Design, synthesis and 3D-QSAR study of cytotoxic flavonoid derivatives

Molecular Diversity

Volumn 15, Issue 3, 2011, Pages 665-675

  Ou, Lili ^a   Han, Shuang ^a   Ding, Wenbo ^a   Chen, Zhe ^a   Ye, Ziqi ^a   Yang, Hongyu ^a   Zhang, Goulin ^a   Lou, Yijia ^a   Chen, Jian Zhong ^a   Yu, Yongping ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

3D QSAR; CoMFA; Comparative molecular field analysis; Cytotoxic activity; Flavonoids

Indexed keywords

(5,7 DIMETHOXY 4 OXO 2 PHENYL 4H CHROMEN 8 YL) ACETALDEHYDE; 1 (2 HYDROXY 4,6 DIMETHOXYPHENYL) 3 (4 METHOXYPHENYL) PROP 2 EN 1 ONE; 1 (2 HYDROXY 4,6 DIMETHOXYPHENYL) 3 PHENYLPROP 2 EN 1 ONE; 1 (3 ALLYL 2 HYDROXY 4,6 DIMETHOXYPHENYL) 3 (4 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 (3 ALLYL 2 HYDROXY 4,6 DIMETHOXYPHENYL) 3 PHENYLPROP 2 EN 1 ONE; 5 HYDROXY 7 DIMETHOXY FLAVONOID DERIVATIVE; 5,7 DIHYDROXY FLAVONOID DERIVATIVE; 5,7 DIMETHOXY 8 (3 METHYL BUT 2 ENYL) 2 PHENYL CHROMEN 4 ONE; 5,7 DIMETHOXY 8 (3 METHYL HEX 2 ENYL) 2 PHENYL CHROMEN 4 ONE; 8 ALLYL 5 HYDROXY 7 METHOXY 2 (4 METHOXY PHENYL) 4H CHROMEN 4 ONE; 8 ALLYL 5 HYDROXY 7 METHOXY 2 PHENYL 4H CHROMEN 4 ONE; 8 ALLYL 5,7 DIHYDROXY 2 (4 HYDROXYPHENYL) 4H; 8 ALLYL 5,7 DIMETHOXY 2 (4 METHOXYPHENYL) 4H CHROMEN 4 ONE; 8 ALLYL 5,7 DIMETHOXY 2 (4 METHOXYPHENYL)CHROMAN 4 ONE; 8 ALLYL 5,7 DIMETHOXY 2 PHENYL 4H CHROMEN 4 ONE; 8 ALLYL 5,7 DIMETHOXY 2 PHENYLCHROMAN 4 ONE; 8 BUT 2 ENYL 5,7 DIMETHOXY 2 PHENYL CHROMEN 4 ONE; [5,7 DIMETHOXY 2 (4 METHOXY PHENYL) 4 OXO 4H CHROMEN 8 YL] ACETALDEHYDE; DIMETHOXY 8 (3 METHYL PENT 2 ENYL) 2 PHENYL CHROMEN 4 ONE; FLAVONOID; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CYTOTOXICITY; DRUG ACTIVITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FLAVONOIDS; HUMANS; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80051595483     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-010-9289-7     Document Type: Article

References (24)

