메뉴 건너뛰기




Volumn 56, Issue 1, 2013, Pages 31-45

Synthesis and insight into the structure-activity relationships of chalcones as antimalarial agents

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXY 5 [3 [7 HYDROXY 2 METHYL 2 (4 METHYL PENT 3 ENYL) 2H CHROMEN 8 YL] 3 OXO PROPENYL]BENZALDEHYDE; ANTIMALARIAL AGENT; CHALCONE DERIVATIVE; FALCIPAIN 2; MEDICAGENIN; MUNCHIWARIN; UNCLASSIFIED DRUG;

EID: 84872325842     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300588j     Document Type: Article
Times cited : (99)

References (59)
  • 1
    • 2542451884 scopus 로고    scopus 로고
    • The global distribution and population at risk of malaria: Past, present, and future
    • Hay, S. I.; Guerra, C. A.; Tatem, A. J.; Noor, A. M.; Snow, R. W. The global distribution and population at risk of malaria: past, present, and future Lancet Infect. Dis. 2004, 4, 327-236
    • (2004) Lancet Infect. Dis. , vol.4 , pp. 327-236
    • Hay, S.I.1    Guerra, C.A.2    Tatem, A.J.3    Noor, A.M.4    Snow, R.W.5
  • 2
    • 79952193925 scopus 로고    scopus 로고
    • World Health Organization: Geneva, December
    • World Malaria Report 2010; World Health Organization: Geneva, December 2010.
    • (2010) World Malaria Report 2010
  • 3
    • 0004580398 scopus 로고    scopus 로고
    • Flavonoids: Old and new aspects of a class of natural therapeutic drugs
    • Di Carlo, G.; Mascolo, N.; Izzo, A. A.; Capasso, F. Flavonoids: old and new aspects of a class of natural therapeutic drugs Life Sci. 1999, 65, 337-353
    • (1999) Life Sci. , vol.65 , pp. 337-353
    • Di Carlo, G.1    Mascolo, N.2    Izzo, A.A.3    Capasso, F.4
  • 4
    • 0034678788 scopus 로고    scopus 로고
    • Antitumor agents. part 202: Novel 2′-amino chalcones: Design, synthesis and biological evaluation
    • Xia, Y.; Yang, Z. Y.; Xia, P.; Bastow, K. F.; Nakanishi, Y.; Lee, K. H. Antitumor agents. part 202: novel 2′-amino chalcones: design, synthesis and biological evaluation Bioorg. Med. Chem. Lett. 2000, 10, 699-701
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 699-701
    • Xia, Y.1    Yang, Z.Y.2    Xia, P.3    Bastow, K.F.4    Nakanishi, Y.5    Lee, K.H.6
  • 5
    • 0032497591 scopus 로고    scopus 로고
    • Halogenated chalcones with high-affinity binding to P-glycoprotein: Potential modulators of multidrug resistance
    • Bois, F.; Beney, C.; Boumendjel, A.; Mariotte, A. M.; Conseil, G.; Di Pietro, A. Halogenated chalcones with high-affinity binding to P-glycoprotein: potential modulators of multidrug resistance J. Med. Chem. 1998, 41, 4161-4164
    • (1998) J. Med. Chem. , vol.41 , pp. 4161-4164
    • Bois, F.1    Beney, C.2    Boumendjel, A.3    Mariotte, A.M.4    Conseil, G.5    Di Pietro, A.6
  • 6
    • 0035818913 scopus 로고    scopus 로고
    • Antimalarial alkoxylated and hydroxylated chalones: Structure-activity relationship analysis
    • Liu, M.; Wilairat, P.; Go, M. L. Antimalarial alkoxylated and hydroxylated chalones: structure-activity relationship analysis J. Med. Chem. 2001, 44, 4443-4452
    • (2001) J. Med. Chem. , vol.44 , pp. 4443-4452
    • Liu, M.1    Wilairat, P.2    Go, M.L.3
  • 8
    • 0031913851 scopus 로고    scopus 로고
