Design, synthesis and biological evaluation of N -((1-benzyl-1 H -1,2,3-triazol-4-yl)methyl)-1,3-diphenyl-1 H -pyrazole-4-carboxamides as CDK1/Cdc2 inhibitors

Reddy, Velma Ganga; Reddy, T. Srinivasa; Nayak, V. Lakshma; Prasad, B.; Reddy, Adiyala Praveen; RaviKumar, Ameeta; Taj, Shaik; Kamal, Ähmed

doi:10.1016/j.ejmech.2016.06.011

Cited by 54 publications

(14 citation statements)

References 43 publications

(34 reference statements)

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“…To investigate the morphological changes induced by compound 4b in SMMC-7721 cells, Hoechst staining was carried out. Hoechst 33258 is a cell membrane permeable dye, which stains the live cells’ nuclei uniformly as light-blue and apoptotic cells’ nuclei as round and bright-blue, on account of karyopyknosis and chromatin condensation [ 31 , 32 ]. SMMC-7721 cells were treated with various concentrations (0, 0.2, 1.0 and 5.0 μM) of compound 4b for 24 h, and stained with Hoechst 33258.…”

Section: Resultsmentioning

confidence: 99%

“…The apoptotic effect of compound 4b was further evaluated by a Annexin V-FITC/propidium iodide (AV/PI) dual staining assay to examine the occurrence of phosphatidylserine externalization, which facilitated the detection of live cells (lower left quadrant; AV−/PI−), early apoptotic cells (lower right quadrant; AV+/PI−), late apoptotic cells (upper right quadrant; AV+/PI+) and necrotic cells (upper left quadrant; AV−/PI+) [ 32 ]. As shown in Figure 3 , the percentage of early apoptotic cells increased from 2.84 ± 0.26% (control) to 17.44 ± 0.68% (5.0 μM), and the percentage of late apoptotic cells also increased from 7.45 ± 0.42% (control) to 52.36 ± 1.23% (5.0 μM).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Evaluation of New Quinoxaline Derivatives of Dehydroabietic Acid as Potential Antitumor Agents

Wang

Jin

et al. 2017

Molecules

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A series of new quinoxaline derivatives of dehydroabietic acid (DAA) were designed and synthesized as potential antitumor agents. Their structures were characterized by IR, 1H-NMR, 13C-NMR, and MS spectra and elemental analyses. All the new compounds were screened for their in vitro antiproliferative activities against three human cancer cell lines (MCF-7, SMMC-7721 and HeLa) and noncancerous human hepatocyte cells (LO2). A cytotoxic assay manifested that compound 4b showed the most potent cytotoxic activity against the three cancer cell lines, with IC50 values of 1.78 ± 0.36, 0.72 ± 0.09 and 1.08 ± 0.12 μM, respectively, and a substantially lower cytotoxicity to LO2 cells (IC50: 11.09 ± 0.57 μM). Moreover, the cell cycle analysis suggested that compound 4b caused cell cycle arrest of SMMC-7721 cells at the G0/G1 phase. In a Hoechst 33258 staining assay, compound 4b caused considerable morphological changes of the nuclei of SMMC-7721 cells, correlated with cell apoptosis. In addition, an Annexin V-FITC/PI dual staining assay confirmed that compound 4b could induce the apoptosis of SMMC-7721 cells in a dose-dependent manner.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of New Quinoxaline Derivatives of Dehydroabietic Acid as Potential Antitumor Agents

Wang

Jin

et al. 2017

Molecules

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“…On the basis of related materials, pyrazoles, especially 3, 5-dimethylpyrazol, occupy a distinct niche in heterocyclic chemistry and represent a key motif in medicinal chemistry because of their capability to exhibit an array of properties and bioactivities, including fungicidal (Wang et al, 2012), anticancer (Ganga-Reddy et al, 2016), anti-inflammatory (Hu et al, 2018), anticonvulsant (Kaymakcioğlu et al, 2003), and nitrification inhibitor (Şahan et al, 2017) activities. Furthermore, we also demonstrated that the benzothiazole nucleus is a unique scaffold for further molecular exploration to synthesize novel compounds.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Benzo[D]Thiazole with Dimethylpyrazol Derivatives

