Relationship between structure and antiproliferative activity of 1-azaflavanones

Anticancer Research

Volumn 32, Issue 7, 2012, Pages 2819-2825

  Kawaii, Satoru ^a   Endo, Kotaro ^a   Tokiwano, Tetsuo ^b   Yoshizawa, Yuko ^b  

^a TOKYO DENKI UNIVERSITY   (Japan)

^b AKITA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

1 Azaflavanone; 2 phenyl 3,4 dihydroquinolin 4(1H) one; Antiproliferative activity; Apoptosis; Cell cycle arrest; HL60 cells

Indexed keywords

1 AZAFLAVANONE DERIVATIVE; 2 (2 HYDROXYPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (2 METHOXYPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (2 METHYLPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (3,4 DIMETHOXYPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (3,4,5 TRIMETHOXYPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (4 FLUOROPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (4 HYDROXYPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (4 METHOXYPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (4 METHYLPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (4 TERT BUTYLPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (4 TRIFLUOROMETHYLPHENYL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (FURAN 2 YL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (PYRIDIN 2 YL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (PYRIDIN 3 YL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (PYRIDIN 4 YL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 (THIOPHEN 2 YL) 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 [2 (3 METHYLBUT 2 ENYLOXY)PHENYL] 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 [4 (3 METHYLBUT 2 ENYLOXY)PHENYL] 2,3 DIHYDROQUINOLIN 4(1H) ONE; 2 PHENYL 3,4 DIHYDROQUINOLIN 4(1H) ONE; FLAVANONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CELL CYCLE ARREST; CELL PROLIFERATION; CONTROLLED STUDY; DRUG POTENTIATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FLOW CYTOMETRY; LEUKEMIA; LEUKEMIA CELL; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS; AZA COMPOUNDS; CELL GROWTH PROCESSES; DRUG SCREENING ASSAYS, ANTITUMOR; FLAVANONES; HL-60 CELLS; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84865685383     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. Erdman JW Jr., Balentine D, Arab L, Beecher G, Dwyer JT, Folts J, Harnly J, Hollman P, Keen CL, Mazza G, Messina M, Scalbert A, Vita J, Williamson G and Burrowes J: Flavonoids and heart health: proceedings of the ILSI North America Flavonoids Workshop, May 31-June 1, 2005, Washington, DC. J Nutr 137: 718S-737S, 2007. (Pubitemid 46397511)
2. Kawaii S, Tomono Y, Katase E, Ogawa K, Nonomura-Nakano M, Nesumi H, Yoshida T, Sugiura M and Yano M: Quantitative study of fruit flavonoids in citrus hybrids of King (C. nobilis) and Mukaku Kishu (C. kinokuni). J Agric Food Chem 49: 3982-3986, 2001. (Pubitemid 32822726)
3. Kawaii S, Tomono Y, Katase E, Ogawa K, Yano M, Koizumi M, Ito C and Furukawa H: Quantitative study of flavonoids in leaves of citrus plants. J Agric Food Chem 48: 3865-3871, 2000.
4. Kawaii S, Tomono Y, Katase E, Ogawa K and Yano M: Quantitation of flavonoid constituents in citrus fruits. J Agric Food Chem 47: 3565-3571, 1999. (Pubitemid 29449470)
5. Prasain JK, Carlson SH and Wyss JM: Flavonoids and age-related disease: risk, benefits and critical windows. Maturitas 66: 163-171, 2010.
6. Ekström AM, Serafini M, Nyrén O, Wolk A, Bosetti C and Bellocco R: Dietary quercetin intake and risk of gastric cancer: results from a population-based study in Sweden. Ann Oncol 22: 438-443, 2011.
