메뉴 건너뛰기




Volumn 16, Issue 3, 2012, Pages 181-193

Synthesis, characterization and antiviral evaluation of 1,3-Thiazolidine-4-one derivatives bearing L-Valine side chain;L-Valin yan zinciri taşıyan 1,3-tiyazolidin-4-on türevlerinin sentezi, yapılarının aydınlatılması ve antiviral etkilerinin tespiti

Author keywords

4 Thiazolidinones; Anti HCV activity; Anti HIV activity; L valine

Indexed keywords


EID: 84878776107     PISSN: None     EISSN: 13090801     Source Type: Journal    
DOI: 10.12991/201216397     Document Type: Article
Times cited : (10)

References (54)
  • 3
    • 33646447042 scopus 로고    scopus 로고
    • Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide
    • Küçükgüzel G, Kocatepe A, De Clercq E, Sahin F, Güllüce M. Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide. Eur J Med Chem 2006; 41: 353-9.
    • (2006) Eur J Med Chem , vol.41 , pp. 353-359
    • Küçükgüzel, G.1    Kocatepe, A.2    de Clercq, E.3    Sahin, F.4    Güllüce, M.5
  • 4
    • 81355135532 scopus 로고    scopus 로고
    • Synthesis, in vitro antitubercular activity and 3D-QSAR of novel quinoxaline derivatives
    • Puratchikody A, Natarajan R, Jayapal M, Doble M. Synthesis, in vitro antitubercular activity and 3D-QSAR of novel quinoxaline derivatives. Chem Biol Drug Des 2011; 78: 988-98.
    • (2011) Chem Biol Drug Des , vol.78 , pp. 988-998
    • Puratchikody, A.1    Natarajan, R.2    Jayapal, M.3    Doble, M.4
  • 5
    • 77955574023 scopus 로고    scopus 로고
    • Identification of thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of the Mycobacterium tuberculosis protein tyrosine phosphatase B
    • Vintonyak VV, Warburg K, Kruse H, Grimme S, Hübel K, Rauh D, Waldmann H. Identification of thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of the Mycobacterium tuberculosis protein tyrosine phosphatase B. Angew Chem Int Ed Engl 2010; 49: 5902-5.
    • (2010) Angew Chem Int Ed Engl , vol.49 , pp. 5902-5905
    • Vintonyak, V.V.1    Warburg, K.2    Kruse, H.3    Grimme, S.4    Hübel, K.5    Rauh, D.6    Waldmann, H.7
  • 7
    • 0036501101 scopus 로고    scopus 로고
    • Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds
    • Küçükgüzel SG, Oruç EE, Rollas S, Sahin F, Özbek A. Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 2002; 37: 197-206.
    • (2002) Eur J Med Chem , vol.37 , pp. 197-206
    • Küçükgüzel, S.G.1    Oruç, E.E.2    Rollas, S.3    Sahin, F.4    Özbek, A.5
  • 8
    • 82955178692 scopus 로고    scopus 로고
    • Antiviral and anticancer Efficient regioselective three-component domino synthesis of 3-(1,2,4-triazol-5-yl)-1,3-thiazolidin-4-ones as potent antifungal and antituberculosis agents
    • El Bialy SA, Nagy MM, Abdel-Rahman HM. antiviral and anticancer. Efficient regioselective three-component domino synthesis of 3-(1,2,4-triazol-5-yl)-1,3-thiazolidin-4-ones as potent antifungal and antituberculosis agents. Arch Pharm (Weinheim) 2011; 344: 821-9.
    • (2011) Arch Pharm (Weinheim) , vol.344 , pp. 821-829
    • El Bialy, S.A.1    Nagy, M.M.2    Abdel-Rahman, H.M.3
  • 10
    • 80051590689 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of thiazolidinone derivatives as antimicrobial and anti-viral agents
    • Ravichandran V, Jain A, Kumar KS, Rajak H, Agrawal RK. Design, synthesis, and evaluation of thiazolidinone derivatives as antimicrobial and anti-viral agents. Chem Biol Drug Des 2011; 78: 464-70.
    • (2011) Chem Biol Drug Des , vol.78 , pp. 464-470
    • Ravichandran, V.1    Jain, A.2    Kumar, K.S.3    Rajak, H.4    Agrawal, R.K.5
  • 14
    • 27644537621 scopus 로고    scopus 로고
    • 2-(Aryl)-3-furan-2-ylmethyl-thiazolidin-4-ones as selective HIVRT inhibitors
    • Rawal RK, Prabhakar YS, Katti SB, De Clercq E. 2-(Aryl)-3-furan-2-ylmethyl-thiazolidin-4-ones as selective HIVRT inhibitors. Bioorg Med Chem 2005; 13: 6771-6.
