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Volumn 82, Issue , 2014, Pages 506-520

Design, synthesis and structure-activity relationship of novel semi-synthetic flavonoids as antiproliferative agents

Author keywords

Cytotoxicity; Furoaurones; Furochalcones; Furoflavones; Furostyrylfurochromones; Kinase inhibition

Indexed keywords

1 (6 HYDROXY 4 METHOXY 1 BENZOFURAN 5 YL) 3 (2 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 (6 HYDROXY 4 METHOXY 1 BENZOFURAN 5 YL) 3 (SUBSTITUTED)PHENYLPROP 2 EN 1 ONE; 1 (7 ALLYL 6 HYDROXY 4 METHOXY 1 BENZOFURAN 5 YL) 3 (4 CHLOROPHENYL) PROP 2 EN 1 ONE; 1 (7 ALLYL 6 HYDROXY 4 METHOXY 1 BENZOFURAN 5 YL) 3 (SUBSTITUTED)PHENYL PROP 2 EN 1 ONE; 1 (7 ALLYL 6 HYDROXY 4 METHOXYBENZOFURAN 5 YL) 3 (2METHOXYPHENYL)PROP 2 EN 1 ONE; 1 (7 BROMO 6 HYDROXY 4 METHOXY 1 BENZOFURAN 5 YL) 3 (2 METHOXY PHENYL)PROP 2 EN 1 ONE; 1 (7 BROMO 6 HYDROXY 4 METHOXY 1 BENZOFURAN 5 YL) 3 (4 METHOXY PHENYL)PROP 2 EN 1 ONE; 1 (7 BROMO 6 HYDROXY 4 METHOXY 1 BENZOFURAN 5 YL) 3 (CHLOROPHENYL)PROP 2 EN 1 ONE; 1 (7 BROMO 6 HYDROXY 4 METHOXY 1 BENZOFURAN-5 YL) 3 PHENYLPROP 2 EN 1 ONE; 1 (7 BROMO 6 HYDROXY 4 METHOXY 1 BENZOFURAN-5 YL) 3 SUBSTITUTED PHENYLPROP 2 EN 1 ONE; 3 (4 METHOXY 5 OXO 7 (SUBSTITUTED)PHENYL 5H FURO[3,2 G]CHROMEN 9 YL)ACRYLALDEHYDE; 3 (4 METHOXY 5 OXO 7 PHENYL 5H FURO[3,2 G]CHROMEN 9 YL) ACRYLALDEHYDE; 3 [4 METHOXY 7 (4 METHOXYPHENYL) 5 OXO 5H FURO[3,2 G] CHROMEN 9 YL]ACRYL ALDEHYDE; 3 [7 (4 CHLOROPHENYL) 4 METHOXY 5 OXO 5H FURO[3,2 G] CHROMEN 9 YL]ACRYLALDEHYDE; 4 METHOXY 7 (2 METHOXYPHENYL) 5H FURO[3,2 G]CHROMEN 5 ONE; 4 METHOXY 7 (SUBSTITUTED)PHENYL FURO[3,2 G]CHROMEN 5 ONE; 4,9 DIMETHOXY 7 [2 (4 DIMETHYLAMINOPHENYL)VINYL] 6 (MORPHOLIN 4 YLMETHYL) 5H FURO [3,2 G]CHROMEN 5 ONE; 9 BROMO 4 METHOXY 7 (2 METHOXYPHENYL) 5H FURO[3,2 G] CHROMEN 5 ONE; 9 BROMO 4 METHOXY 7 (4 METHOXYPHENYL) 5H FURO[3,2 G] CHROMEN 5 ONE; 9 BROMO 4 METHOXY 7 (SUBSTITUTED)PHENYL FURO[3,2 G]CHROMEN 5 ONE; 9 BROMO 4 METHOXY 7 PHENYL 5H FURO[3,2 G]CHROMEN 5 ONE; 9 BROMO 7 (4 CHLOROPHENYL) 4 METHOXY 5H FURO[3,2 G]CHROMEN 5 ONE; ANTINEOPLASTIC AGENT; CYCLIN D1; CYCLIN DEPENDENT KINASE 2; CYCLIN DEPENDENT KINASE 4; CYCLIN E; FLAVONOID; GLYCOGEN SYNTHASE KINASE 3BETA; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84902657942     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.06.007     Document Type: Article
Times cited : (50)

References (45)
  • 1
    • 0036146735 scopus 로고    scopus 로고
    • Dietary flavonols: Chemistry, food content, and metabolism
    • DOI 10.1016/S0899-9007(01)00695-5, PII S0899900701006955
    • S.A. Aherne, and N.M. O'Brien Dietary flavonols: chemistry, food content, and metabolism Nutrition 18 2002 75 81 (Pubitemid 34097718)
    • (2002) Nutrition , vol.18 , Issue.1 , pp. 75-81
    • Aherne, S.A.1    O'Brien, N.M.2
  • 2
    • 0032817487 scopus 로고    scopus 로고
