메뉴 건너뛰기




Volumn 4, Issue 1, 2002, Pages 23-32

Design, synthesis, and biological evaluation of a library of 1-(2-Thiazolyl)-5-(trifluoromethyl)pyrazole-4-carboxamides

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ANTINEMATODAL AGENT; CARBAMIC ACID DERIVATIVE; FLUORINATED HYDROCARBON; PYRAZOLE DERIVATIVE; THIAZOLE DERIVATIVE;

EID: 0036367291     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc010035a     Document Type: Review
Times cited : (46)

References (41)
  • 1
    • 0003132804 scopus 로고
    • Fluorinated agrochemicals
    • Chemistry of Organic Fluorine Compounds 11
    • Lang, R. W. Fluorinated Agrochemicals. ACS Monogr. 1995, 187, 1143-1147 (Chemistry of Organic Fluorine Compounds 11).
    • (1995) ACS Monogr. , vol.187 , pp. 1143-1147
    • Lang, R.W.1
  • 4
    • 84986527695 scopus 로고
    • Selective instability of trifluoromethyl linked to carbon. A prerequisite for new heterocyclizations with ethyl 4,4,4-trifluoroacetoacetate arylhydrazones
    • Pilgram, K. H.; Skiles, R. D. Selective Instability of Trifluoromethyl Linked to Carbon. A Prerequisite for New Heterocyclizations with Ethyl 4,4,4-Trifluoroacetoacetate Arylhydrazones. J. Heterocycl. Chem. 1988, 25, 139-143.
    • (1988) J. Heterocycl. Chem. , vol.25 , pp. 139-143
    • Pilgram, K.H.1    Skiles, R.D.2
  • 5
    • 84986469572 scopus 로고
    • Synthesis of 1-Aryl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acids and esters
    • Beck, J. R.; Wright, F. L. Synthesis of 1-Aryl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acids and esters. J. Heterocycl. Chem. 1987, 24, 739-740.
    • (1987) J. Heterocycl. Chem. , vol.24 , pp. 739-740
    • Beck, J.R.1    Wright, F.L.2
  • 7
    • 0027933345 scopus 로고
    • An efficient entry to perfluoroalkyl substituted azoles starting from β-perfluoroalkyl-β-dicarbonyl compounds
    • Bravo, P.; Diliddo, D.; Resnati, G. An Efficient Entry to Perfluoroalkyl Substituted Azoles Starting from β-Perfluoroalkyl-β-dicarbonyl Compounds. Tetrahedron 1994, 50, 8827-8836.
    • (1994) Tetrahedron , vol.50 , pp. 8827-8836
    • Bravo, P.1    Diliddo, D.2    Resnati, G.3
  • 9
    • 0000390894 scopus 로고
    • Syntheses and reactions of 2-Halo-5-thiazolecarboxylates
    • Lee, L. F.; Schleppnik, F. M.; Howe, R. K. Syntheses and Reactions of 2-Halo-5-thiazolecarboxylates. J. Heterocycl. Chem. 1985, 22, 1621-1630.
    • (1985) J. Heterocycl. Chem. , vol.22 , pp. 1621-1630
    • Lee, L.F.1    Schleppnik, F.M.2    Howe, R.K.3
  • 10
    • 0025144028 scopus 로고
    • A novel dehydrofluorination of 2-(Trifluoromethyl)dihydro-3,5-pyridinecarboxylates to 2-(Difluoromethyl)-3,5-pyridinedicarboxylates
    • Lee, L. F.; Stikes, G. L.; Molyneaux, J. M.; Sing, Y. L.; Chupp, J. P.; Woodard, S. S. A Novel Dehydrofluorination of 2-(Trifluoromethyl)dihydro-3,5-pyridinecarboxylates to 2-(Difluoromethyl)-3,5-pyridinedicarboxylates. J. Org. Chem. 1990, 55, 2872-2877.