    • (2005) Bioorg Med Chem , vol.13 , pp. 6771-6776
    • Rawal, R.K.1    Prabhakar, Y.S.2    Katti, S.B.3    de Clercq, E.4
  • 15
    • 33847781693 scopus 로고    scopus 로고
    • Design, synthesis and evaluation of 2-aryl-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents
    • Rawal RK, Tripathi R, Kati SB, Pannecouque C, De Clercq E. Design, synthesis and evaluation of 2-aryl-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents. Bioorg Med Chem 2007; 15: 1725-31.
    • (2007) Bioorg Med Chem , vol.15 , pp. 1725-1731
    • Rawal, R.K.1    Tripathi, R.2    Kati, S.B.3    Pannecouque, C.4    de Clercq, E.5
  • 16
    • 37849187619 scopus 로고    scopus 로고
    • Molecular docking studies on 4-thiazolidinones as HIV-1 RT inhibitors
    • Rawal RK, Kumar A, Siddiqi MI, Katti SB. Molecular docking studies on 4-thiazolidinones as HIV-1 RT inhibitors. J Mol Model 2007; 13: 155-61.
    • (2007) J Mol Model , vol.13 , pp. 155-161
    • Rawal, R.K.1    Kumar, A.2    Siddiqi, M.I.3    Katti, S.B.4
  • 17
    • 47949096992 scopus 로고    scopus 로고
    • Design and synthesis of 2-(2,6-dibromophenyl)-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents
    • Rawal RK, Tripathi R, Katti SB, Pannecouque C, De Clercq E. Design and synthesis of 2-(2,6-dibromophenyl)-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents. Eur J Med Chem 2008; 43: 2800-6.
    • (2008) Eur J Med Chem , vol.43 , pp. 2800-2806
    • Rawal, R.K.1    Tripathi, R.2    Katti, S.B.3    Pannecouque, C.4    de Clercq, E.5
  • 18
    • 65649125313 scopus 로고    scopus 로고
    • Design, microwave-assisted synthesis and HIV-RT inhibitory activity of 2-(2,6-dihalophenyl)-3-(4,6-dimethyl-5-(un)substituted-pyrimidin-2-yl)thiazolidin-4-ones
    • Chen H, Bai J, Jiao L, Guo Z, Yin Q, Li X. Design, microwave-assisted synthesis and HIV-RT inhibitory activity of 2-(2,6-dihalophenyl)-3-(4,6-dimethyl-5-(un)substituted-pyrimidin-2-yl)thiazolidin-4-ones. Bioorg Med Chem 2009; 17: 3980-6.
    • (2009) Bioorg Med Chem , vol.17 , pp. 3980-3986
    • Chen, H.1    Bai, J.2    Jiao, L.3    Guo, Z.4    Yin, Q.5    Li, X.6
  • 19
    • 57949109639 scopus 로고    scopus 로고
    • Synthesis and anti-HIV studies of 2-and 3-adamantyl-substituted thiazolidin-4-ones
    • Balzarini J, Orzeszko-Krzesińska B, Maurin JK, Orzeszko A. Synthesis and anti-HIV studies of 2-and 3-adamantyl-substituted thiazolidin-4-ones. Eur J Med Chem 2009; 44: 303-11.
    • (2009) Eur J Med Chem , vol.44 , pp. 303-311
    • Balzarini, J.1    Orzeszko-Krzesińska, B.2    Maurin, J.K.3    Orzeszko, A.4
  • 21
    • 55549132596 scopus 로고    scopus 로고
    • Non-nucleoside inhibitors of the hepatitis C virus NS5B RNA-dependent RNA polymerase: 2-Aryl-3-heteroaryl-1,3-thiazolidin-4-one derivatives
    • Rawal RK, Kati SB, Kaushik-Basu N, Arora P, Pan Z. Non-nucleoside inhibitors of the hepatitis C virus NS5B RNA-dependent RNA polymerase: 2-Aryl-3-heteroaryl-1,3-thiazolidin-4-one derivatives. Bioorg Med Chem Lett 2008; 18: 6110-4.
