Synthesis and evaluation of benzoxazinones as HIV-1 reverse transcriptase inhibitors. Analogs of Efavirenz (Sustiva(TM))

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 22, 1999, Pages 3221-3224

  Patel, Mona ^a   McHugh Jr , Robert J ^a   Cordova, Beverly C ^a   Klabe, Ronald M ^a   Erickson Viitanen, Susan ^a   Trainor, George L ^a   Ko, Soo S ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZINONE DERIVATIVE; DRUG ANALOG; EFAVIRENZ; FLUORINE; NITROGEN; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ANTIVIRAL ACTIVITY; ARTICLE; CELL; CHEMICAL MODIFICATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION;

HUMAN IMMUNODEFICIENCY VIRUS 1; RNA VIRUSES;

EID: 0033571566     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00565-X     Document Type: Article

References (9)

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2. Patel, M.; Ko, S. S.; McHugh, R. J.; Markwalder, J. A.; Srivastava, A. S.; Cordova, B. C.; Klabe, R. M.; Erickson- Viitanen, S.; Trainor, G. L.; Seitz, S. P. Bioorg. Med. Chem. Lett. 1999, 9, 2805.
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4. Surya Prakash, G. K.; Yudin, A. K. Chem. Rev. 1997, 97, 757. Since completion of the work described herein, the following communication describing the direct conversion of carboxylic esters to the corresponding trifluoromethyl ketones was published. Wiedemann, J.; Heiner, T.; Mloston, G.; Surya Prakash, G. K.; Olah, G. A. Angew. Chem. Int. Ed. 1998, 37, 820.
5. Surya Prakash, G. K.; Yudin, A. K. Chem. Rev. 1997, 97, 757. Since completion of the work described herein, the following communication describing the direct conversion of carboxylic esters to the corresponding trifluoromethyl ketones was published. Wiedemann, J.; Heiner, T.; Mloston, G.; Surya Prakash, G. K.; Olah, G. A. Angew. Chem. Int. Ed. 1998, 37, 820.
6. Ko, S. S.; Cocuzza, A. J.; Patel, M.; Srivastava, A. S.; Tanabe, K.; Chidester, D. R.; Parsons, R. L.; Cordova, B. C.; Klabe, R. M.; Erickson-Viitanen, S.; Trainor, G. L. Manuscript in preparation.
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8. 90) according to the protocol described in: Bacheler, L. T.; Paul, M.; Jadhav, P. K.; Otto, M.; Miller, J. Antiviral Chem. Chemo. 1994, 5, 111.
9. The data presented for Efavirenz reflects values determined for a single enantiomer, whereas the data shown for 5a-8b are that of racemic mixtures. The biological evaluation of each enantiomer of Efavirenz and other benzoxazinones had determined that only the S enantiomer was active.