    • Health-promoting properties of common herbs
    • W.J. Craig Health-promoting properties of common herbs Am. J. Clin. Nutr. 70 1999 491S 499S (Pubitemid 29407127)
    • (1999) American Journal of Clinical Nutrition , vol.70 , Issue.3 SUPPL.
    • Craig, W.J.1
  • 4
    • 0036401813 scopus 로고    scopus 로고
    • Flavonoids as anticancer agents: Structure-activity relationship study
    • DOI 10.2174/1568011023353714
    • M. Lopez-Lazaro Flavonoids as anticancer agents: structure-activity relationship study Curr. Med. Chem. Anticancer Agents 2 2002 691 714 (Pubitemid 35175268)
    • (2002) Current Medicinal Chemistry - Anti-Cancer Agents , vol.2 , Issue.6 , pp. 691-714
    • Lopez-Lazaro, M.1
  • 5
    • 0031590969 scopus 로고    scopus 로고
    • Inhibition of proliferation of estrogen receptor-positive MCF-7 human breast cancer cells by flavonoids in the presence and absence of excess estrogen
    • DOI 10.1016/S0304-3835(96)04557-0, PII S0304383596045570
    • F.V. So, N. Guthrie, A.F. Chambers, and K.K. Carroll Inhibition of proliferation of estrogen receptor-positive MCF-7 human breast cancer cells by flavonoids in the presence and absence of excess estrogen Cancer Lett. 112 1997 127 133 (Pubitemid 27104286)
    • (1997) Cancer Letters , vol.112 , Issue.2 , pp. 127-133
    • So, F.V.1    Guthrie, N.2    Chambers, A.F.3    Carroll, K.K.4
  • 8
    • 0028959192 scopus 로고
    • Estrogenic flavonoids: Structural requirements for biological activity
    • R.J. Miksicek Estrogenic flavonoids: structural requirements for biological activity Proc. Soc. Exp. Biol. Med. 208 1995 44 50
    • (1995) Proc. Soc. Exp. Biol. Med. , vol.208 , pp. 44-50
    • Miksicek, R.J.1
  • 10
    • 0036318722 scopus 로고    scopus 로고
    • Review of flavopiridol, a cyclin-dependent kinase inhibitor, as breast cancer therapy
    • A.R. Tan, and S.M. Swain Review of flavopiridol, a cyclin-dependent kinase inhibitor, as breast cancer therapy Semin. Oncol. 29 2002 77 85 (Pubitemid 34816069)
    • (2002) Seminars in Oncology , vol.29 , Issue.3 SUPPL. 11 , pp. 77-85
    • Tan, A.R.1    Swain, S.M.2
  • 11
    • 0022651316 scopus 로고
    • Hormothamnione, a novel cytotoxic styrylchromone from the marine cyanophyte Hormothamnion enteromorphoides Grunow
    • DOI 10.1016/S0040-4039(00)84426-3
    • W.H. Gerwik, A. Lopez, G.D. Van-Duyne, J. Clardy, W. Ortiz, and A. Baez Hormothamnione, a novel cytotoxic styrylchromone from the marine cyanophyte Hormothamnion enteromorphoides Grunow Tetrahedron Lett. 27 1986 1979 1982 (Pubitemid 16104308)
    • (1986) Tetrahedron Letters , vol.27 , Issue.18 , pp. 1979-1982
    • Gerwick, W.H.1    Lopez, A.2    Van Duyne, G.D.3
  • 12
    • 0024515662 scopus 로고
    • 6-Desmethoxyhormothamnione, a new cytotoxic styrylchromone from the marine cryptophyte Chrysophaeum taylori
