Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

被引：81

作者：

Karabacak, Muhammed ^{[1
]}

Altintop, Mehlika Dilek ^{[1
]}

Ciftci, Halil Ibrahim ^{[2
]}

Koga, Ryoko ^{[2
]}

Otsuka, Masami ^{[2
]}

Fujita, Mikako ^{[3
]}

Ozdemir, Ahmet ^{[1
]}

机构：

[1] Anadolu Univ, Fac Pharm, Dept Pharmaceut Chem, TR-26470 Eskisehir, Turkey

[2] Kumamoto Univ, Sch Pharm, Dept Bioorgan Med Chem, Kumamoto 8620973, Japan

[3] Kumamoto Univ, Sch Pharm, Res Inst Drug Discovery, Kumamoto 8620973, Japan

来源：

MOLECULES | 2015年 / 20卷 / 10期

关键词：

pyrazoline; oxadiazole; anticancer activity; apoptosis; DNA cleavage; BEARING BENZENE SULFONAMIDE; VITRO ANTITUMOR-ACTIVITY; BIOLOGICAL EVALUATION; ANTIFUNGAL ACTIVITIES; MOIETY; INHIBITORS; CARCINOMA; SCAFFOLD; HYBRIDS; DESIGN;

D O I：

10.3390/molecules201019066

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

New pyrazoline derivatives were synthesized and evaluated for their cytotoxic effects on AsPC-1 human pancreatic adenocarcinoma, U87 and U251 human glioblastoma cell lines. 1-[((5-(4-Methylphenyl)-1,3,4-oxadiazol-2-yl)thio)acetyl]-3-(2-thienyl)-5-(4-chlorophenyl)-2-pyrazoline (11) was found to be the most effective anticancer agent against AsPC-1 and U251 cell lines, with IC50 values of 16.8 mu M and 11.9 mu M, respectively. Tumor selectivity of compound 11 was clearly seen between Jurkat human leukemic T-cell line and human peripheral blood mononuclear cells (PBMC). Due to its promising anticancer activity, compound 11 was chosen for apoptosis/necrosis evaluation and DNA-cleavage analysis in U251 cells. Compound 11-treated U251 cells exhibited apoptotic phenotype at low concentration (1.5 mu M). DNA-cleaving efficiency of this ligand was more significant than cisplatin and was clearly enhanced by Fe(II)-H2O2-ascorbic acid systems. This result pointed out the relationship between the DNA cleavage and the cell death.

引用

页码：19066 / 19084

页数：19

共 41 条

[1]

a PK S Garima Mathur S.N., 2015, Academic Journal of Cancer Research, V8, P01, DOI DOI 10.5829/IDOSI.AJCR.2015.8.1.9336

[2] Synthesis and Anticancer Activity of Some Novel Tetralin-6-yl-pyrazoline, 2-Thioxopyrimidine, 2-Oxopyridine, 2-Thioxo-pyridine and 2-Iminopyridine Derivatives [J].

Al-Abdullah, Ebtehal S. .

MOLECULES, 2011, 16 (04) :3410-3419

[3] 4,5-Dihydro-1H-pyrazole: an indispensable scaffold [J].

Alex, Jimi Marin ;

Kumar, Raj .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2014, 29 (03) :427-442

[4] Synthesis and Biological Evaluation of Some Pyrazoline Derivatives Bearing a Dithiocarbamate Moiety as New Cholinesterase Inhibitors [J].

Altintop, Mehlika D. ;

Ozdemir, Ahmet ;

Kaplancikli, Zafer A. ;

Turan-Zitouni, Guelhan ;

Temel, Halide E. ;

Ciftci, Guelsen A. .

ARCHIV DER PHARMAZIE, 2013, 346 (03) :189-199

[5] A novel series of thiazolyl-pyrazoline derivatives: Synthesis and evaluation of antifungal activity, cytotoxicity and genotoxicity [J].

Altintop, Mehlika Dilek ;

Ozdemir, Ahmet ;

Turan-Zitouni, Gulhan ;

Ilgm, Sinem ;

Atli, Ozlem ;

Demirel, Rasime ;

Kaplancikli, Zafer Asim .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 :342-352

[6] Synthesis and anticancer activity of some 8-substituted-7-methoxy-2H-chromen-2-one derivatives toward hepatocellular carcinoma HepG2 cells [J].

Amin, Kamilia M. ;

Abou-Seri, Sahar M. ;

Awadallah, Fadi M. ;

Eissa, Amal A. M. ;

Hassan, Ghaneya S. ;

Abdulla, Mohamed M. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 90 :221-231

[7] Synthesis and biological evaluation of novel coumarin-pyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents [J].

Amin, Kamilia M. ;

Eissa, Amal A. M. ;

Abou-Seri, Sahar M. ;

Awadallah, Fadi M. ;

Hassan, Ghaneya S. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 60 :187-198

[8] 1,3,4-Oxadiazoles: An emerging scaffold to target growth factors, enzymes and kinases as anticancer agents [J].

Bajaj, Shalini ;

Asati, Vivek ;

Singh, Jagadish ;

Roy, Partha Pratim .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :124-141

[9] Synthesis and biological evaluation of some new 2-pyrazolines bearing benzene sulfonamide moiety as potential anti-inflammatory and anti-cancer agents [J].

Bano, Sameena ;

Javed, Kalim ;

Ahmad, Shamim ;

Rathish, I. G. ;

Singh, Surender ;

Alam, M. S. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (12) :5763-5768

[10] Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents [J].

Bashir, Rafia ;

Ovais, Syed ;

Yaseen, Shafiya ;

Hamid, Hinna ;

Alam, M. S. ;

Samim, Mohammad ;

Singh, Surender ;

Javed, Kalim .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (14) :4301-4305

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