Synthesis and crystal structure of chalcones as well as on cytotoxicity and antibacterial properties

Medicinal Chemistry Research

Volumn 21, Issue 4, 2012, Pages 444-452

  Wu, Jianzhang ^a,b   Wang, Cong ^a,c   Cai, Yuepiao ^a   Peng, Jing ^a   Liang, Donglou ^a   Zhao, Yunjie ^a   Yang, Shulin ^b   Li, Xiaokun ^a,b   Wu, Xiaoping ^a,c   Liang, Guang ^a,b  

^a WENZHOU MEDICAL UNIVERSITY   (China)

^b NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c JINAN UNIVERSITY   (China)

Author keywords

Antibacterial activity; Chalcones; Crystal structure; Cytotoxicity; Synthesis

Indexed keywords

(E) 2 BROMO 3',4' DIMETHOXYCHALCONE; (E) 2 BROMO 4' AMINOCHALCONE; (E) 2 CHLORO 3',4' DIMETHOXYCHALCONE; (E) 2 FLUORO 4' AMINOCHALCONE; (E) 2 TRIFLUOROMETHYL 4' AMINOCHALCONE; (E) 2,3 DIMETHOXY 3',4' DIMETHOXYCHALCONE; (E) 2,4 DICHLORO 4' AMINOCHALCONE; (E) 2,4 DIMETHOXY 3',5' DIFLUOROCHALCONE; (E) 2,6 DIFLUORO 4' METHOXYCHALCONE; (E) 4 DIMETHYLAMINO 3',5' DIFLUOROCHALCONE; (E) 4 METHOXY 3',5' DIFLUOROCHALCONE; CHALCONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL; CELL STRAIN HT29; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MULTIDRUG RESISTANCE; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

EID: 84861857293     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9549-9     Document Type: Article

References (31)