    • Synthesis and anti-inflammatory effect of chalcones and related compounds
    • Hsieh, H. K.; Lee, T. H.; Wang, J. P.; Wang, J. J.; Lin, C. N. Synthesis and anti-inflammatory effect of chalcones and related compounds Pharm. Res. 1998, 15, 39-46
    • (1998) Pharm. Res. , vol.15 , pp. 39-46
    • Hsieh, H.K.1    Lee, T.H.2    Wang, J.P.3    Wang, J.J.4    Lin, C.N.5
  • 11
    • 57349124054 scopus 로고    scopus 로고
    • Synthesis and anti-inflammatory activity of chalcones and related mannich bases
    • Maria, K.; Dimitra, H. L.; Maria, G. Synthesis and anti-inflammatory activity of chalcones and related mannich bases Med. Chem. 2008, 4, 586-596
    • (2008) Med. Chem. , vol.4 , pp. 586-596
    • Maria, K.1    Dimitra, H.L.2    Maria, G.3
  • 12
    • 0037358112 scopus 로고    scopus 로고
    • Analgesic and antiinflammatory effects of chalcones isolated from Myracrodruon urundeuva Allemão
    • Vianaa, G. S.; Bandeiraa, M. A.; Matosa, F. J. Analgesic and antiinflammatory effects of chalcones isolated from Myracrodruon urundeuva Allemão Phytomedicine 2003, 10, 189-195
    • (2003) Phytomedicine , vol.10 , pp. 189-195
    • Vianaa, G.S.1    Bandeiraa, M.A.2    Matosa, F.J.3
  • 13
    • 48449096245 scopus 로고    scopus 로고
    • Synthesis and cytotoxic, anti-inflammatory, and anti-oxidant activities of 2′,5′-dialkoxylchalcones as cancer chemopreventive agents
    • Cheng, J. H.; Hung, C. F.; Yang, S. C.; Wang, J. P.; Won, S. J.; Lin, C. N. Synthesis and cytotoxic, anti-inflammatory, and anti-oxidant activities of 2′,5′-dialkoxylchalcones as cancer chemopreventive agents Bioorg. Med. Chem. 2008, 16, 7270-7276
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 7270-7276
    • Cheng, J.H.1    Hung, C.F.2    Yang, S.C.3    Wang, J.P.4    Won, S.J.5    Lin, C.N.6
  • 15
    • 34548010319 scopus 로고    scopus 로고
    • Anti-inflammatory activity of the synthetic chalcone derivatives: Inhibition of inducible nitric oxide synthase-catalyzed nitric oxide production from lipopolysaccharide-treated RAW 264.7 cells
    • Kim, Y. H.; Kim, J.; Park, H.; Kim, H. P. Anti-inflammatory activity of the synthetic chalcone derivatives: inhibition of inducible nitric oxide synthase-catalyzed nitric oxide production from lipopolysaccharide-treated RAW 264.7 cells Biol. Pharm. Bull. 2007, 30, 1450-1455
    • (2007) Biol. Pharm. Bull. , vol.30 , pp. 1450-1455
    • Kim, Y.H.1    Kim, J.2    Park, H.3    Kim, H.P.4
  • 18
    • 0037025444 scopus 로고    scopus 로고
    • The synthesis and effect of fluorinated chalcone derivatives on nitric oxide production
    • Rojas, J.; Payá, M.; Dominguez, J. N.; Ferrándiz, M. The synthesis and effect of fluorinated chalcone derivatives on nitric oxide production Bioorg. Med. Chem. Lett. 2002, 12, 1951-1954
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1951-1954
    • Rojas, J.1    Payá, M.2    Dominguez, J.N.3    Ferrándiz, M.4
  • 24
    • 78650219690 scopus 로고    scopus 로고
    • Antimicrobial activity of phenolics and glucosinolate hydrolysis products and their synergy with streptomycin against pathogenic bacteria
