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Volumn 49, Issue 4, 2006, Pages 1291-1312

Synthesis and structure-activity relationship studies of CD4 down-modulating cyclotriazadisulfonamide (CADA) analogues

Author keywords

[No Author keywords available]

Indexed keywords

9 BENZYL 3 METHYLENE 1,5 DI 4 TOLUENESULFONYL 1,5,9 TRIAZACYCLODODECANE; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33144467275     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0582524     Document Type: Article
Times cited : (35)

References (46)
  • 1
    • 0023028190 scopus 로고
    • The T4 gene encodes the AIDS virus receptor and is expressed in the immune system and the brain
    • Maddon, P. J.; Dalgleish, A. G.; McDougal, J. S.; Clapham, P. R.; Weiss, R. A.; Axel. R. The T4 gene encodes the AIDS virus receptor and is expressed in the immune system and the brain. Cell 1986, 47, 333-348.
    • (1986) Cell , vol.47 , pp. 333-348
    • Maddon, P.J.1    Dalgleish, A.G.2    McDougal, J.S.3    Clapham, P.R.4    Weiss, R.A.5    Axel, R.6
  • 2
    • 45149142941 scopus 로고
    • The role of CD4 in T-cell activation: Accessory molecule or co-receptor?
    • Janeway, C. A., Jr. The role of CD4 in T-cell activation: accessory molecule or co-receptor? Immunol. Today 1989, 10, 234-238.
    • (1989) Immunol. Today , vol.10 , pp. 234-238
    • Janeway Jr., C.A.1
  • 3
    • 0033006012 scopus 로고    scopus 로고
    • The regulation of CD4 and CD8 coreceptor gene expression during T cell development
    • Ellmeier, W.; Sawada, S.; Littman, D. R. The regulation of CD4 and CD8 coreceptor gene expression during T cell development. Annu. Rev. Immunol. 1999, 17, 523-554.
    • (1999) Annu. Rev. Immunol. , vol.17 , pp. 523-554
    • Ellmeier, W.1    Sawada, S.2    Littman, D.R.3
  • 5
    • 0036888572 scopus 로고    scopus 로고
    • Therapy of autoimmune diseases: Clinical trials and new biologies
    • Nepom, G. T. Therapy of autoimmune diseases: clinical trials and new biologies. Curr. Opin. Immunol. 2002, 14, 812-815.
    • (2002) Curr. Opin. Immunol. , vol.14 , pp. 812-815
    • Nepom, G.T.1
  • 6
    • 0038516689 scopus 로고    scopus 로고
    • Antibody therapy for rheumatoid arthritis
    • Taylor, P. C. Antibody therapy for rheumatoid arthritis. Curr. Opin. Pharmacol. 2003, 3, 323-328.
    • (2003) Curr. Opin. Pharmacol. , vol.3 , pp. 323-328
    • Taylor, P.C.1
  • 7
    • 0242570736 scopus 로고    scopus 로고
    • Nondepleting anti-CD4 monoclonal antibody prevents diabetes and blocks induction of insulin autoantibodies following insulin peptide B:9-23 immunization in the NOD mouse
    • Liu, E.; Moriyama, H.; Paronen, J.; Abiru, N.; Miao, D.; Yu, L.; Taylor, R. M.; Eisenbarth, G. S. Nondepleting anti-CD4 monoclonal antibody prevents diabetes and blocks induction of insulin autoantibodies following insulin peptide B:9-23 immunization in the NOD mouse. J. Autoimmun. 2003, 21, 213-219.
    • (2003) J. Autoimmun. , vol.21 , pp. 213-219
    • Liu, E.1    Moriyama, H.2    Paronen, J.3    Abiru, N.4    Miao, D.5    Yu, L.6    Taylor, R.M.7    Eisenbarth, G.S.8
  • 8
    • 0043235644 scopus 로고    scopus 로고
    • T-cell-activation inhibitors in rheumatoid arthritis
    • Hanns-Martin, L. T-cell-activation inhibitors in rheumatoid arthritis. BioDrugs 2003, 17, 263-270.
