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Volumn 52, Issue 23, 2009, Pages 7473-7487

Synthesis and biological evaluation of C-5 methyl substituted 4-arylthio and 4-aryloxy-3-iodopyridin-2(1H)-one type anti-HIV agents

Author keywords

[No Author keywords available]

Indexed keywords

1 [4 (3,5 DIMETHYLPHENOXY)5 IODO 2 METHYL 6 OXO 1,6 DIHYDROPYRIDIN 3 YLMETHYL]PIPERIDIN 4 YLCARBAMATE; 3 (3,5 DIMETHYLPHENOXY) 5 (FURAN 2 YLMETHYLTHIOMETHYL) 3 IODO 6 METHYL PYRIDIN 2 (1H)ONE; 4 (3,5 DIMETHYLPHENOXY) 3 IODO 5 (2 METHOXY ETHOXYMETHYL) 5 METHYLPYRIDIN 2 (1H)ONE; 4 (3,5 DIMETHYLPHENOXY) 3 IODO 5 (THIOPHEN 2 YL METHOXYMETHYL) 6 METHYLPYRIDIN 2 (1H)ONE; 4 (3,5 DIMETHYLPHENOXY) 5 (2 HYDROXY ETHOXYMETHYL) 3 IODO 6 METHYLPYRIDIN 2 (1H)ONE; 4 (3,5 DIMETHYLPHENOXY) 5 (ETHANESULFONYLMETHYL) 3 IODO 6 METHYLPYRIDINE 2 (1H)ONE; 4 (3,5 DIMETHYLPHENOXY) 5 (FURAN 2 YLMETHYLTHIOMETHYL) 3 IODO 6 METHYL PYRIDIN 2(1H) ONE; 4 (3,5 DIMETHYLPHENOXY) 5 [N(FURAN 2 YLMETHYL)N METHYL]AMINOMETHYL 3 IODO 6 METHYLPYRIDINE 2 (1H)ONE; 4 (3,5 DIMETHYLPHENYLSULFANYL) 2 METHYL 6 OXO 1,6 DIHYDROPYRIDIN 3 YLCARBONITRILE; 4 (3,5 DIMETHYLPHENYLSULFANYL) 3 IODO 6 METHYL 5 (1H PYRROL 2 YLMETHYL)PYRIDIN 2 (1H)ONE; 4 (3,5 DIMETHYLPHENYLSULFANYL) 3 IODO 6 METHYL 5 (TETRAZOL YL METHYL)PYRIDIN 2(1H)ONE; 4 (3,5 DIMETHYLPHENYLSULFANYL) 3 IODO 6 METHYL 5 (TETRAZOL YLMETHYL)PYRIDIN 2(1H)ONE; 4 (3,5 DIMETHYLPHENYLSULFANYL) 3 IODO 6 METHYL 5 [3 METHYL(1,2,4)TRIAZOL 1 YLMETHYL)PYRIDIN 2 (1H)ONE; 4 (3,5 DIMETHYLPHENYLSULFANYL) 5 IODO 2 METHYL 6 OXO 1,6 DIHYDROPYRIDINE 3 YLCARBONITRILE; 4 CHLORO 2 METHYL 6 OXO 1,6 DIHYDROPYRIDIN 3YLCARBONITRILE; 5 CHLOROMETHYL 3 IODO 6 METHYL 4 (3,5 DIMETHYLPHENYLSULFANYL)PYRIDIN 2 (1H)ONE; 5 CHLOROMETHYL 6 METHYL 4 (3,5 DIMETHYLPHENYLSULFANYL)PYRIDIN 2 (1H) ONE; 5 ETHOXYMETHYL 3 IODO 6 METHYL 4 (3,5 DIMETHYLPHENOXY)PYRIDIN 2 (1H)ONE; 5 ETHOXYMETHYL 3 IODO 6 METHYL 4 (3,5 DIMETHYLPHENYLSULFANYL)PYRIDIN 2 (1H)ONE; 5 ETHOXYMETHYL 6 METHYL 4 (3,5 DIMETHYLPHENYLSULFANYL)PYRIDIN 2 (1H) ONE; 5 HYDROXYMETHYL 3 IODO 6 METHYL 4 (3,5 DIMETHYLPHENYLSULFANYL)PYRIDIN 2 (1H)ONE; 5 HYDROXYMETHYL 3 IODO 6 METHYL 4 (3,5 DIMETHYLPHENYLSULFANYL)PYRIDIN 2(1H) ONE; 5 HYDROXYMETHYL 5 METHYL 4 (3,5 DIMETHYLPHENYLSULFANYL)PYRIDIN 2 (1H)ONE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; EFAVIRENZ; ETHYL 4 (3,5 DIMETHYLPHENYLSULFANYL) 2 METHYL 6 OXO 1,6 DIHYDROPYRIDIN 3 YL CARBOXYLATE; ETHYL 4 (3,5 DIMETHYLPHEYLSULFANYL) 5 IODO 2 METHYL 6 OXO 1,6 DIHYDROPYRIDIN 3 YLCARBOXYLATE; ETHYL 4 CHLORO 2 METHYL 6 OXO 1,6 DIHYDROPYRIDIN 3YLCARBOXYLATE; NEVIRAPINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 72249123164     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900802y     Document Type: Article
