Evaluation of retro-inverso modifications of HTLV-1 protease inhibitors containing a hydroxyethylamine isoster

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 7, 2010, Pages 2720-2727

  Tatsumi, Tadashi ^a   Awahara, Chiyuki ^a   Naka, Hiromi ^b   Aimoto, Saburo ^b   Konno, Hiroyuki ^a   Nosaka, Kazuto ^a   Akaji, Kenichi ^a  

^a KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

HTLV 1 protease; Hydroxyethylamine isoster; Inhibitor; Retro inverso

Indexed keywords

ETHANOLAMINE DERIVATIVE; HYDROXYL GROUP; PROTEINASE; PROTEINASE INHIBITOR;

ALDOL REACTION; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DIASTEREOISOMER; HUMAN T CELL LEUKEMIA VIRUS 1; IC 50; NONHUMAN; STEREOCHEMISTRY; VIRUS INHIBITION;

ASPARTIC ACID ENDOPEPTIDASES; DEANOL; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMAN T-LYMPHOTROPIC VIRUS 1; INDICATORS AND REAGENTS; MUTATION; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN T-LYMPHOTROPIC VIRUS 1;

EID: 77950042973     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.02.019     Document Type: Article

References (24)

1. Chorev M., and Goodman M. Acc. Chem. Rev. 26 (1993) 266
2. Chorev M. Biopolymers (Pept. Sci.) 80 (2005) 67
3. Verdini A.S., and Viscomi G.C. J. Chem. Soc., Perkin Trans. I (1985) 697
4. Fuller W.D., Goodman M., and Verlander M.S. J. Am. Chem. Soc. 109 (1987) 4712
5. Verdini A.S., Dilvestri S., Becherucci C., Longobardi M.G., Parente L., Peppoloni S., Perretti M., Pileri P., Pinori M., Viscomi G.C., and Nencioni L. J. Med. Chem. 34 (1991) 3372
6. Gaston F., Granados G.C., Madurga S., Rabanal F., Lakhdar-Ghazal F., Giralt E., and Bahraoui E. ChemMedChem 4 (2009) 570
7. Lee Y.S., Agnes R.S., Davis P., Ma S., Badghisi H., Lai J., Porreca F., and Hruby V. J. Med. Chem. 50 (2007) 165
8. Sakurai K., Chung H.S., and Kahne D. J. Am. Chem. Soc. 126 (2004) 16288
9. Matsuoka M. Oncogene 22 (2003) 5131
10. Akaji K., Teruya K., and Aimoto S. J. Org. Chem. 68 (2003) 4755
11. Naka H., Teruya K., Bang J.K., Aimoto S., Tatsumi T., Konno H., Nosaka K., and Akaji K. Bioorg. Med. Chem. Lett. 16 (2006) 3761
12. Babine R.E., and Bender S.L. Chem. Rev. 97 (1997) 1359
13. Bang J.K., Naka H., Teruya K., Aimoto S., Konno H., Nosaka K., Tatsumi T., and Akaji K. J. Org. Chem. 70 (2005) 10596
14. Bang J.K., Teruya K., Aimoto S., Konno H., Nosaka K., Tatsumi T., and Akaji K. Int. J. Pept. Res. Ther. 13 (2007) 173
15. Ghosh A.K., and Onishi M. J. Am. Chem. Soc. 118 (1996) 2527
16. Ghosh A.K., and Fidanze S. J. Org. Chem. 63 (1998) 6146
17. Matsueda G.R., and Stewart J.M. Peptides 2 (1981) 45
18. Carpino L.A. J. Am. Chem. Soc. 115 (1993) 4397
19. 17 (see the Supplementary data).
20. Kopple K.D., and Nitecki D.E. J. Am. Chem. Soc. 84 (1962) 4457
21. Teruya K., Kawakami T., Akaji K., and Aimoto S. Tetrahedron Lett. 43 (2002) 1487
22. 50 values is shown in the Supplementary data.
23. Abdalla S., Bayer E., and Frank H. Chromatographia 23 (1987) 83
24. Frank H., Woiwode W., Nicholson G., and Bayer E. Liebigs Ann. Chem. (1981) 345