메뉴 건너뛰기




Volumn 15, Issue 6, 2010, Pages 3958-3992

Design, synthesis and structure-activity studies of rhodanine derivatives as HIV-1 integrase inhibitors

Author keywords

2 thioxo 4 thiazolidinone; APE1; Docking; HIV 1; Integrase; Rhodanine

Indexed keywords

APEX1 PROTEIN, HUMAN; DNA (APURINIC OR APYRIMIDINIC SITE) LYASE; INTEGRASE INHIBITOR; RHODANINE;

EID: 77954296650     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15063958     Document Type: Article
Times cited : (41)

References (41)
  • 1
    • 63649087422 scopus 로고    scopus 로고
    • Raltegravir: The first HIV type 1 integrase inhibitor
    • Hicks, C.; Gulick, R. M. Raltegravir: the first HIV type 1 integrase inhibitor. Clin. Infect. Dis. 2009, 48, 931-939.
    • (2009) Clin. Infect. Dis. , vol.48 , pp. 931-939
    • Hicks, C.1    Gulick, R.M.2
  • 2
    • 77954257512 scopus 로고    scopus 로고
    • Raltegravir: The evidence of its therapeutic value in HIV-1 infection
    • Ramkumar, K.; Neamati, N. Raltegravir: The evidence of its therapeutic value in HIV-1 infection. Core Evidence 2009, 4, 131-147.
    • (2009) Core Evidence , vol.4 , pp. 131-147
    • Ramkumar, K.1    Neamati, N.2
  • 3
    • 0026034790 scopus 로고
    • Activities of human immunodeficiency virus (HIV) integration protein in vitro: Specific cleavage and integration of HIV DNA
    • Bushman, F. D.; Craigie, R. Activities of human immunodeficiency virus (HIV) integration protein in vitro: specific cleavage and integration of HIV DNA. Proc. Natl. Acad. Sci. USA 1991, 88, 1339-1343.
    • (1991) Proc. Natl. Acad. Sci. USA , vol.88 , pp. 1339-1343
    • Bushman, F.D.1    Craigie, R.2
  • 4
    • 0035968306 scopus 로고    scopus 로고
    • HIV integrase, a brief overview from chemistry to therapeutics
    • Craigie, R. HIV integrase, a brief overview from chemistry to therapeutics. J. Biol. Chem. 2001, 276, 23213-23216.
    • (2001) J. Biol. Chem. , vol.276 , pp. 23213-23216
    • Craigie, R.1
  • 5
    • 33847648769 scopus 로고    scopus 로고
    • Molecular mechanisms of HIV integration and therapeutic intervention
    • Vandegraaff, N.; Engelman, A. Molecular mechanisms of HIV integration and therapeutic intervention. Expert Rev. Mol. Med. 2007, 9, 1-19.
    • (2007) Expert Rev. Mol. Med. , vol.9 , pp. 1-19
    • Vandegraaff, N.1    Engelman, A.2
  • 6
    • 63549089353 scopus 로고    scopus 로고
    • Raltegravir, elvitegravir, and metoogravir: The birth of "me-too" HIV-1 integrase inhibitors
    • Serrao, E.; Odde, S.; Ramkumar, K.; Neamati, N. Raltegravir, elvitegravir, and metoogravir: the birth of "me-too" HIV-1 integrase inhibitors. Retrovirology 2009, 6, 25-49.
    • (2009) Retrovirology , vol.6 , pp. 25-49
    • Serrao, E.1    Odde, S.2    Ramkumar, K.3    Neamati, N.4
  • 8
    • 34447548922 scopus 로고    scopus 로고
    • HIV integrase inhibitors as therapeutic agents in AIDS
    • Nair, V.; Chi, G. HIV integrase inhibitors as therapeutic agents in AIDS. Rev. Med. Virol. 2007, 17, 277-295.
    • (2007) Rev. Med. Virol. , vol.17 , pp. 277-295
    • Nair, V.1    Chi, G.2
  • 10
    • 34547108566 scopus 로고    scopus 로고
    • New developments in diketo-containing inhibitors of HIV-1 integrase
    • Zhao, G.; Wang, C.; Liu, C.; Lou, H. New developments in diketo-containing inhibitors of HIV-1 integrase. Mini Rev. Med. Chem. 2007, 7, 707-725.
    • (2007) Mini Rev. Med. Chem. , vol.7 , pp. 707-725
