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Volumn 101, Issue 1, 2011, Pages 6-15

Synthesis and bioactivity of novel sulfone derivatives containing 2,4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase inhibitors

Author keywords

2,4 Dichlorophenyl; Antifungal activity; Chitinase inhibitors; Mechanism; Rhizoctonia solani; Sulfone

Indexed keywords

FUNGI; HYPHOMYCETES; THANATEPHORUS CUCUMERIS;

EID: 80052262006     PISSN: 00483575     EISSN: 10959939     Source Type: Journal    
DOI: 10.1016/j.pestbp.2011.05.006     Document Type: Article
Times cited : (78)

References (30)
  • 1
    • 0026594882 scopus 로고
    • Chitinase and chitin synthase 1: counterbalancing activities in cell separation of Saccharomyces cerevisiae
    • Cabib E., Silverman S.J., Shaw J.A. Chitinase and chitin synthase 1: counterbalancing activities in cell separation of Saccharomyces cerevisiae. J. Gen. Microbiol. 1992, 138:97-102.
    • (1992) J. Gen. Microbiol. , vol.138 , pp. 97-102
    • Cabib, E.1    Silverman, S.J.2    Shaw, J.A.3
  • 2
    • 0032557232 scopus 로고    scopus 로고
    • Substrate distortion to a boat conformation at subsite -1 is critical in the mechanism of family 18 chitinases
    • Brameld K.A., Goddard W.A. Substrate distortion to a boat conformation at subsite -1 is critical in the mechanism of family 18 chitinases. J. Am. Chem. Soc. 1998, 120:3571-3580.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3571-3580
    • Brameld, K.A.1    Goddard, W.A.2
  • 3
    • 0029884662 scopus 로고    scopus 로고
    • Comparative studies of chitinases A and B from Serratia marcescens
    • Brurberg M.B., Nes I.F., Eijsink V.G.H. Comparative studies of chitinases A and B from Serratia marcescens. Microbiology 1996, 142:1581-1589.
    • (1996) Microbiology , vol.142 , pp. 1581-1589
    • Brurberg, M.B.1    Nes, I.F.2    Eijsink, V.G.H.3
  • 4
    • 0027401151 scopus 로고
    • Detection and quantification of N-Acetyl-β-d-glucosaminidase, chitobiosidase, and endochitinase in solutions and on gels
    • Tronsmo A., Harman G.E. Detection and quantification of N-Acetyl-β-d-glucosaminidase, chitobiosidase, and endochitinase in solutions and on gels. Anal. Biochem. 1993, 208:74-79.
    • (1993) Anal. Biochem. , vol.208 , pp. 74-79
    • Tronsmo, A.1    Harman, G.E.2
  • 5
    • 0024345556 scopus 로고
    • Chitinase activity from Candida albicans and its inhibition by allosamidin
    • Dickinson K., Keer V., Hitchcock C.A., Adams D.J. Chitinase activity from Candida albicans and its inhibition by allosamidin. J. Gen. Microbiol. 1989, 135:1417-1421.
    • (1989) J. Gen. Microbiol. , vol.135 , pp. 1417-1421
    • Dickinson, K.1    Keer, V.2    Hitchcock, C.A.3    Adams, D.J.4
  • 6
    • 0033920903 scopus 로고    scopus 로고
    • Argifin, a new chitinase inhibitor, produced by Gliodadium sp. FTD-0668
    • Omura S., Aria N., Yamaguchi Y. Argifin, a new chitinase inhibitor, produced by Gliodadium sp. FTD-0668. J. Antibiot. 2000, 53:603-608.
    • (2000) J. Antibiot. , vol.53 , pp. 603-608
    • Omura, S.1    Aria, N.2    Yamaguchi, Y.3
  • 9
    • 0242286892 scopus 로고
    • Chitin metabolism as a target for antifungal and antiparasitic drugs and agrochemicals
    • Elsevier, Amsterdam, M.E. Bushell, U. Gräfe (Eds.)
