Synthesis, Spectroscopic Analysis and Assessment of the Biological Activity of New Hydrazine and Hydrazide Derivatives of 3-Formylchromone

Słomiak, Krzysztof; Łazarenkow, Andrzej; Chęcińska, Lilianna; Kusz, Joachim; Ochocki, Justyn; Nawrot‐Modranka, Jolanta

doi:10.3390/molecules23082067

Cited by 18 publications

(8 citation statements)

References 39 publications

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“…The chromone moiety revealed its characteristic aromatic carbons signatures in the range 144.3–118.1 ppm. [ 30 ] Two resonance peaks at 31.3 and 21.1 ppm were attributed to CH 2 and CH 3 carbon atoms of ethoxy group. The appearance of resonance signals centered at 24.5 and 19.1 ppm was attributed to carbon atoms of –CH– and –CH 3 groups of p ‐cymene unit, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structural investigations, and cytotoxic evaluation of a half‐sandwich Ru(II)‐arene complex

Yousuf

Bashir

2020

Applied Organom Chemis

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We report the design, synthesis, and cytotoxic evaluation of a new organoruthenium(II) complex (1). Complex 1 was characterized by analytical and spectroscopic methods including single crystal X‐ray diffraction studies. Complex 1 crystallized in an orthorhombic crystal system with Pca21 space group with Ru(II) ion p‐cymene arene unit in a usual “piano‐stool” geometry. The DFT and TDFT studies were carried out to provide better insight about the spectral properties of the complex. The Hirshfeld surface analysis plots revealed significant intermolecular interactions within the crystal structure that essentially involve a network of N–H···H, O–H···O, and C–H···O linkages. DNA photocleavage activity revealed oxidative mechanistic pathway with preferential affinity toward minor groove. Cytotoxic studies of complex 1 via SRB assay revealed moderate but selective activity toward pancreatic and cervical cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Synthesis, structural investigations, and cytotoxic evaluation of a half‐sandwich Ru(II)‐arene complex

Yousuf

Bashir

2020

Applied Organom Chemis

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“…In the beginning, 3-formylchromone was prepared based on a known method [41]. Then, we focused our initial study on the preparation of the (arylhydrazono)methyl-4 H -chromen-4-one via the reaction of 3-formylchromone and phenylhydrazine [42–43]. Subjecting (arylhydrazono)methyl-4 H -chromen-4-one ( 1a ), benzylamine ( 2a ), and malononitrile ( 3 ) in the presence of 40% triethylamine was stirred at room temperature in ethanol.…”

Section: Resultsmentioning

confidence: 99%

Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

Navari¹,

Balalaie²,

Mehrparvar³

et al. 2019

Beilstein J. Org. Chem.

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An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

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“…Interesting results of research on the synthesis, structure and biological activity of hydrazine and hydrazide derivatives of 3-formylchromone were presented by Słomiak et al [ 98 ]. They synthesized a number of hydrazine derivatives and a hydrazide derivative which they complexed with Cu (II) ( Figure 14 ).…”

Section: Hydrazidesmentioning

confidence: 99%

Different Schiff Bases—Structure, Importance and Classification

et al. 2022

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Schiff bases are a vast group of compounds characterized by the presence of a double bond linking carbon and nitrogen atoms, the versatility of which is generated in the many ways to combine a variety of alkyl or aryl substituents. Compounds of this type are both found in nature and synthesized in the laboratory. For years, Schiff bases have been greatly inspiring to many chemists and biochemists. In this article, we attempt to present a new take on this group of compounds, underlining of the importance of various types of Schiff bases. Among the different types of compounds that can be classified as Schiff bases, we chose hydrazides, dihydrazides, hydrazones and mixed derivatives such as hydrazide–hydrazones. For these compounds, we presented the elements of their structure that allow them to be classified as Schiff bases. While hydrazones are typical examples of Schiff bases, including hydrazides among them may be surprising for some. In their case, this is possible due to the amide-iminol tautomerism. The carbon–nitrogen double bond present in the iminol tautomer is a typical element found in Schiff bases. In addition to the characteristics of the structure of these selected derivatives, and sometimes their classification, we presented selected literature items which, in our opinion, represent their importance in various fields well.

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Synthesis, Spectroscopic Analysis and Assessment of the Biological Activity of New Hydrazine and Hydrazide Derivatives of 3-Formylchromone

Cited by 18 publications

References 39 publications

Synthesis, structural investigations, and cytotoxic evaluation of a half‐sandwich Ru(II)‐arene complex

Synthesis, structural investigations, and cytotoxic evaluation of a half‐sandwich Ru(II)‐arene complex

Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

Different Schiff Bases—Structure, Importance and Classification

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