Synthesis and screening of anti-cancer, antioxidant, and anti-inflammatory activities of novel galloyl pyrazoline derivatives

Pharmaceutical Biology

Volumn 47, Issue 9, 2009, Pages 854-863

  Abdel Aziz, Mohamed ^a   Gamal Eldeen, Amira M ^b  

^a Minia University   (Egypt)

^b NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

2 Pyrazoline; Anti cancer; Anti inflammatory; Antioxidant; Galloyl derivatives

Indexed keywords

1 (3,4,5 TRIHYDROXYBENZOYL) 4,5 DIHYDRO 5 (4 METHOXYPHENYL) 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 1,1 DIPHENYL 2 PICRYLHYDRAZYL; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 5 (2 FURYL) 4,5 DIHYDRO 1 (3,4,5 TRIHYDROXYBENZOYL) 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 5 (2,6 DICHLOROPHENYL) 4,5 DIHYDRO 1 (3,4,5 TRIHYDROXYBENZOYL) 3 (3,4 DIMETHOXYPHENYL) 1H PYRAZOLE; 5 (4 CYANOPHENYL) 4,5 DIHYDRO 1 (3,4,5 TRIHYDROXYBENZOYL) 3 (3,4 DIMETHOXY PHENYL) 1H PYRAZOLE; LIPOPOLYSACCHARIDE; NITRIC OXIDE; NITRITE; PYRAZOLINE DERIVATIVE; RADICAL; REAGENT; SCAVENGER; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; ASSAY; CANCER CELL CULTURE; CELL PROLIFERATION; CELL STRAIN HCT116; CELL STRAIN HEPG2; CYTOTOXICITY; DOSE RESPONSE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MACROPHAGE; SCREENING;

EID: 77149178470     PISSN: 13880209     EISSN: 17445116     Source Type: Journal    
DOI: 10.1080/13880200902946452     Document Type: Article

References (30)