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 6110-6114
    • Rawal, R.K.1    Kati, S.B.2    Kaushik-Basu, N.3    Arora, P.4    Pan, Z.5
  • 24
    • 79961014405 scopus 로고    scopus 로고
    • Anti-infectives: Can cellular screening deliver?
    • Keller TH, Shi PY, Wang QY. Anti-infectives: can cellular screening deliver? Curr Opin Chem Biol 2011; 15: 529-33.
    • (2011) Curr Opin Chem Biol , vol.15 , pp. 529-533
    • Keller, T.H.1    Shi, P.Y.2    Wang, Q.Y.3
  • 25
    • 84862776775 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of piperidinesubstituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors
    • Chen X, Zhan P, Pannecouque C, Balzarini J, De Clercq E, Liu X. Synthesis and biological evaluation of piperidinesubstituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors. Eur J Med Chem 2012; 51:60-6.
    • (2012) Eur J Med Chem , vol.51 , pp. 60-66
    • Chen, X.1    Zhan, P.2    Pannecouque, C.3    Balzarini, J.4    de Clercq, E.5    Liu, X.6
  • 26
    • 61449189645 scopus 로고    scopus 로고
    • Anti-HIV drugs: 25 compounds approved within 25 years after the discovery of HIV
    • De Clercq E. Anti-HIV drugs: 25 compounds approved within 25 years after the discovery of HIV. Int J Antimicrob Agents 2009; 33: 307-20.
    • (2009) Int J Antimicrob Agents , vol.33 , pp. 307-320
    • de Clercq, E.1
  • 27
    • 33747116051 scopus 로고    scopus 로고
    • Dimerization inhibitors of HIV-1 reverse transcriptase, protease and integrase: A single mode of inhibition for the three HIV enzymes
    • Camarasa MJ, Velázquez S, San-Félix A, Pérez-Pérez MJ, Gago F. Dimerization inhibitors of HIV-1 reverse transcriptase, protease and integrase: a single mode of inhibition for the three HIV enzymes. Antiviral Res 2006; 71: 260-7.
    • (2006) Antiviral Res , vol.71 , pp. 260-267
    • Camarasa, M.J.1    Velázquez, S.2    San-Félix, A.3    Pérez-Pérez, M.J.4    Gago, F.5
  • 28
    • 79951968104 scopus 로고    scopus 로고
    • A 40-year journey in search of selective antiviral chemotherapy
    • De Clercq E. A 40-year journey in search of selective antiviral chemotherapy. Annu Rev Pharmacol Toxicol 2011; 51: 1-24.
    • (2011) Annu Rev Pharmacol Toxicol , vol.51 , pp. 1-24
    • de Clercq, E.1
  • 30
    • 80054865518 scopus 로고    scopus 로고
    • HIV-1 reverse transcriptase connection subdomain mutations involved in resistance to approved non-nucleoside inhibitors
    • Menéndez-Arias L, Betancor G, Matamoros T. HIV-1 reverse transcriptase connection subdomain mutations involved in resistance to approved non-nucleoside inhibitors. Antiviral Res 2011; 92: 139-49.
    • (2011) Antiviral Res , vol.92 , pp. 139-149
    • Menéndez-Arias, L.1    Betancor, G.2    Matamoros, T.3
  • 31
    • 84861229590 scopus 로고    scopus 로고
    • Docking, molecular dynamics and quantitative structure-activity relationship studies for HEPTs and DABOs as HIV-1 reverse transcriptase inhibitors
    • Mao Y, Li Y, Hao M, Zhang S, Ai C. Docking, molecular dynamics and quantitative structure-activity relationship studies for HEPTs and DABOs as HIV-1 reverse transcriptase inhibitors. J Mol Model 2012; 18: 2185-98.
    • (2012) J Mol Model , vol.18 , pp. 2185-2198
    • Mao, Y.1    Li, Y.2    Hao, M.3    Zhang, S.4    Ai, C.5
  • 32
    • 84878788687 scopus 로고    scopus 로고
    • 3-[2-(Arylamino)-3-methylbutanamido]-2-aryl-5-substituted/non-substituted-1,3-thiazolidine-4-ones as antiviral agents
    • September 5-7, 2007, İstanbul, Turkey, Published in: Turkish Journal of Pharmaceutical Sciences, Special Issue
    • Tatar E, Küçükgüzel İ, De Clercq E. 3-[2-(Arylamino)-3-methylbutanamido]-2-aryl-5-substituted/non-substituted-1,3-thiazolidine-4-ones as antiviral agents. 5th International Symposium on Pharmaceutical Chemistry, September 5-7, 2007, İstanbul, Turkey, Published in: Turkish Journal of Pharmaceutical Sciences, Special Issue, 2007.