    • W.H. Gerwik 6-Desmethoxyhormothamnione, a new cytotoxic styrylchromone from the marine cryptophyte Chrysophaeum taylori J. Nat. Prod. 52 1989 252 256
    • (1989) J. Nat. Prod. , vol.52 , pp. 252-256
    • Gerwik, W.H.1
  • 13
    • 33747001295 scopus 로고    scopus 로고
    • Synthesis and anticancer activity of lavendustin A derivatives containing arylethenylchromone substituents
    • DOI 10.1016/j.ejmech.2006.04.008, PII S0223523406001541
    • K.Y. Lee, D.H. Nam, C.S. Moon, S.H. Seo, J.Y. Lee, and Y.S. Lee Synthesis and anticancer activity of lavendustin A derivatives containing arylethenylchromone substituents Eur. J. Med. Chem. 41 2006 991 996 (Pubitemid 44202637)
    • (2006) European Journal of Medicinal Chemistry , vol.41 , Issue.8 , pp. 991-996
    • Lee, K.Y.1    Nam, D.H.2    Moon, C.S.3    Seo, S.H.4    Lee, J.Y.5    Lee, Y.S.6
  • 14
  • 16
    • 16844372227 scopus 로고    scopus 로고
    • Sequence dependent potentiation of gemcitabine by flavopiridol in human breast cancer cells
    • DOI 10.1007/s10549-004-2179-x
    • S. Ali, B.F. El-Rayes, O. Aranha, F.H. Sarkar, and P.A. Philip Sequence dependent potentiation of gemcitabine by flavopiridol in human breast cancer cells Breast Cancer Res. Treat. 90 2005 25 31 (Pubitemid 40486998)
    • (2005) Breast Cancer Research and Treatment , vol.90 , Issue.1 , pp. 25-31
    • Ali, S.1    El-Rayes, B.F.2    Aranha, O.3    Sarkar, F.H.4    Philip, P.A.5
  • 17
    • 0037383322 scopus 로고    scopus 로고
    • GSK-3: Tricks of the trade for a multi-tasking kinase
    • DOI 10.1242/jcs.00384
    • B.W. Doble, and J.R. Woodgett GSK-3: tricks of the trade for a multitasking kinase J. Cell Sci. 116 2003 1175 1186 (Pubitemid 36410657)
    • (2003) Journal of Cell Science , vol.116 , Issue.7 , pp. 1175-1186
    • Doble, B.W.1    Woodgett, J.R.2
  • 18
    • 0034859101 scopus 로고    scopus 로고
    • The multifaceted roles of glycogen synthase kinase 3β in cellular signaling
    • DOI 10.1016/S0301-0082(01)00011-9, PII S0301008201000119
    • C.A. Grimes, and R.S. Jope The multifaceted roles of glycogen synthase kinase 3beta in cellular signaling Prog. Neurobiol. 65 2001 391 426 (Pubitemid 32781670)
    • (2001) Progress in Neurobiology , vol.65 , Issue.4 , pp. 391-426
    • Grimes, C.A.1    Jope, R.S.2
  • 19
    • 57349143530 scopus 로고    scopus 로고
    • Glycogen synthase kinase 3beta (GSK3beta) in tumorigenesis and cancer chemotherapy
    • J. Luo Glycogen synthase kinase 3beta (GSK3beta) in tumorigenesis and cancer chemotherapy Cancer Lett. 273 2009 194 200
    • (2009) Cancer Lett. , vol.273 , pp. 194-200
    • Luo, J.1
  • 20
    • 0029921317 scopus 로고    scopus 로고
    • Genetic alterations of cyclins, cyclin-dependent kinases, and Cdk inhibitors in human cancer
    • M. Hall, and G. Peters Genetic alterations of cyclins, cyclin-dependent kinases, and Cdk inhibitors in human cancer Adv. Cancer Res. 68 1996 67 108 (Pubitemid 26099813)
