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Volumn 23, Issue 1, 2014, Pages 158-167

Synthesis and antibacterial activity of 4,4′-(aryl or alkyl methylene)-bis(1H-pyrazol-5-ol) derivatives

Author keywords

1 Aryl 3 alkyl 1H pyrazol 5 ol; 4,4 Aryl or alkyl methylene bis(1H pyrazol 5 ol); Ammonium acetate; Antibacterial activity

Indexed keywords


EID: 84893643742     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0623-3     Document Type: Article
Times cited : (36)

References (39)
  • 1
    • 28244439978 scopus 로고    scopus 로고
    • Synthesis of N-heteroaryl(trifluoromethyl)hydroxyalkanoic acid esters by highly efficient solid acid-catalyzed hydroxyalkylation of indoles and pyrroles wih activated trifluoromethyl ketones
    • 1:CAS:528:DC%2BD2MXht1OgtrjM 10.1002/adsc.200505117
    • Abid M, Torok B (2005) Synthesis of N-heteroaryl(trifluoromethyl) hydroxyalkanoic acid esters by highly efficient solid acid-catalyzed hydroxyalkylation of indoles and pyrroles wih activated trifluoromethyl ketones. Adv Synth Catal 347:1797-1803
    • (2005) Adv Synth Catal , vol.347 , pp. 1797-1803
    • Abid, M.1    Torok, B.2
  • 4
    • 84860425971 scopus 로고    scopus 로고
    • Synthesis, biological evaluation and molecular modelling study of pyrazole and pyrazoline derivatives as selective COX-2 inhibitors and anti-inflammatory agents
    • 10.1016/j.bmc.2012.03.044
    • EI-Sayed MA-A, Abdel-Aziz NI, Abdel-Aziz AA-M, EI-Azab AS, ELTahir KEH (2012) Synthesis, biological evaluation and molecular modelling study of pyrazole and pyrazoline derivatives as selective COX-2 inhibitors and anti-inflammatory agents. Bioorg Med Chem 20(10):3306-3316
    • (2012) Bioorg Med Chem , vol.20 , Issue.10 , pp. 3306-3316
    • Ei-Sayed, M.-A.1    Abdel-Aziz, N.I.2    Abdel-Aziz, A.-M.3    Ei-Azab, A.S.4    Keh, E.5
  • 5
    • 46649096443 scopus 로고    scopus 로고
    • Facile and convenient synthesis of 4′4′-(arylmethylene) bis(1H-pyrazol-5-ols) by electrocatalytic tandem Knoevenagel-Michael reaction
    • 10.1055/s-2008-1067079
    • Elinson MN, Dorofeev AS, Nasybullin RF, Nikishin GI (2008) Facile and convenient synthesis of 4′4′-(arylmethylene)bis(1H-pyrazol-5-ols) by electrocatalytic tandem Knoevenagel-Michael reaction. Synthesis 12:1933-1937
    • (2008) Synthesis , vol.12 , pp. 1933-1937
    • Elinson, M.N.1    Dorofeev, A.S.2    Nasybullin, R.F.3    Nikishin, G.I.4
  • 6
    • 72049096999 scopus 로고    scopus 로고
    • Fluorine in medicinal chemistry: A century of progress and a 60-year retrospective of selected highlights
    • 1:CAS:528:DC%2BD1MXhtFCjs7bO 21426080 10.4155/fmc.09.65
    • Filler R, Saha R (2009) Fluorine in medicinal chemistry: a century of progress and a 60-year retrospective of selected highlights. Future Med Chem 1:777-791
    • (2009) Future Med Chem , vol.1 , pp. 777-791
    • Filler, R.1    Saha, R.2
  • 7
    • 18944397659 scopus 로고    scopus 로고
    • Management of Xanthomonas leaf blight of onion with a plant activator, biological control agents, and copper bactericides
    • 1:CAS:528:DC%2BD2MXltlOgu7g%3D 10.1094/PD-89-0631
    • Gent DH, Schwartz HF (2005) Management of Xanthomonas leaf blight of onion with a plant activator, biological control agents, and copper bactericides. Plant Dis 89:631-639
    • (2005) Plant Dis , vol.89 , pp. 631-639
