Pharmacological Activity of 4,5-Dihydropyrazole Derivatives (Review)

Korablina, Diana D.; Ворожцов, Н. И.; Свиридова, Л. А.; Kalenikova, E. I.; Медведев, О. С.

doi:10.1007/s11094-016-1438-6

Cited by 24 publications

(3 citation statements)

References 91 publications

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“…Pleasingly, 3a underwent selective benzylic substitution utilizing NaSCN, thiophenol, or NaN 3 as nucleophiles to furnish the functionalized gem -diiodides 4a – 4c in 68–90% yield in up to gram quantities. Employing the binucleophile phenylhydrazine gave access to the 2-pyrazoline derivative 5 in 60% yield, representing a privileged and valuable aza-heterocycle found in many bioactive compounds . Next, we targeted aforementioned functionalized gem -diiodides for further reactivity.…”

mentioning

confidence: 69%

Copper Makes the Difference: Visible Light-Mediated Atom Transfer Radical Addition Reactions of Iodoform with Olefins

Engl

Reiser

2020

ACS Catal.

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Herein, we report a visible light-mediated coppercatalyzed protocol enabling the highly economic, vicinal difunctionalization of olefins utilizing the readily available bulk chemical iodoform. This protocol is characterized by high yields under environmentally benign reaction conditions and allows the regioselective and chemoselective functionalization of activated double bonds. Besides the synthetic utility of the shown transformation, this study undergirds the exclusive role of copper in photoredox catalysis as the title transformation is not possible via the most commonly employed ruthenium, iridium, or organic dye-based photocatalysts owing to the ability of copper to stabilize and interact with radical intermediates in its coordination sphere. Furthermore, the protocol can be smoothly scaled to gram quantities of the product, which offers manifold possibilities for further transformations, for example, heterocycle synthesis or intramolecular cyclopropanation.

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confidence: 69%

Copper Makes the Difference: Visible Light-Mediated Atom Transfer Radical Addition Reactions of Iodoform with Olefins

Engl

Reiser

2020

ACS Catal.

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“…Pyrazoline, an important heterocycle that widely exists in numerous biologically active molecules and pharmaceuticals, exhibits several properties such as antimicrobial, antitumor, anti-inflammatory, antiviral, antimalarial, and antituberculosis activity . Accordingly, significant research endeavors have been dedicated to their synthesis, and remarkable advances have been achieved in their construction, such as catalytic [3+2] and [4+1] cycloadditions, cyclocondensations, and 5-exo annulations .…”

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confidence: 99%

Photoinduced [3+2] Cycloaddition of Alkyl–Acceptor Diazoalkanes: Diversity-Oriented Synthesis of Pyrazolines Containing a Quaternary Center

He,

Sun,

et al. 2024

Org. Lett.

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We present a new [3+2] cycloaddition reaction between alkyl−acceptor diazoalkanes under visible light irradiation. By employing easily accessible alkyl−acceptor-type diazoalkanes or their precursor hydrazones as both 1,3-dipoles and dipolarophiles, a diverse range of pyrazoline derivatives featuring a quaternary center have been efficiently synthesized in a predictable manner, with excellent functional group tolerance and good yields. Furthermore, scale-up experiments and downstream transformations of the product were also detailed.

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“…Pyrazolines, the partially saturated counterpart of pyrazoles, represent an essential class of N -heterocycles as they offer an excellent opportunity for structural modifications in modern drug discovery and development (Figure ). Parallelly, pyrazolines have several biological significances, including antifungal, anti-inflammatory, and antimicrobial activities . Also, they have been known for treating a wide range of diseases such as malaria, diabetes, and cancer. , Due to their significant applications in different fields, processes leading to the pyrazoline scaffold are vital.…”

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confidence: 99%

Cu(II)-Catalyzed Aminocyclization of N-Propargyl Hydrazones to Substituted Pyrazolines

Sharma,

Das,

Guru

2023

J. Org. Chem.

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An efficient route for the copper(II)-catalyzed synthesis of substituted pyrazolines from readily accessible N-propargyl hydrazones has been reported under open flask conditions via intramolecular C–N bond formation. N-acyl and N-tosyl-substituted pyrazolines have been prepared in moderate to excellent yields. Mechanistic investigations using NMR, high-resolution mass spectrometry (HRMS), and Hammett analyses suggest that the Cu(II) catalyst generally acts as a Lewis acid to form an iminium-ion intermediate via cyclization, which afforded the desired pyrazolines upon hydrolysis. One progesterone receptor antagonist has also been synthesized utilizing this reaction methodology.

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Pharmacological Activity of 4,5-Dihydropyrazole Derivatives (Review)

Cited by 24 publications

References 91 publications

Copper Makes the Difference: Visible Light-Mediated Atom Transfer Radical Addition Reactions of Iodoform with Olefins

Copper Makes the Difference: Visible Light-Mediated Atom Transfer Radical Addition Reactions of Iodoform with Olefins

Photoinduced [3+2] Cycloaddition of Alkyl–Acceptor Diazoalkanes: Diversity-Oriented Synthesis of Pyrazolines Containing a Quaternary Center

Cu(II)-Catalyzed Aminocyclization of N-Propargyl Hydrazones to Substituted Pyrazolines

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