Times cited : (26)

References (32)
  • 1
    • 0033587510 scopus 로고    scopus 로고
    • Highly active anti-retroviral therapy in a large urban clinic: Risk factors for virologic failure and adverse drug reactions
    • Lucas, G. M.; Chaisson, R. E.; Moore, R. D. Highly active anti-retroviral therapy in a large urban clinic: risk factors for virologic failure and adverse drug reactions. Ann. Intern.Med. 1999, 13, 81-87.
    • (1999) Ann. Intern.Med. , vol.13 , pp. 81-87
    • Lucas, G.M.1    Chaisson, R.E.2    Moore, R.D.3
  • 2
    • 0033612928 scopus 로고    scopus 로고
    • Transmission of antiretroviral-drug-resistant HIV-1 variants
    • Yerly, S.; Kaiser, L.; Race, E.; Bru, J. P.; Clavel, F.; Perrin, L. Transmission of antiretroviral-drug-resistant HIV-1 variants. Lancet 1999, 354, 729-733.
    • (1999) Lancet , vol.354 , pp. 729-733
    • Yerly, S.1    Kaiser, L.2    Race, E.3    Bru, J.P.4    Clavel, F.5    Perrin, L.6
  • 3
    • 0033583977 scopus 로고    scopus 로고
    • Prediction, and natural course of HIV-1 protease inhibitor associated lipodystrophy, hyperlipidaemia, and diabetes mellitus: A cohort study
    • Carr, A.; Samaras, C. K.; Thorisdottir, A.; Kaufmann, G. R.; Ghisholm, D. J.; Cooper, D. A. Diagnosis, prediction, and natural course of HIV-1 protease inhibitor associated lipodystrophy, hyperlipidaemia, and diabetes mellitus: a cohort study. Lancet 1999, 353, 2093-2099.
    • (1999) Lancet , vol.353 , pp. 2093-2099
    • Carr, A.1    Samaras, C.K.2    Thorisdottir, A.3    Kaufmann, G.R.4    Ghisholm, D.J.5    Diagnosis, C.D.A.6
  • 4
    • 0034699898 scopus 로고    scopus 로고
    • Adverse effects of antiviral therapy
    • Carr, A.; Cooper, D. A. Adverse effects of antiviral therapy. Lancet 2000, 356, 1423-1430.
    • (2000) Lancet , vol.356 , pp. 1423-1430
    • Carr, A.1    Cooper, D.A.2
  • 5
    • 0037161026 scopus 로고    scopus 로고
    • Association between altered expression of adipogenic factor SREBP1 in lipotrophic adipose tissue from HIV-1 infected patients and abnormal adipocyte differentiation and insulin resistance
    • Bastard, J.-P.; Caron, M.; Vidal, H.; Jan, V.; Auclair,M.; Vigouroux, C.;Luboinski, J.;Laville,M.;Maachi, M.;Girard, P.-M.; Rozenbaum, W.; Levan, P.; Capeau, J. Association between altered expression of adipogenic factor SREBP1 in lipotrophic adipose tissue from HIV-1 infected patients and abnormal adipocyte differentiation and insulin resistance. Lancet 2002, 359, 1026-1031.
