메뉴 건너뛰기




Volumn 62, Issue 46, 2014, Pages 11080-11088

Design, synthesis, and biological activities of aromatic gossypol schiff base derivatives

Author keywords

anti TMV activity; gossypol; Schiff base; structure activity relationships; synthesis

Indexed keywords

AROMATIC COMPOUNDS; BIOASSAY; CHEMICAL MODIFICATION; SYNTHESIS (CHEMICAL); VIRUSES;

EID: 84913526232     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf504411g     Document Type: Article
Times cited : (75)

References (42)
  • 1
    • 33744461697 scopus 로고
    • Anticancer activity of some alkaloids
    • Vermel, E. M.; Kruglyak, S. A. Anticancer activity of some alkaloids Vopr. Onkol. 1962, 8, 9-17
    • (1962) Vopr. Onkol. , vol.8 , pp. 9-17
    • Vermel, E.M.1    Kruglyak, S.A.2
  • 3
    • 51049106854 scopus 로고    scopus 로고
    • Natural BH3 mimetic (-)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa
    • Meng, Y.; Tang, W.; Dai, Y.; Wu, X.; Liu, M.; Ji, Q.; Ji, M.; Pienta, K.; Lawrence, T.; Xu, L. Natural BH3 mimetic (-)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa Mol. Cancer Ther. 2008, 7, 2192-2202
    • (2008) Mol. Cancer Ther. , vol.7 , pp. 2192-2202
    • Meng, Y.1    Tang, W.2    Dai, Y.3    Wu, X.4    Liu, M.5    Ji, Q.6    Ji, M.7    Pienta, K.8    Lawrence, T.9    Xu, L.10
  • 6
    • 0032741299 scopus 로고    scopus 로고
    • The phytoalexins desoxyhemigossypol and hemigossypol are elicited by Xanthomonas in Gossypium cotyledons
    • Abraham, K. J.; Pierce, M. L.; Essenberg, M. The phytoalexins desoxyhemigossypol and hemigossypol are elicited by Xanthomonas in Gossypium cotyledons Phytochemistry 1999, 52, 829-836
    • (1999) Phytochemistry , vol.52 , pp. 829-836
    • Abraham, K.J.1    Pierce, M.L.2    Essenberg, M.3
  • 7
    • 0032733493 scopus 로고    scopus 로고
    • Purification and characterization of S -adenosyl- l -methionine: Desoxyhemigossypol-6- O -methyltransferase from cotton plants
    • Liu, J.; Benedict, C. R.; Stipanovic, R. D.; Bell, A. A. Purification and characterization of S -adenosyl- l -methionine: desoxyhemigossypol-6- O -methyltransferase from cotton plants Plant Physiol. 1999, 121, 1017-1024
    • (1999) Plant Physiol. , vol.121 , pp. 1017-1024
    • Liu, J.1    Benedict, C.R.2    Stipanovic, R.D.3    Bell, A.A.4
  • 8
    • 0037145927 scopus 로고    scopus 로고
    • Toxicity of (+) and (-)-gossypol to the plant pathogen Rhizoctonia solani
    • Puckhaber, L. S.; Dowd, M. K.; Stipanovic, R. D.; Howell, C. R. Toxicity of (+) and (-)-gossypol to the plant pathogen Rhizoctonia solani J. Agric. Food Chem. 2002, 50, 7017-7021
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 7017-7021
    • Puckhaber, L.S.1    Dowd, M.K.2    Stipanovic, R.D.3    Howell, C.R.4
  • 10
    • 84876148121 scopus 로고    scopus 로고
    • Synthesis and anti-H5N1 activity of chiral gossypol derivatives and its analogs implicated by a viral entry blocking mechanism
    • Yang, J.; Chen, G.; Li, L. L.; Pan, W.; Zhang, F.; Yang, J.; Wu, S.; Tien, P. Synthesis and anti-H5N1 activity of chiral gossypol derivatives and its analogs implicated by a viral entry blocking mechanism Bioorg. Med. Chem. Lett. 2013, 23, 2619-2623
    • (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 2619-2623
    • Yang, J.1    Chen, G.2    Li, L.L.3    Pan, W.4    Zhang, F.5    Yang, J.6    Wu, S.7    Tien, P.8
  • 12
    • 0020057855 scopus 로고