    • Gent, D.H.1    Schwartz, H.F.2
  • 8
    • 33748206790 scopus 로고    scopus 로고
    • Emergence and resurgence of methicillinresistant Staphylococcus aureus as a public-health threat
    • 16950365 10.1016/S0140-6736(06)68853-3
    • Grundmann H, Aires-de-Sousa, Boyce J, Tiemersma E (2006) Emergence and resurgence of methicillinresistant Staphylococcus aureus as a public-health threat. Lancet 368:874
    • (2006) Lancet , vol.368 , pp. 874
    • Grundmann, H.1    Aires-De-Sousa2    Boyce, J.3    Tiemersma, E.4
  • 9
    • 0034933737 scopus 로고    scopus 로고
    • Pyrazolones as versatile precursors for the synthesis of fused and binary heterocycles
    • 1:CAS:528:DC%2BD3MXlsVClsrw%3D 10.1081/SCC-100104042
    • Hamama WS (2001) Pyrazolones as versatile precursors for the synthesis of fused and binary heterocycles. Synth Commun 31:1335-1345
    • (2001) Synth Commun , vol.31 , pp. 1335-1345
    • Hamama, W.S.1
  • 11
    • 13944265524 scopus 로고    scopus 로고
    • A clean and simple synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl- 1,4-dihydropyrano[2,3-c] pyrazole in Water
    • 1:CAS:528:DC%2BD2MXit1Sksbw%3D 10.1081/SCC-200046527
    • Jin TS, Wang AQ, Cheng ZL, Zhang JS, Li TS (2005) A clean and simple synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c] pyrazole in Water. Synth Commun 35:137-140
    • (2005) Synth Commun , vol.35 , pp. 137-140
    • Jin, T.S.1    Wang, A.Q.2    Cheng, Z.L.3    Zhang, J.S.4    Li, T.S.5
  • 12
    • 84857604330 scopus 로고    scopus 로고
    • Phosphomolybdic acid: An efficient and recyclable solid acid catalyst for the synthesis of 4,4′- (arylmethylene)bis(1H-pyrazol-5-ols)
    • 10.1080/00397911.2010.539759
    • Kiran RP, Vikas SP, Vinod DG, Vikas SP, Prashant GU, Sekar N (2012) Phosphomolybdic acid: an efficient and recyclable solid acid catalyst for the synthesis of 4,4′- (arylmethylene)bis(1H-pyrazol-5-ols). Synth Commun 42:1349-1358
    • (2012) Synth Commun , vol.42 , pp. 1349-1358
    • Kiran, R.P.1    Vikas, S.P.2    Vinod, D.G.3    Vikas, S.P.4    Prashant, G.U.5    Sekar, N.6
  • 13
    • 25444462248 scopus 로고    scopus 로고
    • Synthesis of hantsch 1,4-dihydropyridines by fermenting bakers' yeast
    • 1:CAS:528:DC%2BD2MXhtVantbfL 10.1016/j.tetlet.2005.08.137
    • Lee JH (2005) Synthesis of hantsch 1,4-dihydropyridines by fermenting bakers' yeast. Tetrahedron Lett 46:7329-7330
    • (2005) Tetrahedron Lett , vol.46 , pp. 7329-7330
    • Lee, J.H.1
  • 14
    • 0007326878 scopus 로고    scopus 로고
    • The solid-state Michael addition of 3-methyl-1-phenyl-5-pyrazolone
    • 1:CAS:528:DyaK1cXhvFWhs70%3D 10.1002/jhet.5570350124
    • Li X-L, Wang Y-M, Tian B, Matsuura T, Meng J-B (1998) The solid-state Michael addition of 3-methyl-1-phenyl-5-pyrazolone. J Heterocycl Chem 35:129-134
    • (1998) J Heterocycl Chem , vol.35 , pp. 129-134
    • Li, X.-L.1    Wang, Y.-M.2    Tian, B.3    Matsuura, T.4    Meng, J.-B.5
  • 16
    • 79959896279 scopus 로고    scopus 로고
    • Synthesis and anti-inflammatory activity of some novel 3-phenyl-N-[3-(4-phenylpiperazin-1yl)propyl]-1H-pyrazole-5-carboxamide derivative
    • 10.1016/j.bmcl.2011.05.105
    • Lingaiah N, Jhansi M, Hanmant KG, Rajashaker B, Rani MS, Subhashini NJP (2011) Synthesis and anti-inflammatory activity of some novel 3-phenyl-N-[3-(4-phenylpiperazin-1yl)propyl]-1H-pyrazole-5-carboxamide derivative. Bioorg Med Chem Lett 21:4138-4140