    • (2003) BioDrugs , vol.17 , pp. 263-270
    • Hanns-Martin, L.1
  • 9
    • 0021751840 scopus 로고
    • The CD4 (T4) antigen is an essential component of the receptor for the AIDS retrovirus
    • Dalgleish, A. G.; Beverley, P. C.; Clapham, P. R.; Crawford, D. H.; Greaves, M. F.; Weiss, R. A. The CD4 (T4) antigen is an essential component of the receptor for the AIDS retrovirus. Nature 1984, 312, 763-767.
    • (1984) Nature , vol.312 , pp. 763-767
    • Dalgleish, A.G.1    Beverley, P.C.2    Clapham, P.R.3    Crawford, D.H.4    Greaves, M.F.5    Weiss, R.A.6
  • 11
    • 2942627670 scopus 로고    scopus 로고
    • HIV-chemotherapy and -prophylaxis: New drugs, leads and approaches
    • De Clercq, E. HIV-chemotherapy and -prophylaxis: new drugs, leads and approaches. Int. J. Biochem. Cell Biol. 2004, 36, 1800-1822.
    • (2004) Int. J. Biochem. Cell Biol. , vol.36 , pp. 1800-1822
    • De Clercq, E.1
  • 12
    • 77956849100 scopus 로고    scopus 로고
    • New anti-HIV agents in preclinical or clinical development
    • De Clercq, E., Ed.; Elsevier: Amsterdam
    • De Clercq, E. New anti-HIV agents in preclinical or clinical development. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; Elsevier: Amsterdam, 2004; Vol. 4, pp 1-62.
    • (2004) Advances in Antiviral Drug Design , vol.4 , pp. 1-62
    • De Clercq, E.1
  • 13
    • 14944344464 scopus 로고    scopus 로고
    • New approaches to anti-HIV chemotherapy
    • De Clercq, E. New approaches to anti-HIV chemotherapy. J. Med. Chem. 2005, 48, 1297-1313.
    • (2005) J. Med. Chem. , vol.48 , pp. 1297-1313
    • De Clercq, E.1
  • 15
    • 0036343301 scopus 로고    scopus 로고
    • A humanized, nondepleting anti-CD4 antibody that blocks virus entry inhibits virus replication in rhesus monkeys chronically infected with simian immunodeficiency virus
    • Reimann, K. A.; Khunkhun, R.; Lin, W.; Gordon, W.; Fung, M. A humanized, nondepleting anti-CD4 antibody that blocks virus entry inhibits virus replication in rhesus monkeys chronically infected with simian immunodeficiency virus. AIDS Res. Hum. Retroviruses 2002, 18, 747-755.
    • (2002) AIDS Res. Hum. Retroviruses , vol.18 , pp. 747-755
    • Reimann, K.A.1    Khunkhun, R.2    Lin, W.3    Gordon, W.4    Fung, M.5
  • 16
    • 0032775435 scopus 로고    scopus 로고
    • Bicyclams, selective antagonists of the human chemokine receptor CXCR4, potently inhibit feline immunodeficiency virus replication
    • Egberink, H. F.; De Clercq, E.; Van Vliet, A. L. W.; Balzarini, J.; Bridger, G. J., Henson, G.; Horzinek, M. C.; Schols, D. Bicyclams, selective antagonists of the human chemokine receptor CXCR4, potently inhibit feline immunodeficiency virus replication. J. Virol. 1999, 73, 6346-6352.
    • (1999) J. Virol. , vol.73 , pp. 6346-6352
    • Egberink, H.F.1    De Clercq, E.2    Van Vliet, A.L.W.3    Balzarini, J.4    Bridger, G.J.5    Henson, G.6    Horzinek, M.C.7    Schols, D.8
  • 17
    • 2942555662 scopus 로고    scopus 로고
    • HIV co-receptors as targets for antiviral therapy
    • Schols, D. HIV co-receptors as targets for antiviral therapy. Curr. Topics Med. Chem. 2004, 4, 883-893.
    • (2004) Curr. Topics Med. Chem. , vol.4 , pp. 883-893
    • Schols, D.1
  • 18
    • 0025994353 scopus 로고
    • Several CD4 domains can play a role in human immunodeficiency virus infection in cells
    • Poulin, L.; Evans, L. A.; Tang, S. B.; Barboza, A.; Legg, H.; Littman, D. R.; Levy, J. A. Several CD4 domains can play a role in human immunodeficiency virus infection in cells. J. Virol. 1991, 65, 4893-4901.