    • Inhibiting herpes simplex virus type 2 infection in human epithelial cells by gossypol, a potent spermicidal and contraceptive agent
    • Wichmann, K.; Vaheri, A.; Luukkainen, T. Inhibiting herpes simplex virus type 2 infection in human epithelial cells by gossypol, a potent spermicidal and contraceptive agent Am. J. Obstet. Gynecol. 1982, 142, 593-594
    • (1982) Am. J. Obstet. Gynecol. , vol.142 , pp. 593-594
    • Wichmann, K.1    Vaheri, A.2    Luukkainen, T.3
  • 13
    • 0022899737 scopus 로고
    • Antiviral activities of gossypol and its derivatives against herpes simplex virus type II
    • Radloff, R. J.; Deck, L. M.; Royer, R. E.; Vander Jagt, D. L. Antiviral activities of gossypol and its derivatives against herpes simplex virus type II Pharmacol. Res. Commun. 1986, 18, 1063-1067
    • (1986) Pharmacol. Res. Commun. , vol.18 , pp. 1063-1067
    • Radloff, R.J.1    Deck, L.M.2    Royer, R.E.3    Vander Jagt, D.L.4
  • 14
    • 0014910553 scopus 로고
    • Antiviral properties of gossypol in experimental influenza pneumonia
    • Vichkanova, S. A.; Oifa, A. I.; Goryunova, L. V. Antiviral properties of gossypol in experimental influenza pneumonia Antibiotiki 1970, 15, 1071-1073
    • (1970) Antibiotiki , vol.15 , pp. 1071-1073
    • Vichkanova, S.A.1    Oifa, A.I.2    Goryunova, L.V.3
  • 16
    • 17044424644 scopus 로고    scopus 로고
    • Resistance to plant viruses: Old issue, news answers?
    • Ritzenthaler, C. Resistance to plant viruses: old issue, news answers? Curr. Opin. Biotechnol. 2005, 16, 118-122
    • (2005) Curr. Opin. Biotechnol. , vol.16 , pp. 118-122
    • Ritzenthaler, C.1
  • 18
    • 64549109038 scopus 로고    scopus 로고
    • Synthesis and antiviral activities of chiral thiourea derivatives containing an α-aminophosphonate moiety
    • Chen, M. H.; Chen, Z.; Song, B. A.; Bhadury, P. S.; Yang, S.; Cai, X. J.; Hu, D. Y.; Xue, W.; Zeng, S. Synthesis and antiviral activities of chiral thiourea derivatives containing an α-aminophosphonate moiety J. Agric. Food Chem. 2009, 57, 1383-1388
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 1383-1388
    • Chen, M.H.1    Chen, Z.2    Song, B.A.3    Bhadury, P.S.4    Yang, S.5    Cai, X.J.6    Hu, D.Y.7    Xue, W.8    Zeng, S.9
  • 20
    • 34547662510 scopus 로고    scopus 로고
    • Antiviral activity of oxidized polyamines
    • Bachrach, U. Antiviral activity of oxidized polyamines Amino Acids 2007, 33, 267-272
    • (2007) Amino Acids , vol.33 , pp. 267-272
    • Bachrach, U.1
  • 21
    • 84894145407 scopus 로고    scopus 로고
    • Design, synthesis, antiviral activity, and structure-activity relationships (SARs) of two types of structurally novel phenanthroindo/quinolizidine analogues
    • Su, B.; Chen, F.; Wang, L.; Wang, Q. Design, synthesis, antiviral activity, and structure-activity relationships (SARs) of two types of structurally novel phenanthroindo/quinolizidine analogues J. Agric. Food Chem. 2014, 62, 1233-1239
    • (2014) J. Agric. Food Chem. , vol.62 , pp. 1233-1239
    • Su, B.1    Chen, F.2    Wang, L.3    Wang, Q.4
  • 22
    • 84893677357 scopus 로고    scopus 로고
    • Synthesis and antiviral and fungicidal activity evaluation of β-carboline, dihydro-β-carboline, tetrahydro-β-carboline alkaloids, and their derivatives
    • Song, H.; Liu, Y.; Liu, Y.; Wang, L.; Wang, Q. Synthesis and antiviral and fungicidal activity evaluation of β-carboline, dihydro-β-carboline, tetrahydro-β-carboline alkaloids, and their derivatives J. Agric. Food Chem. 2014, 62, 1010-1018