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 4138-4140
    • Lingaiah, N.1    Jhansi, M.2    Hanmant, K.G.3    Rajashaker, B.4    Rani, M.S.5    Subhashini, N.J.P.6
  • 17
    • 28544451673 scopus 로고    scopus 로고
    • Studies on the biginelli reaction: A mild and selective route to 3,4-dihydropyrimidin-2(1H)-ones via enamine intermediates
    • 1:CAS:528:DC%2BD2MXht1OisbzO 10.1016/j.tetlet.2005.10.124
    • Mabry M, Ganem B (2006) Studies on the biginelli reaction: a mild and selective route to 3,4-dihydropyrimidin-2(1H)-ones via enamine intermediates. Tetrahedron Lett 47:55-56
    • (2006) Tetrahedron Lett , vol.47 , pp. 55-56
    • Mabry, M.1    Ganem, B.2
  • 19
    • 0040470252 scopus 로고
    • Tautomeric products of condensation of aldehydes with pyrazolone
    • Mitra AS, Rout MK (1961) Tautomeric products of condensation of aldehydes with pyrazolone. J Indian Chem Soc 38:893-895
    • (1961) J Indian Chem Soc , vol.38 , pp. 893-895
    • Mitra, A.S.1    Rout, M.K.2
  • 20
    • 31944446866 scopus 로고    scopus 로고
    • Direct asymmetric anti-mannich-type reactions catalyzed by a designed amino acid
    • 1:CAS:528:DC%2BD28XitVymsg%3D%3D 2532695 16433496 10.1021/ja056984f
    • Mitsumori S, Zhang HL, Cheong PH, Houk KN, Tanaka F, Barbas CF (2006) Direct asymmetric anti-mannich-type reactions catalyzed by a designed amino acid. J Am Chem Soc 128:1040-1041
    • (2006) J Am Chem Soc , vol.128 , pp. 1040-1041
    • Mitsumori, S.1    Zhang, H.L.2    Cheong, P.H.3    Houk, K.N.4    Tanaka, F.5    Barbas, C.F.6
  • 21
    • 72149102674 scopus 로고    scopus 로고
    • Silica-bonded S-sulfonic acid: An efficient and recyclable catalyst for the synthesis of 4.4′-(arylmethylene)bis(1H-pyrazol-5-ols)
    • 1:CAS:528:DC%2BD1MXhs1SqtrbE 10.1016/j.tetlet.2009.11.114
    • Niknam K, Saberi D, Sadegheyan M, Deris A (2010) Silica-bonded S-sulfonic acid: an efficient and recyclable catalyst for the synthesis of 4.4′-(arylmethylene)bis(1H-pyrazol-5-ols). Tetrahedron Lett 51:692-694
    • (2010) Tetrahedron Lett , vol.51 , pp. 692-694
    • Niknam, K.1    Saberi, D.2    Sadegheyan, M.3    Deris, A.4
  • 22
    • 84856091368 scopus 로고    scopus 로고
    • Brahmbhatt di (2012) Synthesis, characterization and biological evaluation of some pyridine and quinoline fused chromenone derivatives
    • 1:CAS:528:DC%2BC38XhtlOksr4%3D 10.1007/s00044-012-9978-0
    • Patel MA, Bhila VG, Patel NH, Patel AK (2012) Brahmbhatt DI (2012) Synthesis, characterization and biological evaluation of some pyridine and quinoline fused chromenone derivatives. Med Chem Res 21:4381-4388
    • (2012) Med Chem Res , vol.21 , pp. 4381-4388
    • Patel, M.A.1    Bhila, V.G.2    Patel, N.H.3    Patel, A.K.4
  • 25
    • 77951138173 scopus 로고    scopus 로고
    • Synthesis and antibacterial activity of some new derivatives of pyrazole
    • 1:CAS:528:DC%2BC3cXjslKjsQ%3D%3D 10.1007/s11274-009-0178-0
    • Rahimizadeh Md, Pordel M, Bakavoli M, Rezaeian S, Sadeghian A (2010) Synthesis and antibacterial activity of some new derivatives of pyrazole. World J Microbiol Biotechnol 26:317-321
    • (2010) World J Microbiol Biotechnol , vol.26 , pp. 317-321
    • Rahimizadeh, M.1    Pordel, M.2    Bakavoli, M.3    Rezaeian, S.4    Sadeghian, A.5
  • 26