    • Zhao, G.1    Wang, C.2    Liu, C.3    Lou, H.4
  • 11
    • 41649096265 scopus 로고    scopus 로고
    • Quinolone 3-carboxylic acid pharmacophore: Design of second generation HIV-1 integrase inhibitors
    • Dayam, R.; Al-Mawsawi, L. Q.; Zawahir, Z.; Witvrouw, M.; Debyser, Z.; Neamati, N. Quinolone 3-carboxylic acid pharmacophore: design of second generation HIV-1 integrase inhibitors. J. Med. Chem. 2008, 51, 1136-1144.
    • (2008) J. Med. Chem. , vol.51 , pp. 1136-1144
    • Dayam, R.1    Al-Mawsawi, L.Q.2    Zawahir, Z.3    Witvrouw, M.4    Debyser, Z.5    Neamati, N.6
  • 12
    • 29144509688 scopus 로고    scopus 로고
    • Diketo acid pharmacophore. 2. Discovery of structurally diverse inhibitors of HIV-1 integrase
    • DOI 10.1021/jm050837a
    • Dayam, R.; Sanchez, T.; Neamati, N. Diketo acid pharmacophore. 2. Discovery of structurally diverse inhibitors of HIV-1 integrase. J. Med. Chem. 2005, 48, 8009-8015. (Pubitemid 41798431)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.25 , pp. 8009-8015
    • Dayam, R.1    Sanchez, T.2    Neamati, N.3
  • 13
    • 33846164748 scopus 로고    scopus 로고
    • Design of second generation HIV-1 integrase inhibitors
    • DOI 10.2174/138161207779313687
    • Deng, J.; Dayam, R.; Al-Mawsawi, L. Q.; Neamati, N. Design of second generation HIV-1 integrase inhibitors. Curr. Pharm. Des. 2007, 13, 129-141. (Pubitemid 46085288)
    • (2007) Current Pharmaceutical Design , vol.13 , Issue.2 , pp. 129-141
    • Deng, J.1    Dayam, R.2    Al-Mawsawi, L.Q.3    Neamati, N.4
  • 14
    • 12144254795 scopus 로고    scopus 로고
    • Beta-diketo acid pharmacophore hypothesis. 1. Discovery of a novel class of HIV-1 integrase inhibitors
    • Dayam, R.; Sanchez, T.; Clement, O.; Shoemaker, R.; Sei, S.; Neamati, N. Beta-diketo acid pharmacophore hypothesis. 1. Discovery of a novel class of HIV-1 integrase inhibitors. J. Med. Chem. 2005, 48, 111-120.
    • (2005) J. Med. Chem. , vol.48 , pp. 111-120
    • Dayam, R.1    Sanchez, T.2    Clement, O.3    Shoemaker, R.4    Sei, S.5    Neamati, N.6
  • 19
    • 0035931471 scopus 로고    scopus 로고
    • Arylalkylidene rhodanine with bulky and hydrophobic functional group as selective HCV NS3 protease inhibitor
    • Sing, W. T.; Lee, C. L.; Yeo, S. L.; Lim, S. P.; Sim, M. M. Arylalkylidene rhodanine with bulky and hydrophobic functional group as selective HCV NS3 protease inhibitor. Bioorg. Med. Chem. Lett. 2001, 11, 91-94.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 91-94
    • Sing, W.T.1    Lee, C.L.2    Yeo, S.L.3    Lim, S.P.4    Sim, M.M.5
  • 21
    • 34548131106 scopus 로고    scopus 로고
    • Structure-activity relationships of phenyl-furanyl-rhodanines as inhibitors of RNA polymerase with antibacterial activity on biofilms
    • Villain-Guillot, P.; Gualtieri, M.; Bastide, L.; Roquet, F.; Martinez, J.; Amblard, M.; Pugniere, M.; Leonetti, J. P. Structure-activity relationships of phenyl-furanyl-rhodanines as inhibitors of RNA polymerase with antibacterial activity on biofilms. J. Med. Chem. 2007, 50, 4195-4204.
    • (2007) J. Med. Chem. , vol.50 , pp. 4195-4204
    • Villain-Guillot, P.1    Gualtieri, M.2    Bastide, L.3    Roquet, F.4    Martinez, J.5    Amblard, M.6    Pugniere, M.7    Leonetti, J.P.8
  • 22
    • 67650261319 scopus 로고    scopus 로고
    • Rhodanine as a privileged scaffold in drug discovery curr
