ye, H.¹⁴ Lichtenstein, M.A.¹⁵ Andries, K.¹⁶ Pauwels, R.¹⁷ De Béthune, M.-P.¹⁸ Boyer, P.L.¹⁹ Clark, P.²⁰ more..

33
- 40349091258
- K. Das, J.D. Bauman, A.D. Clark, Y.V. Frenkel, P.J. Lewi, A.J. Shatkin, S.H. Hughes, and E. Arnold Proc. Natl. Acad. Sci. U.S.A. 105 2008 1466 1471
- (2008) Proc. Natl. Acad. Sci. U.S.A. , vol.105 , pp. 1466-1471
- Das, K.¹ Bauman, J.D.² Clark, A.D.³ Frenkel, Y.V.⁴ Lewi, P.J.⁵ Shatkin, A.J.⁶ Hughes, S.H.⁷ Arnold, E.⁸

34
- 0030255303
- A.N. Jain, and J. Comput Aided Mol. Des. 10 1996 427 440
- (1996) Aided Mol. Des. , vol.10 , pp. 427-440
- Jain, A.N.¹ Comput, J.²

35
- 0037434582
- A.N. Jain J. Med. Chem. 46 2003 499 511
- (2003) J. Med. Chem. , vol.46 , pp. 499-511
- Jain, A.N.¹

36
- 35848947985
- Q. Liu, B. Masek, K. Smith, and J. Smith J. Med. Chem. 50 2007 5392 5402
- (2007) J. Med. Chem. , vol.50 , pp. 5392-5402
- Liu, Q.¹ Masek, B.² Smith, K.³ Smith, J.⁴

38
- 79954987862
- M. Yu, Z. Li, S. Liu, E. Fan, C. Pannecouque, E. De Clercq, and X. Liu ChemMedChem 6 2011 826 833
- (2011) ChemMedChem , vol.6 , pp. 826-833
- Yu, M.¹ Li, Z.² Liu, S.³ Fan, E.⁴ Pannecouque, C.⁵ De Clercq, E.⁶ Liu, X.⁷

39
- 34547691007
- J.Z. Chen, J. Wang, and X.Q. Xie J. Chem Inf. Model. 47 2007 1626 1637
- (2007) J. Chem Inf. Model. , vol.47 , pp. 1626-1637
- Chen, J.Z.¹ Wang, J.² Xie, X.Q.³

40
- 33744916587
- S. Raduner, A. Majewska, J.Z. Chen, X.Q. Xie, J. Hamon, B. Faller, K.H. Altmann, and J. Gertsch J. Biol. Chem. 281 2006 14192 14206
- (2006) J. Biol. Chem. , vol.281 , pp. 14192-14206
- Raduner, S.¹ Majewska, A.² Chen, J.Z.³ Xie, X.Q.⁴ Hamon, J.⁵ Faller, B.⁶ Altmann, K.H.⁷ Gertsch, J.⁸

41
- 0030979125
- J. Ruppert, W. Welch, and A.N. Jain Protein Sci. 6 1997 524 533
- (1997) Protein Sci. , vol.6 , pp. 524-533
- Ruppert, J.¹ Welch, W.² Jain, A.N.³

42
- 0030154893
- W. Welch, J. Ruppert, and A.N. Jain Chem. Biol. 3 1996 449 462
- (1996) Chem. Biol. , vol.3 , pp. 449-462
- Welch, W.¹ Ruppert, J.² Jain, A.N.³

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