    • (1996) Advances in Cancer Research , vol.68 , pp. 67-108
    • Hall, M.1    Peters, G.2
  • 21
    • 0036146815 scopus 로고    scopus 로고
    • Cyclin D1 and mammary carcinoma: New insights from transgenic mouse models
    • DOI 10.1186/bcr411
    • R.L. Sutherland, and E.A. Musgrove Cyclin D1 and mammary carcinoma: new insights from transgenic mouse models Breast Cancer Res. 4 2002 14 17 (Pubitemid 34097551)
    • (2002) Breast Cancer Research , vol.4 , Issue.1 , pp. 14-17
    • Sutherland, R.L.1    Musgrove, E.A.2
  • 22
    • 33644975749 scopus 로고    scopus 로고
    • Antitumor activity of some natural flavonoids and synthetic derivatives on various human and murine cancer cell lines
    • M. Cárdenas, M. Marder, V.C. Blank, and L.P. Roguin Antitumor activity of some natural flavonoids and synthetic derivatives on various human and murine cancer cell lines Bioorg. Med. Chem. 14 2006 2966 2971
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 2966-2971
    • Cárdenas, M.1    Marder, M.2    Blank, V.C.3    Roguin, L.P.4
  • 24
    • 0022529486 scopus 로고
    • Phase I and pharmacokinetic study of LM985 (flavone acetic acid ester)
    • D.J. Kerr, S.B. Kaye, J. Graham, J. Cassidy, M. Harding, A.J. Setanoians, C. McGrath, W.R. Vezin, D. Cunningham, G. Forrest, and M. Soukop Phase I and pharmacokinetic study of LM985 (flavone acetic acid ester) Cancer Res. 46 1986 3142 3146 (Pubitemid 16074341)
    • (1986) Cancer Research , vol.46 , Issue.6 , pp. 3142-3146
    • Kerr, D.J.1    Kaye, S.B.2    Graham, J.3
  • 25
  • 28
    • 34250861273 scopus 로고    scopus 로고
    • Synthesis of 4′-hydroxy-3′-piperidinomethylchalcone derivatives and their cytotoxicity against PC-3 cell lines
    • DOI 10.1002/ardp.200600072
    • I. Halise, H.I. Gul, K.O. Yerdelen, M. Gul, U. Das, B. Pandit, P.-K. Li, H. Secen, and F. Sahin Synthesis of 4′-hydroxy-3′- piperidinomethylchalcone derivatives and their cytotoxicity against PC-3 cell lines Arch. Pharm. Chem. Life Sci. 340 2007 195 201 (Pubitemid 46972891)
    • (2007) Archiv der Pharmazie , vol.340 , Issue.4 , pp. 195-201
    • Gul, H.I.1    Yerdelen, K.O.2    Gul, M.3    Das, U.4    Pandit, B.5    Li, P.-K.6    Secen, H.7    Sahin, F.8
  • 29
    • 33947452329 scopus 로고
    • Khellin and allied compounds
    • A. Schonberg, and A. Sina Khellin and allied compounds J. Am. Chem. Soc. 72 1950 1611 1616
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 1611-1616
    • Schonberg, A.1    Sina, A.2
  • 31
    • 2642598498 scopus 로고
    • Addition of urea, thiourea and iodine to the natural benzopyrones of Ammi. Visnaga Linn. and Ammi. Majus Linn
    • N.A. Starkowsky Addition of urea, thiourea and iodine to the natural benzopyrones of Ammi. Visnaga Linn. and Ammi. Majus Linn Egypt. J. Chem. 2 1959 111 117
    • (1959) Egypt. J. Chem. , vol.2 , pp. 111-117
    • Starkowsky, N.A.1
  • 32
