Synthesis of 2‐pyrazolines by the reactions of α,β‐unsaturated aldehydes, ketones, and esters with diazoalkanes, nitrile imines, and hydrazines

Léavai, Albert

doi:10.1002/jhet.5570390101

Cited by 126 publications

(23 citation statements)

References 117 publications

(131 reference statements)

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“…Pyrazolines and pyrazoles represent important nitrogencontaining five membered heterocyclic compounds and various methods have been worked out for their synthesis [1][2][3][4]. Derivatives of pyrazolines and pyrazoles have played a crucial role in the history of heterocyclic chemistry and have been used extensively as important pharmacophores and synthons in the field of organic chemistry and drug design.…”

Section: Introductionmentioning

confidence: 99%

An Efficient One Pot Synthesis of New Indanopyrazoline and Indanopyrazole Derivatives

Jelizi¹,

Askri²,

Rammah³

et al. 2011

LOC

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Section: Introductionmentioning

confidence: 99%

An Efficient One Pot Synthesis of New Indanopyrazoline and Indanopyrazole Derivatives

Jelizi¹,

Askri²,

Rammah³

et al. 2011

LOC

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“…Previously, the reaction of chromanone and flavanone derivatives with substituted hydrazines has been investigated in different conditions [16,17]. Kállay et al have been reported that the flavanone hydrazones are predominantly obtained under acidic conditions while alkaline conditions give the pyrazolines and the 2-hydroxychalcone derivatives due to the ring cleavage of the hetero ring of chromanone [16].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, in vitro antifungal evaluation and in silico study of 3-azolyl-4-chromanone phenylhydrazones

et al. 2012

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BackgroundThe currently available antifungal drugs suffer from toxicity, greatest potential drug interactions with other drugs, insufficient pharmacokinetics properties, and development of resistance. Thus, development of new antifungal agents with optimum pharmacokinetics and less toxicity is urgent task. In the search for new azole antifungals, we have been previously described azolylchromanone oxime ethers as rigid analogs of oxiconazole. In continuation of our work, we incorporated phenylhydrazone moiety instead of oxime ether fragment in azolylchromanone derivatives.MethodsThe 3-azolyl-4-chromanone phenylhydrazones were synthesized via ring closure of 2-azolyl-2'-hydroxyacetophenones and subsequent reaction with phenylhydrazine. The biological activity of title compounds was evaluated against different pathogenic fungi including Candida albicans, Saccharomyces cerevisiae, Aspergillus niger, and Microsporum gypseum. Docking study, in silico toxicity risks and drug-likeness predictions were used to better define of title compounds as antifungal agents.ResultsThe in vitro antifungal activity of compounds based on MIC values revealed that all compounds showed good antifungal activity against C. albicans, S. cerevisiae and M. gypseum at concentrations less than 16 μg/mL. Among the test compounds, 2-methyl-3-imidazolyl derivative 3b showed the highest values of drug-likeness and drug-score.ConclusionThe 3-azolyl-4-chromanone phenylhydrazones considered as analogs of 3-azolyl-4-chromanone oxime ethers basically designed as antifungal agents. The antifungal activity of title compounds was comparable to that of standard drug fluconazole. The drug-likeness data of synthesized compounds make them promising leads for future development of antifungal agents.

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“…The pyrazolines are the five membered heterocyclic compounds and extensive important synthons which have attracted the attentions of organic chemists in the past decades due to their immense biological applications. These kind of compounds have played an important role in the development of theoretical heterocyclic chemistry and some of their various spectra of biological activities are antiinflammatory, antidepressant, antibacterial, antiviral, anticancer activities [7][8][9] and antidiabetic activities [10].…”

Section: Figure 1 Structure Of Dehydrozingeronementioning

confidence: 99%

Dehydrozingerone analogues in synthesis attractive sulfonamide compounds as potential antitumor agents

Muškinja

Ratković

Popović

et al. 2019

Proceedings of the 23rd International Electronic Conference on Synthetic Organic Chemistry

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Sulfonamides are very important scaffold in design of different compounds with potential biological activity. They are the basis of several groups of drugs and could be called sulfa drugs. Starting from this fact, we wanted to synthesize some new types of sulfonamides, prepared from derivatives of natural product vanillin. In light of this, we synthesized dehydrozingerone, 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one, and its alkyl derivatives. These compounds served as good substrates in the synthesis of new sulfonamide compounds. The structures of the new compounds were determined by IR and NMR methods. Cytotoxicity screening of fourteen new organic compounds against SW480, Hela and MRC-5 was measured by colorimetric MTT assay after 48h of treatment. Cytotoxicity ratio (CR) was calculated as % of cytotoxicity of each compound on normal cells and % of cytotoxicity of the same compounds on tumor cell line. CR is pointed to some new compounds as promising candidates for further experiments.

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Synthesis of 2‐pyrazolines by the reactions of α,β‐unsaturated aldehydes, ketones, and esters with diazoalkanes, nitrile imines, and hydrazines

Cited by 126 publications

References 117 publications

An Efficient One Pot Synthesis of New Indanopyrazoline and Indanopyrazole Derivatives

An Efficient One Pot Synthesis of New Indanopyrazoline and Indanopyrazole Derivatives

Synthesis, in vitro antifungal evaluation and in silico study of 3-azolyl-4-chromanone phenylhydrazones

Dehydrozingerone analogues in synthesis attractive sulfonamide compounds as potential antitumor agents

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