7. Williamson G and Manach C: Bioavailability and bioefficacy of polyphenols in humans. II. Review of 93 intervention studies. Am J Clin Nutr 81: 243S-255S, 2005.
8. Manach C, Williamson G, Morand C, Scalbert A and Rémésy C: Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am J Clin Nutr 81: 230S-242S, 2005.
9. Kawaii S, Tomono Y, Katase E, Ogawa K and Yano M: Antiproliferative activity of flavonoids on several cancer cell lines. Biosci Biotechnol Biochem 63: 896-899, 1999. (Pubitemid 129562768)
10. Tsimplouli C, Demetzos C, Hadzopoulou-Cladaras M, Pantazis P and Dimas K: In vitro activity of dietary flavonol congeners against human cancer cell lines. Eur J Nutr 51: 181-190, 2012.
11. Terao J: Dietary flavonoids as antioxidants. Forum Nutr 61: 87-94, 2009.
12. González R, Ballester I, López-Posadas R, Suárez MD, Zarzuelo A, Martínez-Augustin O and Sánchez de Medina F: Effects of flavonoids and other polyphenols on inflammation. Crit Rev Food Sci Nutr 51: 331-362, 2011.
13. Korkina L, Kostyuk V, De Luca C and Pastore S: Plant phenylpropanoids as emerging anti-inflammatory agents. Mini Rev Med Chem 11: 823-835, 2011.
14. Kawaii S, Tomono Y, Katase E, Ogawa K and Yano M: HL-60 differentiating activity and flavonoid content of the readily extractable fraction prepared from citrus juices. J Agric Food Chem 47: 128-135, 1999. (Pubitemid 29179634)
15. Kawaii S, Tomono Y, Katase E, Ogawa K and Yano M: Effect of citrus flavonoids on HL-60 cell differentiation. Anticancer Res 19: 1261-1269, 1999. (Pubitemid 29257569)
16. Xia Y, Yang ZY, Xia P, Bastow KF, Tachibana Y, Kuo SC, Hamel E, Hackl T and Lee KH: Antitumor agents. 181. Synthesis and biological evaluation of 6,7,2′,3′,4′-substituted-1,2,3,4-tetrahydro-2-phenyl-4- quinolones as a new class of antimitotic antitumor agents. J Med Chem 41: 1155-1162, 1998. (Pubitemid 28207391)
17. Zhang SX, Feng J, Kuo SC, Brossi A, Hamel E, Tropsha A and Lee KH: Antitumor agents. 199. Three-dimensional quantitative structure-activity relationship study of the colchicine binding site ligands using comparative molecular field analysis. J Med Chem 43: 167-176, 2000. (Pubitemid 30078148)
18. Pejović A, Damljanović I, Stevanović D, Vukićević M, Novaković SB, Bogdanović GA, Radulović N and Vukićević RD: Antimicrobial ferrocene containing quinolinones: Synthesis, spectral, electrochemical and structural characterization of 2-ferrocenyl-2,3-dihydroquinolin-4(1H)-one and its 6-chloro and 6-bromo derivatives. Polyhedron 31: 789-795, 2012.
19. Jiang C, Yang L, Wu WT, Guo QL and You QD: De novo design, synthesis and biological evaluation of 1,4-dihydroquinolin-4-ones and 1,2,3,4- tetrahydroquinazolin-4-ones as potent kinesin spindle protein (KSP) inhibitors. Bioorg Med Chem 19: 5612-5627, 2011.
20. Mphahlele MJ and Oyeyiola FA: Suzuki-Miyaura cross-coupling of 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones and subsequent dehydrogenation and oxidative aromatization of the resulting 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones. Tetrahedron 67: 6819-6825, 2011.
21. Chandrasekhar S, Vijeender K and Sridhar C: L-Proline-catalyzed one-pot synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones. Tetrahedron Lett 48: 4935-4937, 2007. (Pubitemid 46891534)
22. Donnelly JA and Farrell DF: The chemistry of 2′-amino analogs of 2′-hydroxychalcone and its derivatives. J Org Chem 55: 1757-1761, 1990.
23. Uzunoglu S, Karaca B, Atmaca H, Kisim A, Sezgin C, Karabulut B and Uslu R: Comparison of XTT and alamar blue assays in the assessment of the viability of various human cancer cell lines by AT-101 (-/- gossypol). Toxicol Mech Methods 20: 482-486, 2010.