    • (1991) J. Virol. , vol.65 , pp. 4893-4901
    • Poulin, L.1    Evans, L.A.2    Tang, S.B.3    Barboza, A.4    Legg, H.5    Littman, D.R.6    Levy, J.A.7
  • 19
    • 0347320929 scopus 로고    scopus 로고
    • Specific CD4 down-modulating compounds with potent anti-HIV activity
    • Vermeire, K.; Schols, D. Specific CD4 down-modulating compounds with potent anti-HIV activity. J. Leukoc. Biol. 2003, 74, 667-675.
    • (2003) J. Leukoc. Biol. , vol.74 , pp. 667-675
    • Vermeire, K.1    Schols, D.2
  • 20
    • 2442618847 scopus 로고    scopus 로고
    • CD4 down-modulating compounds with potent anti-HIV activitiy
    • Vermeire, K.; Schols, D.; Bell, T. W. CD4 down-modulating compounds with potent anti-HIV activitiy. Curr. Pharm. Des. 2004, 10, 1795-1803.
    • (2004) Curr. Pharm. Des. , vol.10 , pp. 1795-1803
    • Vermeire, K.1    Schols, D.2    Bell, T.W.3
  • 21
  • 23
    • 0030046536 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of phenylenebis(methylene) -linked bis-tetraazamacrocyles that inhibit human immunodeficiency virus replication. 2. Effect of heteroaromatic linkers on the activity of bicyclams
    • Bridger, G. J.; Skerlj, R. T.; Padmanabhan, S.; Martellucci, S. A.; Henson, G. W.; Abrams, M. J.; Joao, H. C.; Witvrouw, M.; De Vreese, K.; Pauwels, R.; De Clercq, E. Synthesis and structure-activity relationships of phenylenebis(methylene)-linked bis-tetraazamacrocyles that inhibit human immunodeficiency virus replication. 2. Effect of heteroaromatic linkers on the activity of bicyclams. J. Med. Chem. 1996, 39, 109-119.
    • (1996) J. Med. Chem. , vol.39 , pp. 109-119
    • Bridger, G.J.1    Skerlj, R.T.2    Padmanabhan, S.3    Martellucci, S.A.4    Henson, G.W.5    Abrams, M.J.6    Joao, H.C.7    Witvrouw, M.8    De Vreese, K.9    Pauwels, R.10    De Clercq, E.11
  • 24
    • 7744237428 scopus 로고    scopus 로고
    • CADA, a novel CD4-targeted HIV inhibitor, is synergistic with various anti-HIV drugs in vitro
    • Vermeire, K.; Princen, K.; Hatse, S.; De Clercq, E.; Dey, K.; Bell, T. W.; Schols, D. CADA, a novel CD4-targeted HIV inhibitor, is synergistic with various anti-HIV drugs in vitro. AIDS 2004, 18, 2115-2125.
    • (2004) AIDS , vol.18 , pp. 2115-2125
    • Vermeire, K.1    Princen, K.2    Hatse, S.3    De Clercq, E.4    Dey, K.5    Bell, T.W.6    Schols, D.7
  • 25
    • 0037220770 scopus 로고    scopus 로고
    • The anti-HIV potency of cyclotriazadisulfonamide analogs is directly correlated with their ability to down-modulate the CD4 receptor
    • Vermeire, K.; Bell, T. W.; Choi, H. J.; Jin, Q.; Samala, M. F.; Sodoma, A.; De Clercq, E.; Schols, D. The anti-HIV potency of cyclotriazadisulfonamide analogs is directly correlated with their ability to down-modulate the CD4 receptor. Mol. Pharm. 2003, 63, 203-210.
