Synthesis and pharmacological evaluation of some new fluorine containing hydroxypyrazolines as potential anticancer and antioxidant agents

Dinesha,; Viveka, S.; Priya, Keerthi; Pai, K. Sreedhara Ranganath; Naveen, S.; Lokanath, N.K.; Nagaraja, G. K.

doi:10.1016/j.ejmech.2015.09.029

Cited by 40 publications

(13 citation statements)

References 38 publications

(29 reference statements)

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“…It is characterized by unsuppressed, uncontrolled, rapid, and pathological proliferation of abnormal cells, and is responsible for serious health‐related repercussions globally. [ 1,2 ] According to various surveys or statistical data, cancer is second among the leading causes of mortality and accounts for millions of deaths every year preceded only by heart diseases. [ 3 ] Despite perennial efforts or despite very significant progress from diagnosis to remedy, a consolidated cure still remains largely elusive due to either patients not reacting to therapy or an intermittent initial response.…”

Section: Introductionmentioning

confidence: 99%

3′‐(4‐(Benzyloxy)phenyl)‐1′‐phenyl‐5‐(heteroaryl/aryl)‐3,4‐dihydro‐1′H,2H‐[3,4′‐bipyrazole]‐2‐carboxamides as EGFR kinase inhibitors: Synthesis, anticancer evaluation, and molecular docking studies

Nawaz

Alam

Perwez

et al. 2020

Archiv der Pharmazie

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Pyrazoline‐linked carboxamide derivatives were designed, synthesized, and evaluated for potential epidermal growth factor receptor (EGFR) kinase inhibition, anticancer activity, and apoptotic and cardiomyopathy toxicity. Compounds 6m and 6n inhibit EGFR kinase at a concentration of 6.5 ± 2.91 and 3.65 ± 0.54 µM, respectively. Some of these compounds showed effects on proliferation, which were also then evaluated against four different human cancer cell lines, that is, MCF‐7 (breast cancer), A549 (non‐small‐cell lung tumor), HCT‐116 (colon cancer), and SiHa cells (cancerous tissues of the cervix uteri). The results showed that certain synthetic compounds showed significant inhibitor activity; compounds 6m and 6n were more cytotoxic than doxorubicin against A549 cancer cells, with IC50 values of 10.3 ± 1.07 and 4.6 ± 0.57 µM, respectively. Additionally, compounds 6m and 6n induced apoptosis in A549 cancer cells, as evidenced by 4′,6‐diamidino‐2‐phenylindole (DAPI) staining and phase‐contrast microscopy. Potency to induce apoptosis by compound 6n was further confirmed by fluorescence‐activated cell sorting using Annexin V‐FITC and propidium iodide labeling. Compound 6n showed normal cardiomyocytes with no marked sign of pyknotic nuclei in cardiomyopathy and also normal histological appearance of the renal cortex when compared with that of control. Results of molecular docking studies suggested that compounds 6m and 6n can bind to the hinge region of the adenosine triphosphate‐binding site of EGFR kinase, like the standard drug erlotinib. Therefore, the present study suggests that compounds 6m and 6n have potent in vitro antitumor activities against the human non‐small‐cell lung tumor cell line A549, which can be further explored in other cancer cell lines and in animal studies.

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Section: Introductionmentioning

confidence: 99%

3′‐(4‐(Benzyloxy)phenyl)‐1′‐phenyl‐5‐(heteroaryl/aryl)‐3,4‐dihydro‐1′H,2H‐[3,4′‐bipyrazole]‐2‐carboxamides as EGFR kinase inhibitors: Synthesis, anticancer evaluation, and molecular docking studies

Nawaz

Alam

Perwez

et al. 2020

Archiv der Pharmazie

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“…Nsubstituted phthalazin-1-amine derivatives reported to have epidermal growth factor receptor inhibitors [12]. Furthermore, pyrazole containing heterocyclic are great interest because they show plenty pharmacological activities such as antidepressant [13], antioxidant [14], anti-inflammatory [15], anticancer [16], antimicrobial [17][18][19], antiviral [20,21], anticonvulsant [22], and insecticidal activities [23]. Recently, Sangani et al [24] reported one-pot synthesis of pyrazolo [1,2-b]phthalazine-5,10-diones as antimicrobial, antituberculosis, and antioxidant agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel Heterocycles Utilizing 3‐(1,4‐Dioxo‐3,4‐dihydrophthalazin‐2(1H)‐yl)‐3‐oxopropanenitrile as Precursors