    • 70350071885 scopus 로고    scopus 로고
    • Synthesis, characterization and antimicrobial activity of some new 1-(fluorobenzoyl)-3-(fluorophenyl) thioureas
    • 1:CAS:528:DC%2BD1MXhtlWlu7fE 10.1016/j.jfluchem.2009.09.003
    • Saeed A, Shaheen U, Hameed A, Haider Naqvi SZ (2009) Synthesis, characterization and antimicrobial activity of some new 1-(fluorobenzoyl)-3- (fluorophenyl) thioureas. J Fluor Chem 130:1028-1034
    • (2009) J Fluor Chem , vol.130 , pp. 1028-1034
    • Saeed, A.1    Shaheen, U.2    Hameed, A.3    Haider Naqvi, S.Z.4
  • 27
    • 15444375592 scopus 로고    scopus 로고
    • Photo-controllable tristability of a dithiolato-bipyridine-Pt(II) complex molecule containing two azobenzene moieties
    • 10.1039/b415293j
    • Sakamoto R, Ryoto M, Kume S, Sampei H, Sugimoto M, Nishihara H (2005) Photo-controllable tristability of a dithiolato-bipyridine-Pt(II) complex molecule containing two azobenzene moieties. Chem Commun 9:1215-1217
    • (2005) Chem Commun , vol.9 , pp. 1215-1217
    • Sakamoto, R.1    Ryoto, M.2    Kume, S.3    Sampei, H.4    Sugimoto, M.5    Nishihara, H.6
  • 28
    • 80054860498 scopus 로고    scopus 로고
    • The state of the art of pyrazole derivatives as monoamine oxidase inhibitors and antidepressant/anticonvulsant agents
    • 1:CAS:528:DC%2BC3MXhs1ShtrzO 22050759 10.2174/092986711797636090
    • Secci D, Bolasco A, Chimenti P, Carradori S (2011) The state of the art of pyrazole derivatives as monoamine oxidase inhibitors and antidepressant/ anticonvulsant agents. Curr Med Chem 18:5114-5144
    • (2011) Curr Med Chem , vol.18 , pp. 5114-5144
    • Secci, D.1    Bolasco, A.2    Chimenti, P.3    Carradori, S.4
  • 29
    • 34547201983 scopus 로고    scopus 로고
    • Synthesis, isomerization, and antimicrobial evaluation of some pyrazolopyrano triazolo pyrimidine derivatives
    • 1:CAS:528:DC%2BD2sXosV2gsLc%3D 10.1002/ardp.200700007
    • Shamroukh AH, Zaki MEA, Morsy EMH, Abdel-Motti FM, Abdel Megeid FME (2007) Synthesis, isomerization, and antimicrobial evaluation of some pyrazolopyrano triazolo pyrimidine derivatives. Arch de Pharma 340:345-351
    • (2007) Arch de Pharma , vol.340 , pp. 345-351
    • Shamroukh, A.H.1    Zaki, M.E.A.2    Morsy, E.M.H.3    Abdel-Motti, F.M.4    Abdel Megeid, F.M.E.5
  • 30
    • 11144238099 scopus 로고
    • Synthesis of 1,3-disubstituted 4-arylidenepyrazoln-5-ones and the keto and enol forms of 4,4′-arylidenebis(1,3-disubstituted pyrazolin-5-ones)
    • 1:CAS:528:DyaL2cXksFCqur0%3D 10.1021/je00037a040
    • Singh D, Singh D (1984) Synthesis of 1,3-disubstituted 4-arylidenepyrazoln-5-ones and the keto and enol forms of 4,4′- arylidenebis(1,3-disubstituted pyrazolin-5-ones). J Chem Eng Data 29:355-356
    • (1984) J Chem Eng Data , vol.29 , pp. 355-356
    • Singh, D.1    Singh, D.2
  • 31
    • 0034926661 scopus 로고    scopus 로고
    • Fluorine substituent effects (on bioactivity)
    • 1:CAS:528:DC%2BD3MXksFKltbY%3D 10.1016/S0022-1139(01)00375-X
    • Smart BE (2001) Fluorine substituent effects (on bioactivity). J Fluor Chem 109:3-11
    • (2001) J Fluor Chem , vol.109 , pp. 3-11
    • Smart, B.E.1
  • 32
    • 84859720043 scopus 로고    scopus 로고
    • Tandem Knoevenagel-Michael reaction of 1-phenyl-3methyl-5-pyrazolone with aldehydes using 3-aminopropylated silica gel as an efficient and reusable heterogeneous catalyst