    • (2003) Mol. Pharm. , vol.63 , pp. 203-210
    • Vermeire, K.1    Bell, T.W.2    Choi, H.J.3    Jin, Q.4    Samala, M.F.5    Sodoma, A.6    De Clercq, E.7    Schols, D.8
  • 26
    • 0141992302 scopus 로고    scopus 로고
    • Syntheses, conformations and basicities of bicyclic triamines
    • Bell, T. W.; Choi, H.-J.; Harte, W.; Drew, M. G. B. Syntheses, conformations and basicities of bicyclic triamines. J. Am. Chem. Soc. 2003, 125, 12196-12210.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12196-12210
    • Bell, T.W.1    Choi, H.-J.2    Harte, W.3    Drew, M.G.B.4
  • 27
    • 2842529620 scopus 로고
    • Nitrogen analogues of crown ethers
    • Richman, J.; Atkins, T. J. Nitrogen analogues of crown ethers. J. Am. Chem. Soc. 1974, 96, 2268-2270.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 2268-2270
    • Richman, J.1    Atkins, T.J.2
  • 28
    • 0002521819 scopus 로고
    • Macrocyclic polyamines: 1,4,7,10,13,16-hexaäzacycloöctadecane
    • Wiley: New York
    • Atkins, T. J.; Richman, J. E.; Oettle, W. F. Macrocyclic polyamines: 1,4,7,10,13,16-hexaäzacycloöctadecane. In Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 652-662.
    • (1988) Organic Syntheses , vol.6 , pp. 652-662
    • Atkins, T.J.1    Richman, J.E.2    Oettle, W.F.3
  • 29
    • 0021260262 scopus 로고
    • A new reagent for the selective, high-yield N-dealkylation of tertiary amines: Improved synthesis of naltrexone and nalbuphine
    • Olofsen, R. A.; Martz, J. T.; Senet, J.-P.; Piteau, M.; Malfroot, T. A new reagent for the selective, high-yield N-dealkylation of tertiary amines: improved synthesis of naltrexone and nalbuphine. J. Org. Chem. 1984, 49, 2081-2082.
    • (1984) J. Org. Chem. , vol.49 , pp. 2081-2082
    • Olofsen, R.A.1    Martz, J.T.2    Senet, J.-P.3    Piteau, M.4    Malfroot, T.5
  • 30
    • 0001413754 scopus 로고
    • Tests of a piperidino mask for the protection of functionalized carbon sites in multistep syntheses
    • Olofsen, R. A.; Abbott, D. E. Tests of a piperidino mask for the protection of functionalized carbon sites in multistep syntheses. J. Org. Chem. 1984, 49, 2795-2799.
    • (1984) J. Org. Chem. , vol.49 , pp. 2795-2799
    • Olofsen, R.A.1    Abbott, D.E.2
  • 31
    • 0028212736 scopus 로고
    • Convenient method for N-debenzylation of tertiary amines
    • Kanth, J. V. B.; Reddy, C. K.; Periasamy, M. Convenient method for N-debenzylation of tertiary amines. Synth. Commun. 1994, 24, 313-319.
    • (1994) Synth. Commun. , vol.24 , pp. 313-319
    • Kanth, J.V.B.1    Reddy, C.K.2    Periasamy, M.3
  • 32
    • 33947339438 scopus 로고
    • The action of formaldehyde on amines and amino acids
    • Clarke, H. T.; Gillespie, H. B.; Weisshaus, S. Z. The action of formaldehyde on amines and amino acids. J. Am. Chem. Soc. 1933, 55, 4571-4587.
    • (1933) J. Am. Chem. Soc. , vol.55 , pp. 4571-4587
    • Clarke, H.T.1    Gillespie, H.B.2    Weisshaus, S.Z.3
  • 33
    • 33947089510 scopus 로고
    • A new method for the methylation of amines
    • Borch, R. F.; Hassid, A. I. A new method for the methylation of amines. J. Org. Chem. 1972, 37, 1673-1674.
    • (1972) J. Org. Chem. , vol.37 , pp. 1673-1674
    • Borch, R.F.1    Hassid, A.I.2
  • 34
    • 33845378961 scopus 로고
    • Zinc-modified cyanoborohydride as a selective reducing agent
    • Kim, S.; Oh, C. H.; Ko, J. S.; Ahn, K. H.; Kim, Y. J. Zinc-modified cyanoborohydride as a selective reducing agent. J. Org. Chem. 1985, 30, 1927-1932.
    • (1985) J. Org. Chem. , vol.30 , pp. 1927-1932
    • Kim, S.1    Oh, C.H.2    Ko, J.S.3    Ahn, K.H.4    Kim, Y.J.5
  • 35
    • 37049111987 scopus 로고
    • 1H NMR spectroscopy of hexahydropyrimidines from spermidine and propane-1.3-diamines
    • 1H NMR spectroscopy of hexahydropyrimidines from spermidine and propane-1.3-diamines. J. Chem. Soc., Perkin Trans. 1 1985, 2011-2015.