    • Tomasic, T.; Masic, L. P. Rhodanine as a Privileged Scaffold in Drug Discovery Curr. Med. Chem. 2009, 16, 1596-1629.
    • (2009) Med. Chem. , vol.16 , pp. 1596-1629
    • Tomasic, T.1    Masic, L.P.2
  • 24
    • 34548276529 scopus 로고    scopus 로고
    • The DNA base excision repair protein Ape1/Ref-1 as a therapeutic and chemopreventive target
    • Fishel, M. L.; Kelley, M. R. The DNA base excision repair protein Ape1/Ref-1 as a therapeutic and chemopreventive target. Mol. Aspects Med. 2007, 28, 375-395.
    • (2007) Mol. Aspects Med. , vol.28 , pp. 375-395
    • Fishel, M.L.1    Kelley, M.R.2
  • 25
    • 51349134457 scopus 로고    scopus 로고
    • Role of the multifunctional DNA repair and redox signaling protein Ape1/Ref-1 in cancer and endothelial cells: Small-molecule inhibition of the redox function of Ape1
    • Luo, M.; Delaplane, S.; Jiang, A.; Reed, A.; He, Y.; Fishel, M.; Nyland, R. L. 2nd; Borch, R. F.; Qiao, X.; Georgiadis, M. M.; Kelley, M. R. Role of the multifunctional DNA repair and redox signaling protein Ape1/Ref-1 in cancer and endothelial cells: small-molecule inhibition of the redox function of Ape1. Antioxid. Redox Signal. 2008, 10, 1853-1867.
    • (2008) Antioxid. Redox Signal , vol.10 , pp. 1853-1867
    • Luo, M.1    Delaplane, S.2    Jiang, A.3    Reed, A.4    He, Y.5    Fishel, M.6    Nyland II, R.L.7    Borch, R.F.8    Qiao, X.9    Georgiadis, M.M.10    Kelley, M.R.11
  • 26
    • 59449097875 scopus 로고    scopus 로고
    • Pharmacophore guided discovery of small-molecule human apurinic/apyrimidinic endonuclease 1 inhibitors
    • Zawahir, Z.; Dayam, R.; Deng, J.; Pereira, C.; Neamati, N. Pharmacophore guided discovery of small-molecule human apurinic/apyrimidinic endonuclease 1 inhibitors. J. Med. Chem. 2009, 52, 20-32.
    • (2009) J. Med. Chem. , vol.52 , pp. 20-32
    • Zawahir, Z.1    Dayam, R.2    Deng, J.3    Pereira, C.4    Neamati, N.5
  • 27
    • 0034461768 scopus 로고    scopus 로고
    • Drug-like properties and the causes of poor solubility and poor permeability
    • Lipinski, C. A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 2000, 44, 235-249.
    • (2000) J. Pharmacol. Toxicol. Methods , vol.44 , pp. 235-249
    • Lipinski, C.A.1
  • 28
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • DOI 10.1016/S0169-409X(00)00129-0, PII S0169409X00001290
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 2001, 46, 3-26. (Pubitemid 33653411)
    • (2000) Advanced Drug Delivery Reviews , vol.46 , Issue.1-3 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 29
    • 0037204547 scopus 로고    scopus 로고
    • Prediction of intestinal permeability
    • Egan, W. J.; Lauri, G. Prediction of intestinal permeability. Adv. Drug Deliv. Rev. 2002, 54, 273-289.
    • (2002) Adv. Drug Deliv. Rev. , vol.54 , pp. 273-289
    • Egan, W.J.1    Lauri, G.2
  • 30
    • 0034687231 scopus 로고    scopus 로고
    • Prediction of drug absorption using multivariate statistics
    • Egan, W. J.; Merz, K. M., Jr.; Baldwin, J. J. Prediction of drug absorption using multivariate statistics. J. Med. Chem. 2000, 43, 3867-3877.
    • (2000) J. Med. Chem. , vol.43 , pp. 3867-3877
    • Egan, W.J.1    Merz, K.M.J.2    Baldwin Jr., J.3
  • 32
    • 0032585545 scopus 로고    scopus 로고
    • Evaluation of dynamic polar molecular surface area as predictor of drug absorption: Comparison with other computational and experimental predictors
