Synthesis and cytotoxic activity of novel benzopyrano [3,2-c]chromene-6,8- dione derivatives

Medicinal Chemistry Research

Volumn 20, Issue 4, 2011, Pages 466-474

  Shafiee, Abbas ^a,b   Motamedi, Radineh ^c   Firuzi, Omidreza ^d   Meili, Savis ^d   Mehdipour, Ahmad Reza ^d   Miri, Ramin ^d  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c PAYAME NOOR UNIVERSITY   (Iran)

^d SHIRAZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

4 Hydroxycoumarin; Benzopyran; Chromene; Cytotoxicity

Indexed keywords

9,10 DIHYDRO 7 (3 METHOXYPHENYL) 7H,11H BENZOPYRANO[3,2 C]CHROMENE 6,8 DIONE; BENZOPYRAN DERIVATIVE; BENZOPYRANO[3,2 C]CHROMENE 6,8 DIONE DERIVATIVE; CHROMENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 80052033941     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9340-3     Document Type: Article

References (30)

1. Bedair AH, El-Hady NA, El-Latif MSA, Fakery AH, El-Agrody AM (2000) Synthesis of some new pyrano[2, 3-d]pyrimidine, 2-substituted[ 1,2,4]triazolo[1,5-c]pyrimidine and pyrimido[1,6-b] [1,2,4]triazine derivatives. Farmaco 55:708-714 (Pubitemid 32037102)
2. Colotta V, Cecchi L, Melani F, Filacchioni G, Martini C, Giannaccini G, Lucacchini A (1990) Tricyclic heteroaromatic systems. [1]benzopyranopyrrol-4- ones and [1]benzopyrano-1,2,3-triazol- 4-ones as benzodiazepine receptor ligands. Synthesis and structure-activity relationships. J Med Chem 33:2646-2651 (Pubitemid 20274227)
3. Colotta V, Cecchi L, Melani F, Filacchioni G, Martini C, Gelli S, Lucacchini A (1991a) Tricyclic heteroaromatic systems. Synthesis of 1, 3 and 1, 2 disubstituted [1]benzopyrano[4, 3-b]pyrrol- 4-ones and structure-activity relationships as benzodiazepine receptor ligands. Il Farmaco 46:1139-1154
4. Colotta V, Cecchi L, Melani F, Filacchioni G, Martini C, Gelli S, Lucacchini A (1991b) Tricyclic heteroaromatic systems: [1]benzopyrano- pyrazol-4-ones as benzodiazepine receptor ligands. J Pharm Sci 80:276-279
5. Cravottoo G, Nano GM, Palmisano G, Tagliapietra S (2001) An asymmetric approach to coumarin anticoagulants via hetero- Diels-Alder cycloaddition. Tetrahedron Asymmetr 12:707-709 (Pubitemid 32497083)
6. Crow FW, Doholke WK, Farley KA, Hadden CE, Hahn DA, Kaluzny BD, Mallory CS, Martin GE, Smith RF, Thamann TJ (1999) Complete spectroscopic structural characterization of novobiocin, isonovobiocin, decarbamylnovobiocin, 2-(O-carbamyl) novobiocin, and novobiocin-2,3-carbonate. J Heterocycl Chem 36:365-370 (Pubitemid 29220942)
7. Ermili A, Roma G, Buonamici M, Cuttica A, Galante M, Orsini G, Passerini N (1979) Psychopharmacological study with K 8409, a 1H-naphtho[2, 1-b]pyran 3-dialkylamino substituted derivative. Farmaco Ed Sci 34:535-544 (Pubitemid 9214859)
8. Farag NA, El-Tayeb W (2010) Design, synthesis and docking studies of new furobenzopyranones and pyranobenzopyranones as photoreagent towards DNA and as antimicrobial agents. Eur J Med Chem 45:317-325
9. Feuer G (1974) The metabolism and biological actions of coumarins. Prog Med Chem 10:85-158
10. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al- Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong WM, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA.
11. Georgiadis MP, Couladouros EA, Delitheos AK (1992) Synthesis and antimicrobial properties of 2H-pyran-3(6H)-one derivatives and related compounds. J Phar Sci 81:1126-1131 (Pubitemid 23021439)
12. Halland N, Velgoard T, Jørgensen KA (2003) Direct asymmetric Michael reactions of cyclic 1,3-dicarbonyl compounds and enamines catalyzed by chiral bisoxazoline-copper(II) complexes. J Org Chem 68:5067-5074 (Pubitemid 36750173)