    • (1985) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2011-2015
    • Golding, B.T.1    Nasseereddin, I.K.2
  • 36
    • 0001428369 scopus 로고    scopus 로고
    • Selective synthesis of polyamine derivatives: Efficient derivatization of the secondary amino group of N-monosubstituted 1.3-diamines
    • Jentgens, C.; Hofmann, R.; Guggisberg, A.; Bienz, S.; Hesse, M. Selective synthesis of polyamine derivatives: efficient derivatization of the secondary amino group of N-monosubstituted 1.3-diamines. Helv. Chim. Acta 1997, 80, 966-977.
    • (1997) Helv. Chim. Acta , vol.80 , pp. 966-977
    • Jentgens, C.1    Hofmann, R.2    Guggisberg, A.3    Bienz, S.4    Hesse, M.5
  • 37
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoFMA). 1. Effect of shape on binding of steroids to carrier proteins
    • Cramer, R. D., III.; Patterson, D. E.; Bunce, J. D. Comparative molecular field analysis (CoFMA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5959-5967
    • Cramer III, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 38
    • 0027944195 scopus 로고
    • Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity
    • Klebe, G.; Abraham, U.; Mietzner, T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J. Med. Chem. 1994, 37, 4130-4146, 102, 1239-1248.
    • (1994) J. Med. Chem. , vol.37 , pp. 4130-4146
    • Klebe, G.1    Abraham, U.2    Mietzner, T.3
  • 39
    • 0033022163 scopus 로고    scopus 로고
    • Comparative molecular similarity index analysis (CoMSIA) to study hydrogen-bonding properties and to score combinatorial libraries
    • Klebe, G.; Abraham, U. Comparative molecular similarity index analysis (CoMSIA) to study hydrogen-bonding properties and to score combinatorial libraries. J. Comput.-Aided Mol. Design 1999, 13, 1-10.
    • (1999) J. Comput.-Aided Mol. Design , vol.13 , pp. 1-10
    • Klebe, G.1    Abraham, U.2
  • 40
    • 0037920567 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationship analysis using comparative molecular field analysis and comparative molecular similarity indices analysis to elucidate selectivity differences of inhibitors binding to trypsin, thrombin, and factor Xa
    • Böhm, M.; Stürzebecher, J.; Klebe, G. Three-dimensional quantitative structure-activity relationship analysis using comparative molecular field analysis and comparative molecular similarity indices analysis to elucidate selectivity differences of inhibitors binding to trypsin, thrombin, and factor Xa. J. Med. Chem. 1999, 42, 458-477.
    • (1999) J. Med. Chem. , vol.42 , pp. 458-477
    • Böhm, M.1    Stürzebecher, J.2    Klebe, G.3
  • 41
    • 0017873623 scopus 로고
    • Inactivation of trypsin-like proteases by sulfonylation. Variation of partially charged group and inhibitor length
    • Wong, S.-C.; Green, G. D. J.; Shaw, E. Inactivation of trypsin-like proteases by sulfonylation. Variation of partially charged group and inhibitor length. J. Med Chem. 1978, 21, 456-459.
    • (1978) J. Med Chem. , vol.21 , pp. 456-459
    • Wong, S.-C.1    Green, G.D.J.2    Shaw, E.3
  • 42
    • 84872266105 scopus 로고    scopus 로고
    • Tripos, Inc., 1699 Hanley Road, St. Louis, MO 63144
    • SYBYL 6.5, Tripos, Inc., 1699 Hanley Road, St. Louis, MO 63144.
    • SYBYL 6.5
  • 45
    • 85152373811 scopus 로고    scopus 로고
    • Notes on the history and nature of partial least-squares analysis
    • Geladi, P. Notes on the history and nature of partial least-squares analysis. J. Chemom. 1998, 2, 231.
    • (1998) J. Chemom. , vol.2 , pp. 231
    • Geladi, P.1
  • 46
    • 84951601886 scopus 로고
    • Cross-validation estimation of number of components in factor and principal components models
    • Wold, S. Cross-validation estimation of number of components in factor and principal components models. Technometrics 1978, 4, 397.
    • (1978) Technometrics , vol.4 , pp. 397
    • Wold, S.1


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