    • (2002) Lancet , vol.359 , pp. 1026-1031
    • Bastard, J.-P.1    Caron, M.2    Vidal, H.3    Jan, V.4    Auclair, M.5    Vigouroux, C.6    Luboinski, J.7    Laville, M.8    Maachi, M.9    Girard, P.-M.10    Rozenbaum, W.11    Levan, P.12    Capeau, J.13
  • 7
    • 0034687250 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of 4-benzyl pyridinone derivatives as potent and selective non-nucleoside human immunodeficiency virus type 1 reverse transcriptase inhibitors
    • Dollé, V.; Nguyen, C. H.; Legraverend, M.;Aubertin,A.-M.;Kirn, A.; Andreola, M. L.; Ventura, M.; Tarrago-Litvak, L.; Bisagni, E. Synthesis and antiviral activity of 4-benzyl pyridinone derivatives as potent and selective non-nucleoside human immunodeficiency virus type 1 reverse transcriptase inhibitors. J.Med. Chem. 2000, 43, 3949-3962.
    • (2000) J.Med. Chem. , vol.43 , pp. 3949-3962
    • Dollé, V.1    Nguyen, C.H.2    Legraverend, M.3    Aubertin, A.-M.4    Kirn, A.5    Andreola, M.L.6    Ventura, M.7    Tarrago-Litvak, L.8    Bisagni, E.9
  • 10
    • 33846378472 scopus 로고    scopus 로고
    • Structure - Activity Relationship in the 3-Iodo-4-phenoxypyridinone (IOPY) Series: The Nature of the C-3 Substituent on Anti-HIV Activity
    • Benjahad, A.; Oumouch, S.; Guillemont, J.; Pasquier, E.; Mabire, D.; Andries, K.; Nguyen, C. H.; Grierson, D.S. Structure - Activity Relationship in the 3-Iodo-4-phenoxypyridinone (IOPY) Series: The Nature of the C-3 Substituent on Anti-HIV Activity. Bioorg. Med. Chem. Lett. 2007, 17, 712-716.
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 712-716
    • Benjahad, A.1    Oumouch, S.2    Guillemont, J.3    Pasquier, E.4    Mabire, D.5    Andries, K.6    Nguyen, C.H.7    Grierson, D.S.8
  • 12
    • 0029096567 scopus 로고
    • Synthesis and antiviral activity of 6-benzyl analogs of 1-[(2-hydroxyethoxy) methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents
    • Tanaka, H.; Takashima, H.; Ubasawa,M.; Sekiya, K.; Inouye, N.; Baba, M.; Shigeta, S.; Walker, R. T.; De Clercq, E.; Miyasaka, T. Synthesis and antiviral activity of 6-benzyl analogs of 1-[(2-hydroxyethoxy) methyl]-6-(phenylthio) thymine (HEPT) as potent and selective anti-HIV-1 agents. J. Med. Chem. 1995, 38, 2860-2865.