    • Saavedra, M. J.; Borges, A.; Dias, C.; Aires, A.; Bennett, R. N.; Rosa, E. S.; Simoes, M. Antimicrobial activity of phenolics and glucosinolate hydrolysis products and their synergy with streptomycin against pathogenic bacteria Med. Chem. 2010, 6, 174-183
    • (2010) Med. Chem. , vol.6 , pp. 174-183
    • Saavedra, M.J.1    Borges, A.2    Dias, C.3    Aires, A.4    Bennett, R.N.5    Rosa, E.S.6    Simoes, M.7
  • 26
    • 77950854525 scopus 로고    scopus 로고
    • Trends in utilization of the pharmacological potential of chalcones
    • Batovska, D. I.; Todorova, I. T. Trends in utilization of the pharmacological potential of chalcones Curr. Clin. Pharmacol. 2010, 5, 1-29
    • (2010) Curr. Clin. Pharmacol. , vol.5 , pp. 1-29
    • Batovska, D.I.1    Todorova, I.T.2
  • 27
    • 0020961795 scopus 로고
    • Anti-mutagenic chalcones: Antagonizing the mutagenicity of benzo-(a) pyrene on Salmonella typhimurium
    • Torigoe, T.; Arisawa, M.; Itoh, S.; Fujiu, M.; Maruyama, H. B. Anti-mutagenic chalcones: antagonizing the mutagenicity of benzo-(a) pyrene on Salmonella typhimurium Biochem. Biophys. Res. Commun. 1983, 112, 833-842
    • (1983) Biochem. Biophys. Res. Commun. , vol.112 , pp. 833-842
    • Torigoe, T.1    Arisawa, M.2    Itoh, S.3    Fujiu, M.4    Maruyama, H.B.5
  • 28
    • 65449132740 scopus 로고    scopus 로고
    • Blockade of four transmembrane L6 family member 5 (TM4SF5)-mediated tumorogenicity in hepatocytes by a synthetic chalcone derivative
    • Lee, S. A.; Ryu, H. W.; Kim, Y. M.; Choi, S.; Lee, M. J.; Kwak, T. K.; Kim, H. J.; Cho, M.; Park, K. H.; Lee, J. W. Blockade of four transmembrane L6 family member 5 (TM4SF5)-mediated tumorogenicity in hepatocytes by a synthetic chalcone derivative Hepatology 2009, 49, 1316-1325
    • (2009) Hepatology , vol.49 , pp. 1316-1325
    • Lee, S.A.1    Ryu, H.W.2    Kim, Y.M.3    Choi, S.4    Lee, M.J.5    Kwak, T.K.6    Kim, H.J.7    Cho, M.8    Park, K.H.9    Lee, J.W.10
  • 29
    • 0028012440 scopus 로고
    • Anti-tumerogenic chaclones
    • Shibata, S. Anti-tumerogenic chaclones Stem Cells 1994, 12, 44-52
    • (1994) Stem Cells , vol.12 , pp. 44-52
    • Shibata, S.1
  • 30
    • 0028357495 scopus 로고
    • A new antimalarial agent, inhibits in vitro growth of the human malaria parasite Plasmodium falciparum and protects mice from P. yoelii infection
    • Chen, M.; Theander, T. G.; Christensen, S. B.; Hviid, L.; Zhai, L.; Kharazmi, A.; Licochalcone, A. a new antimalarial agent, inhibits in vitro growth of the human malaria parasite Plasmodium falciparum and protects mice from P. yoelii infection Antimicrob. Agents Chemother. 1994, 38, 1470-1475
    • (1994) Antimicrob. Agents Chemother. , vol.38 , pp. 1470-1475
    • Chen, M.1    Theander, T.G.2    Christensen, S.B.3    Hviid, L.4    Zhai, L.5    Kharazmi, A.6    Licochalcone, A.7
  • 31
    • 79151480340 scopus 로고    scopus 로고
    • Concise synthesis of licochalcone A through water-accelerated [3,3]-sigmatropic rearrangement of an aryl prenyl ether
    • Jun, J. -G.; Jeon, J. -H.; Kim, M. Concise synthesis of licochalcone A through water-accelerated [3,3]-sigmatropic rearrangement of an aryl prenyl ether Synthesis 2011, 3, 370-376
    • (2011) Synthesis , vol.3 , pp. 370-376
    • Jun, J.-G.1    Jeon, J.-H.2    Kim, M.3
  • 32
