Indolizine studies, part 5: Indolizine-2-carboxamides as potential HIV-1 protease inhibitors[1]

Synthetic Communications

Volumn 40, Issue 13, 2010, Pages 2018-2028

  Tukulula, Matshawandile ^a   Klein, Rosalyn ^a   Kaye, Perry T ^a  

^a RHODES UNIVERSITY   (South Africa)

Author keywords

Baylis Hillman reaction; HIV 1 protease inhibitors; Indolizine 2 carboxamides

Indexed keywords

1 (INDOLIZIN 2 YL) 7 CARBOMETHOXY 1,9,12 TRIOXO 2,8,11 TRIAZATRIDECANE; AMINE; AMINO ACID DERIVATIVE; ETHYL(2) 3 HYDROXY 2 (5 METHYLINDOLIZINE 2 CARBOXAMIDO)PROPANOATE; ETHYL(2) 3 HYDROXY 2 (INDOLIZINE 2 CARBOXAMIDO)PROPANOATE; ETHYL(2) 3 HYDROXY 2 {PYRROLO[1,2 A]QUINOLINE 2 CARBOXAMIDO}PROPANOATE; INDOLIZINE 2 CARBOXAMIDE; INDOLIZINE 2 CARBOXYLATE ESTER; INDOLIZINE DERIVATIVE; METHYL(2) 1 [(5 METHYLINDOLIZIN 2 YL)CARBONYL]PYRROLIDINE 2 CARBOXYLATE; N (CARBOMETHOXYMETHYL)PYRROLO[1,2 A]QUINOLINE 2 CARBOXAMIDE; N [2 (BENZYLTHIO)ETHYL] 5 METHYLINDOLIZINE 2 CARBOXAMIDE; N [2 (BENZYLTHIO)ETHYL]INDOLIZINE 2 CARBOXAMIDE; N [2 (BENZYLTHIO)ETHYL]PYRROLO[1,2 A]QUINOLINE 2 CARBOXAMIDE; N [4 (DIETHYLAMINO) 1 METHYLBUTYL]INDOLIZINE 2 CARBOXAMIDE; N CARBETHOXYMETHYL 5 METHYLINDOLIZINE 2 CARBOXAMIDE; N CARBETHOXYMETHYLINDOLIZINE 2 CARBOXAMIDE; N CARBOMETHOXYMETHYL 5 METHYLINDOLIZINE 2 CARBOXAMIDE; RITONAVIR; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL BOND; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 77953377264     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903219450     Document Type: Article

References (21)