Liu

Cheng

Wang

2019

Asian Pac J Cancer Prev

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A series of new benzothiazole derivatives containing dimethylpyrazole were synthesized and evaluated for their anticonvulsant activity, neurotoxicity and cytotoxicity by using the maximal electroshock (MES), rotarod neurotoxicity (TOX) and MTT colorimetric assay. Among the compounds studied, four compounds (6a, 6b, 6g and 6m) showed better anticonvulsant than the others at 300 mg/kg and they also showed anticonvulsant activity at the dose of 100 mg/ kg. All the synthetic compounds showed lower neurotoxicity and little cytotoxicity, so that the compounds, which with better activities, also had higher protective index. In particular, the compound 6g, 2-(3,5-dimethyl-1H-pyrazol-1-yl)-6-((2-fluorobenzyl)oxy)benzo[d]thiazole showed better activity with an ED 50 value of 160.4 mg/kg and higher protective index (PI) values of 2.74 in the MES test than the standard drugs sodium valproate, which used as positive controls in this study. After that the compound 6g demonstrated antagonistic activity against seizures induced by pentylenetetrazol, which proved 6g maybe exert activity through effecting GABAergic neurotransmission.

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“…Pyrazole and its derivatives are a class of bioactive nitrogenous heterocycles that a key scaffold in medicinal chemistry owns an array of most pharmacological activities . Due to that pyrazole derivatives have fruitful applications in pharmaceutical fields, pyrazole has been widely intricate in the development of diverse bioactive molecules such as antioxidant , analgesic, lipid peroxidation, ulcerogenic , anticancer , immunosuppressive agents , antibacterial , and antimitotic . In the present study, we report simple and efficient synthetic approaches to pyrazolo[3,4‐ c ][1,2]diazepine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antioxidant Evaluation of Some Novel Pyrazolo[3,4‐c][1,2]diazepine and Pyrazolo[3,4‐c]pyrazole Derivatives

Mohammed

Elbeily

El‐Taweel

et al. 2018

Journal of Heterocyclic Chem

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5‐Hydrazineyl‐3‐methyl‐1H‐pyrazole (1) was used as a starting material for the synthesis of novel pyrazolo[3,4‐c][1,2]diazepine derivatives 3, 4, and 6a,b by its reaction with acetylacetone, ethyl acetoacetate, and isatylidene derivatives 5a,b, respectively. Also, pyrazolo[3,4‐c][1,2]diazepine derivative 11 was synthesized via multicomponent reaction of 1, benzaldehyde, and malononitrile. Moreover, compound 1 was used for synthesis novel pyrazolo[3,4‐c]pyrazole derivative 7 by its reaction with isatin. In addition, pyrazolo[3,4‐c]pyrazole derivatives 18a–c were synthesized by treatment of 2‐cyano‐N′‐(3‐methyl‐1H‐pyrazol‐5‐yl)acetohydrazide (13) with aromatic aldehydes 16a–c. The newly synthesized compounds were valeted by means of analytical and spectral data. All newly synthesized compounds were screened for their antioxidant activities. Compounds 3, 13, 18b, and 18c showed higher radical‐scavenging activities.

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Design, synthesis and biological evaluation of N -((1-benzyl-1 H -1,2,3-triazol-4-yl)methyl)-1,3-diphenyl-1 H -pyrazole-4-carboxamides as CDK1/Cdc2 inhibitors

Cited by 54 publications

References 43 publications

Synthesis and Evaluation of New Quinoxaline Derivatives of Dehydroabietic Acid as Potential Antitumor Agents

Synthesis and Evaluation of New Quinoxaline Derivatives of Dehydroabietic Acid as Potential Antitumor Agents

Design, Synthesis and Biological Evaluation of Benzo[D]Thiazole with Dimethylpyrazol Derivatives

Synthesis, Characterization, and Antioxidant Evaluation of Some Novel Pyrazolo[3,4‐c][1,2]diazepine and Pyrazolo[3,4‐c]pyrazole Derivatives

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