    • 0040099970 scopus 로고
    • Furochromones and coumarins VII. Degradation of visnagin, khellin and related substances, experiments with chromic acid and hydrogen peroxide, and synthesis of eugenitin
    • A. Schonberg, N. Badran, and N.A. Starkovesky Furochromones and coumarins VII. Degradation of visnagin, khellin and related substances, experiments with chromic acid and hydrogen peroxide, and synthesis of eugenitin J. Am. Chem. Soc. 75 1953 4992 4995
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 4992-4995
    • Schonberg, A.1    Badran, N.2    Starkovesky, N.A.3
  • 33
    • 38949170754 scopus 로고    scopus 로고
    • Synthesis and reactions of some new allyl furobenzopyranone derivatives
    • E.-S.I. El-Desoky Synthesis and reactions of some new allyl furobenzo-pyranone derivatives J. Heterocyclic Chem. 44 2007 1309 1315 (Pubitemid 351225763)
    • (2007) Journal of Heterocyclic Chemistry , vol.44 , Issue.6 , pp. 1309-1315
    • El-Desoky, E.-S.I.1
  • 34
    • 37049150684 scopus 로고
    • Synthetical experiments in the chromone group. Part XVI. Chalkones and flavanones and their oxidation to flavones by means of selenium dioxide
    • H. Mahal, H. Rai, and K. Venkatarama Synthetical experiments in the chromone group. Part XVI. Chalkones and flavanones and their oxidation to flavones by means of selenium dioxide J. Chem. Soc. 1935 866 868
    • (1935) J. Chem. Soc. , pp. 866-868
    • Mahal, H.1    Rai, H.2    Venkatarama, K.3
  • 35
    • 0008803172 scopus 로고
    • Flavonones and gelated compounds
    • T.A. Geissman, and D.K. Fukushima Flavonones and gelated compounds. V. the oxidation of 2′-hydroxchalcones with alkaline hydrogen peroxide J. Am. Chem. Soc. 70m 1948 1686 1689
    • (1948) J. Am. Chem. Soc. , vol.70 M , pp. 1686-1689
    • Geissman, T.A.1    Fukushima, D.K.2
  • 36
    • 0142198745 scopus 로고
    • Furo-chromones and -coumarins. XII. Synthesis of fraxinol from bergapten and of baicalein from visnagin
    • A. Schonberg, N. Badran, and N.A. Starkowsky Furo-chromones and -coumarins. XII. Synthesis of fraxinol from bergapten and of baicalein from visnagin J. Am. Chem. Soc. 77 1955 5390 5392
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 5390-5392
    • Schonberg, A.1    Badran, N.2    Starkowsky, N.A.3
  • 37
    • 0039539407 scopus 로고
    • Diels-Alder reaction. II. Experiments with 2-styrylchromones. on the nature of the dimer of 1,3-diphenylisobenzofuran
    • A. Schonberg, A. Mustafa, and G. Aziz Diels-Alder reaction. II. Experiments with 2-styrylchromones. On the nature of the dimer of 1,3-diphenylisobenzofuran J. Am. Chem. Soc. 76 1954 4576 4577
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 4576-4577
    • Schonberg, A.1    Mustafa, A.2    Aziz, G.3
  • 38
    • 0000499715 scopus 로고
    • On visnagin and khellin and related compounds. A simple synthesis of chromone
