메뉴 건너뛰기




Volumn 19, Issue 6, 2014, Pages 7104-7121

Synthesis and biological evaluation of novel 2-Arylalkylthio-5-iodine-6- substituted-benzyl-pyrimidine-4(3H)-ones as Potent HIV-1 Non-Nucleoside reverse transcriptase inhibitors

Author keywords

Docking; HIV; IC50; NNRTIs; S DABOs

Indexed keywords

RNA DIRECTED DNA POLYMERASE INHIBITOR;

EID: 84903308128     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19067104     Document Type: Article
Times cited : (11)

References (27)
  • 2
    • 10644257857 scopus 로고    scopus 로고
    • Progress in HIV non-nucleoside reverse transcriptase inhibitors (NNRTIs
    • Ting, Z.; Lan, X. Progress in HIV non-nucleoside reverse transcriptase inhibitors (NNRTIs). Acta Pharm. Sin. 2004, 39, 666-672.
    • (2004) Acta Pharm. Sin. , vol.39 , pp. 666-672
    • Ting, Z.1    Lan, X.2
  • 4
    • 77950920637 scopus 로고    scopus 로고
    • The newest developments in anti-HIV-1 drugs
    • Zhang, X. The newest developments in anti-HIV-1 drugs. Acta Pharm. Sin. 2010, 45, 194-204.
    • (2010) Acta Pharm. Sin. , vol.45 , pp. 194-204
    • Zhang, X.1
  • 5
    • 12144265244 scopus 로고    scopus 로고
    • Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs): Past present, and future
    • De Clercq, E. Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs): Past, Present, and Future. Chem. Biodivers. 2004, 1, 44-64.
    • (2004) Chem. Biodivers. , vol.1 , pp. 44-64
    • De Clercq, E.1
  • 6
    • 0027521797 scopus 로고
    • 3.4-Dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines(DABOs): A new class of specific inhibitors of human immunodeficiency virus type
    • Artico, M.; Massa, S.; Mai, A.; Marongiu, M.E .; Piras, G.; Tramontano, E.; la Colla, P. 3.4-Dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines(DABOs): A new class of specific inhibitors of human immunodeficiency virus type Antivir. Chem. Chemother. 1993, 4, 361-368.
    • (1993) Antivir. Chem. Chemother , vol.4 , pp. 361-368
    • Artico, M.1    Massa, S.2    Mai, A.3    Marongiu, M.E.4    Piras, G.5    Tramontano, E.6    La Colla, P.7
  • 8
    • 60549105209 scopus 로고    scopus 로고
    • Synthesis and in vitro anti-HIV evaluation of a new series of 6-arylmethyl-s ubstituted S-DABOs as potential non-nucleoside HIV-1 reverse transcriptase inhibitors
    • Wang, Y.; Chen, F.; de Clercq, E.; Balzarini, J.; Pannecouque, C. Synthesis and in vitro anti-HIV evaluation of a new series of 6-arylmethyl-s ubstituted S-DABOs as potential non-nucleoside HIV-1 reverse transcriptase inhibitors. Eur. J. Med. Chem. 2009, 44, 1016-1023.
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 1016-1023
    • Wang, Y.1    Chen, F.2    De Clercq, E.3    Balzarini, J.4    Pannecouque, C.5
  • 9
    • 10744230514 scopus 로고    scopus 로고
    • Computer-aided design, syn thesis and anti-hiv-1 activity in vitro of 2-alkylamino-6-[1-(2,6-difluorophenyl)alkyl]-3,4-dihydro-5-alkylpyrimidin-4(3H) -ones as novel potent n on-nucleoside reverse transcriptase inhibitors, also active against the Y181C variant
    • Ragno R.Mai A.Sbardella S.Artico M.Massa S.Musiu C.Mura M.Marceddu T.Cadeddu A.la Colla P. Computer-aided design, syn thesis and anti-hiv-1 activity in vitro of 2-alkylamino-6-[1-(2,6-difluorophenyl)alkyl]-3,4-dihydro-5- alkylpyrimidin-4(3H)-ones as novel potent n on-nucleoside reverse transcriptase inhibitors, also active against the Y181C variant, J. Med. Chem. 2004,47,928-934.