    • (1990) J. Org. Chem. , vol.55 , pp. 2872-2877
    • Lee, L.F.1    Stikes, G.L.2    Molyneaux, J.M.3    Sing, Y.L.4    Chupp, J.P.5    Woodard, S.S.6
  • 12
    • 0343067114 scopus 로고    scopus 로고
    • Synthesis of 4-thiazolidinone and 2-azetidinone derivatives of 2-trifluoromethyl-1,8-naphthyridine as antibacterial agents
    • Mogilaiah, K.; Rao, R. B.; Reddy, K. N. Synthesis of 4-thiazolidinone and 2-azetidinone derivatives of 2-trifluoromethyl-1,8-naphthyridine as antibacterial agents. Indian J. Chem., Sect. B 1999, 38, 818-822.
    • (1999) Indian J. Chem., Sect. B , vol.38 , pp. 818-822
    • Mogilaiah, K.1    Rao, R.B.2    Reddy, K.N.3
  • 13
    • 0033526095 scopus 로고    scopus 로고
    • Switching androgen receptor antagonists to agonists by modifying C-ring substituents on piperidino[3,2-g]quinolinone
    • Zhi, L.; Tegley, C, M.; Marschke, K. B.; Jones, T. K. Switching Androgen Receptor Antagonists to Agonists by Modifying C-Ring Substituents on Piperidino[3,2-g]quinolinone. Bioorg. Med. Chem. Lett. 1999, 9, 1008-1012.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 1008-1012
    • Zhi, L.1    Tegley, C.M.2    Marschke, K.B.3    Jones, T.K.4
  • 14
    • 0032492668 scopus 로고    scopus 로고
    • New nonsteroidal androgen receptor modulators based on 4-(Trifluoromethyl)-2(1H)-pyrrolidino[3,2-g]quinolinone
    • Edwards, J. P.; West, S. J.; Pooley, C. L. F.; Marschke, K. B.; Farmer, L. J.; Jones, T. K. New Nonsteroidal Androgen Receptor Modulators Based on 4-(Trifluoromethyl)-2(1H)-pyrrolidino[3,2-g]quinolinone. Bioorg. Med. Chem. Lett. 1998, 8, 745-750.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 745-750
    • Edwards, J.P.1    West, S.J.2    Pooley, C.L.F.3    Marschke, K.B.4    Farmer, L.J.5    Jones, T.K.6
  • 15
    • 0039891072 scopus 로고
    • Some diazinon analogs containing the 4-Trifluoromethyl group
    • Gershon, H.; Clarke, D. D.; Grefig, A. T.; Anderson, T. E. Some Diazinon Analogs Containing the 4-Trifluoromethyl Group. Monatsh. Chem. 1990, 121, 289-292.
    • (1990) Monatsh. Chem. , vol.121 , pp. 289-292
    • Gershon, H.1    Clarke, D.D.2    Grefig, A.T.3    Anderson, T.E.4
  • 16
    • 0035795083 scopus 로고    scopus 로고
    • Regiocontrolled synthesis of 3-Substituted-6-trifluoromethyl-4(3H)-pyrimidinones
    • Tice, C. M.; Bryman, L. M. Regiocontrolled Synthesis of 3-Substituted-6-trifluoromethyl-4(3H)-pyrimidinones. Tetrahedron 2001, 57, 2689-2700.
    • (2001) Tetrahedron , vol.57 , pp. 2689-2700
    • Tice, C.M.1    Bryman, L.M.2
  • 18
    • 0032854156 scopus 로고    scopus 로고
    • Isolation, conformational analysis and x-ray structure determination of a trifluoromethyl-stabilized hexahydropyrimidinone - An intermediate in the biginelli reaction
    • Kappe, C. O.; Falsone, S. F.; Fabian, W. M. F.; Belaj, F. Isolation, Conformational Analysis and X-ray Structure Determination of a Trifluoromethyl-Stabilized Hexahydropyrimidinone - An Intermediate in the Biginelli Reaction. Heterocycles 1999, 51, 77-84.