    • (1995) J. Med. Chem. , vol.38 , pp. 2860-2865
    • Tanaka, H.1    Takashima, H.2    Ubasawa, M.3    Sekiya, K.4    Inouye, N.5    Baba, M.6    Shigeta, S.7    Walker, R.T.8    De Clercq, E.9    Miyasaka, T.10
  • 13
    • 0033524008 scopus 로고    scopus 로고
    • Design of MKC-442 (Emivirine) analogues with improved activity against drug-resistant HIV mutants
    • Hopkins, A. L.; Ren, J.; Tanaka, H.; Baba, M.; Okamato, M.; Stuart, D. I.; Stammers, D. K. Design of MKC-442 (Emivirine) analogues with improved activity against drug-resistant HIV mutants. J. Med. Chem. 1999, 42, 4500-14005
    • (1999) J. Med. Chem. , vol.42 , pp. 4500-14005
    • Hopkins, A.L.1    Ren, J.2    Tanaka, H.3    Baba, M.4    Okamato, M.5    Stuart, D.I.6    Stammers, D.K.7
  • 14
    • 0037137588 scopus 로고    scopus 로고
    • Synthesis of novel N-1 (allyloxymethyl) analogues of MKC-442 (Emivirine) with improved activity against HIV-1 and its mutants
    • (a) El-Brollosy, N. R.; Jrgensen, P. T.; Dahan, B.; Boel, A.-M.; Pedersen, E. B.; Nielsen, C. Synthesis of novel N-1 (allyloxymethyl) analogues of MKC-442 (Emivirine) with improved activity against HIV-1 and its mutants. J. Med. Chem. 2002, 45, 5721-5726.
    • (2002) J. Med. Chem. , vol.45 , pp. 5721-5726
    • El-Brollosy, N.R.1    Jrgensen, P.T.2    Dahan, B.3    Boel, A.-M.4    Pedersen, E.B.5    Nielsen, C.6
  • 17
    • 8744299855 scopus 로고
    • Synthese von Pyridonen aus Enaminen und Cyanessigsauren
    • (a) Kappe, T.; Stelzel, H. P.; Ziegler, E. Synthese von Pyridonen aus Enaminen und Cyanessigsauren. Monatsh. Chem. 1983, 114, 953-963.
    • (1983) Monatsh. Chem. , vol.114 , pp. 953-963
    • Kappe, T.1    Stelzel, H.P.2    Ziegler, E.3
  • 18
    • 0345567614 scopus 로고
    • Potential nonsteroidal estrogens and antiestrogens. I. Synthesis of some 7-methoxy-2-(1H)-quinolone derivatives
    • (b) El-Mariah, F. A. A.; Kappe, T. Potential nonsteroidal estrogens and antiestrogens. I. Synthesis of some 7-methoxy-2-(1H)-quinolone derivatives. Croat. Chem. Acta 1986, 59 (1), 171-176.
    • (1986) Croat. Chem. Acta , vol.59 , Issue.1 , pp. 171-176
    • El-Mariah, F.A.A.1    Kappe, T.2
  • 19
    • 0034699898 scopus 로고    scopus 로고
    • Adverse effects of antiretroviral therapy
    • Carr, A.; Cooper, D. A. Adverse effects of antiretroviral therapy. Lancet 2000, 356, 1423.
    • (2000) Lancet , vol.356 , pp. 1423
    • Carr, A.1    Cooper, D.A.2
  • 20
    • 0030048748 scopus 로고    scopus 로고
    • Multidrug-resistant human immunodeficiency virus type 1 strains resulting from combination antiretroviral therapy
    • Iversen, A. K.; Shafer, R. W.; Wehrly, K.; Winters, M. A.; Chesebro, B.; Merigan, T. C.; Mullins, J. Multidrug-resistant human immunodeficiency virus type 1 strains resulting from combination antiretroviral therapy. J. Virol. 1996, 70, 1086. (Pubitemid 26029028)
    • (1996) Journal of Virology , vol.70 , Issue.2 , pp. 1086-1090
    • Iversen, A.K.N.1    Shafer, R.W.2    Wehrly, K.3    Winters, M.A.4    Mullins, J.I.5    Chesebro, B.6    Merigan, T.C.7
  • 21
    • 0001039344 scopus 로고
    • A synthesis of 2-hydroxyquinolizinones-(4)
    • Kappe, T. A synthesis of 2-hydroxyquinolizinones-(4). Monatsh. Chem. 1967, 98, 874-886.
    • (1967) Monatsh. Chem. , vol.98 , pp. 874-886
    • Kappe, T.1
  • 22
    • 0017385485 scopus 로고
    • Synthesis of 1-cyano-2-hydroxy-4-quinolizinones and corresponding 5-cyano-4-hydroxy-2-pyridones. Part 187: Synthesis of heterocycles. Part 9: Quinolizines and indolizines
    • Soliman, F. S. G.; Kappe, T. Synthesis of 1-cyano-2-hydroxy-4- quinolizinones and corresponding 5-cyano-4-hydroxy-2-pyridones. Part 187: Synthesis of heterocycles. Part 9: Quinolizines and indolizines. Pharmazie 1977, 32 (5), 278-279.