    • (2004) J. Med. Chem. , vol.47 , pp. 928-934
    • Ragno, R.1    Mai, A.2    Sbardella, S.3    Artico, M.4    Massa, S.5    Musiu, C.6    Mura, M.7    Marceddu, T.8    Cadeddu, A.9    La Colla, P.10
  • 10
    • 17544387814 scopus 로고    scopus 로고
    • Mo dels which explain the inhibition of reverse transcriptase by HIV-1 specific (thio)carboxaanilide derivatives
    • Esnouf, R.M.; Stuart, D.I.; de Clercq, E.; Schwartz, E.; Balzarini, J. Mo dels which explain the inhibition of reverse transcriptase by HIV-1 specific (thio)carboxaanilide derivatives. Biochem. Biophys. Res. Commn. 1997, 234, 458-464.
    • (1997) Biochem. Biophys. Res. Commn. , vol.234 , pp. 458-464
    • Esnouf, R.M.1    Stuart, D.I.2    De Clercq, E.3    Schwartz, E.4    Balzarini, J.5
  • 11
    • 0028172345 scopus 로고
    • Locations of anti-AIDS drug binding sites and resistance mutations in the three-dimensional structure of HIV-1 reverse transcriptas e. Implications for mechanisms of drug inhibition and resistance
    • Tantillo, C.; Ding, J.; Jacobo-Molina, A.; Nanni, R.G.; Boyer, P.L.; Hughes, S.H.; Pauwels, R.; Andries, K.; Janssen, P.A.; Arnold, E. Locations of anti-AIDS drug binding sites and resistance mutations in the three-dimensional structure of HIV-1 reverse transcriptas e. Implications for mechanisms of drug inhibition and resistance. J. Mol. Boil. 1994, 243, 369-387.
    • (1994) J. Mol. Boil. , vol.243 , pp. 369-387
    • Tantillo, C.1    Ding, J.2    Jacobo-Molina, A.3    Nanni, R.G.4    Boyer, P.L.5    Hughes, S.H.6    Pauwels, R.7    Andries, K.8    Janssen, P.A.9    Arnold, E.10
  • 12
    • 84865651416 scopus 로고    scopus 로고
    • Research progress of HEPT analogs as nonnucleoside HIV-1 reverse transcriptase inhibitors
    • Meng, G.; Chen, F. Research progress of HEPT analogs as nonnucleoside HIV-1 reverse transcriptase inhibitors. Chin. J. Med. Chem. 2004, 14, 56-64.
    • (2004) Chin. J. Med. Chem. , vol.14 , pp. 56-64
    • Meng, G.1    Chen, F.2
  • 13
    • 0026693137 scopus 로고
    • Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed wi th an inhibitor
    • Kohlstaedt, L.A.; Wang, J.; Friedman, J.M.; Rice, P.A.; Steits, T.A. Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed wi th an inhibitor. Science 1992, 256, 1783-1790.
    • (1992) Science , vol.256 , pp. 1783-1790
    • Kohlstaedt, L.A.1    Wang, J.2    Friedman, J.M.3    Rice, P.A.4    Steits, T.A.5
  • 14
    • 9744258219 scopus 로고    scopus 로고
    • Crystallography and the design of anti-AIDS drugs: Conformational flexibility and positional adapt ability are important in the design of non-nucleoside HIV-1 reverse transcriptase inhibitors
    • Das, K.; Lewi, P.J.; Hughes, S.H.; Arnold, E. Crystallography and the design of anti-AIDS drugs: Conformational flexibility and positional adapt ability are important in the design of non-nucleoside HIV-1 reverse transcriptase inhibitors. Prog. Biophys. Mol. Biol. 2005, 88, 209-231.
    • (2005) Prog. Biophys. Mol. Biol. , vol.88 , pp. 209-231
    • Das, K.1    Lewi, P.J.2    Hughes, S.H.3    Arnold, E.4
  • 15
    • 78651248497 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel dihydro-aryl/alkylsulfanyl- cyclohexylmethyl oxopyrimidines (S-DACOs) as high active anti-HIV agents