    • (1999) Heterocycles , vol.51 , pp. 77-84
    • Kappe, C.O.1    Falsone, S.F.2    Fabian, W.M.F.3    Belaj, F.4
  • 21
    • 0032541999 scopus 로고    scopus 로고
    • Synthesis of novel fluorinated coumarins: Excellent UV-light excitable fluorescent dyes
    • Sun, W.-C.; Gee, K. R.; Haugland, R. P. Synthesis of Novel Fluorinated Coumarins: Excellent UV-Light Excitable Fluorescent Dyes. Bioorg. Med. Chem. Lett. 1998, 8, 3107-3110.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 3107-3110
    • Sun, W.-C.1    Gee, K.R.2    Haugland, R.P.3
  • 24
    • 84989692374 scopus 로고
    • Thiazole carboxanilide fungicides: A new structure - Activity relationship for succinate dehydrogenase inhibitors
    • Phillips, W. G.; Rejda-Heath, J. M. Thiazole carboxanilide fungicides: a new structure - activity relationship for succinate dehydrogenase inhibitors. Pestic. Sci. 1993, 38, 1-7.
    • (1993) Pestic. Sci. , vol.38 , pp. 1-7
    • Phillips, W.G.1    Rejda-Heath, J.M.2
  • 25
    • 0039298932 scopus 로고
    • Process for treating hyperglycemia using trifluoromethyl substituted 3H-pyrazol-3-ones
    • U.S. Patent 5,264,451, 1993
    • Kees, K. L. Process for treating hyperglycemia using trifluoromethyl substituted 3H-pyrazol-3-ones. U.S. Patent 5,264,451, 1993 (Chem. Abstr. 1994, 120, 95803).
    • (1994) Chem. Abstr. , vol.120 , pp. 95803
    • Kees, K.L.1
  • 26
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • 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 Delivery Rev. 1997, 23, 3-25.
    • (1997) Adv. Drug Delivery Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 27
    • 0035132705 scopus 로고    scopus 로고
    • Selecting the right compounds for screening: Does Lipinski's rule of 5 for pharmaceuticals apply to agrochemicals?
    • Tice, C. M. Selecting the Right Compounds for Screening: Does Lipinski's Rule of 5 for Pharmaceuticals Apply to Agrochemicals? Pest Manage. Sci. 2001, 57, 3-16.
    • (2001) Pest Manage. Sci. , vol.57 , pp. 3-16
    • Tice, C.M.1
  • 29
    • 0030200397 scopus 로고    scopus 로고
    • Approaches to combinatorial synthesis of heterocycles: Solid-phase synthesis of pyridines and pyrido[2,3-d]pyrimidines
    • Gordeev, M. F.; Patel, D. V.; Wu, J.; Gordon, E. M. Approaches to Combinatorial Synthesis of Heterocycles: Solid-Phase Synthesis of Pyridines and Pyrido[2,3-d]pyrimidines. Tetrahedron Lett. 1996, 37, 4643-4646.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4643-4646
    • Gordeev, M.F.1    Patel, D.V.2    Wu, J.3    Gordon, E.M.4
  • 30
    • 33947294569 scopus 로고
    • Modified support for solid-phase peptide synthesis which permits the synthesis of protected peptide fragments
    • Marshall, D. L.; Liener, I. E. Modified support for solid-phase peptide synthesis which permits the synthesis of protected peptide fragments. J. Org. Chem. 1970, 35, 867-868.
    • (1970) J. Org. Chem. , vol.35 , pp. 867-868
    • Marshall, D.L.1    Liener, I.E.2
  • 31
    • 0001176887 scopus 로고    scopus 로고
    • Activation method to prepare a highly reactive acylsulfonamide "safety-catch" linker for solid-phase synthesis
    • Backes, B. J.; Virgilio, A. A.; Ellman, J. A. Activation Method To Prepare a Highly Reactive Acylsulfonamide "Safety-Catch" Linker for Solid-Phase Synthesis. J. Am. Chem. Soc. 1996, 118, 3055-3056.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3055-3056
    • Backes, B.J.1    Virgilio, A.A.2    Ellman, J.A.3
  • 32
    • 0030700807 scopus 로고    scopus 로고
    • Alkylation of rink's amide linker on polystyrene resin: A reductive amination approach to modified amine-linkers for the solid-phase synthesis of N-substituted amide derivatives
    • Brown, E. G.; Nuss, J. M. Alkylation of Rink's amide linker on polystyrene resin: a reductive amination approach to modified amine-linkers for the solid-phase synthesis of N-substituted amide derivatives. Tetrahedron Lett. 1997, 38, 8457-8460.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8457-8460
    • Brown, E.G.1    Nuss, J.M.2
  • 33
    • 0012664399 scopus 로고
    • Synthesis of derivatives of pyrazoles, 1,2,4,5-tetrazine and 1,2,4-triazole from thiocarbonylhydrazides and β-dicarbonyl compounds
    • Alexiev, V. V.; Zelenin, K. N.; Yakimovich, S. I. Synthesis of derivatives of pyrazoles, 1,2,4,5-tetrazine and 1,2,4-triazole from thiocarbonylhydrazides and β-dicarbonyl compounds. Zh. Org. Chim. 1995, 31, 937-943.
