Synthesis of functionalized fluoroalkyl pyrimidines and pyrazoles from fluoroalkyl enones

Shaitanova, Elena N.; Balabon, Olga; Rybakova, Antonina N.; Khlebnicova, Tatyana S.; Лахвич, Ф. А.; Gerus, Igor I.

doi:10.1016/j.jfluchem.2021.109905

Cited by 2 publications

(1 citation statement)

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“…Since the structural features have extremely significant effects on the physical and drug-like properties of pyrazole and pyridazine derivatives, the starting materials for the However, there are some limitations associated with reactions of unsymmetrical diketones and their synthetic equivalents with substituted hydrazines. The major difficulty is that they can sometimes suffer from regioselectivity issues, leading to the formation of multiple isomeric products [64][65][66][67][68]. In some cases, using specific catalysts along with varying the reaction parameters allow for the precise manipulation of the reactivity of different carbonyl groups.…”

Section: Introductionmentioning

confidence: 99%

Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

Edilova,

Osipova,

Slepukhin

et al. 2023

IJMS

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A convenient approach to substituted pyrazoles and pyridazinones based on 1,2,4-triketones is presented. Chemo- and regiocontrol in condensations of t-Bu, Ph-, 2-thienyl-, and CO2Et-substituted 1,2,4-triketone analogs with hydrazines are described. The direction of preferential nucleophilic attack was shown to be switched depending on the substituent nature in triketone as well as the reaction conditions. The acid and temperature effects on the selectivity of condensations were revealed. Regiochemistry of heterocyclic core formation was confirmed by NMR and XRD studies. The facile construction of heterocyclic motifs bearing acetyl and (or) carbethoxy groups suggests them as promising mono- or bifunctional building blocks for subsequent transformations.

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Section: Introductionmentioning

confidence: 99%

Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

Edilova,

Osipova,

Slepukhin

et al. 2023

IJMS

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Investigating the Synthesis Methods of 3,5-dione Pyrazolidine and 3,5-dione 1-phenylpyrazolidine in the Presence and Absence of Ultrasound Bath and their Anticancer Effects on MCF-7 Breast Cancer Cells

Nadipour,

Salahvarzi,

Dadgar

2024

CBC

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Background: Pyrazolidine 5,3-dione derivatives have a wide range of biological and pharmacological activities and play an important role in the sub-structures of various drugs. They also have inhibitory and antimicrobial properties, anti-tumor, anti-inflammatory, analgesic, anti-tuberculosis, anti-hypertensive, anti-cancer, and anti-Alzheimer. The purpose of the current study was to investigate a number of synthesis methods of pyrazolidine-3,5-dione and 1 phenylpyrazolidine-3,5-dione in the presence and absence of ultrasound bath and their anti-cancer effects on mcf-7 breast cancer cells. Methods: In this study, pyrazolidine-3,5-dione and 1-phenylpyrazolidine-3,5-dione were synthesized using hydrazine, phenylhydrazine, and diethyl malonate by different methods. The advantage of this research compared to other studies is the use of different methods (3 methods and each method were performed in two different conditions, toalling 6 methods) for the synthesis of these two derivatives. The effect of two synthesized derivatives on MCF-7 cell line breast cancer cells was also investigated using MTT (methylthiazole tetrazolium) test. IR, 13CNMR, and HNMR spectroscopy methods have also been used to determine the structure of products. Results: The results of FT-IR and NMR spectrum analysis confirm the synthesized pyrazolidine-3,5-dione and 1-phenylpyrazolidine-3,5-dione. Based on the results in zero doses (control group) and 10 μM of all Samples after 24 hours, no significant difference in the number of cells was observed. However, the number of cells significantly decreased after treatment with 20 μM dose of both pyrazolidine-3,5-dione and 1-phenylpyrazolidine-3,5-dione. Also, there was no significant difference in reducing cancer cell proliferation between pyrazolidine-3,5-dione and 1-phenylpyrazolidine-3,5-dione samples. In addition, treatment of cancer cells with 40 μM of both hydrazine and phenylhydrazine samples after 24 hours caused approximately 50% cell death and reduced the number of cancer cells by approximately half compared to the control group. Conclusion: According to the results of this study, treatment of cancer cells with a dose of 40 μM in both samples of pyrazolidine-3,5-dione and 1-phenylpyrazolidine-3,5-dione after 24 hours caused cell death in approximately 50% of cells and the number of cancer cells is almost half that of the control group.

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Synthesis of functionalized fluoroalkyl pyrimidines and pyrazoles from fluoroalkyl enones

Cited by 2 publications

References 40 publications

Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

Investigating the Synthesis Methods of 3,5-dione Pyrazolidine and 3,5-dione 1-phenylpyrazolidine in the Presence and Absence of Ultrasound Bath and their Anticancer Effects on MCF-7 Breast Cancer Cells

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