    • 1:CAS:528:DC%2BC38XlsVWlur4%3D 10.1080/00397911.2011.555589
    • Sobhani S, Hasaninejad A-R, Maleki MF, Parizi ZP (2012) Tandem Knoevenagel-Michael reaction of 1-phenyl-3methyl-5-pyrazolone with aldehydes using 3-aminopropylated silica gel as an efficient and reusable heterogeneous catalyst. Synth Commun 42:2245-2255
    • (2012) Synth Commun , vol.42 , pp. 2245-2255
    • Sobhani, S.1    Hasaninejad, A.-R.2    Maleki, M.F.3    Parizi, Z.P.4
  • 33
    • 67649968893 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of 4,4′-(arylmethylene)bis(1H- pyrazol-5-ols) against peste des petits ruminant virus (PPRV)
    • 1:CAS:528:DC%2BD1MXosVGlsLk%3D 19482473 10.1016/j.bmcl.2009.02.113
    • Sujatha K, Shanthi G, Selvam NP, Manoharan S, Perumal PT, Rajendran M (2009) Synthesis and antiviral activity of 4,4′-(arylmethylene)bis(1H- pyrazol-5-ols) against peste des petits ruminant virus (PPRV). Bioorg Med Chem Lett 19:4501-4503
    • (2009) Bioorg Med Chem Lett , vol.19 , pp. 4501-4503
    • Sujatha, K.1    Shanthi, G.2    Selvam, N.P.3    Manoharan, S.4    Perumal, P.T.5    Rajendran, M.6
  • 34
    • 4644346774 scopus 로고    scopus 로고
    • A clean one-pot Synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by hexadecyltrimethyl ammonium bromide in aqueous media
    • Tong-Shou J, Ai-Qing W, Xin W, Jian-She Z, Tong-Shuang L (2004) A clean one-pot Synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by hexadecyltrimethyl ammonium bromide in aqueous media. Synlet 5:871-873
    • (2004) Synlet , vol.5 , pp. 871-873
    • Tong-Shou, J.1    Ai-Qing, W.2    Xin, W.3    Jian-She, Z.4    Tong-Shuang, L.5
  • 35
    • 48049104380 scopus 로고    scopus 로고
    • Point-of-use filtration reduces endemic Pseudomonas aeruginosa infections on a surgical intensive care unit
    • 18675148 10.1016/j.ajic.2007.09.012
    • Trautmann M, Halder S, Hoegel J, Royer H, Haller M (2008) Point-of-use filtration reduces endemic Pseudomonas aeruginosa infections on a surgical intensive care unit. Am J Infect Control 36:421-429
    • (2008) Am J Infect Control , vol.36 , pp. 421-429
    • Trautmann, M.1    Halder, S.2    Hoegel, J.3    Royer, H.4    Haller, M.5
  • 38
    • 18744366642 scopus 로고    scopus 로고
    • Reaction of aldehyde and pyrazolones in the presence of sodium dodecyl sulphate in aqueous media
    • 1:CAS:528:DC%2BD2MXks12msrs%3D 10.1081/SCC-200054854
    • Wang W, Wang SX, Qin XY, Li JT (2005) Reaction of aldehyde and pyrazolones in the presence of sodium dodecyl sulphate in aqueous media. Synth Commun 35:1263-1269
    • (2005) Synth Commun , vol.35 , pp. 1263-1269
    • Wang, W.1    Wang, S.X.2    Qin, X.Y.3    Li, J.T.4
  • 39
    • 9344260831 scopus 로고    scopus 로고
    • A novel l-Proline catalyzed biginelli reaction: One-pot synthesis of 3,4-dihydropyrimidine-2(1H)-ones under solvent-free conditions
    • 1:CAS:528:DC%2BD2cXnslSru7o%3D 10.1246/cl.2004.1168
    • Yadav JS, Kumar SP, Kondaji G, Rao RS, Nagaiah K (2004) A novel l-Proline catalyzed biginelli reaction: one-pot synthesis of 3,4-dihydropyrimidine-2(1H)- ones under solvent-free conditions. Chem Lett 33:1168-1169
    • (2004) Chem Lett , vol.33 , pp. 1168-1169
    • Yadav, J.S.1    Kumar, S.P.2    Kondaji, G.3    Rao, R.S.4    Nagaiah, K.5


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