Synthesis of novel pyrazoline derivatives and the evaluation of death mechanisms involved in their antileukemic activity

Stefanes, Natália Marcéli; Toigo, Jéssica; Maioral, Mariana Franzoni; Jacques, Amanda Virtuoso; Chiaradia-Delatorre, Louise Domeneghini; Perondi, Daiane; Ribeiro, Amanda Abdalla Biasi; Bigolin, Álisson; Pirath, Iris Mattos Santos; Duarte, Bruna Fischer; Nunes, Ricardo José; Santos-Silva, Maria Cláudia

doi:10.1016/j.bmc.2018.12.012

Cited by 27 publications

(11 citation statements)

References 32 publications

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“…Pyrazoline derivatives as a kind of important five-member nitrogen-containing compound are ubiquitous in natural products. , With the CNNHC functional group, pyrazoline derivatives possess a broad spectrum of biological activities and have attracted considerable interests in functional materials such as medicine, − fluorescent substances, − and energetic fuel precursors. , …”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl₃

Xia

Zhang²,

Liu

et al. 2020

Ind. Eng. Chem. Res.

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Pyrazoline derivatives as valuable five-membered heterocyclic compounds could be readily prepared through the intramolecular cyclization of ketazines. In this paper, transition metals (Zn 2+ , Cu 2+ , Cr 3+ , Mn 2+ , Co 2+ , Ni 2+ , and Fe 3+ ) were applied for the catalytic synthesis of 3,5,5-trimethyl-2-pyrazoline, and FeCl 3 showed the best catalytic performance with 95% conversion and 99% selectivity. Substrate screening exhibited that the steric hindrance of ketazines is a key factor on the conversions of R-substituted pyrazolines, following the order of R as methyl (95%) > ethyl (83%) > propyl (68%) > butyl (55%). Moreover, the mechanism of the cyclization of ketazines catalyzed by FeCl 3 is calculated by density functional theory. The energetic profile shows that the cyclization reaction consists of two steps and FeCl 3 can efficiently reduce their barrier energies. This work provides a feasible method for the preparation of pyrazoline derivatives using inexpensive, less toxic, and environmentally friendly FeCl 3 as a catalyst.

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Section: Introductionmentioning

confidence: 99%

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl₃

Xia

Zhang²,

Liu

et al. 2020

Ind. Eng. Chem. Res.

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“…Several classes of biologically active 2‐pyrazolines (or 4,5‐dihydropyrazoles) have been developed with anti‐inflammatory, [21] anticancer, [22,23] antidepressant, [24] anticonvulsant, [25] antibacterial, [26,27] and antimalarial activities [27] . There are also some studies showing that compounds with 2‐pyrazoline scaffold have selective COX‐2 inhibitory effects [19,28–31] …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of 1,3,5‐Trisubstituted 2‐Pyrazolines as Novel Cyclooxygenase‐2 Inhibitors with Antiproliferative Activity

Vahedpour

Kaur

Hemmati

et al. 2021

Chemistry & Biodiversity

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A new series of 1,3,5‐trisubstituted 2‐pyrazolines for the inhibition of cyclooxygenase‐2 (COX‐2) were synthesized. The designed structures include a COX‐2 pharmacophore SO2CH3 at the para‐position of the phenyl ring located at C‐5 of a pyrazoline scaffold. The synthesized compounds were tested for in vitro COX‐1/COX‐2 inhibition and cell toxicity against human colorectal adenocarcinoma cell lines HT‐29. The lead compound (4‐chlorophenyl){5‐[4‐(methanesulfonyl)phenyl]‐3‐phenyl‐4,5‐dihydro‐1H‐pyrazol‐1‐yl}methanone (16) showed significant COX‐2 inhibition (IC50=0.05±0.01 μM), and antiproliferative activity (IC50=5.46±4.71 μM). Molecular docking studies showed that new pyrazoline‐based compounds interact via multiple hydrophobic and hydrogen‐bond interactions with key binding site residues of the COX‐2 enzyme.

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“…Pyrazolines have been reported to display quality of biological activities as a reactive heterocyclic structure, especially about the anti-tubercular (Ahmad et al, 2016), anti-viral (Yar et al, 2009), anti-bacterial (Solanki et al, 2012), anti-fungal (Hassan, 2013) and anti-cancer (Jainey and Bhat, 2012) activities. Stefans et al (2019) explored the antileukemic potential against neoplastic cells of pyrazoline derivatives which have been obtained from various chalcones.…”

Section: Introductionmentioning

confidence: 99%

Yeni pirazolin türevlerinin sentezi ve yapı karakterizasyonu

Çelik¹

2021

Gümüşhane Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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Pyrazolines, which are nitrogen including five-membered heterocyclic structures, have been used in the organic and pharmaceutical industries. This study aimed was to synthesize and characterizes new series of 3,5-diphenyl-4,5-dihydro-1H-pyrazole derivatives. The new pyrazoline compounds have been synthesized from chalcones and hydrazine hydrate in two steps. In the first step, chalcones were synthesized from 2-amino acetophenone and various substituted benzaldehyde by Claisen-Schmidt condensation at room temperature. In second step, starting from various substituted chalcones derivatives with hydrazine hydrate and glacial acetic acid in anhydrous ethanol were synthesized six novel 3,5diphenyl-4,5-dihydro-1H-pyrazole derivatives utilizing intramolecular Michael addition reaction in good yields. The structures of the newly synthesized 3,5-diphenyl-4,5-dihydro-1H-pyrazole derivatives are identified via 1H NMR, 13C NMR, FT-IR, and HRMS.

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Synthesis of novel pyrazoline derivatives and the evaluation of death mechanisms involved in their antileukemic activity

Cited by 27 publications

References 32 publications

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl₃

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl₃

Synthesis and Biological Evaluation of 1,3,5‐Trisubstituted 2‐Pyrazolines as Novel Cyclooxygenase‐2 Inhibitors with Antiproliferative Activity

Yeni pirazolin türevlerinin sentezi ve yapı karakterizasyonu

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Synthesis of novel pyrazoline derivatives and the evaluation of death mechanisms involved in their antileukemic activity

Cited by 27 publications

References 32 publications

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl3

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl3

Synthesis and Biological Evaluation of 1,3,5‐Trisubstituted 2‐Pyrazolines as Novel Cyclooxygenase‐2 Inhibitors with Antiproliferative Activity

Yeni pirazolin türevlerinin sentezi ve yapı karakterizasyonu

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Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl₃

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl₃