13. Hermodson MA, Barker WM, Link KP (1971) Studies on the 4-hydroxycoumarins. Synthesis of the metabolites and some other derivatives of warfarin. J Med Chem 14:167-169
14. Jabbar SA, Twentyman PR, Watson JV (1989) The MTT assay underestimates the growth inhibitory effects of interferons. Br J Cancer 60:523-528 (Pubitemid 19251443)
15. Jin LW, Hua DH, Shie FS, Maezawa I, Sopher B, Martin GM (2002) Novel tricyclic pyrone compounds prevent intracellular APP C99-induced cell death. J Mol Neurosci 19:57-61 (Pubitemid 35013335)
16. Kang SS, Kim HJ, Jin C, Lee YS (2009) Synthesis of tyrosinase inhibitory (4-oxo-4H-pyran-2-yl)acrylic acid ester derivatives. Bioorg Med Chem Lett 19:188-191
17. Kasaplar P, Yilmazer O, Caǧir A (2009) 6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: asymmetric synthesis, and anti-proliferative properties. Bioorg Med Chem 17:311-318
18. Kesten SR, Heffner TG, Johnson SJ, Pgsley TA, Wright JL, Wise LD (1999) Design, synthesis, and evaluation of chromen-2-ones as potent and selective human dopamine D4 antagonists. J Med Chem 42:3718-3725 (Pubitemid 29445105)
19. Mahajan DH, Pannecouque C, De Clercq E, Chikhalia KH (2009) Synthesis and studies of new 2-(coumarin-4-yloxy)-4,6-(substituted)- S-triazine derivatives as potential anti-HIV agents. Arch Pharm (Weinheim) 342:281-290
20. Matos MJ, Viña D, Picciau C, Orallo F, Santana L, Uriarte E (2009) Synthesis and evaluation of 6-methyl-3-phenylcoumarins as potent and selective MAO-B inhibitors. Bioorg Med Chem Lett 19:5053-5055
21. Mehdipour AR, Javidnia K, Hemateenejad B, Amirghofran Z, Miri R(2007) Dihydropyridine derivatives to overcome atypical multidrug resistance: design, synthesis, QSAR studies, and evaluation of their cytotoxic and pharmacological activities. Chem Biol Drug Des 70:337-346 (Pubitemid 47537694)
22. Miri R, Javidnia K, Hemmateenejad B, Azarpira A, Amirghofran Z (2004) Synthesis, cytotoxicity, QSAR, and intercalation study of new diindenopyridine derivatives. Bioorg Med Chem 12:2529-2536 (Pubitemid 38542778)
23. Miri R, Javidnia K, Sarkarzadeh H, Hemmateenejad B (2006) Synthesis, study of 3D structures, and pharmacological activities of lipophilic nitroimidazolyl-1,4-dihydropyridines as calcium channel antagonist. Bioorg Med Chem 14:4842-4849
24. Obaseki AO, Porter WR (1982) 4-Hydroxycoumarin/2-hydroxychromone tautomerism: infrared spectra of 2-13C and 3-D labeled 4-hydroxycoumarin and its anion. J Heterocycl Chem 19:385-390 (Pubitemid 12016098)
25. Robinson A, Liu HY, Feaster J (1996) The first practical asymmetric synthesis of R and S-Warfarin. Tetrahedron Lett 37:8321-8324 (Pubitemid 26373111)
26. Sagar R, Singh P, Kumar R, Maulik PR, Shaw AK (2005) Diastereoselective annulation of 4-hydroxypyran-2H-ones with enantiopure 2,3-dideoxy-alpha, beta-unsaturated sugar aldehydes derived from respective glycals. Carbohydrate Res 340:1287-1300. (Pubitemid 40602283)
27. Stanchev S, Momekov G, Jensen F, Manolov I (2008) Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives. Eur J Med Chem 43:694-706 (Pubitemid 351447326)
28. Su CR, Yeh SF, Liu CM, Damu AG, Kuo TH, Chiang PC, Bastow KF, Lee KH, Wu TS (2009) Anti-HBV and cytotoxic activities of pyranocoumarin derivatives. Bioorg Med Chem 17:6137-6143
29. Tallarida RJ, Murray RP (1986) Manual of pharmacologic calculations with computer programs. Springer, New York.
30. Trivedi KN, Madhava Rao SS, Mistry SV, Desai SM (2001) Chemistry of 4-hydroxycoumarin. J Ind Chem Soc 78:579-595 (Pubitemid 34292671)