    • Gooday G.W. Chitin metabolism as a target for antifungal and antiparasitic drugs and agrochemicals. Bioactive metabolites from microorganisms progress in industrial microbiology 1989, 139-150. Elsevier, Amsterdam. M.E. Bushell, U. Gräfe (Eds.).
    • (1989) Bioactive metabolites from microorganisms progress in industrial microbiology , pp. 139-150
    • Gooday, G.W.1
  • 10
    • 0242287992 scopus 로고    scopus 로고
    • Glycosidase inhibitors: update and perspectives on practical use
    • Asano N. Glycosidase inhibitors: update and perspectives on practical use. Glycobiology 2003, 13:93R-104R.
    • (2003) Glycobiology , vol.13
    • Asano, N.1
  • 11
    • 0036297773 scopus 로고    scopus 로고
    • The structure of an allosamidin complex with the Coccidioides immitis chitinase defines a role for a second acid residue in substrate-assisted mechanism
    • Bortone K., Monzingo A.F., Ernst S., Robertus J.D. The structure of an allosamidin complex with the Coccidioides immitis chitinase defines a role for a second acid residue in substrate-assisted mechanism. J. Mol. Biol. 2002, 320:293-302.
    • (2002) J. Mol. Biol. , vol.320 , pp. 293-302
    • Bortone, K.1    Monzingo, A.F.2    Ernst, S.3    Robertus, J.D.4
  • 13
    • 34249285483 scopus 로고    scopus 로고
    • Rapid synthesis of sulfone derivatives as potential anti-infectious agents
    • Curti C., Laget M., Ortiz Carle A., Vanelle P. Rapid synthesis of sulfone derivatives as potential anti-infectious agents. Eur. J. Med. Chem. 2007, 42:880-884.
    • (2007) Eur. J. Med. Chem. , vol.42 , pp. 880-884
    • Curti, C.1    Laget, M.2    Ortiz Carle, A.3    Vanelle, P.4
  • 14
    • 1342321756 scopus 로고    scopus 로고
    • Anti-HIV-1 activity of pyrryl aryl sulfone (PAS) derivatives: synthesis and SAR studies of novel esters and amides at the position 2 of the pyrrole nucleus
    • Silvestri R., Artico M., Regina G.L. Anti-HIV-1 activity of pyrryl aryl sulfone (PAS) derivatives: synthesis and SAR studies of novel esters and amides at the position 2 of the pyrrole nucleus. Il Farmaco. 2004, 59:201-210.
    • (2004) Il Farmaco. , vol.59 , pp. 201-210
    • Silvestri, R.1    Artico, M.2    Regina, G.L.3
  • 15
    • 0004034476 scopus 로고
    • Benzoxazole and benzothiazole derivatives, WO Patent 9406783, 121 9394f.
    • S. Fitzjohn, M. P. Robinson, Benzoxazole and benzothiazole derivatives, WO Patent 9406783(1994), Chem. Abstr. 121 9394f.
    • (1994) Chem. Abstr.
    • Fitzjohn, S.1    Robinson, M.P.2
  • 16
    • 80052260528 scopus 로고    scopus 로고
    • Isoxazoline derivatives and their preparation, herbicidal composition, and use as herbicides to control weeds or plant growth inhibition, WO Patent 2006024820, Chem. Abstr. 144 274262v.
    • P. Andrew, E. B. Jutta, B. Janice, D. S. Timothy, Isoxazoline derivatives and their preparation, herbicidal composition, and use as herbicides to control weeds or plant growth inhibition, WO Patent 2006024820(2006), Chem. Abstr. 144 274262v.
    • (2006)
    • Andrew, P.1    Jutta, E.B.2    Janice, B.3    Timothy, D.S.4
  • 18
    • 0034748113 scopus 로고    scopus 로고
    • Syntheses, biological activities of novel diheterocyclic compounds containing 1,2,4-triazolo[1,5-α]pyrimidine and 1,3,4-oxadiazole