    • (2007) 5th International Symposium on Pharmaceutical Chemistry
    • Tatar, E.1    Küçükgüzel, I.2    de Clercq, E.3
  • 33
    • 84878781972 scopus 로고    scopus 로고
    • Synthesis, characterisation and antiviral activity of novel 1,3-thiazolidine-4-ones derived from new 1-[2-(benzoylamino)-3-metylbutyryl]-4-alkyl/arylalkyl thiosemicarbazides
    • September 5-7, 2007, İstanbul, Turkey, Published in: Turkish Journal of Pharmaceutical Sciences, Special Issue
    • Tatar E, Küçükgüzel İ, De Clercq E. Synthesis, characterisation and antiviral activity of novel 1,3-thiazolidine-4-ones derived from new 1-[2-(benzoylamino)-3-metylbutyryl]-4-alkyl/arylalkyl thiosemicarbazides. 5th International Symposium on Pharmaceutical Chemistry, September 5-7, 2007, İstanbul, Turkey, Published in: Turkish Journal of Pharmaceutical Sciences, Special Issue, 2007.
    • (2007) 5th International Symposium on Pharmaceutical Chemistry
    • Tatar, E.1    Küçükgüzel, I.2    de Clercq, E.3
  • 34
    • 38949189604 scopus 로고    scopus 로고
    • Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/ aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents
    • Küçükgüzel İ, Tatar E, Küçükgüzel ŞG, Rollas S, De Clercq E. Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/ aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents. Eur J Med Chem 2008; 43: 381-92.
    • (2008) Eur J Med Chem , vol.43 , pp. 381-392
    • Küçükgüzel, I.1    Tatar, E.2    Küçükgüzel, S.G.3    Rollas, S.4    de Clercq, E.5
  • 35
    • 54949141808 scopus 로고    scopus 로고
    • Synthesis, characterization and screening of antimicrobial, antituberculosis, antiviral and anticancer activity of novel 1,3-thiazolidine-4-ones derived from 1-[2-(benzoylamino)-4-(methylthio)butyryl]-4-alkyl/ arylalkyl thiosemicarbazides
    • Tatar E, Küçükgüzel İ, De Clercq E, Şahin F, Güllüce M. Synthesis, characterization and screening of antimicrobial, antituberculosis, antiviral and anticancer activity of novel 1,3-thiazolidine-4-ones derived from 1-[2-(benzoylamino)-4-(methylthio)butyryl]-4-alkyl/ arylalkyl thiosemicarbazides. Arkivoc 2008; 14: 191-210.
    • (2008) Arkivoc , vol.14 , pp. 191-210
    • Tatar, E.1    Küçükgüzel, I.2    de Clercq, E.3    Şahin, F.4    Güllüce, M.5
  • 36
    • 84858994359 scopus 로고    scopus 로고
    • GBV-C: State of the art and future prospects
    • Giret MT, Kallas EG. GBV-C: state of the art and future prospects. Curr HIV/AIDS Rep 2012; 9: 26-33.
    • (2012) Curr HIV/AIDS Rep , vol.9 , pp. 26-33
    • Giret, M.T.1    Kallas, E.G.2
  • 37
    • 80054938642 scopus 로고    scopus 로고
    • Management of HCV and HIV infections among people who inject drugs
    • Grebely J, Tyndall MW. Management of HCV and HIV infections among people who inject drugs. Curr Opin HIV AIDS 2011; 6: 501-7.
    • (2011) Curr Opin HIV AIDS , vol.6 , pp. 501-507
    • Grebely, J.1    Tyndall, M.W.2
  • 38
    • 80051791963 scopus 로고    scopus 로고
    • The role of coinfections in HIV epidemic trajectory and positive prevention: A systematic review and meta-analysis
    • Barnabas RV, Webb EL, Weiss HA, Wasserheit JN. The role of coinfections in HIV epidemic trajectory and positive prevention: a systematic review and meta-analysis. AIDS 2011; 25: 1559-73.
    • (2011) AIDS , vol.25 , pp. 1559-1573
    • Barnabas, R.V.1    Webb, E.L.2    Weiss, H.A.3    Wasserheit, J.N.4
  • 40
    • 0000880849 scopus 로고
    • α-Chymotrypsincatalysed hydrolysis of acetyl-, chloroacetyl-, and benzoyl-L-valine methyl ester
    • Applewhite TH, White H, Niemann C. α-Chymotrypsincatalysed hydrolysis of acetyl-, chloroacetyl-, and benzoyl-L-valine methyl ester. J Am Chem Soc 1958; 80: 1465-9.