    • 0038548308 scopus 로고    scopus 로고
    • Structure-activity relationships of antileishmanial and antimalarial chalcones
    • Liu, M.; Wilairat, P.; Croft, S. L.; Tan, A. L.; Go, M.-L. Structure-activity relationships of antileishmanial and antimalarial chalcones Bioorg. Med. Chem. 2003, 11, 2729-2738
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 2729-2738
    • Liu, M.1    Wilairat, P.2    Croft, S.L.3    Tan, A.L.4    Go, M.-L.5
  • 34
    • 18144375933 scopus 로고    scopus 로고
    • Prenylated chalcones isolated from Crotalaria genus inhibits in vitro growth of the human malaria parasite Plasmodium falciparum
    • Narender, T.; Shweta.; Tanvir, K.; Rao, M. S.; Srivastava, K.; Puri, S. K. Prenylated chalcones isolated from Crotalaria genus inhibits in vitro growth of the human malaria parasite Plasmodium falciparum Bioorg. Med. Chem. Lett. 2005, 15, 2453-2455
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 2453-2455
    • Narender, T.1    Shweta2    Tanvir, K.3    Rao, M.S.4    Srivastava, K.5    Puri, S.K.6
  • 35
    • 38349128558 scopus 로고    scopus 로고
    • Total synthesis of munchiwarin, a triprenylated chalcone from Crotalaria medicagenia
    • Narender, T.; Reddy, K. P.; Shweta.; Srivastava, K.; Mishra, D. K.; Puri, S. K. Total synthesis of munchiwarin, a triprenylated chalcone from Crotalaria medicagenia Org. Lett. 2007, 9, 5369-5372
    • (2007) Org. Lett. , vol.9 , pp. 5369-5372
    • Narender, T.1    Reddy, K.P.2    Shweta3    Srivastava, K.4    Mishra, D.K.5    Puri, S.K.6
  • 36
    • 0000911615 scopus 로고
    • A study of nuclear prenylation of β-resacetophenone II: Synthesis of bavachalcone, 4′- O -methylbavachalcone and bavachin
    • Jain, A. C.; Lal, P.; Seshadri, T. R. A study of nuclear prenylation of β-resacetophenone II: synthesis of bavachalcone, 4′- O -methylbavachalcone and bavachin Tetrahedron 1970, 26, 2631-2635
    • (1970) Tetrahedron , vol.26 , pp. 2631-2635
    • Jain, A.C.1    Lal, P.2    Seshadri, T.R.3
  • 37
    • 84993884851 scopus 로고
    • An improved procedure for the preparation of chalcones and related enones
    • Wattanasin, S.; Murphy, W. S. An improved procedure for the preparation of chalcones and related enones Synthesis 1980, 647-650
    • (1980) Synthesis , pp. 647-650
    • Wattanasin, S.1    Murphy, W.S.2
  • 38
    • 61649106775 scopus 로고    scopus 로고
    • 2O Mediated one-pot synthesis of acetylchromans from polyhydroxyacetophenones and isoprene/allyl alcohol
    • 2O Mediated one-pot synthesis of acetylchromans from polyhydroxyacetophenones and isoprene/allyl alcohol Synth. Commun. 2009, 39, 384-394
    • (2009) Synth. Commun. , vol.39 , pp. 384-394
    • Narender, T.1    Reddy, K.P.2
  • 39
    • 37049125432 scopus 로고
    • Pyridine-catalyzed chromenylation of mono-chelated meta -dihydric phenols with mono-, sesqui- and di-terpene aldehydes: Synthesis of rubranine and flemingins A-, B- and C-methyl ethers
    • Bandaranayke, W. M.; Crumbier, L.; Whiting, D. A. Pyridine-catalyzed chromenylation of mono-chelated meta -dihydric phenols with mono-, sesqui- and di-terpene aldehydes: synthesis of rubranine and flemingins A-, B- and C-methyl ethers J. Chem. Soc., C 1971, 804-810
