Recent advancements in the development of bioactive pyrazoline derivatives

Nehra, Bhupender; Rulhania, Sandeep; Jaswal, Shalini; Kumar, Bhupinder; Singh, Gurpreet; Monga, Vikramdeep

doi:10.1016/j.ejmech.2020.112666

Cited by 77 publications

(52 citation statements)

References 118 publications

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“…Amongst these heterocyclic ring-containing scaffolds, pyrazolines as a class of electron-rich nitrogen heterocyclic compounds play an important role due to their extensive use as pharmacophore and synthon. Interestingly, 2-pyrazoline derivatives synthesized from chalcones have shown a variety of biological activities, such as antibacterial, antitumor, antifungal, anti-inflammatory, antioxidant, and antimalarial [18][19][20][21][22][23][24]. Previously it has been reported that 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-(multi-substituted-4-hydroxyphenyl)-2-pyrazoli nes showed significant human LDL-antioxidant activities (Figure 1) [25].…”

Section: Introductionmentioning

confidence: 99%

Isobornylchalcones as Scaffold for the Synthesis of Diarylpyrazolines with Antioxidant Activity

et al. 2021

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The pyrazoline ring is defined as a “privileged structure” in medicinal chemistry. A variety of pharmacological properties of pyrazolines is associated with the nature and position of various substituents, which is especially evident in diarylpyrazolines. Compounds with a chalcone fragment show a wide range of biological properties as well as high reactivity which is primarily due to the presence of an α, β-unsaturated carbonyl system. At the same time, bicyclic monoterpenoids deserve special attention as a source of a key structural block or as one of the pharmacophore components of biologically active molecules. A series of new diarylpyrazoline derivatives based on isobornylchalcones with different substitutes (MeO, Hal, NO2, N(Me)2) was synthesized. Antioxidant properties of the obtained compounds were comparatively evaluated using in vitro model Fe2+/ascorbate-initiated lipid peroxidation in the substrate containing brain lipids of laboratory mice. It was demonstrated that the combination of the electron-donating group in the para-position of ring B and OH-group in the ring A in the structure of chalcone fragment provides significant antioxidant activity of synthesized diarylpyrazoline derivatives.

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Section: Introductionmentioning

confidence: 99%

Isobornylchalcones as Scaffold for the Synthesis of Diarylpyrazolines with Antioxidant Activity

et al. 2021

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“…There are numerous examples where different applications of 2‐pyrazolines have been explored [2b] . Some of these applications in drug discovery, industry, and agriculture, in conjunction with their synthetic pathways, are provided in the following sections.…”

Section: Important Applications Of 2‐pyrazolinesmentioning

confidence: 99%

Synthesis of 2‐Pyrazolines from Hydrazines: Mechanisms Explained

et al. 2021

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2-Pyrazoline core is a very interesting five-membered heterocycle, which has been explored in recent years due to its vast applications as the core structure of bioactive and industrial agents. Based on literature studies, versatile synthetic approaches have been employed for the preparation of 2pyrazolines, among them the reaction between hydrazines and α,β-unsaturated enones as the most used method. In this review article, different methods for the synthesis of 2-pyrazolines using hydrazine derivatives were classified and presented.Initially, numerous catalytic methods for the preparation of 2pyrazolines from hydrazines and α,β-unsaturated enones are reviewed and various aspects of these methods discussed including catalyst efficiency, catalyst recovery, green chemistry, cost-effectiveness, scope of the method, enantioselectivity, and yield. In addition, reactions between hydrazines and other reagents in multicomponent and two-component reactions, developed recently, are discussed. Finally, some of the important applications of 2-pyrazolines are summarized.

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“…Even 100 years after the first reports on the synthesis of pyrazoles, this heterocyclic structure is still used as a model for designing selective protocols in cyclocondensation reactions, and also for biological/pharmacological assays [24–29] . Scheme 3 shows the general synthetic pathway for the regioselective synthesis of pyrazolines 5 and pyrazoles 6 (obtained from dehydration of 5 ), using enones 4 and substituted hydrazines or hydrazides.…”

Section: Synthesis Of Pyrazolines and Pyrazoles Using Nn‐dinucleophilesmentioning

confidence: 99%

Haloacetylated Enol Ethers: a Way Out for the Regioselective Synthesis of Biologically Active Heterocycles

2021

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This review describes advances in the synthesis of heterocyclic scaffolds (associated with their biological activity), using haloacetylated enol ethers as precursors. The wide variety of heterocycles that can be prepared using these precursors, together with the high regioselectivity they usually provide, in [3+2] and [3+3] cyclocondensation reactions, make these starting materials powerful tools. The biological evaluation is also highlighted, given that several analogues of commercially available drugs can be easily accessed.

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Recent advancements in the development of bioactive pyrazoline derivatives

Cited by 77 publications

References 118 publications

Isobornylchalcones as Scaffold for the Synthesis of Diarylpyrazolines with Antioxidant Activity

Isobornylchalcones as Scaffold for the Synthesis of Diarylpyrazolines with Antioxidant Activity

Synthesis of 2‐Pyrazolines from Hydrazines: Mechanisms Explained

Haloacetylated Enol Ethers: a Way Out for the Regioselective Synthesis of Biologically Active Heterocycles

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