    • (1977) Pharmazie , vol.32 , Issue.5 , pp. 278-279
    • Soliman, F.S.G.1    Kappe, T.2
  • 24
    • 33947451350 scopus 로고
    • 1-Phenyl-2-(N-methyl-N-benzylamino)ethanol and Related Compounds
    • Beck, W.; Kaye, I. A.; Kogon, I. C.; Klein, H. C.; Burlant, W. J. 1-Phenyl-2-(N-methyl-N-benzylamino)ethanol and Related Compounds. J. Org. Chem. 1951, 16 (9), 1434-1441.
    • (1951) J. Org. Chem. , vol.16 , Issue.9 , pp. 1434-1441
    • Beck, W.1    Kaye, I.A.2    Kogon, I.C.3    Klein, H.C.4    Burlant, W.J.5
  • 25
  • 26
    • 0001184477 scopus 로고
    • A convenient synthesis of 3,5-disubstituted-1,2,4-triazoles
    • Francis, J. E.; Gorczyca, L. A.; Mazzenga, G. C.; Meckler, H. A convenient synthesis of 3,5-disubstituted-1,2,4-triazoles. Tetrahedron Lett. 1987, 28 (43), 5133-5136.
    • (1987) Tetrahedron Lett. , vol.28 , Issue.43 , pp. 5133-5136
    • Francis, J.E.1    Gorczyca, L.A.2    Mazzenga, G.C.3    Meckler, H.4
  • 27
    • 37049058402 scopus 로고
    • Triazoles. Part VII. Syntheses of substituted 1,2,4-triazoles
    • Browne, E. J.; Polya, J. B. Triazoles. Part VII. Syntheses of substituted 1,2,4-triazoles. J. Chem. Soc. 1962, 5149-5152.
    • (1962) J. Chem. Soc. , pp. 5149-5152
    • Browne, E.J.1    Polya, J.B.2
  • 28
    • 14444269869 scopus 로고
    • Triazoles. Part III. Mono- And di-methyl(phenyl)-1:2:4-triazoles
    • Atkinson, M. R.; Polya, J. B. Triazoles. Part III. Mono- and di-methyl(phenyl)-1:2:4-triazoles. J. Chem. Soc. 1954, 3319-3324.
    • (1954) J. Chem. Soc. , pp. 3319-3324
    • Atkinson, M.R.1    Polya, J.B.2
  • 29
    • 0025275481 scopus 로고
    • Novel benzamides as selective and potent gastric prokinetic agents. 1. Synthesis and structure-activity relationships of N-[(2-morpholinyl)alkyl] benzamides
    • Kato, S.; Morie, T.; Hino, K.; Kon, T.; Naruto, S.; Yoshida, N.; Karasawa, T.; Matsumoto, J. Novel benzamides as selective and potent gastric prokinetic agents. 1. Synthesis and structure-activity relationships of N-[(2-morpholinyl)alkyl]benzamides. J. Med. Chem. 1990, 33 (5), 1406-1413.
    • (1990) J. Med. Chem. , vol.33 , Issue.5 , pp. 1406-1413
    • Kato, S.1    Morie, T.2    Hino, K.3    Kon, T.4    Naruto, S.5    Yoshida, N.6    Karasawa, T.7    Matsumoto, J.8
  • 30
    • 72249109598 scopus 로고
    • Benzoic acid compound and use thereof as medicine
    • PCT Int. Appl. WO 9526953
    • Kawakita, T.; Kuroita, T.; Murozono, T.; Hakira, H.; Haga, K. Benzoic acid compound and use thereof as medicine. PCT Int. Appl. WO 9526953, 1995.
    • (1995)
    • Kawakita, T.1    Kuroita, T.2    Murozono, T.3    Hakira, H.4    Haga, K.5


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