    • (1971) J. Chem. Soc., C , pp. 804-810
    • Bandaranayke, W.M.1    Crumbier, L.2    Whiting, D.A.3
  • 40
    • 27544446099 scopus 로고    scopus 로고
    • Synthesis of chromenochalcones and evaluation of their in vitro antileishmanial activity
    • Narender, T.; Khaliq, T.; Shweta.; Nishi.; Goyal, N.; Gupta, S. Synthesis of chromenochalcones and evaluation of their in vitro antileishmanial activity Bioorg. Med. Chem. 2005, 13, 6543-6550
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 6543-6550
    • Narender, T.1    Khaliq, T.2    Shweta3    Nishi4    Goyal, N.5    Gupta, S.6
  • 41
    • 0030599686 scopus 로고    scopus 로고
    • 5-Formyl salicylaldehyde as a linker for the synthesis of benzofuran containing insulin sensitivity enhancer compounds
    • Stille, J. R.; Ward, J. A.; Leffelman, C.; Sullivan, K. A. 5-Formyl salicylaldehyde as a linker for the synthesis of benzofuran containing insulin sensitivity enhancer compounds Tetrahedron Lett. 1996, 37, 9267-9270
    • (1996) Tetrahedron Lett. , vol.37 , pp. 9267-9270
    • Stille, J.R.1    Ward, J.A.2    Leffelman, C.3    Sullivan, K.A.4
  • 43
    • 78650526350 scopus 로고    scopus 로고
    • In vitro culture of Plasmodium falciparum: Utility of modified (RPNI) medium for drug-sensitivity studies using SYBR Green i assay
    • Singh, S.; Srivastava, R. K.; Srivastava, M.; Puri, S. K.; Srivastava, K. In vitro culture of Plasmodium falciparum: utility of modified (RPNI) medium for drug-sensitivity studies using SYBR Green I assay Exp. Parasitol. 2011, 127, 318-321
    • (2011) Exp. Parasitol. , vol.127 , pp. 318-321
    • Singh, S.1    Srivastava, R.K.2    Srivastava, M.3    Puri, S.K.4    Srivastava, K.5
  • 44
    • 70349780547 scopus 로고    scopus 로고
    • Search for new pharmacophores for antimalarial activity. Part III: Synthesis and bioevaluation of new 6-thioureido-4-anilinoquinazolines
    • Mishra, A.; Srivastava, K.; Tripathi, R.; Puri, S. K.; Batra., S. Search for new pharmacophores for antimalarial activity. Part III: synthesis and bioevaluation of new 6-thioureido-4-anilinoquinazolines Eur. J. Med. Chem. 2009, 44, 4404-4412
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 4404-4412
    • Mishra, A.1    Srivastava, K.2    Tripathi, R.3    Puri, S.K.4    Batra, S.5
  • 45
    • 7444258497 scopus 로고    scopus 로고
    • Plasmodium falciparum: Modified medium composition supports continuous cultivation with foetal bovine serum
    • Srivastava, K.; Puri, S. K. Plasmodium falciparum: modified medium composition supports continuous cultivation with foetal bovine serum Exp. Parasitol. 2004, 108, 74-75
    • (2004) Exp. Parasitol. , vol.108 , pp. 74-75
    • Srivastava, K.1    Puri, S.K.2
  • 46
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays
    • Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65, 55-63
    • (1983) J. Immunol. Methods , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 48
    • 0033973112 scopus 로고    scopus 로고
    • Azithromycin: Antimalarial profile against blood- and sporozoite-induced infections in mice and monkeys
    • Puri, S. K.; Singh, N. Azithromycin: antimalarial profile against blood- and sporozoite-induced infections in mice and monkeys Exp. Parasitol. 2000, 94, 8-14
