메뉴 건너뛰기




Volumn 76, Issue 4, 2010, Pages 330-339

Synthesis, biological evaluation and molecular modeling studies of N-aryl-2-arylthioacetamides as non-nucleoside HIV-1 reverse transcriptase inhibitors

Author keywords

antiviral agents; molecular docking; N aryl 2 arylthioacetamides; non nucleoside reverse transcriptase inhibitors; structure activity relationships

Indexed keywords

N (5 CHLORO 2 PYRIDINYL) N' [2 (4 ETHOXY 3 FLUORO 2 PYRIDINYL)ETHYL]THIOUREA; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; THIOACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG; VRX 480773;

EID: 77956400880     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2010.01017.x     Document Type: Article
Times cited : (12)

References (34)
  • 1
    • 0023091963 scopus 로고
    • Strategies for antiviral therapy in AIDS
    • Mitsuya H., Broder S. (1987) Strategies for antiviral therapy in AIDS. Nature 325 : 773 778.
    • (1987) Nature , vol.325 , pp. 773-778
    • Mitsuya, H.1    Broder, S.2
  • 2
    • 0032437454 scopus 로고    scopus 로고
    • The role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection
    • De Clercq E. (1998) The role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection. Antiviral Res 38 : 153 179.
    • (1998) Antiviral Res , vol.38 , pp. 153-179
    • De Clercq, E.1
  • 3
    • 33747162419 scopus 로고    scopus 로고
    • The regulation of HIV-1 transcription: Molecular targets for chemotherapeutic intervention
    • Stevens M., De Clercq E., Balzarini J. (2006) The regulation of HIV-1 transcription: molecular targets for chemotherapeutic intervention. Med Chem Rev 26 : 595 625.
    • (2006) Med Chem Rev , vol.26 , pp. 595-625
    • Stevens, M.1    De Clercq, E.2    Balzarini, J.3
  • 4
    • 33646848691 scopus 로고    scopus 로고
    • Current developments in HIV chemotherapy
    • Meadows D.C., Gervay H.J. (2006) Current developments in HIV chemotherapy. Chem Med Chem 1 : 16 29.
    • (2006) Chem Med Chem , vol.1 , pp. 16-29
    • Meadows, D.C.1    Gervay, H.J.2
  • 5
    • 0028925773 scopus 로고
    • Mechanism of inhibition of HIV-1 reverse transcriptase by nonnucleoside inhibitors
    • Spence R.A., Kati W.M., Anderson K.S., Johnson K.A. (1995) Mechanism of inhibition of HIV-1 reverse transcriptase by nonnucleoside inhibitors. Science 267 : 988 993.
    • (1995) Science , vol.267 , pp. 988-993
    • Spence, R.A.1    Kati, W.M.2    Anderson, K.S.3    Johnson, K.A.4
  • 6
    • 18744416007 scopus 로고    scopus 로고
    • Highly active antiretroviral therapy: Current state of the art new agents and their pharmacological interactions useful for improving therapeutic outcome
    • Barbaro G., Scozzafava A., Mastrolorenzo A., Supuran C.T. (2005) Highly active antiretroviral therapy: current state of the art new agents and their pharmacological interactions useful for improving therapeutic outcome. Curr Pharm Des 11 : 1805 1843.
    • (2005) Curr Pharm des , vol.11 , pp. 1805-1843
    • Barbaro, G.1    Scozzafava, A.2    Mastrolorenzo, A.3    Supuran, C.T.4
  • 7
  • 8
    • 0028785708 scopus 로고
    • L-743, 726 (DMP-266): A novel, highly potent nonnucleoside inhibitor of the human immunodeficiency virus type 1 reverse transcriptase