1. Deane, P. O'G.; George, R.; Kaye, P. T. Indolizine studies, part 4: Kinetics and mechanism for the formation of indolizines via thermal cyclisation of 2-pyridyl derivatives. Tetrahedron 1998, 54, 3871-3876.
2. Perez, M. A. S.; Fernandes, P. A.; Ramos, M. Drug design: New inhibitors for HIV-1 protease based on nelfinavir as lead. J. J. Mol. Graph. Model. 2007, 26, 634-642.
3. Aversa, S. M. L.; Cattelan, A. M.; Salvagno, L.; Crivellari, G.; Banna, G.; Trevenzoli, M.; Chiarion-Sileni, V.; Monfardini, S. Treatments of AIDS-related Kaposi's sarcoma. Crit. Rev. Oncol.=Hematol. 2005, 53, 253-265.
4. Turner, B. G.; Summers, M. F. Structural biology of HIV. J. Mol. Biol. 1999, 285, 1-32.
5. Nijhuis, M.; van Maarseveen, N. M.; Lastere, S.; Schipper, P.; Coakley, E.; Glass, B.; Rovenska, M.; de Jong, D.; Chappey, C.; Goedegebuure, I. W.; Heilek-Snyder, G.; Dulude, D.; Cammack, N.; Brakier-Gingras, L.; Konvalika, J.; Parkin, N.; Krausslic, H.; Brun-Vezinet, F.; Boucher, C. A. A novel substrate-based HIV-1 protease inhibitor drug resistance mechanism. Medicine 2007, 4, 0152-0163.
6. Maeda, K.; Mitsuya, H. Development of therapeutics for AIDS: Structure-based molecular targeting. Tuberculosis 2007, 87, S31-S34.
7. Kaye, P. T.; Musa, M. A.; Nchinda, A. T.; Nocanda, X. W. Novel heterocyclic analogues of the HIV-1 protease inhibitor, ritonavir. Synth. Commun. 2004, 34, 2575-2589.
8. Kaloko, Jr., J.; Hayford, A. Direct synthesis of monofunctionalized indolizine derivatives bearing alkoxymethyl substituents at C-3 and their benzofused analogues. Org. Lett. 2005, 7, 4305-4308.
9. Katritzky, A. R.; Qiu, G.; Yang, B.; He, H. Novel syntheses of indolizines and pyrrolo[2,1-a]isoquinolines via benzotriazole methodology. J. Org. Chem. 1999, 64, 7618-7621.
10. Cingolani, G. M.; Claudi, F.; Massi, M.; Venturi, F. Indolizine derivatives with biological activity, VI: 1-(2-Aminoethyl)-3-benzyl-7-methoxy-2- methylindolizine, benanserine structural analog. Eur. J. Med. Chem. 1990, 25, 709-712.
11. Troll, T.; Beckel, H.; Lentner-Boehm, C. Electrochemical synthesis of substituted indoli-zines: UV and fluorescence spectra. Tetrahedron 1997, 53, 81-90.
12. Gundersen, L.-L.; Charnock, C.; Negussie, A. H.; Rise, F.; Teklu, S. Synthesis of indoli-zine derivatives with selective antibacterial activity against Mycobacterium tuberculosis. Eur. J. Pharm. Sci. 2007, 30, 26-35.
13. Przewloka, T.; Chen, S.; Xia, Z.; Li, H.; Zhang, S.; Chimmanamada, D.; Kostik, E.; James, D.; Koya, K.; Sun, L. Application of DMF-methyl sulfate adduct in the regio-selective synthesis of 3-acylated indolizines. Tetrahedron Lett. 2007, 48, 5739-5742.
14. Weide, T.; Arve, L.; Prinz, H.; Waldmann, H.; Kessler, H. 3-Substituted indolizine-1-carbonitrile derivatives as phosphatase inhibitors. Bioorg. Med. Chem. 2006, 16, 59-63.
15. Uchida, T.; Matsumoto, K. Methods for the construction of the indolizine nucleus. Synthesis 1976, 209-236.
16. Kostik, E. I.; Abiko, A.; Oku, A. Chichibabin indolizine synthesis revisited: Synthesis of indolizinones by solvolysis of 4-alkoxycarbonyl-3- oxotetrahydroquinolizinium ylides. J. Org. Chem. 2001, 66, 2618-2623.
17. Wang, B.; Zhang, X.; Li, J.; Jiang, X.; Hu, Y.; Hu, H. Preparation of indolizine-3-carboxamides and indolizine-3-carbonitriles by 1,3-dipolar cycloaddition of N-(cyanomethyl)pyridinium ylides to alkenes in the presence of tetrakispyridinecobalt(II) dichromate or manganese(IV) oxide. J. Chem. Soc., Perkin Trans. 1 1999, 1571-1575;
18. Mmutlane, E. M.; Harris, J. M.; Padwa, A. 1,3-Dipolar cycloaddition chemistry for the preparation of novel indolizinone-based compounds. J. Org. Chem. 2005, 70, 8055-8063.
19. Bode, M. L.; Kaye, P. T. A new synthesis of indolizines via thermal cyclisation of 2-pyridyl derivatives. J. Chem. Soc., Perkin Trans. 1 1990, 2612-2613;
20. Bode, M. L.; Kaye, P. T. Indolizine studies, part 2: Synthesis and NMR spectroscopic analysis of 2-substituted indolizines. J. Chem. Soc., Perkin Trans. 1 1993, 1809-1815.
21. Bode, M. L.; Kaye, P. T.; George, R. Indolizine studies, part 3: Synthesis and dynamic NMR analysis of indolizine-2-carboxamides. J. Chem. Soc., Perkin Trans. 1 1994, 3023-3027.