Synthesis of imine-pyrazolopyrimidinones and their mechanistic interventions on anticancer activity

Baviskar, Ashish T.; Banerjee, Uttam Chand; Gupta, Mukesh; Singh, Rajveer; Kumar, Sunil; Gupta, Manish Kumar; Kumar, Sanjeev; Raut, Satish K; Khullar, Madhu; Singh, Sandeep; Kumar, Raj

doi:10.1016/j.bmc.2013.07.016

Cited by 44 publications

(35 citation statements)

References 34 publications

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“…Results were expressed as inhibitory potential possessed by the synthesized compounds. Etoposide was used as standard anticancer agent . The synthesized target compounds when tested on peripheral human blood lymphocytes were found to be non‐toxic indicating that compounds had no effect on the normal cells.…”

Section: Resultsmentioning

confidence: 99%

1‐Acetyl‐3,5‐diaryl‐4,5‐dihydro(1H)pyrazoles: Exhibiting Anticancer Activity through Intracellular ROS Scavenging and the Mitochondria‐Dependent Death Pathway

Alex

Singh

Kumar

2014

Archiv der Pharmazie

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A series of 17 analogs of 1-acetyl-4,5-dihydro(1H)pyrazoles (JP-1 to JP-17) bearing two aromatic rings at positions 3 and 5, either of which ought to be heterocyclic, were synthesized and evaluated for their anti-proliferative potential against breast cancer (MCF-7 and T-47D) and lung cancer (H-460 and A-549) cell lines for the first time. JP-1-7, -10, -11, -14, and -15 were observed to exhibit significant anti-proliferative activity against MCF-7 cells. Some notions about structure-activity relationships are reported. The investigated compounds were found to lower the intracellular reactive oxygen species in the H2 DCFDA assay and also caused mitochondria-dependent cell death in the MCF-7 cell line, indicating a plausible mechanism of their anticancer effect.

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Section: Resultsmentioning

confidence: 99%

1‐Acetyl‐3,5‐diaryl‐4,5‐dihydro(1H)pyrazoles: Exhibiting Anticancer Activity through Intracellular ROS Scavenging and the Mitochondria‐Dependent Death Pathway

Alex

Singh

Kumar

2014

Archiv der Pharmazie

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“…Some pyrazole‐based drugs are depicted in Figure . Pyrazole derivatives show anticancer activity due to their inhibition of various targets such as EGFR , IGF‐1R , tubulin , B‐raf , mTOR , HDAC , ALK , topoisomerase II , JAK2 , ROS 1 , among others. Hence, incorporation of the pyrazole moiety is an important synthetic strategy in rational drug development process.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Evaluation of Some Novel Heterocycles Bearing Pyrazole Moiety as Potential Anticancer Agents

Abdelgawad

Ismail

Hekal

et al. 2019

Journal of Heterocyclic Chem

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1,3‐Diphenylpyrazole‐4‐carboxylaldehyde and o‐hydroxyacetophenone were exploited as starting materials for the synthesis of novel substituted chalconated pyrazole derivative. The proclivity of this compound towards carbon and nitrogen nucleophiles such as malononitrile, diethyl malonate, ethyl cyanoacetate, ethyl acetoacetate, semicarbazide, thiosemicarbazide, and hydroxylamine has been investigated. The structures of all synthesized compounds were ascertained by analytical and spectral data. The antitumor activity of the target synthesized compounds was tested against a panel of two human tumor cell lines, namely, hepatocellular carcinoma (liver) HepG2 and mammary gland breast MCF‐7.

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“…Since many guanidines were reported to possess cytotoxic and apoptosis inducing activities [28][29][30] , we deemed it interesting to explore the effect of introducing guanidino and aminoguanidino moieties at position 6. Moreover, due to the reported anti-tumor and apoptosis inducing activities of some hydrazones 12,[31][32][33][34][35] it was considered worthwhile to extend substitution at position 6 to include the structural elements of hydrazones. These combinations were suggested in an attempt to investigate the possible synergistic influence of such structure hybridizations on the anticipated biological activity, hoping to discover and develop apoptosis inducers as potential new anti-cancer agents.…”

Section: Introductionmentioning

confidence: 99%

Novel 1,5-diphenyl-6-substituted 1H-pyrazolo[3,4-d]pyrimidin-4(5H)-ones induced apoptosis in RKO colon cancer cells

Malki

Ashour

Elbayaa

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Novel 1,5-diphenyl-6-substituted-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-ones were synthesized and characterized. All compounds were screened for their anti-proliferative activities in five different cancer cell lines. The results showed that compounds 7a and 7b comprising aminoguanidino or guanidino moiety at position 6 inhibited proliferation of RKO colon cancer cells with IC 50 of 8 and 4 mM, respectively. Compounds 7a and 7b induced apoptosis in RKO cells, which was confirmed by TUNEL and annexin V-FITC assays. Flow cytometric analysis indicated that compounds 7a and 7b arrested RKO cells in the G1 phase and the most active compound 7b increased levels of p53, p21, Bax, ERK1/2 and reduced levels of Bcl2 and Akt. Compound 7b also activates release of cytochrome c, which is consistent with activation of caspase-9. Additionally, compound 7b increased caspase-3 activity and cleaved PARP-1 in RKO cells. Collectively, these findings could establish a molecular basis for the development of new anti-cancer agents.

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Synthesis of imine-pyrazolopyrimidinones and their mechanistic interventions on anticancer activity

Cited by 44 publications

References 34 publications

1‐Acetyl‐3,5‐diaryl‐4,5‐dihydro(1H)pyrazoles: Exhibiting Anticancer Activity through Intracellular ROS Scavenging and the Mitochondria‐Dependent Death Pathway

1‐Acetyl‐3,5‐diaryl‐4,5‐dihydro(1H)pyrazoles: Exhibiting Anticancer Activity through Intracellular ROS Scavenging and the Mitochondria‐Dependent Death Pathway

Design, Synthesis, and Evaluation of Some Novel Heterocycles Bearing Pyrazole Moiety as Potential Anticancer Agents

Novel 1,5-diphenyl-6-substituted 1H-pyrazolo[3,4-d]pyrimidin-4(5H)-ones induced apoptosis in RKO colon cancer cells

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