    • Young S.D., Britcher S.F., Tran L.O., Payne L.S., Lumma W.C., Lyle T.A., Huff J.R. et al. (1995) L-743, 726 (DMP-266): a novel, highly potent nonnucleoside inhibitor of the human immunodeficiency virus type 1 reverse transcriptase. Antimicrob Agents Chemother 39 : 2602 2605.
    • (1995) Antimicrob Agents Chemother , vol.39 , pp. 2602-2605
    • Young, S.D.1    Britcher, S.F.2    Tran, L.O.3    Payne, L.S.4    Lumma, W.C.5    Lyle, T.A.6    Huff, J.R.7
  • 9
    • 0029928409 scopus 로고    scopus 로고
    • Delavirdine mesylate, a potent non-nucleoside HIV-1 reverse transcriptase inhibitor
    • Freimuth W.W. (1996) Delavirdine mesylate, a potent non-nucleoside HIV-1 reverse transcriptase inhibitor. Adv Exp Med Bio 394 : 279 289.
    • (1996) Adv Exp Med Bio , vol.394 , pp. 279-289
    • Freimuth, W.W.1
  • 11
    • 0029809694 scopus 로고    scopus 로고
    • Highly favorable antiviral activity and resistance profile of the novel thiocarboxanilide pentenyloxy ether derivatives UC-781 and UC-82 as inhibitors of human immunodeficiency virus type 1 replication
    • Balzarini J., Pelemans H., Aquaro S., Perno C.F., Witvrouw M., Schols D., De Clercq E., Karlsson A. (1996) Highly favorable antiviral activity and resistance profile of the novel thiocarboxanilide pentenyloxy ether derivatives UC-781 and UC-82 as inhibitors of human immunodeficiency virus type 1 replication. Mol Pharmacol 50 : 394 401.
    • (1996) Mol Pharmacol , vol.50 , pp. 394-401
    • Balzarini, J.1    Pelemans, H.2    Aquaro, S.3    Perno, C.F.4    Witvrouw, M.5    Schols, D.6    De Clercq, E.7    Karlsson, A.8
  • 14
    • 0032918170 scopus 로고    scopus 로고
    • Perspectives of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection
    • De Clercq E. (1999) Perspectives of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection. Farmaco 54 : 26 45.
    • (1999) Farmaco , vol.54 , pp. 26-45
    • De Clercq, E.1
  • 15
    • 37249019061 scopus 로고    scopus 로고
    • Inhibitors of HIV-I reverse transcriptase
    • Ilina T., Parniak M.A. (2008) Inhibitors of HIV-I reverse transcriptase. Adv Pharmacol 56 : 121 167.
    • (2008) Adv Pharmacol , vol.56 , pp. 121-167
    • Ilina, T.1    Parniak, M.A.2
  • 16
    • 33745727133 scopus 로고    scopus 로고
    • Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors
    • Wang Z., Wu B., Kuhen K.L., Bursulaya B., Nguyen T.N., Nguyen D.G., He Y. (2006) Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorg Med Chem Lett 16 : 4174 4177.
    • (2006) Bioorg Med Chem Lett , vol.16 , pp. 4174-4177
    • Wang, Z.1    Wu, B.2    Kuhen, K.L.3    Bursulaya, B.4    Nguyen, T.N.5    Nguyen, D.G.6    He, Y.7
  • 18
    • 53349162138 scopus 로고    scopus 로고
    • 123-Thiadiazole thioacetanilides as a novel class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors
    • Zhan P., Liu X., Cao Y., Wang Y., Pannecouque C., De Clercq E. (2008) 123-Thiadiazole thioacetanilides as a novel class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorg Med Chem Lett 18 : 5368 5371.
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 5368-5371
    • Zhan, P.1    Liu, X.2    Cao, Y.3    Wang, Y.4    Pannecouque, C.5    De Clercq, E.6
  • 19
    • 33846637261 scopus 로고    scopus 로고