    • (2014) J. Agric. Food Chem. , vol.62 , pp. 1010-1018
    • Song, H.1    Liu, Y.2    Liu, Y.3    Wang, L.4    Wang, Q.5
  • 23
    • 27744431949 scopus 로고    scopus 로고
    • Investigations on gossypol: Past and present developments
    • Dodou, K. Investigations on gossypol: past and present developments Expert Opin. Invest. Drugs 2005, 14, 1419-1434
    • (2005) Expert Opin. Invest. Drugs , vol.14 , pp. 1419-1434
    • Dodou, K.1
  • 24
    • 0344824649 scopus 로고    scopus 로고
    • Mechanism of drug and toxic actions of gossypol: Focus on reactive oxygen species and electron transfer
    • Kovacic, P. Mechanism of drug and toxic actions of gossypol: focus on reactive oxygen species and electron transfer Curr. Med. Chem. 2003, 10, 2711-2718
    • (2003) Curr. Med. Chem. , vol.10 , pp. 2711-2718
    • Kovacic, P.1
  • 25
    • 79957834040 scopus 로고    scopus 로고
    • Inhibition of virus replication and symptom expression by reactive oxygen species in tobacco infected with tobacco mosaic virus
    • Bacso, R. Y.; Hafez, M.; Király, Z.; Király, L. Inhibition of virus replication and symptom expression by reactive oxygen species in tobacco infected with tobacco mosaic virus Acta Phytopathol. Entomol. 2011, 46, 1-10
    • (2011) Acta Phytopathol. Entomol. , vol.46 , pp. 1-10
    • Bacso, R.Y.1    Hafez, M.2    Király, Z.3    Király, L.4
  • 26
    • 33744490651 scopus 로고    scopus 로고
    • Reaction chemistry of gossypol and its derivatives
    • Kenar, J. A. Reaction chemistry of gossypol and its derivatives J. Am. Oil Chem. Soc. 2006, 83, 269-302
    • (2006) J. Am. Oil Chem. Soc. , vol.83 , pp. 269-302
    • Kenar, J.A.1
  • 29
    • 67651180554 scopus 로고    scopus 로고
    • Chiral gossypol derivatives: Evaluation of their anticancer activity and molecular modeling
    • Zhang, L.; Jiang, H.; Cao, X.; Zhao, H.; Wang, F.; Cui, Y.; Jiang, B. Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling Eur. J. Med. Chem. 2009, 44, 3961-3972
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 3961-3972
    • Zhang, L.1    Jiang, H.2    Cao, X.3    Zhao, H.4    Wang, F.5    Cui, Y.6    Jiang, B.7
  • 30
    • 70349902333 scopus 로고    scopus 로고
    • Synthesis, crystal structures and antibacterial activity studies of aza-derivatives of phytoalexin from cotton plant - Gossypol
    • Przybylski, P.; Pyta, K.; Stefanska, J.; Ratajczak-Sitarz, M.; Katrusiak, A.; Huczynski, A.; Brzezinski, B. Synthesis, crystal structures and antibacterial activity studies of aza-derivatives of phytoalexin from cotton plant-gossypol Eur. J. Med. Chem. 2009, 44, 4393-4403
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 4393-4403
    • Przybylski, P.1    Pyta, K.2    Stefanska, J.3    Ratajczak-Sitarz, M.4    Katrusiak, A.5    Huczynski, A.6    Brzezinski, B.7
  • 32
    • 23444458422 scopus 로고    scopus 로고
    • Spectroscopic and semiempirical studies of new Schiff base of gossypol with allylamine in solution
    • Przybylski, P.; Maluszynska, M.; Brzezinski, B. Spectroscopic and semiempirical studies of new Schiff base of gossypol with allylamine in solution J. Mol. Struct. 2005, 750, 152-157
    • (2005) J. Mol. Struct. , vol.750 , pp. 152-157
    • Przybylski, P.1    Maluszynska, M.2    Brzezinski, B.3
  • 33
    • 0011238238 scopus 로고