1. Avila HP, Smania Ede F, Monache FD, Smania A (2008) Structureactivity relationship of antibacterial chalcones. Bioorg Med Chem 16:9790-9794
2. Batovska D, Parushev S, Stamboliyska B, Tsvetkova I, Ninova M, Najdenski H (2009) Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted. Eur J Med Chem 44:2211-2218
3. Bhattacharya A, Mishra LC, Sharma M, Awasthi SK, Bhasin VK (2009) Antimalarial pharmacodynamics of chalcone derivatives in combination with artemisinin against Plasmodium falciparum in vitro. Eur J Med Chem 44:3388-3393
4. Boumendjel A, Boccard J, Carrupt P, Nicolle E, Blanc M, Geze A, Choisnard L, Wouessidjewe D, Matera E, Dumontet C (2008) Antimitotic and antiproliferative activities of chalcones: forward structure-activity relationship. J Med Chem 51:2307-2310 (Pubitemid 351503287)
5. Bruker (1997) SHELXTL Version 5.1, Bruker AXS Inc., Madison, Wisconsin, USA
6. Bruker (1999) SAINT Version 6.02, Bruker AXS Inc., Madison, Wisconsin, USA
7. Dominguez JN, Leon C, Rodrigues J, Gamboa de Dominguez N, Gut J, Rosenthal PJ (2005) Synthesis of chlorovinyl sulfones as structural analogs of chalcones and their antiplasmodial activities. J Med Chem 48:3654-3658
8. Ducki S (2009) Antimitotic chalcones and related compounds as inhibitors of tubulin assembly. Anticancer Agents Med Chem 9:336-347
9. Ghosh A, Mandal S, Banerji A, Kar M, Banerji J (2009) A new chalcone from Pongamia pinnata and its antioxidant properties. Nat Prod Commun 4:209-210
10. Heidari MR, Foroumadi A, Noroozi H, Samzadeh-Kermani A, Azimzadeh BS (2009) Study of the anti-inflammatory and analgesic effects of novel rigid benzofuran-3, 4-dihydroxy chalcone by formalin, hot-plate and carrageenan tests in mice. Pak J Pharm Sci 22:395-401
11. Henmi K, Hiwatashi Y, Hikita E, Toyama N, Hirano T (2009) Methoxy-and fluoro-chalcone derivatives arrest cell cycle progression and induce apoptosis in human melanoma cell A375. Biol Pharm Bull 32:1109-1113
12. Hua SZ, Luo JK, Wang XB, Wang JS, Kong LY (2009) Two novel monoterpene-chalcone conjugates isolated from the seeds of Alpinia katsumadai. Bioorg Med Chem Lett 19:2728-2730
13. Kamal A, Shankaraiah N, Prabhakar S, Reddy ChR, Markandeya N, Reddy KL, Devaiah V (2008) Solid-phase synthesis of new pyrrolobenzodiazepine-chalcone conjugates: DNA-binding affinity and anticancer activity. Bioorg Med Chem Lett 18:2434-2439 (Pubitemid 351444875)
14. Ko HH, Tsao LT, Yu KL, Liu CT, Wang JP, Lin CN (2003) Structure-activity relationship of antibacterial chalcones. Bioorg Med Chem 11:105-111
15. Kumar SK, Hager E, Pettit C, Gurulingappa H, Davidson NE, Khan SR (2003) Design, synthesis and evolution of novel boronicchalcone derivatives as antitumor agents. J Med Chem 46:2813-2815 (Pubitemid 36775907)
16. Lee CM, Yeh SC, Lim HK, Liu CP, Tseng HK (2009) High prevalence rate of multidrug resistance among nosocomial pathogens in the respiratory care center of a tertiary hospital. J Microbiol Immunol Infect 42:401-404
17. Liang G, Shao LL, Wang Y, Zhao CG, Chu YH, Xiao J, Zhao Y, Li XK, Yang SL (2009) Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents. Bioorg Med Chem 17:2623-2631
18. Liu X, Xu Y, Go M (2008) Functionalized chalcones with basic functionalities have antibacterial activity against drug sensitive Staphylococcus aureus. Eur J Med Chem 43:1681-1687
19. Nielsen SF, Larsen M, Boesen T, Schonning K, Kromann H (2005) Cationic chalcone antibiotics design, synthesis, and mechanism of action. J Med Chem 48:2667-2677 (Pubitemid 40516456)
20. Nowakowska Z (2007) A review of anti-infective and anti-inflammatory chalcones. Eur J Med Chem 42:125-137 (Pubitemid 46282233)
21. Nowakowska Z, Kdzia B, Schroeder G (2008) Functionalized chalcones with basic functionalities have antibacterial activity against drug sensitive Staphylococcus aureus. Eur J Med Chem 43:707-713
22. Padhye S, Ahmad A, Oswal N, Sarkar FH, Hematol J (2009) Emerging role of Garcinol, the antioxidant chalcone from Garcinia indica Choisy and its synthetic analogs. Oncol 2:38
23. Park PH, Kim HS, Jin XY, Jin F, Hur J, Ko G, Sohn DH (2009) KB- 34, a newly synthesized chalcone derivative, inhibits lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages via heme oxygenase-1 induction and blockade of activator protein-1. Eur J Pharmacol 606:215-224
24. Rao Y, Fang S, Tzeng Y (2004) Structure-activity relationship of antibacterial chalcones. Bioorg Med Chem 12:2679-2686
25. Ratkovic Z, Juranic ZD, Stanojkovic T, Manojlovic D, Vukicevic RD, Radulovic N, Joksovic MD (2010) Synthesis, characterization, electrochemical studies and antitumor activity of some new chalcone analogues containing ferrocenyl pyrazole moiety. Bioorg Chem 38:26-32
26. Rizvi SU, Siddiqui HL, Parvez M, Ahmad M, Siddiqui WA, Yasinzai MM (2010) Antimicrobial and antileishmanial studies of novel(2E)-3-(2-chloro-6-methyl/ methoxyquinolin-3-yl)-1-(aryl)prop-2-en-1-ones. Chem Pharm Bull 58:301-306
27. Rodriguez CH, De Ambrosio A, Bajuk M, Spinozzi M, Nastro M, Bombicino K, Radice M, Gutkind G, Vay C, Famiglietti A (2010) In vitro antimicrobials activity against endemic Acinetobacter baumannii multiresistant clones. J Infect Dev Ctries 4:164-167
28. Tanaka H, Nakamura S, Onda K, Tazaki T, Hirano T (2009) Sofalcone, an anti-ulcer chalcone derivative, suppresses inflammatory crosstalk between macrophages and adipocytes and adipocyte differentiation: implication of heme-oxygenase-1 induction. Biochem Biophys Res Commun 381:566-570
29. Tang Y, Simoneau AR, Xie J, Shahandeh B, Zi X (2008) Effects of the kava chalcone flavokawain a differ in bladder cancer cells with wild-type versus mutant p53. Cancer Prev Res 1:439-451
30. Tomar V, Bhattacharjee G, Rajakumar S, Kamaluddin, Srivastava K, Puri SK (2010) Synthesis of new chalcone derivatives containing acridinyl moiety with potential antimalarial activity. Eur J Med Chem 45:745-751
31. Tsukiyama R, Katsura H, Tokuriki N, Kobayashi M (2002) Antibacterial activity of licochalcone A against spore-forming bacteria. Antimicrob Agents Chemother 46:1226-1230 (Pubitemid 34415295)