    • A novel nonnucleoside analogue that inhibits human immunodeficiency virus type 1 isolates resistant to current nonnucleoside reverse transcriptase inhibitors
    • Zhang Z., Xu W., Koh Y.H., Shim J.H., Girardet J.L., Yeh L.T., Hamatake R.K., Hong Z. (2007) A novel nonnucleoside analogue that inhibits human immunodeficiency virus type 1 isolates resistant to current nonnucleoside reverse transcriptase inhibitors. Antimicrob Agents Chemother 51 : 429 437.
    • (2007) Antimicrob Agents Chemother , vol.51 , pp. 429-437
    • Zhang, Z.1    Xu, W.2    Koh, Y.H.3    Shim, J.H.4    Girardet, J.L.5    Yeh, L.T.6    Hamatake, R.K.7    Hong, Z.8
  • 20
    • 62549102032 scopus 로고    scopus 로고
    • Receptor- and ligand-based 3D-QSAR study for a series of non-nucleoside HIV-1 reverse transcriptase inhibitors
    • Hu R., Barbault F., Delamar M., Zhang R. (2009) Receptor- and ligand-based 3D-QSAR study for a series of non-nucleoside HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem 17 : 2400 2409.
    • (2009) Bioorg Med Chem , vol.17 , pp. 2400-2409
    • Hu, R.1    Barbault, F.2    Delamar, M.3    Zhang, R.4
  • 21
    • 34248562794 scopus 로고    scopus 로고
    • Synthesis of novel 3′-spirocyclic-oxindole derivatives and assessment of their cytostatic activities
    • Yong S.R., Ung A.T., Pyne S.G., Skelton B.W., White A.H. (2007) Synthesis of novel 3′-spirocyclic-oxindole derivatives and assessment of their cytostatic activities. Tetrahedron 63 : 5579 5586.
    • (2007) Tetrahedron , vol.63 , pp. 5579-5586
    • Yong, S.R.1    Ung, A.T.2    Pyne, S.G.3    Skelton, B.W.4    White, A.H.5
  • 22
    • 42449105761 scopus 로고    scopus 로고
    • One-pot synthesis of diverse 4-di(tri)fluoromethyl-3-cyanopyridine-2(1H)- thiones and their utilities in the cascade synthesis of annulated heterocycles
    • Rodinovskaya L.A., Shestopalov A.M., Gromova A.V., Shestopalov A.A. (2008) One-pot synthesis of diverse 4-di(tri)fluoromethyl-3-cyanopyridine-2(1H)- thiones and their utilities in the cascade synthesis of annulated heterocycles. J Comb Chem 10 : 313 322.
    • (2008) J Comb Chem , vol.10 , pp. 313-322
    • Rodinovskaya, L.A.1    Shestopalov, A.M.2    Gromova, A.V.3    Shestopalov, A.A.4
  • 23
    • 58149090406 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of N-carboxyphenylpyrrole derivatives as potent HIV fusion inhibitors targeting gp41
    • Liu K., Lu H., Hou L., Qi Z., Teixeira C., Barbault F., Fan B.T., Liu S., Jiang S., Xie L. (2008) Design, synthesis, and biological evaluation of N-carboxyphenylpyrrole derivatives as potent HIV fusion inhibitors targeting gp41. J Med Chem 51 : 7843 7854.
    • (2008) J Med Chem , vol.51 , pp. 7843-7854
    • Liu, K.1    Lu, H.2    Hou, L.3    Qi, Z.4    Teixeira, C.5    Barbault, F.6    Fan, B.T.7    Liu, S.8    Jiang, S.9    Xie, L.10
  • 24
    • 0035087062 scopus 로고    scopus 로고
    • Anti-human immunodeficiency virus activity of YK-FH312 (a betulinic acid derivative), a novel compound blocking viral maturation
    • Kanamoto T., Kashiwada Y., Kanbara K., Gotoh K., Yoshimori M., Goto T., Sano K., Nakashima H. (2001) Anti-human immunodeficiency virus activity of YK-FH312 (a betulinic acid derivative), a novel compound blocking viral maturation. Antimicrob Agents Chemother 45 : 1225 1230.