    • Substituted arylimino derivatives of gossypol
    • Dechary, J. M.; Brown, L. E. Substituted arylimino derivatives of gossypol J. Am. Oil Chem. Soc. 1956, 33, 76-78
    • (1956) J. Am. Oil Chem. Soc. , vol.33 , pp. 76-78
    • Dechary, J.M.1    Brown, L.E.2
  • 34
    • 20344407837 scopus 로고    scopus 로고
    • Schiff bases of gossypol: An NMR and DFT study
    • That, Q. T.; Nguyen, K. P. P.; Hansen, P. E. Schiff bases of gossypol: an NMR and DFT study Magn. Reson. Chem. 2005, 43, 302-308
    • (2005) Magn. Reson. Chem. , vol.43 , pp. 302-308
    • That, Q.T.1    Nguyen, K.P.P.2    Hansen, P.E.3
  • 35
    • 33744469981 scopus 로고
    • NMR investigation of bis-4-fluoroaniline Schiff base of gossypol
    • Zhou, X.; Wang, W.; Gu, J. NMR investigation of bis-4-fluoroaniline Schiff base of gossypol Acta Chim. Sinica 1986, 44, 357-359
    • (1986) Acta Chim. Sinica , vol.44 , pp. 357-359
    • Zhou, X.1    Wang, W.2    Gu, J.3
  • 36
    • 33744503006 scopus 로고
    • Novel fluorine-containing derivatives of gossypol
    • Zhou, X.; Wang, W.; Gu, J. Novel fluorine-containing derivatives of gossypol Acta Chim. Sinica 1988, 46, 375-378
    • (1988) Acta Chim. Sinica , vol.46 , pp. 375-378
    • Zhou, X.1    Wang, W.2    Gu, J.3
  • 37
    • 77949354150 scopus 로고    scopus 로고
    • Synthesis and antiviral activities of phenanthroindolizidine alkaloids and their derivatives
    • Wang, K. L.; Su, B.; Wang, Z. W.; Wu, M.; Li, Z.; Hu, Y. N.; Fan, Z. J.; Mi, N.; Wang, Q. M. Synthesis and antiviral activities of phenanthroindolizidine alkaloids and their derivatives J. Agric. Food Chem. 2010, 58, 2703-2709
    • (2010) J. Agric. Food Chem. , vol.58 , pp. 2703-2709
    • Wang, K.L.1    Su, B.2    Wang, Z.W.3    Wu, M.4    Li, Z.5    Hu, Y.N.6    Fan, Z.J.7    Mi, N.8    Wang, Q.M.9
  • 38
    • 84889083348 scopus 로고    scopus 로고
    • Regioselective oxidative dehydrogenation in nonenzymatic condition: A synthetic route to gossypol
    • Li, L.; Liu, Y. X.; Wang, Q. M. Regioselective oxidative dehydrogenation in nonenzymatic condition: a synthetic route to gossypol Eur. J. Org. Chem. 2013, 2013, 8014-8021
    • (2013) Eur. J. Org. Chem. , vol.2013 , pp. 8014-8021
    • Li, L.1    Liu, Y.X.2    Wang, Q.M.3
  • 40
    • 67649651798 scopus 로고    scopus 로고
    • Structure of a new Schiff base of gossypol with ethyl 4-amino-1-piperidine carboxylate in the solid and in the solution
    • Przybylski, P.; Pyta, K.; Ratajczak-Sitarz, M.; Katrusiak, A.; Brzezinski, B. Structure of a new Schiff base of gossypol with ethyl 4-amino-1-piperidine carboxylate in the solid and in the solution Polym. J. Chem. 2009, 83, 747-759
    • (2009) Polym. J. Chem. , vol.83 , pp. 747-759
    • Przybylski, P.1    Pyta, K.2    Ratajczak-Sitarz, M.3    Katrusiak, A.4    Brzezinski, B.5
  • 41
    • 44449101254 scopus 로고    scopus 로고
    • CP/MAS spectroscopy in the determination of the tautomeric forms of gossypol, its Schiff bases and hydrazones in the solid state
    • Przybylski, P.; Schilf, W.; Kamienski, B.; Brzezinski, B.; Bartl, F. CP/MAS spectroscopy in the determination of the tautomeric forms of gossypol, its Schiff bases and hydrazones in the solid state Magn. Reson. Chem. 2008, 46, 534-544
    • (2008) Magn. Reson. Chem. , vol.46 , pp. 534-544
    • Przybylski, P.1    Schilf, W.2    Kamienski, B.3    Brzezinski, B.4    Bartl, F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.