    • Liu Z., Yang G., Qin X. Syntheses, biological activities of novel diheterocyclic compounds containing 1,2,4-triazolo[1,5-α]pyrimidine and 1,3,4-oxadiazole. J. Chem. Technol. Biotechnol. 2001, 76:1154-1158.
    • (2001) J. Chem. Technol. Biotechnol. , vol.76 , pp. 1154-1158
    • Liu, Z.1    Yang, G.2    Qin, X.3
  • 19
    • 77949374897 scopus 로고    scopus 로고
    • Design, synthesis, and 3D-QSAR analysis of novel 1,3,4-oxadiazol-2(3H)-ones as protoporphyrinogen oxidase inhibitors
    • Jiang L., Tan Y., Zhu X., Wang Z., Zuo Y., Chen Q., Xi Z., Yang G. Design, synthesis, and 3D-QSAR analysis of novel 1,3,4-oxadiazol-2(3H)-ones as protoporphyrinogen oxidase inhibitors. J. Agric. Food Chem. 2010, 58:2643-2651.
    • (2010) J. Agric. Food Chem. , vol.58 , pp. 2643-2651
    • Jiang, L.1    Tan, Y.2    Zhu, X.3    Wang, Z.4    Zuo, Y.5    Chen, Q.6    Xi, Z.7    Yang, G.8
  • 20
    • 0030272255 scopus 로고    scopus 로고
    • Syntheses and Insecticidal Activities of Novel 2,5-Disubstituted-1,3,4-oxadiazoles
    • Qian X., Zhang R. Syntheses and Insecticidal Activities of Novel 2,5-Disubstituted-1,3,4-oxadiazoles. J. Chem. Tech. Biotech. 1996, 67:124-130.
    • (1996) J. Chem. Tech. Biotech. , vol.67 , pp. 124-130
    • Qian, X.1    Zhang, R.2
  • 21
    • 0037227705 scopus 로고    scopus 로고
    • Synthesis and Antifeedant Activity of New Oxadiazolyl 3(2H)-Pyridazinones
    • Cao S., Qian X., Song G., Chai B., Jiang Z. Synthesis and Antifeedant Activity of New Oxadiazolyl 3(2H)-Pyridazinones. J Agric Food Chem. 2003, 51:152-155.
    • (2003) J Agric Food Chem. , vol.51 , pp. 152-155
    • Cao, S.1    Qian, X.2    Song, G.3    Chai, B.4    Jiang, Z.5
  • 22
    • 34247569863 scopus 로고    scopus 로고
    • Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxy phenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives
    • Chen C.J., Song B.A., Yang S., Xu G.F., Bhadury P.S., Jin L.H., Hu D.Y., Li Q.Z., Liu F., Xue W., Lu P., Chen Z. Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxy phenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives. Bioorg. Med. Chem. 2007, 15:3981-3989.
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 3981-3989
    • Chen, C.J.1    Song, B.A.2    Yang, S.3    Xu, G.F.4    Bhadury, P.S.5    Jin, L.H.6    Hu, D.Y.7    Li, Q.Z.8    Liu, F.9    Xue, W.10    Lu, P.11    Chen, Z.12
  • 23
    • 41649120338 scopus 로고    scopus 로고
    • Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety
    • Liu F., Luo X.Q., Song B.A., Bhadury P.S., Yang S., Jin L.H., Xue W., Hu D.Y. Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety. Bioorg. Med. Chem. 2008, 16:3632-3640.
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 3632-3640
    • Liu, F.1    Luo, X.Q.2    Song, B.A.3    Bhadury, P.S.4    Yang, S.5    Jin, L.H.6    Xue, W.7    Hu, D.Y.8
  • 24
    • 34247326968 scopus 로고    scopus 로고
    • Synthesis and antifungal activity of novel s-substituted 6-fluoro-4-alkyl(aryl) thioquinazoline derivatives
    • Xu G.F., Song B.A., Bhadury P.S., Yang S., Zhang P.Q., Jin L.H., Xue W., Hu D.Y., Lu P. Synthesis and antifungal activity of novel s-substituted 6-fluoro-4-alkyl(aryl) thioquinazoline derivatives. Bioorg. Med. Chem. 2007, 15:3768-3774.