    • (2001) Antimicrob Agents Chemother , vol.45 , pp. 1225-1230
    • Kanamoto, T.1    Kashiwada, Y.2    Kanbara, K.3    Gotoh, K.4    Yoshimori, M.5    Goto, T.6    Sano, K.7    Nakashima, H.8
  • 25
    • 0037061639 scopus 로고    scopus 로고
    • Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase
    • Silvestri R., Artico M., De Martino G., Ragno Ri., Massa S., Loddo R., Murgioni C., Loi A.G., La Colla P., Pani A. (2002) Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5- nitroimidazoles targeted at the HIV-1 reverse transcriptase. J Med Chem 45 : 1567 1576.
    • (2002) J Med Chem , vol.45 , pp. 1567-1576
    • Silvestri, R.1    Artico, M.2    De Martino, G.3    Ragno, R.4    Massa, S.5    Loddo, R.6    Murgioni, C.7    Loi, A.G.8    La Colla, P.9    Pani, A.10
  • 27
    • 53249118917 scopus 로고    scopus 로고
    • Antitumor studies, part 5: Synthesis antitumor activity and molecular docking study of 5-(monosubstituted amino)-2-deoxo-2-phenyl-5-deazaflavins
    • Shrestha A.R., Ali H.I., Ashida N., Nagamatsu T. (2008) Antitumor studies, part 5: synthesis antitumor activity and molecular docking study of 5-(monosubstituted amino)-2-deoxo-2-phenyl-5-deazaflavins. Bioorg Med Chem 16 : 9161 9170.
    • (2008) Bioorg Med Chem , vol.16 , pp. 9161-9170
    • Shrestha, A.R.1    Ali, H.I.2    Ashida, N.3    Nagamatsu, T.4
  • 28
    • 57349130997 scopus 로고    scopus 로고
    • Discovery of new inhibitors of d-Alanine: D-Alanine ligase by structure-based virtual screening
    • Kovac A., Konc J., Vehar B., Bostock J.M., Chopra I., Janezic D., Gobec S. (2008) Discovery of new inhibitors of d-Alanine: d-Alanine ligase by structure-based virtual screening. J Med Chem 51 : 7442 7448.
    • (2008) J Med Chem , vol.51 , pp. 7442-7448
    • Kovac, A.1    Konc, J.2    Vehar, B.3    Bostock, J.M.4    Chopra, I.5    Janezic, D.6    Gobec, S.7
  • 29
    • 0029644484 scopus 로고
    • Structure of HIV-1 reverse transcriptase in a complex with the non-nucleoside inhibitor α-APA R95845 at 2.8 A resolution
    • Ding J., Das K., Tantillo C., Zhang W., Clark A.D.J., Jessen S., Lu X. et al. (1995) Structure of HIV-1 reverse transcriptase in a complex with the non-nucleoside inhibitor α-APA R95845 at 2.8 A resolution. Structure 3 : 365 379.
    • (1995) Structure , vol.3 , pp. 365-379
    • Ding, J.1    Das, K.2    Tantillo, C.3    Zhang, W.4    Clark, A.D.J.5    Jessen, S.6    Lu, X.7
  • 32
    • 0034059835 scopus 로고    scopus 로고
    • The HIV-1 reverse transcription (RT) process as target for RT inhibitors
    • Jonckheere H., Anne J., De Clercq E. (2000) The HIV-1 reverse transcription (RT) process as target for RT inhibitors. Med Res Rev 20 : 129 154.
    • (2000) Med Res Rev , vol.20 , pp. 129-154
    • Jonckheere, H.1    Anne, J.2    De Clercq, E.3
  • 34
    • 33646135276 scopus 로고    scopus 로고
    • Tyrosine kinase-role and significance in cancer
    • Paul M.K., Mukhopadhyay A.K. (2004) Tyrosine kinase-role and significance in cancer. Int J Med Sci 1 : 101 115.
    • (2004) Int J Med Sci , vol.1 , pp. 101-115
    • Paul, M.K.1    Mukhopadhyay, A.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.