    • He, Y.; Long, J.; Zhang, S.; Li, C.; Lai, C.; Zhang, C .; Li, D.; Zhang, D.; Wang, H.; Cai, Q.; et al. Synthesis and biological evaluation of novel dihydro-aryl/alkylsulfanyl-cyclohexylmethyl oxopyrimidines (S-DACOs) as high active anti-HIV agents. Bioorg. Med. Chem. Lett. 2011, 21, 694-697.
    • (2011) Bioorg. Med. Chem. Lett. , vol.221 , pp. 694-697
    • He, Y.1    Long, J.2    Zhang, S.3    Li, C.4    Lai, C.5    Zhang, C.6    Li, D.7    Zhang, D.8    Wang, H.9    Cai, Q.10
  • 16
    • 77951206884 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel C5 halogen-functionalized S-DABO as potent HIV-1 non-nucleoside reverse transcriptase inhibitors
    • Qin, H.; Liu, C.; Guo, Y.; Wang, R.; Zhang, J.; Ma, L.; Zhang, Z.; Wang, X.; Cui, Y.; Liu, J. Synthesis and biological evaluation of novel C5 halogen-functionalized S-DABO as potent HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorg. Med. Chem. 2010, 18, 3231-3237.
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 3231-3237
    • Qin, H.1    Liu, C.2    Guo, Y.3    Wang, R.4    Zhang, J.5    Ma, L.6    Zhang, Z.7    Wang, X.8    Cui, Y.9    Liu, J.10
  • 17
    • 84863290357 scopus 로고    scopus 로고
    • Design, Synthesis and Biological Evaluation of 1-[(2-benzyloxyl/alkoxyl) methyl]-5-halo-6-aryluracils as Potent HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors with Improved Drug Resistance Profile
    • Wang, X.; Zhang, J.; Huang, Y.; Wang, R.; Zhang, L.; Qiao, K.; Li, L.; Liu, C.; Ouyang, Y.; Xu, W.; et al. Design, Synthesis and Biological Evaluation of 1-[(2-benzyloxyl/alkoxyl) methyl]-5-halo-6-aryluracils as Potent HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors with Improved Drug Resistance Profile. J. Med. Chem. 2012, 55, 2242-2250.
    • (2012) J. Med. Chem. , vol.55 , pp. 2242-2250
    • Wang, X.1    Zhang, J.2    Huang, Y.3    Wang, R.4    Zhang, L.5    Qiao, K.6    Li, L.7    Liu, C.8    Ouyang, Y.9    Xu, W.10
  • 18
    • 33947440940 scopus 로고
    • The Structure of Meldrum?s Supposed α-Lacto nic Acid
    • Davidson, D.; Berhardt, S.A. The Structure of Meldrum?s Supposed α-Lacto nic Acid. J. Am. Chem. Soc. 1948, 70, 3426-3428.
    • (1948) J. Am. Chem. Soc. , vol.70 , pp. 3426-3428
    • Davidson, D.1    Berhardt, S.A.2
  • 19
    • 0000681727 scopus 로고
    • Methyl Phenylacetylacetate from Phenylacetyl Chloride and Meldrum?s Acid
    • Oikawa, Y.; Yoshika, T.; Sugano, K.; Yonemitsu, O. Methyl Phenylacetylacetate from Phenylacetyl Chloride and Meldrum?s Acid. Org. Synth. 1985, 63, 198-202.
    • (1985) Org. Synth. , vol.63 , pp. 198-202
    • Oikawa, Y.1    Yoshika, T.2    Sugano, K.3    Yonemitsu, O.4
  • 20
    • 0029111877 scopus 로고
    • Easy synthesis of 5,6-disubstituted acyclouridine derivatives
    • Danel, K.; Larse n, E.; Pedersen, E.B. Easy synthesis of 5,6-disubstituted acyclouridine derivatives. Synthesis 1995, 8, 934-936.
    • (1995) Synthesis , vol.8 , pp. 934-936
    • Danel, K.1    Larsen, E.2    Pedersen, E.B.3
  • 21
    • 37349004798 scopus 로고    scopus 로고
    • Dihydro-alkylthio-benzyl-oxopyrimidines as Inhibitors of reverse transcriptase: Synthesis and rationalization of the biological data on both wild-type enzyme and relevant clinical mutants