Khidre

Radini

2019

Journal of Heterocyclic Chem

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The reaction of 3‐(1,4‐dioxo‐3,4‐dihydrophthalazin‐2(1H)‐yl)‐3‐oxopropanenitrile 1 and salicyladehyde furnished coumarin derivatives 4 and 5. Coupling reaction of 1 with aryl diazonium chlorides and benzene‐1,4‐bis (diazonium) chloride gave the corresponding hydrazones 6a,b and bishydrazone 9, respectively. Hydrazones 6 underwent intramolecular cyclization upon treating with hydrazine hydrate to give 3‐aminopyrazoles 7. Pyranyl phthalazine 13 was prepared from the reaction of 1 with ethyl 2‐cyano‐3‐ethoxyacrylate 10. Enaminonitrile 14 was reacted with hydrazine hydrate/phenylhydrazine and hydroxylamine to afford the corresponding pyrazoles 16 and oxime 17. The antimicrobial evaluation revealed pyrazole derivatives 7a,b and 16a,b displayed a broad spectrum activity against most strains. 3‐Aminopyrazole derivative 7b showed potent antibacterial activity against all tested microorganisms.

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“…The rate of bacterial resistance to antibiotics is higher than the rate of development of new classes of antibiotics [2] so the design and synthesis of new compounds have potential antimicrobial activity are very important issue. Pyrazole derivatives have great attention due to their interesting biological and pharmaceutical activities such as antidepressant [3], antioxidant [4], anti-inflammatory [5], anticancer [6], antimicrobial [7,8,9], antiviral [10,11], anticonvulsant [12], and insecticidal activities [13]. In addition, the natural pyrazole C-glycoside, pyrazofurin (4-hydroxy-3β- d -dribofuranosyl-1 H -pyrazole-5-carboxamide) has a broad spectrum of antimicrobial, antiviral, and antitumor activities [14].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antimicrobial Evaluation of Novel Pyrazoles and Pyrazolyl 1,3,4-Thiadiazine Derivatives

Radini

2018

Molecules

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A novel series of pyrazolyl 1,3,4-thiadiazines 5a–c, 8a–c, 12, 15a–c, 17a–c, and 20 was prepared from the reaction of pyrazole-1-carbothiohydrazide 1a,b with 2-oxo-N′-arylpropanehydrazonoyl chloride, 2-chloro-2-(2-arylhydrazono)acetate, and 3-bromoacetylcoumarin. Moreover, the regioselective reaction of 5-pyrazolone-1-carbothiohydrazide 1a with 4-substituted diazonium salts and 4-(dimethylamino)benzaldehyde gave the corresponding hydrazones 21a–c and 22. The newly prepared compounds were characterized by spectroscopy and elemental analysis. Many new synthesized compounds showed considerable antimicrobial activity against tested microorganisms. Hydrazones 21a–c and 22 showed remarkable antibacterial and antifungal activities. 4-(2-(p-tolyl)hydrazineylidene)-pyrazole-1-carbothiohydrazide 21a displayed the highest antibacterial and antifungal activities with minimum inhibitory concentration (MIC) values lower than standard drugs chloramphenicol and clotrimazole, in the range of 62.5–125 and 2.9–7.8 µg/mL, respectively.

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Synthesis and pharmacological evaluation of some new fluorine containing hydroxypyrazolines as potential anticancer and antioxidant agents

Cited by 40 publications

References 38 publications

3′‐(4‐(Benzyloxy)phenyl)‐1′‐phenyl‐5‐(heteroaryl/aryl)‐3,4‐dihydro‐1′H,2H‐[3,4′‐bipyrazole]‐2‐carboxamides as EGFR kinase inhibitors: Synthesis, anticancer evaluation, and molecular docking studies

3′‐(4‐(Benzyloxy)phenyl)‐1′‐phenyl‐5‐(heteroaryl/aryl)‐3,4‐dihydro‐1′H,2H‐[3,4′‐bipyrazole]‐2‐carboxamides as EGFR kinase inhibitors: Synthesis, anticancer evaluation, and molecular docking studies

Synthesis and Antimicrobial Activity of Novel Heterocycles Utilizing 3‐(1,4‐Dioxo‐3,4‐dihydrophthalazin‐2(1H)‐yl)‐3‐oxopropanenitrile as Precursors

Design, Synthesis, and Antimicrobial Evaluation of Novel Pyrazoles and Pyrazolyl 1,3,4-Thiadiazine Derivatives

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