1. EJ Middleton C Kandaswami TC Theoharides 2000 The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer Pharmacol Rev 52 673 751 11121513 1:CAS:528:DC%2BD3MXislWktw%3D%3D
2. K Suresh Babu T Hari Babu PV Srinivas KH Kishore USN Murthy JM Rao 2006 Synthesis and biological evaluation of novel C (7) modified chrysin analogues as antibacterial agents Bioorg Med Chem Lett 16 221 224 10.1016/j.bmcl.2005.09.009 16213726 10.1016/j.bmcl.2005.09.009 1:STN:280:DC%2BD2MnhtFygsQ%3D%3D (Pubitemid 41625675)
3. AI Khlebnikov IA Schepetkin NG Domina LN Kirpotina MT Quinn 2007 Improved quantitative structure-activity relationship models to predict antioxidant activity of flavonoids in chemical, enzymatic, and cellular systems Bioorg Med Chem 15 1749 1770 10.1016/j.bmc.2006.11.037 17166721 10.1016/j.bmc.2006.11.037 1:CAS:528:DC%2BD2sXmtVeiuw%3D%3D (Pubitemid 46394047)
4. H Park TT Dao HP Kim 2005 Synthesis and inhibition of PGE2 production of 6,8-disubstituted chrysin derivatives Eur J Med Chem 40 943 948 10.1016/j.ejmech.2005.04.013 15963606 10.1016/j.ejmech.2005.04.013 1:CAS:528:DC%2BD2MXhtVCltL3N (Pubitemid 41376310)
5. K Nakagawa-Goto KF Bastow TH Chen SL Morris-Natschke KH Lee 2008 Antitumor agents 260. new desmosdumotin B analogues with improved in vitro anticancer J Med Chem 51 3297 3303 10.1021/jm701208v 18473435 10.1021/jm701208v 1:CAS:528:DC%2BD1cXmtVGgsro%3D (Pubitemid 351821888)
6. M Cárdenas M Marder VC Blank LP Roguin 2006 Antitumor activity of some natural flavonoids and synthetic derivatives on various human and murine cancer cell lines Bioorg Med Chem 14 2966 2971 10.1016/j.bmc.2005.12.021 16412650 10.1016/j.bmc.2005.12.021
7. CL Wang HQ Li WD Meng FL Qing 2005 Trifluoromethylation of flavonoids and anti-tumor activity of the trifluoromethylated flavonoid derivatives Bioorg Med Chem Lett 15 4456 4458 10.1016/j.bmcl.2005.07.047 16137880 10.1016/j.bmcl.2005. 07.047 1:CAS:528:DC%2BD2MXpvVSrs7w%3D (Pubitemid 41258171)
8. R Tundis B Deguin MR Loizzo M Bonesi GA Statti F Tillequinb F. Menichini F Menichini 2005 Potential antitumor agents: flavones and their derivatives from Linaria reflexa Desf Bioorg Med Chem Lett 15 4757 4760 10.1016/j.bmcl.2005.07. 029 16125932 10.1016/j.bmcl.2005.07.029 1:CAS:528:DC%2BD2MXhtVanu7zN (Pubitemid 41354800)
9. B Bauvois ML Puiffe JB Bongui S Paillat C Monneret D Dauzonne 2003 Synthesis and biological evaluation of novel flavone-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13 J Med Chem 46 3900 3913 10.1021/jm021109f 12930151 10.1021/jm021109f 1:CAS:528:DC%2BD3sXmtVSlsrg%3D (Pubitemid 37034139)
10. W Wätjen AK Suckow-Schnitker R Rohrig A Kulawik J Addae-Kyereme CW Wright CM Passreiter 2008 Prenylated flavonoid derivatives from the bark of Erythrina addisoniae J Nat Prod 71 735 738 10.1021/np070417j 18302333 10.1021/np070417j (Pubitemid 351656219)
11. BJ Yoder SG Cao A Norris JS Miller F Ratovoson J Razafitsalama R Andriantsiferana VE Rasamison DGI Kingston 2007 Antiproliferative prenylated stilbenes and flavonoids from macaranga alnifolia from the madagascar rainforest J Nat Prod 70 342 346 10.1021/np060484y 17326683 10.1021/np060484y 1:CAS:528:DC%2BD2sXitFKrtLc%3D (Pubitemid 46603582)
