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

Bashir, Rabia; Ovais, Syed; Yaseen, Shafiya; Hamid, Hinna; Alam, Mohammad Sarwar; Samim, Mohd; Singh, Surender; Javed, Kalim

doi:10.1016/j.bmcl.2011.05.061

Cited by 97 publications

(44 citation statements)

References 22 publications

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“…4-Methoxyacetophenone and suitable aldehyde in 1:1 mol ratio were dissolved in ethanol (10 ml) 23 . Aqueous NaOH solution (10%, 20 ml) was added into the reaction flask.…”

Section: Synthesis Of Chalcone Compounds 1a-6amentioning

confidence: 99%

“…Medicinal chemists have great attention of pyrazolines and substituted pyrazolines because of their various biological activities such as antimicrobial, anticonvulsant, anticancer, anti-inflammatory, antitubercular, antiviral, analgesic and antidepressive activities [13][14][15][16][17] . Sulfonamide is an important functional group in medicinal chemistry having a wide range of bioactivities such as cytotoxic, carbonic anhydrase inhibitory, antibacterial, antimalarial, antihypertensive, antiviral, anti-inflammatory and diuretics activities 8,13,[18][19][20][21][22][23][24][25] .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

Küçükoğlu

Oral

Aydin

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of polymethoxylated-pyrazoline benzene sulfonamides were synthesized, investigated for their cytotoxic activities on tumor and non-tumor cell lines and inhibitory effects on carbonic anhydrase isoenzymes (hCA I and hCA II). Although tumor selectivity (TS) of the compounds were less than the reference compounds 5-Fluorouracil and Melphalan, trimethoxy derivatives 4, 5, and 6 were more selective than dimethoxy derivatives 2 and 3 as judged by the cytotoxicity assay with the cells both types originated from the gingival tissue. The compound 6 (4-[3-(4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl] benzene sulfonamide) showed the highest TS values and can be considered as a lead molecule of the series for further investigations. All compounds synthesized showed superior CA inhibitory activity than the reference compound acetazolamide on hCA I, and II isoenzymes, with inhibition constants in the range of 26.5-55.5 nM against hCA I and of 18.9-28.8 nM against hCA II, respectively.

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“…4-Methoxyacetophenone and suitable aldehyde in 1:1 mol ratio were dissolved in ethanol (10 ml) 23 . Aqueous NaOH solution (10%, 20 ml) was added into the reaction flask.…”

Section: Synthesis Of Chalcone Compounds 1a-6amentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

Küçükoğlu

Oral

Aydin

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…They exhibit a wide spectrum of biological activities such as antimicrobial, anti-inflammatory, antidepressant, and anticancer effects. Among the reported activities, it is important to note that pyrazolines are not only useful in treatment of various cancer types, including brain, bone, mouth, esophagus, stomach, liver, bladder, pancreas, cervix, lung, breast, colon, rectum, and prostate cancers, but also some of them act as cancer chemopreventive agents [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23]. In many studies, pyrazoline derivatives were reported as epidermal growth factor receptor tyrosine kinase (EGFR-TK) inhibitors [19], aurora kinase inhibitors [20], COX-2/B-Raf inhibitors [21], telomerase inhibitors [22], tubulin assembling inhibitors [23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

et al. 2015

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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 µM and 11.9 µM, 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 µM). 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.

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“…Pyrazoline derivatives have been reported to exhibit a wide spectrum of biological effects including anticancer activity [6][7][8][9][10][11][12][13][14][15][16] . Some compounds bearing pyrazole moiety exert their therapeutic action by inhibiting different types of enzymes that play important roles in cell division [16][17][18] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1-acetyl-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives and evaluation of their anticancer activity

Özdemir

Altıntop

Kaplancıklı

et al. 2012

Journal of Enzyme Inhibition and Medicinal Chemistry

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

Cited by 97 publications

References 22 publications

Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

Synthesis and Evaluation of New Pyrazoline Derivatives as Potential Anticancer Agents

Synthesis of 1-acetyl-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives and evaluation of their anticancer activity

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