    • (1958) J Am Chem Soc , vol.80 , pp. 1465-1469
    • Applewhite, T.H.1    White, H.2    Niemann, C.3
  • 41
    • 0013476739 scopus 로고
    • Studies on the kinetics of racemization of 2,4-disubstituted-5(4H)-oxazolones
    • Slebioda M, St-Amand MA, Chen FMF, Benoiton NL. Studies on the kinetics of racemization of 2,4-disubstituted-5(4H)-oxazolones. Can J Chem 1988; 66: 2540-4.
    • (1988) Can J Chem , vol.66 , pp. 2540-2544
    • Slebioda, M.1    St-Amand, M.A.2    Chen, F.M.F.3    Benoiton, N.L.4
  • 42
    • 0023687234 scopus 로고
    • Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds
    • Pauwels R, Balzarini J, Baba M, Snoeck R, Schols D, Herdewijn P. Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. J Virol Methods 1988; 20: 309-21.
    • (1988) J Virol Methods , vol.20 , pp. 309-321
    • Pauwels, R.1    Balzarini, J.2    Baba, M.3    Snoeck, R.4    Schols, D.5    Herdewijn, P.6
  • 43
    • 0021237243 scopus 로고
    • Detection, isolation, and continuous production of cytopathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS
    • Popovic M, Sarngadharan MG, Read E, Gallo RC. Detection, isolation, and continuous production of cytopathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS, Science 1984; 224: 497-500.
    • (1984) Science , vol.224 , pp. 497-500
    • Popovic, M.1    Sarngadharan, M.G.2    Read, E.3    Gallo, R.C.4
  • 47
    • 0021840054 scopus 로고
    • Antiviral and antimetabolic activities of neplanocins
    • De Clercq E. Antiviral and antimetabolic activities of neplanocins. Antimicrob Agents Chemother 1985; 28: 84-9.
    • (1985) Antimicrob Agents Chemother , vol.28 , pp. 84-89
    • de Clercq, E.1
  • 50
    • 1842858323 scopus 로고    scopus 로고
    • Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents
    • Archana, Srivastava VK, Kumar A. Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents. Eur J Med Chem 2002; 37: 873-82.
    • (2002) Eur J Med Chem , vol.37 , pp. 873-882
    • Archana, S.V.K.1    Kumar, A.2
  • 52
    • 84887262203 scopus 로고
    • Z/E Isomerism in Thiazole-and 1,3,4-Thiadiazole-2-nitrosimines
    • Rehse K, Lüdtke E. Z/E Isomerism in Thiazole-and 1,3,4-Thiadiazole-2-nitrosimines. Arch Pharm (Weinheim) 1992; 327: 647-51.
    • (1992) Arch Pharm (Weinheim) , vol.327 , pp. 647-651
    • Rehse, K.1    Lüdtke, E.2
  • 53
    • 0033479370 scopus 로고    scopus 로고
    • New 6-phenylimidazo[2,1-b]thiazole derivatives: Synthesis and antifungal activity
    • Çapan G, Ulusoy N, Ergenç N, Kiraz M. New 6-phenylimidazo[2,1-b]thiazole derivatives: Synthesis and antifungal activity. Monatsh Chem 1999; 130: 1399-407.
    • (1999) Monatsh Chem , vol.130 , pp. 1399-1407
    • Çapan, G.1    Ulusoy, N.2    Ergenç, N.3    Kiraz, M.4
  • 54
    • 33750718764 scopus 로고    scopus 로고
    • 1H-NMR Dynamic study of thermal Z/E isomerization of 5-substituted 2-alkylidene-4-oxothiazolidine derivatives: Barriers to rotation about C=C bond
    • Marković R, Baranac M, Juranić N, Macura S, Cekić I, Minić D. 1H-NMR Dynamic study of thermal Z/E isomerization of 5-substituted 2-alkylidene-4-oxothiazolidine derivatives: Barriers to rotation about C=C bond. J Mol Struc 2006; 800: 85-92.
    • (2006) J Mol Struc , vol.800 , pp. 85-92
    • Marković, R.1    Baranac, M.2    Juranić, N.3    McUra, S.4    Cekić, I.5    Minić, D.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.