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 3768-3774
    • Xu, G.F.1    Song, B.A.2    Bhadury, P.S.3    Yang, S.4    Zhang, P.Q.5    Jin, L.H.6    Xue, W.7    Hu, D.Y.8    Lu, P.9
  • 25
    • 80052271200 scopus 로고    scopus 로고
    • Bromuconazole, fluquinconazole, hexaconazole, tetraconazole, in: The Pesticide Manual, thirteenth ed., The British Crop Protection Council, London, 114, 449, 538, 945.
    • C. Tomlin, Bromuconazole, fluquinconazole, hexaconazole, tetraconazole, in: The Pesticide Manual, thirteenth ed., The British Crop Protection Council, London, 2003, 114, 449, 538, 945.
    • (2003)
    • Tomlin, C.1
  • 26
    • 33645757110 scopus 로고    scopus 로고
    • Antifungal activity of 4-methyl-6-alkyl-2H-pyran-2-ones
    • Tarun K.C., Prem D.J. Antifungal activity of 4-methyl-6-alkyl-2H-pyran-2-ones. J. Agric. Food Chem. 2006, 54:2129-2133.
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 2129-2133
    • Tarun, K.C.1    Prem, D.J.2
  • 27
    • 74849140347 scopus 로고    scopus 로고
    • Inhibitor subnanomolar of cytochrome bc1 complex designed by optimizing interaction with conformationally flexible residues
    • Zhao P.L., Wang L., Zhu X.L., Huang X., Zhao C.G., Wu J.W., Yang G.F. Inhibitor subnanomolar of cytochrome bc1 complex designed by optimizing interaction with conformationally flexible residues. J. Am. Chem. Soc. 2010, 132:185-194.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 185-194
    • Zhao, P.L.1    Wang, L.2    Zhu, X.L.3    Huang, X.4    Zhao, C.G.5    Wu, J.W.6    Yang, G.F.7
  • 28
    • 69549086564 scopus 로고    scopus 로고
    • Computational simulations of the interactions between acetyl-coenzyme-a carboxylase, clodinafop: resistance mechanism due to active and nonactive site mutations
    • Zhu X.L., Gefei H., Zhan C.G., Yang G.F. Computational simulations of the interactions between acetyl-coenzyme-a carboxylase, clodinafop: resistance mechanism due to active and nonactive site mutations. J. Chem. Inf. Model. 2009, 49:1936-1943.
    • (2009) J. Chem. Inf. Model. , vol.49 , pp. 1936-1943
    • Zhu, X.L.1    Gefei, H.2    Zhan, C.G.3    Yang, G.F.4
  • 29
    • 33744980870 scopus 로고    scopus 로고
    • Synthesis, structure and antitumor activity of 2-alkylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole compounds
    • Song B.A., Chen C.J., Yang S., Jin L.H., Xue W., Zhang S.M., Zou Z.H., Hu D.Y., Liu G. Synthesis, structure and antitumor activity of 2-alkylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole compounds. Acta Chim. Sinica. 2005, 63:1720-1726.
    • (2005) Acta Chim. Sinica. , vol.63 , pp. 1720-1726
    • Song, B.A.1    Chen, C.J.2    Yang, S.3    Jin, L.H.4    Xue, W.5    Zhang, S.M.6    Zou, Z.H.7    Hu, D.Y.8    Liu, G.9
  • 30
    • 0035953032 scopus 로고    scopus 로고
    • Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent-and halogen-free conditions
    • Sato K., Hyodo M., Aoki M., Zheng X.Q., Noyori R. Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent-and halogen-free conditions. Tetrahedron 2001, 57:2469-2476.
    • (2001) Tetrahedron , vol.57 , pp. 2469-2476
    • Sato, K.1    Hyodo, M.2    Aoki, M.3    Zheng, X.Q.4    Noyori, R.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.