    • A. Schonberg, and A. Sina On visnagin and khellin and related compounds. A simple synthesis of chromone J. Am. Chem. Soc. 72 1950 3396 3399
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 3396-3399
    • Schonberg, A.1    Sina, A.2
  • 39
    • 84902650685 scopus 로고
    • Synthesis, hypotensive and antispasmodic activities of certain aminomethylchromones
    • F.A. Ragab, and H.A. Abd-El-Latif Synthesis, hypotensive and antispasmodic activities of certain aminomethylchromones Bull. Fac. Phar. Cairo Univ. 30 1992 215 221
    • (1992) Bull. Fac. Phar. Cairo Univ. , vol.30 , pp. 215-221
    • Ragab, F.A.1    Abd-El-Latif, H.A.2
  • 41
    • 16444380336 scopus 로고    scopus 로고
    • Role of glycogen synthase kinase 3β in rapamycin-mediated cell cycle regulation and chemosensitivity
    • DOI 10.1158/0008-5472.CAN-04-2501
    • J. Dong, J. Peng, H. Zhang, W.H. Mondesire, W. Jian, G.B. Mills, M.C. Hung, and B.F. Meric Role of glycogen synthase kinase 3beta in rapamycin-mediated cell cycle regulation and chemosensitivity Cancer Res. 65 2005 1961 1972 (Pubitemid 40478626)
    • (2005) Cancer Research , vol.65 , Issue.5 , pp. 1961-1972
    • Dong, J.1    Peng, J.2    Zhang, H.3    Mondesire, W.H.4    Jian, W.5    Mills, G.B.6    Hung, M.-C.7    Meric-Bernstam, F.8
  • 43
    • 0036264560 scopus 로고    scopus 로고
    • Photochemical reaction of phenanthrenequinone with some new aurones derived from khellin and visnagin
    • DOI 10.1081/SCC-120003624
    • A.A. Nada, M.F. Zayed, N. Khir-eldin, M.M.T. El-saidi, and E. Hefny Photochemical reaction of phenanthrenequinone with some new aurones derived from khellin and visnagin Synth. Comm. 32 2002 1293 1302 (Pubitemid 34556487)
    • (2002) Synthetic Communications , vol.32 , Issue.9 , pp. 1293-1302
    • Nada, A.A.1    Zayed, M.F.2    El Din, N.K.3    El-Saidi, M.M.T.4    Hefny, E.5
  • 44
    • 34447578794 scopus 로고    scopus 로고
    • Synthesis of 6- and 9-alkylaminomethyl furoflavones as gastroprotective agents
    • DOI 10.1016/j.ejmech.2007.01.019, PII S022352340700058X
    • F.A. Ragab, G.S. Hassan, H.A. Yossef, and H.A. Hashem Synthesis of 6- and 9-alkylaminomethyl furoflavones as gastroprotective agents Eur. J. Med. Chem. 42 2007 1117 1127 (Pubitemid 47081247)
    • (2007) European Journal of Medicinal Chemistry , vol.42 , Issue.8 , pp. 1117-1127
    • Ragab, F.A.1    Hassan, G.S.2    Yossef, H.A.3    Hashem, H.A.4
  • 45
    • 0026751099 scopus 로고
    • Nicotinamide can lower tumor interstitial fluid pressure: Mechanistic and therapeutic implications
    • I. Lee, Y. Boucher, and R.K. Jain Nicotinamide can lower tumor interstitial fluid pressure: mechanistic and therapeutic implications Cancer Res. 52 1992 3237 3240
    • (1992) Cancer Res. , vol.52 , pp. 3237-3240
    • Lee, I.1    Boucher, Y.2    Jain, R.K.3


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