Antitumor agents 286. Design, synthesis, and structure-activity relationships of 3'R,4'R -disubstituted-2',2'-dimethyldihydropyrano[2,3- f ]chromone (DSP) analogues as potent chemosensitizers to overcome multidrug resistance

Journal of Medicinal Chemistry

Volumn 53, Issue 24, 2010, Pages 8700-8708

  Zhou, Ting ^a   Shi, Qian ^a   Bastow, Kenneth F ^a   Lee, Kuo Hsiung ^a,b  

^a University of North Carolina   (United States)

^b CHINA MEDICAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

2',2' DIMETHYLDIHYDROPYRANO[2,3 F]CHROMONE DERIVATIVE; 3',4' DI (4 METHOXYBENZOYLOXY) 2',2' DIMETHYL 2 ETHYLDIHYDROPYRANO[2,3 F]CHROMONE; 3',4' DI (4 METHYLBENZYLOXY) 2',2' DIMETHYL 2 ETHYLDIHYDROPYRANO[2,3 F]CHROMONE; 3',4' DI 4 METHOXYPHENYLACRYLOYLOXY 2',2' DIMETHYL 2 ETHYL DIHYDROPYRANO[2,3 F]CHROMONE; ANTINEOPLASTIC AGENT; CHROMONE DERIVATIVE; GLYCOPROTEIN P; PYRAN DERIVATIVE; UNCLASSIFIED DRUG; VERAPAMIL; VINCRISTINE;

ARTICLE; CANCER CELL CULTURE; CHEMOSENSITIZATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MULTIDRUG RESISTANCE; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CHROMONES; DRUG DESIGN; DRUG INTERACTIONS; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; P-GLYCOPROTEIN; PYRANS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78650313335     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101249z     Document Type: Article

References (17)

1. Dalton, W. S. Is p-glycoprotein a potential target for reversing clinical drug resistance? Curr. Opin. Oncol. 1994, 6 (6) 595-600
2. Hindenburg, A. A.; Baker, M. A.; Gleyzer, E.; Stewart, V. J.; Case, N.; Taub, R. N. Effect of verapamil and other agents on the distribution of anthracyclines and on reversal of drug resistance Cancer Res. 1987, 47 (5) 1421-1425
3. Thomas, H.; Coley, H. Overcoming multidrug resistance in cancer: an updated on the clinical strategy of inhibitinf P-glycoprotein Cancer Control 2003, 10, 159-165
4. Szakacs, G.; Paterson, J. K.; Ludwig, J. A.; Booth-Genthe, C.; Gottesman, M. M. Targeting multidrug resistance in cancer Nature Rev Drug Discovery 2006, 5 (3) 219-234
5. Hollt, V.; Kouba, M.; Dietel, M.; Vogt, G. Stereoisomers of calcium antagonists which differ markedly in their potencies as calcium blockers are equally effective in modulating drug transport by P-glycoprotein Biochem. Pharmacol. 1992, 43 (12) 2601-2608
6. Wu, J. Y.; Fong, W. F.; Zhang, J. X.; Leung, C. H.; Kwong, H. L.; Yang, M. S.; Li, D.; Cheung, H. Y. Reversal of multidrug resistance in cancer cells by pyranocoumarins isolated from Radix peucedani Eur. J. Pharmacol. 2003, 473 (1) 9-17
7. Fong, W. F.; Shen, X. L.; Globisch, C.; Wiese, M.; Chen, G. Y.; Zhu, G. Y.; Yu, Z. L.; Tse, A. K.; Hu, Y. J. Methoxylation of 3′,4′-aromatic side chains improves P-glycoprotein inhibitory and multidrug resistance reversal activities of 7,8-pyranocoumarin against cancer cells Bioorg. Med. Chem. 2008, 16 (7) 3694-3703
8. Aller, S. G.; Yu, J.; Ward, A.; Weng, Y.; Chittaboina, S.; Zhuo, R.; Harrell, P. M.; Trinh, Y. T.; Zhang, Q.; Urbatsch, I. L.; Chang, G. Structure of P-glycoprotein reveals a molecular basis for poly-specific drug binding Science 2009, 323 (5922) 1718-1722
9. Pajeva, I. K.; Wiese, M. Pharmacophore model of drugs involved in P-glycoprotein multidrug resistance: explanation of structural variety (hypothesis) J. Med. Chem. 2002, 45, 5671-5686
10. Zhou, T.; Shi, Q.; Chen, C. H.; Zhu, H.; Huang, L.; Ho, P.; Lee, K. H. Anti-AIDS agents 79. Design, synthesis, molecular modeling and structure-activity relationships of novel dicamphanoyl-2′,2′- dimethyldihydropyranochromone (DCP) analogs as potent anti-HIV agents Bioorg. Med. Chem. 2010, 18 (18) 6678-6689
11. Zhou, T.; Shi, Q.; Lee, K. H. Anti-AIDS agent 83. Efficient microwave-assisted one-pot preparation of augular 2,2-dimethyl-2 H -chromone containing compounds Tetrahedron Lett. 2010, 51 (33) 4382-4386
12. Baba, T.; Huang, G.; MInoru, I. Synthesis of the JKLM-ring Fragment of Ciguatoxin Tetrahedron 2003, 59, 6851-6872
13. Nguyen, T. M.; Sittisombut, C.; Boutefnouchet, S.; Lallemand, M.-C.; Michel, S.; Koch, M.; Tillequin, F.; Mizinghien, R.; Lansiaux, A.; David-Cordonnier, M.-H.; Pfeiffer, B.; Kraus-Berthier, L.; Leonce, S.; Pierre, A. Synthesis, antitumor activity, and mechanism of action of benzo[ a ]pyrano[3,2- h ]acridin-7-one analogues of acronycine J. Med. Chem. 2006, 49, 3383-3394
14. Gouaze, V.; Yu, J. Y.; Bleicher, R. J.; Han, T. Y.; Liu, Y. Y.; Wang, H.; Gottesman, M. M.; Bitterman, A.; Giuliano, A. E.; Cabot, M. C. Overexpression of glucosylceramide synthase and P-glycoprotein in cancer cells selected for resistance to natural product chemotherapy Mol. Cancer Ther. 2004, 3 (5) 633-639
15. Armstrong, L.; Sullivan, R.; Mechetner, E., New functional assays for multidrug resistance. http://www.biosciencetechnology.com/ShowPR.aspx?PUBCODE= 090&ACCT=9000009885&ISSUE=0404&RELTYPE=PR&Cat=SubCat=1& PRODCODE=00005949&PRODLETT=A&CALLFROM=PR&CommonCount=0, 2004, (accessed April 28, 2004).
16. Lunney, E. A.; Hagen, S. E.; Domagala, J. M.; Humblet, C.; Kosinski, J.; Tait, B. D.; Warmus, J. S.; Wilson, M.; Ferguson, D.; Hupe, D.; Tummino, P. J.; Baldwin, E. T.; Bhat, T. N.; Liu, B.; Erickson, J. W. A novel nonpeptide HIV-1 protease inhibitor: elucidation of the binding mode and its application in the design of related analogs J. Med. Chem. 1994, 37 (17) 2664-2677
17. Rubinstein, L. V.; Shoemaker, R. H.; Paull, K. D.; Simon, R. M.; Tosini, S.; Skehan, P.; Scudiero, D. A.; Monks, A.; Boyd, M. R. Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines J. Natl. Cancer Inst. 1990, 82 (13) 1113-1118