    • (1995) Zh. Org. Chim. , vol.31 , pp. 937-943
    • Alexiev, V.V.1    Zelenin, K.N.2    Yakimovich, S.I.3
  • 34
    • 0001903629 scopus 로고    scopus 로고
    • Haloacetylated enol ethers 10. Condensation of β-alkoxyvinyl trifluoromethyl ketones with thiosemicarbazide. Synthesis of new trifluoromethyl 4,5-dihydro-1-H-1-pyrazolethiocarboxyamides
    • Bonacorso, H. G.; Wastowski, A. D.; Zanatta, N.; Martins, M. A. P.; Naue, J. A. Haloacetylated enol ethers 10. Condensation of β-alkoxyvinyl trifluoromethyl ketones with thiosemicarbazide. Synthesis of new trifluoromethyl 4,5-dihydro-1-H-1-pyrazolethiocarboxyamides J. Fluorine Chem. 1998, 92, 23-26.
    • (1998) J. Fluorine Chem. , vol.92 , pp. 23-26
    • Bonacorso, H.G.1    Wastowski, A.D.2    Zanatta, N.3    Martins, M.A.P.4    Naue, J.A.5
  • 35
    • 0030952762 scopus 로고    scopus 로고
    • Chemical library purification strategies based on principles of complementary molecular reactivity and molecular recognition
    • Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodard, S. Chemical library purification strategies based on principles of complementary molecular reactivity and molecular recognition. J. Am. Chem. Soc. 1997, 119, 4874-4881.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4874-4881
    • Flynn, D.L.1    Crich, J.Z.2    Devraj, R.V.3    Hockerman, S.L.4    Parlow, J.J.5    South, M.S.6    Woodard, S.7
  • 36
    • 0030987922 scopus 로고    scopus 로고
    • Polymer-supported quenching reagents for parallel purification
    • Booth, R. J.; Hodges, J. C. Polymer-supported quenching reagents for parallel purification. J. Am. Chem. Soc. 1997, 119, 4882-4886.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4882-4886
    • Booth, R.J.1    Hodges, J.C.2
  • 37
    • 0021278642 scopus 로고
    • Palladium(0) mediated β-carboline synthesis: Preparation of the CDE ring system of lavendamycin
    • Boger, D. L.; Panek, J. S. Palladium(0) mediated β-carboline synthesis: Preparation of the CDE ring system of lavendamycin. Tetrahedron Lett. 1984, 25, 3175-3178.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 3175-3178
    • Boger, D.L.1    Panek, J.S.2
  • 38
    • 0033886109 scopus 로고    scopus 로고
    • Bacillus thuringiensis (Bt) toxin susceptibility and isolation of resistance mutants in the nematode caenorhabditis elegans
    • Marroquin, L. D.; Elyassnia, D.; Griffitts, J. S.; Feitelson, J. S.; Aroian, R. V. Bacillus thuringiensis (Bt) toxin susceptibility and isolation of resistance mutants in the nematode Caenorhabditis elegans. Genetics 2000 155, 1693-1699.
    • (2000) Genetics , vol.155 , pp. 1693-1699
    • Marroquin, L.D.1    Elyassnia, D.2    Griffitts, J.S.3    Feitelson, J.S.4    Aroian, R.V.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.