1. Abdel-Aziz M, Matsuda K, Otsuka M, Uyeda M, Okawara T, Suzuki K (2004): Inhibitory activities against topoisomerase I and II by polyhydroxybenzoyl amide derivatives and their structure-activity relationship. Bioorg Med Chem Lett 14: 1669-1672.
2. Amir M, Kumar H, Khan SA (2008): Synthesis and pharmacological evaluation of pyrazoline derivatives as new anti-fand analgesic agents. Bioorg Med Chem Lett 18: 918-922.
3. Bansal E, Srivastava VK, Kumar A (2001): Synthesis and anti-factivity of 1-acetyl-5-substituted aryl-3-(be ta-aminonaphthyl)-2-pyrazolines and beta-(substituted aminoethyl) amidonaphthalenes. Eur J Med Chem 36: 81-92.
4. Barsoum FF, Hosni HM, Girgis AS (2006): Novel bis(1-acyl-2-pyrazolines) of potential anti-fand molluscicidal properties. Bioorg Med Chem 14: 3929-3937.
5. Beckman KB, Ames BN (1998): The free radical theory of aging matures. Physiol Rev 78: 447-581.
6. Bhat BA, Dhar KL, Puri SC, Saxena AK, Shanmugavel M, Qazi GN (2005): Isolation, characterization and biological evaluation of datura lactones as potential immunomodulators. Bioorg Med Chem Lett 15: 3177-3180.
7. Block G (1992): The data support a role for antioxidants in reducing cancer risk. Nutr Rev 50: 207-213.
8. Gazit A, Yaish P, Gilon C, Levitzki A (1989): Tyrphostins I: Synthesis and biological activity of protein tyrosine kinase inhibitors. J Med Chem 32: 2344-2352.
9. Gerhäuser C, Klimo K, Heiss E, Neumann I, Gamal-Eldeen A, Knauft J, Liu JU, Sitthimonchai S, Frank N (2003): Mechanism-based in vitro screening of potential cancer chemopreventive agents. Mutat Res 523-524: 163-172.
10. Girotti M, Evans JH, Burke D, Leslie CC (2004): Cytosolic phospholi-pase A2 translocates to forming phagosomes during phagocytosis of zymosan in macrophages. J Biol Chem 279: 19113-19121.
11. Hansen MB, Nielsen SE, Berg K (1989): Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J Immunol Methods 119: 203-210.
12. Hu L, Gunn C, Beckman J (1992): Bactericidal activity of peroxyni-trite. Arch Biochem Biophys 298: 452-457.
13. Jang M, Cai L, Udeani OG, Slowing VK, Thomas FC, et al. (1997): Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275: 218-220.
14. Karthikeyan MS, Holla BS, Kumari NS (2007): Synthesis and antimicrobial studies on novel chloro-fluorine containing hydroxy pyrazolines. Eur J Med Chem 42: 30-36.
15. MacMicking J, Xie QW, Nathan C (1997): Nitric oxide and macro-phage function. Annu Rev Immunol 15:323-350.
16. Nazir N, Koul S, Qurishi MA, Taneja SC, Ahmad SF, Bani Sg, Qazi GN (2007): Immunomodulatory effect of bergenin and norbergenin against adjuvant-induced arthritis: a fow cytometric study. J Ethnopharmacol 112: 401-405.
17. Oh GS, Pae HO, Oh H, Hong SG, Kim IK, Chai KY, Yun YG, Kwon TO, Chung HT (2001): In vitro anti-proliferative effect of 1,2,3,4,6-penta-O-galloyl- beta-D-glucose on human hepatocellular carcinoma cell line, SK-HEP-1 cells. Cancer Lett 174: 17-24.
18. Okuda T (2005): Systematics and health effects of chemically distinct tannins in medicinal plants. Phytochemistry 66: 2012-2031.
19. Palaska E, Erol D, Demirdamar R (1996): Synthesis and antidepres-sant activities of some 1,3,5-triphenyl-2-pyrazolines. Eur J Med Chem 31: 43-47.
20. Rani P, Srivastava VK, Kumar A (2004): Synthesis and antiinflammatory activity of heterocyclic indole derivatives. Eur J Med Chem 39: 449-452.
21. Rice-Evans AC, Miller NJ, Paganga G (1996): Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20: 933-956.
22. Smith PK, Krohn R, Hermanson GT, Mallia AK, Gartner FH, Provenzano MD, Fujimoto EK, Goeke NM, Olson BJ, Klenk DC (1985): Measurement of protein using bicinchoninic acid. Anal Biochem 150: 76-80.
23. Soni N, Pande K, Kalsi R, Gupta TK, Parmer SS, Barthwal JP (1987): Inhibition of rat brain monoamine oxidase and succinic dehydrogenase by anticonvulsant pyrazolines. Res Commun Chem Pathol Pharm 56: 129-132.
24. Torres de Pinedo A, Peñalver P, Morales JC (2007): New phenolic-based antioxidants: structure-activity relationships. Food Chem 103: 55-61.
25. Van Amsterdam FT, Roveri A, Maiorino M, Ratti E, Ursini F (1992) Lacidipine: A dihydropyridine calcium antagonist with antioxi-dant activity. Bio Med 12: 183-187.
26. Visioli F, Bellomo G, Montedoro G, Galli C (1995): Low density lipo-protein oxidation is inhibited in vitro by olive oil constituents. Atherosclerosis 117: 25-32.
27. Yokozawa T, Chen CP, Dong E, Tanaka T, Nonaka G-I, Nishioka I (1998): Study on the inhibitory effect of tannins and flavonoids against the 1,1-diphenyl-2-picrylhydrazyl radical. Biochem Pharmacol 56: 213-222.
28. Zitouni GT, Chevallet P, Kiliç; FS, Erol K (2000): Synthesis of some thiazolyl-pyrazoline derivatives and preliminary investigation of their hypotensive activity. Eur J Med Chem 35:635-641.
29. Zitouni GT, Özdemir A, Guven K (2005a): Synthesis of Some 1-[(N, N-substituted thiocar bamoylthio)acetyl]-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives and investigation of their antibacterial and antifungal activities. Arch Pharm 338: 96-104.
30. Zitouni GT, Özdemir A, Kaplancikli ZA, Chevallet P, Tunali Y (2005b): Synthesis and antimicrobial activities of some 1-[(N,N- disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines Phosphorus Sulfur Silicon Relat Elem 180:2717-2724.