    • (2000) Exp. Parasitol. , vol.94 , pp. 8-14
    • Puri, S.K.1    Singh, N.2
  • 49
    • 0034966663 scopus 로고    scopus 로고
    • Systematic optimization of expression and refolding of the Plasmodium falciparum cysteine protease falcipain-2
    • Sijwali, P. S.; Brinen, L. S.; Rosenthal., P. J. Systematic optimization of expression and refolding of the Plasmodium falciparum cysteine protease falcipain-2 Protein Express. Purif. 2001, 22, 128-34
    • (2001) Protein Express. Purif. , vol.22 , pp. 128-34
    • Sijwali, P.S.1    Brinen, L.S.2    Rosenthal, P.J.3
  • 50
    • 0035644195 scopus 로고    scopus 로고
    • Expression and characterization of the Plasmodium falciparum haemoglobinase falcipain-3
    • Sijwali, P. S.; Shenai, B. R; Gut, J.; Singh, A.; Rosenthal, P. J. Expression and characterization of the Plasmodium falciparum haemoglobinase falcipain-3 Biochem. J. 2001, 360, 481-489
    • (2001) Biochem. J. , vol.360 , pp. 481-489
    • Sijwali, P.S.1    Shenai, B.R.2    Gut, J.3    Singh, A.4    Rosenthal, P.J.5
  • 52
    • 61449267734 scopus 로고    scopus 로고
    • Structures of falcipain-2 and falcipain-3 bound to small molecule inhibitors: Implications for substrate specificity
    • Kerr, I. D.; Lee, J. H.; Pandey, K. C.; Harrison, A.; Sajid, M.; Rosenthal, P. J.; Brinen, L. S. Structures of falcipain-2 and falcipain-3 bound to small molecule inhibitors: implications for substrate specificity J. Med. Chem. 2009, 52, 852-857
    • (2009) J. Med. Chem. , vol.52 , pp. 852-857
    • Kerr, I.D.1    Lee, J.H.2    Pandey, K.C.3    Harrison, A.4    Sajid, M.5    Rosenthal, P.J.6    Brinen, L.S.7
  • 55
    • 0035163181 scopus 로고    scopus 로고
    • The impact of whole genome sequence data on drug discovery - A malaria case study
    • Joachimiak, M. P.; Chang, C.; Rosenthal, P. J.; Cohen, F. E. The impact of whole genome sequence data on drug discovery-a malaria case study Mol. Med. 2001, 7, 698-710
    • (2001) Mol. Med. , vol.7 , pp. 698-710
    • Joachimiak, M.P.1    Chang, C.2    Rosenthal, P.J.3    Cohen, F.E.4
  • 56
    • 84871456197 scopus 로고    scopus 로고
    • Molecular modeling studies of some substituted chalcone derivatives as cysteine protease inhibitors
    • Sahu, N. K.; Bari, S. B.; Kohli, D. V. Molecular modeling studies of some substituted chalcone derivatives as cysteine protease inhibitors Med. Chem. Res. 2011, 21, 3835-3847
    • (2011) Med. Chem. Res. , vol.21 , pp. 3835-3847
    • Sahu, N.K.1    Bari, S.B.2    Kohli, D.V.3
  • 57
    • 0030599010 scopus 로고    scopus 로고
    • A fast flexible docking method using an incremental algorithm
    • Rarey, M.; Kramer, B.; Lengauer, T.; Klebe, G. A fast flexible docking method using an incremental algorithm J. Mol. Biol. 1996, 261, 470-489
    • (1996) J. Mol. Biol. , vol.261 , pp. 470-489
    • Rarey, M.1    Kramer, B.2    Lengauer, T.3    Klebe, G.4
  • 58
    • 84872291834 scopus 로고    scopus 로고
    • Tripos Inc. 1699 South Hanely Road, St. Louis, Missouri 63114, USA
    • Sybyl7.1; Tripos Inc.: 1699 South Hanely Road, St. Louis, Missouri 63114, USA.
    • Sybyl7.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.