    • Palm, K.; Luthman, K.; Ungell, A. L.; Strandlund, G.; Beigi, F.; Lundahl, P.; Artursson, P. Evaluation of dynamic polar molecular surface area as predictor of drug absorption: comparison with other computational and experimental predictors. J. Med. Chem. 1998, 41, 5382-5392.
    • (1998) J. Med. Chem. , vol.41 , pp. 5382-5392
    • Palm, K.1    Luthman, K.2    Ungell, A.L.3    Strandlund, G.4    Beigi, F.5    Lundahl, P.6    Artursson, P.7
  • 33
    • 0030914681 scopus 로고    scopus 로고
    • Polar molecular surface properties predict the intestinal absorption of drugs in humans
    • Palm, K.; Stenberg, P.; Luthman, K.; Artursson, P. Polar molecular surface properties predict the intestinal absorption of drugs in humans. Pharm. Res. 1997, 14, 568-571.
    • (1997) Pharm. Res. , vol.14 , pp. 568-571
    • Palm, K.1    Stenberg, P.2    Luthman, K.3    Artursson, P.4
  • 34
    • 0032714220 scopus 로고    scopus 로고
    • Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs
    • Kelder, J.; Grootenhuis, P. D.; Bayada, D. M.; Delbressine, L. P.; Ploemen, J. P. Polar Molecular Surface as a Dominating Determinant for Oral Absorption and Brain Penetration of Drugs. Pharm. Res. 1999, 16, 1514-1519.
    • (1999) Pharm. Res. , vol.16 , pp. 1514-1519
    • Kelder, J.1    Grootenhuis, P.D.2    Bayada, D.M.3    Delbressine, L.P.4    Ploemen, J.P.5
  • 35
    • 77954302345 scopus 로고    scopus 로고
    • Catalyst 4.11; Accelrys Inc.: San Diego, CA, USA, GOLD 3.2; CCDC: Cambridge, UK
    • Catalyst 4.11; Accelrys Inc.: San Diego, CA, USA, 2005. 36. GOLD 3.2; CCDC: Cambridge, UK, 2002.
    • (2002) , vol.36
  • 37
    • 1642310340 scopus 로고    scopus 로고
    • Glide: A new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening
    • Halgren, T. A.; Murphy, R. B.; Friesner, R. A.; Beard, H. S.; Frye, L. L.; Pollard, W. T.; Banks, J. L. Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. J. Med. Chem. 2004, 47, 1750-1759.
    • (2004) J. Med. Chem. , vol.47 , pp. 1750-1759
    • Halgren, T.A.1    Murphy, R.B.2    Friesner, R.A.3    Beard, H.S.4    Frye, L.L.5    Pollard, W.T.6    Banks, J.L.7
  • 38
    • 0031226772 scopus 로고    scopus 로고
    • Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes
    • Eldridge, M. D.; Murray, C. W.; Auton, T. R.; Paolini, G. V.; Mee, R. P. Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes. J. Comput. Aided Mol. Des. 1997, 11, 425-445.
    • (1997) J. Comput. Aided Mol. Des. , vol.11 , pp. 425-445
    • Eldridge, M.D.1    Murray, C.W.2    Auton, T.R.3    Paolini, G.V.4    Mee, R.P.5
  • 39
    • 77954289687 scopus 로고    scopus 로고
    • ADMET Predictor 3.0; Simulations Plus, Inc.: Lancaster, CA, USA
    • ADMET Predictor 3.0; Simulations Plus, Inc.: Lancaster, CA, USA, 2008.
    • (2008)
  • 41
    • 23144432272 scopus 로고    scopus 로고
    • Discovery and preclinical evaluation of a novel class of small-molecule compounds in hormonedependent and-independent cancer cell lines
    • Plasencia, C.; Dayam, R.; Wang, Q.; Pinski, J.; Burke, T. R., Jr.; Quinn, D. I.; Neamati, N. Discovery and preclinical evaluation of a novel class of small-molecule compounds in hormonedependent and-independent cancer cell lines. Mol. Cancer Ther. 2005, 4, 1105-1113.
    • (2005) Mol. Cancer Ther. , vol.4 , pp. 1105-1113
    • Plasencia, C.1    Dayam, R.2    Wang, Q.3    Pinski, J.4    Burke Jr., T.R.5    Quinn, D.I.6    Neamati, N.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.