    • Mugnaini, C.; Alongi, M.; Togninelli, A.; Gevariya, H.; Rizzi, A.; Manetti, F.; Bernardini, C.; Angeli, L.; Tafi, A.; Bellucci, L.; et al. Dihydro-alkylthio-benzyl-oxopyrimidines as Inhibitors of reverse transcriptase: synthesis and rationalization of the biological data on both wild-type enzyme and relevant clinical mutants. J. Med. Chem. 2007, 50, 6580-6595.
    • (2007) J. Med. Chem. , vol.50 , pp. 6580-6595
    • Mugnaini, C.1    Alongi, M.2    Togninelli, A.3    Gevariya, H.4    Rizzi, A.5    Manetti, F.6    Bernardini, C.7    Angeli, L.8    Tafi, A.9    Bellucci, L.10
  • 23
    • 77950861081 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel 2-arylalkylthio-4-amino-6- benzyl pyrimidines as potent HIV-1 non-nucleoside reverse t ranscriptase inhibitors
    • Q in, H.; Liu, C.; Zhang, J.; Guo, Y.; Zhang, S.; Zhang, Z.; Wang, X.; Zhang, L.; Liu, J. Synthesis and biological evaluation of novel 2-arylalkylthio-4-amino-6-benzyl pyrimidines as potent HIV-1 non-nucleoside reverse t ranscriptase inhibitors. Bioorg. Med. Chem. Lett. 2010, 20, 3003-3005.
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 3003-3005
    • Qin, H.1    Liu, C.2    Zhang, J.3    Guo, Y.4    Zhang, S.5    Zhang, Z.6    Wang, X.7    Zhang, L.8    Liu, J.9
  • 24
    • 0024999263 scopus 로고
    • Cerium(iv-mediated halogenation at c-5 of uracil derivatives
    • Asakura, J.; Robins, M.J. Cerium(IV)-Mediated Halogenation at C-5 of Uracil Derivatives. J. Org. Chem. 1990, 55, 4928-4933.
    • (1990) J. Org. Chem. , vol.55 , pp. 4928-4933
    • Asakura, J.1    Robins, M.J.2
  • 25
    • 2942553016 scopus 로고    scopus 로고
    • Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 1: Discovery of novel orally active inhibitors of human thymidine phosphorylase
    • Yano, S.; Kazuno, H.; Suzuki, N.; Emura, T.; Wierzba, K.; Yamashita, J.; Tada, Y.; Yamada, Y.; Fukushima, M.; Asao, T. Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 1: Discovery of novel orally active inhibitors of human thymidine phosphorylase. Bioorg. Med. Chem. 2004, 12, 3431-3441.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 3431-3441
    • Yano, S.1    Kazuno, H.2    Suzuki, N.3    Emura, T.4    Wierzba, K.5    Yamashita, J.6    Tada, Y.7    Yamada, Y.8    Fukushima, M.9    Asao, T.10
  • 26
    • 35148883143 scopus 로고    scopus 로고
    • The design and synthesis of N-1-alkylated-5-aminoaryalkylsubstituted-6- methyl uracils as potential non-nucleoside HIV-1 RT inhibitors
    • Lu, X .; Chen, Y.; Guo, Y.; Liu, Z.; Shi, Y.; Xu, Y.; Wang, X.; Zhang, Z.; Liu, J. The design and synthesis of N-1-alkylated-5- aminoaryalkylsubstituted-6-methyl uracils as potential non-nucleoside HIV-1 RT inhibitors. Bioorg . Med. Chem. 2007, 15, 7399-7407.
    • (2007) Bioorg . Med. Chem. , vol.15 , pp. 7399-7407
    • Lu, X.1    Chen, Y.2    Guo, Y.3    Liu, Z.4    Shi, Y.5    Xu, Y.6    Wang, X.7    Zhang, Z.8    Liu, J.9
  • 27
    • 11644261806 scopus 로고    scopus 로고
    • Complexes of HIV-1 reverse transcriptase with inhibitors o f the HEPT series reveal conformational changes relevant to the design of potent non-nucleoside inhibitors
    • Morris, G.M.; Goodsell, D.S.; Halliday, R.S.; Huey, R.; Hart, W.E.; Belew, R.K.; Olson, A.J. Complexes of HIV-1 reverse transcriptase with inhibitors o f the HEPT series reveal conformational changes relevant to the design of potent non-nucleoside inhibitors. J. Comput. Chem. 1998, 19, 1639-1662.
    • (1998) J. Comput. Chem. , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.