Novel 2H-pyrazolo[4,3-c]hexahydropyridine derivatives: Synthesis, crystal structure, fluorescence properties and cytotoxicity evaluation against human breast cancer cells

Chuncheng, PANG; Sun, Chengbo; Wang, Jing; Xiao, Di; Ding, Li; Bu, Hongfei

doi:10.1007/s11426-013-4840-x

Cited by 10 publications

(7 citation statements)

References 20 publications

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“…Whereas, in other pyrazolo-piperidine derivatives [9], less close to ideal chair conformations can be observed, in which the N(5) atoms of the piperidine ring leave the plane of 4 carbon atoms in the range from 0.288 (5) to 0.409 (5) Å, and the C(8) atom is in the range of 0.373 (6) and 0.463 (4) Å. In general, the geometric parameters (Table 1) of the compounds are in good agreement with related compounds described in the literature [9][10][11].…”

Section: Resultssupporting

confidence: 80%

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Novel 7-Aryliden-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridine Hydrochloride: Synthesis and Structure

Koshetova¹,

Yu²,

Iskakova³

et al. 2022

Eurasian Chem. Tech. J.

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A Claisen-Schmidt type reaction of 1-(2-ethoxyethyl)piperidin-4-one with differ¬ent aromatic aldehydes led to corresponding dienones with a yield of 65‒71%. 7-Arylidene-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridines were synthesized by heterocyclization of 3,5-dia¬rylidene-piperidin-4-ones with phenylhydrazine hydrochloride in methanol at 70 °C over 4‒6 h. The X-ray crystal structure determination of 7-(p-methoxy¬benzyliden)-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-(p-methoxy¬phenyl)-2H-pyrazolo[4,3-c]pyridine hydrochloride (the deposition number is CCDC 862410) was completed. The piperidine and pyrazoline rings are close to a chair and envelope conformations, respectively.

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Section: Resultssupporting

confidence: 80%

“…Chalcones can usually be prepared by the treatment of cyclic ketones with aromatic aldehydes [7][8]. Moreover, the molecular structures, supramolecular interactions and vibrational properties of several pyrazolopiperidine derivatives have been recently determined [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Novel 7-Aryliden-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridine Hydrochloride: Synthesis and Structure

Koshetova¹,

Yu²,

Iskakova³

et al. 2022

Eurasian Chem. Tech. J.

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“…Moreover, Pang et al prepared a novel series of pyrazolo[4,3-c]hexahydropyridine derivatives and studied their anti-proliferative activity against two breast cancer cell lines, MDA-MB-231 and MCF-7. The results showed that compound 31 (Figure 5) displayed excellent cytotoxic activity against MDA-MB-231 and MCF-7 with IC 50 values of 4.2 µM and 2.4 µM, respectively, compared to standard drug 5-fluorouracil that showed IC 50 values of 9.6 µM and 4.8 µM, respectively [55]. Further mechanistic insights, via cell cycle analysis, acridine orange/ethidium bromide (A.O./Et.Br.)…”

Section: Pyridine and Fused Pyridine Derivativesmentioning

confidence: 99%

Recent Advancements in the Development of Anti-Breast Cancer Synthetic Small Molecules

Elkaeed

Salam²,

Sabt³

et al. 2021

Molecules

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Among all cancer types, breast cancer (BC) still stands as one of the most serious diseases responsible for a large number of cancer-associated deaths among women worldwide, and diagnosed cases are increasing year by year worldwide. For a very long time, hormonal therapy, surgery, chemotherapy, and radiotherapy were used for breast cancer treatment. However, these treatment approaches are becoming progressively futile because of multidrug resistance and serious side effects. Consequently, there is a pressing demand to develop more efficient and safer agents that can fight breast cancer belligerence and inhibit cancer cell proliferation, invasion and metastasis. Currently, there is an avalanche of newly designed and synthesized molecular entities targeting multiple types of breast cancer. This review highlights several important synthesized compounds with promising anti-BC activity that are categorized according to their chemical structures.

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“…The unique properties of fluoro organic molecules may arise due to some factors to affect the pharmacological properties of the fluorinated molecules such as electronegativity, strength in the carbon-fluorine bond, low polarizability, the smallest atomic radius of the fluorine atom, in well studied anticancer agents (for example, 5-fluorouracil (5-FU) and 5-fluoro-2-deoxyuridine) [55][56][57][58]. The bioavailability of the pyridine ring has been evaluated and was found to be most active against two human BC cell lines and was explained the cytotoxic potency to induce the apoptosis of MCF-7 cells (for example, Trovirdin hydrochloride as anticancer agent contains two pyridine rings) [59,60]. Previous research has suggested contrasting effects of methoxy substitutions in chemical entities: it has been reported that they may have unfavorable steric effects and the enhanced potency of some of the lead scaffold is most likely the result of methoxylation leading to improved pharmacokinetic properties and increased stability [61].…”

Section: Sar (Structure-activity Relationship) For Used Substituentsmentioning

confidence: 99%

Anti-Cancer Activity of Gabapentin and Chiral Amino Acids-Based Hybrid-Peptides against MCF-7 Breast Cancer Cell-Line

Pansuriya

Kapadiya

Rathod

et al. 2021

JPRI

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Aims: Herein, we report the cytotoxicity of gabapentin-based peptides (11a-11j) using L-alanine and L-phenyl alanine chiral amino acids for peptide bond formation in ten efficient and straightforward steps. The in vitro MTT assays of derived molecules on the MCF-7 cell line (a human breast adenocarcinoma cell line) exhibited enhanced antitumor activity compared to the control (100% cell proliferation). Methods: The ten steps synthetic methods were adapted for the synthesis of the Gabapentin-based peptide derivatives through BOC- deBOC methods and using EDC-HCl, DMAP and commercially available solvents. All the synthesized peptides were unambiguously characterized with the help of spectroscopic (IR, 1H NMR, 13C-NMR, mass spectra, and elemental) data analysis. Results: The Compounds 11a, 11b, 11h,11i, and 11j showed a remarkable antiproliferative (cell death) activity, with % cell proliferation values ranging from 25-38 %. Conclusion: The study showed that the compounds with some specific functionalities like, benzylic and trifluoromethyl functionality enhanced the potency with comparable %cell proliferation and cell death. Based on the findings in this work and their easily accessible molecular structures, compounds 11a and 11j are worthy of further biological investigations.

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Novel 2H-pyrazolo[4,3-c]hexahydropyridine derivatives: Synthesis, crystal structure, fluorescence properties and cytotoxicity evaluation against human breast cancer cells

Cited by 10 publications

References 20 publications

Novel 7-Aryliden-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridine Hydrochloride: Synthesis and Structure

Novel 7-Aryliden-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridine Hydrochloride: Synthesis and Structure

Recent Advancements in the Development of Anti-Breast Cancer Synthetic Small Molecules

Anti-Cancer Activity of Gabapentin and Chiral Amino Acids-Based Hybrid-Peptides against MCF-7 Breast Cancer Cell-Line

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