12. W Wätjen N Weber YJ Lou ZQ Wang Y Chovolou A Kampkötter R Kahl P Proksch 2007 Prenylation enhances cytotoxicity of apigenin and liquiritigeninin rat H4IIE hepatoma and C6 glioma cells Food Chem Toxicol 45 119 124 10.1016/j.fct.2006.08.008 17045382 10.1016/j.fct.2006.08.008 (Pubitemid 44792321)
13. F Roelens N Heldring W Dhooge M Bengtsson F Comhaire JÅ Gustafsson E Treuter DD Keukeleire 2006 Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors α and β J Med Chem 49 7357 7365 10.1021/jm060692n 17149865 10.1021/jm060692n 1:CAS:528:DC%2BD28Xht1SqtL3I (Pubitemid 44920186)
14. M Maitrejea G Comte D Barron KE Kirat G Conseil AD Pietro 2000 The flavanolignan silybin and its hemisynthetic derivatives, a novel series of potential modulators of P-Glycoprotein Bioorg Med Chem Lett 10 157 160 10.1016/S0960-894(99)00636-8 10.1016/S0960-894X(99)00636-8 (Pubitemid 30055446)
15. AS Lin K Nakagawa-Goto FR Chang DL Yu SL Morris-Natschke CC Wu SL Chen YC Wu KH Lee 2007 First total synthesis of protoapigenone and its analogues as potent cytotoxic agents J Med Chem 50 3921 3927 10.1021/jm070363a 17622129 10.1021/jm070363a 1:CAS:528:DC%2BD2sXnsVymur4%3D (Pubitemid 47292055)
16. KC Gulati SR Seth K Venkataraman 1943 Phloroacetophenone Org Synth 2 522 523
17. Juntend KYT, Junte TST (1988) Anti-ulcerous agent containing chalcone derivative as effective ingredient and novel chalcone derivatives. Patent EP 292576
18. X Bu L Zhao Y Li 1997 A facile synthesis of 6-C-Prenylflavanones Synthesis 11 1246 1248 10.1055/s-1997-1348 10.1055/s-1997-1348 (Pubitemid 27501320)
19. MK Schwaebe TJ Moran JP Whitten 2005 Total synthesis of psorospermin Tetrahedron Lett 46 827 829 10.1016/j.tetlet.2004.12.006 10.1016/j.tetlet.2004. 12.006 1:CAS:528:DC%2BD2MXjtFOktQ%3D%3D (Pubitemid 40091682)
20. J Quintin C Roullier S Thoret G Lewin 2006 Synthesis and anti-tubulin evaluation of chromone-based analogues of combretastatins Tetrahedron 62 4038 4051 10.1016/j.tet.2006.02.024 10.1016/j.tet.2006.02.024 1:CAS:528: DC%2BD28XjslCgsrw%3D
21. 5-Methyl-(±) -(2'R, 3'S)-psorospermin J Org Chem 52 342 347 10.1021/jo00379a005 10.1021/jo00379a005 1:CAS:528:DyaL2sXhslGqur0%3D (Pubitemid 17010343)
22. ME Meza-Avina M Ordonez M Fernandez-Zertuche L Rodriguez- Fragoso J Reyes-Esparza AA de Los Rios-Corsino 2005 Synthesis of some monocyclic analogues of mycophenolic acid via the Johnson ortho ester Claisen rearrangement Bioorg Med Chem 13 6521 6528 10.1016/j.bmc.2005.07.013 16122928 10.1016/j.bmc.2005.07. 013 1:CAS:528:DC%2BD2MXhtFKhsLbJ (Pubitemid 41539316)
23. X Guo W Hu S Cheng L Wang J Chang 2006 Synthesis of novel murrapanine analogues by microwave irradiation Syn Commun 36 781 788 10.1080/ 00397910500451159 10.1080/00397910500451159 1:CAS:528:DC%2BD28Xit1Omsrs%3D (Pubitemid 43247221)
24. G Solladié N Gehrold J Maignan 1999 Synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8- methylflavanone Tetrahedron Asymmetry 10 2739 2747 10.1016/S0957-4166(99)00266-9 10.1016/S0957-4166(99) 00266-9 (Pubitemid 29423381)