Regioselective role of the hydrazide moiety in the formation of complex pyrrole–pyrazole systems

Attanasi, Orazio A.; Fïlippone, Paolino; Perrulli, Francesca R.; Santeusanio, Stefania

doi:10.1016/s0040-4020(00)01125-x

Cited by 22 publications

(13 citation statements)

References 45 publications

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“…Finally, the starting materials used are readily available and stable compounds and can be kept for any time required. This is a considerable advantage of this procedure, since the described methods [8,9] use certain labile and difficult to store azoalkenes 2 [3,15] or diazo ketones 7. [9] Further investigations were directed to extending the scope of the method for preparation of the corresponding 1-arylsulfonylamino derivatives.…”

Section: Resultsmentioning

confidence: 99%

A New and Convenient Synthesis of 1,2-Diamino-3-hetarylpyrrole Derivatives

et al. 2002

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Section: Resultsmentioning

confidence: 99%

A New and Convenient Synthesis of 1,2-Diamino-3-hetarylpyrrole Derivatives

et al. 2002

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“…All compounds were dissolved in the DMSO then diluted in the buffer and the DMSO does not exceed 1% in the mixture. After that, 25 mL of acetylthiocholine iodide solution were added to the initial mixture and the final mixture was incubated, for 15 min, at 25 C, then the absorbance was determined at 412 nm. Control contained all components except the tested compounds.…”

Section: Ache Inhibitory Activity Assaymentioning

confidence: 99%

“…They are useful as a precursor for the construction of several organic compounds with a broad spectrum of biological activities 19 . For instance, hydrazides are used for the synthesis of several heterocyclic compounds such as pyrroles 20 , pyrazoles 21 , 1,3-thiazoles 22 , thiadiazoles 23 , 1,2,4-triazolo [3,4-b]-1,3,4-thiadiazines 24 and hydrazones 25 . On the other hand, hydrazones are molecules containing azomethine group 26 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, cytotoxic, anti-lipoxygenase and anti-acetylcholinesterase capacities of novel derivatives from harmine

Filali

Belkacem

Nejma

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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We synthesized two series of new hydrazide harmine derivatives. The reaction of harmine 1 with ethyl acetate chloride afforded the corresponding ethyl ester 2. The treatment of 2 with hydrazine hydrate gave the hydrazide 3 which further converted into hydrazones 4a-j and dihydrazides 5a-c. A series of new triazoles 7a-f has also been prepared from the suitable propargyl harmine 6. The synthesized derivatives were characterized by 1 H-NMR, 13 C-NMR, and HRMS and evaluated for their activities against MCF7, HCT116 OVCAR-3, acetylcholinesterase and 5-lipoxygenase. The most hydrazones derivatives 4a-j have a good cytotoxic activity against all cell lines, when 4a, 4d, 4f and 4 g are more active than 1 (against OVCAR-3 IC 50 16.7-2.5 mM). The compound 6 was the most active (IC 50 ¼ 1.9 mM) against acetylcholinesterase. Some compounds exhibited significant activity against 5-lipoxygenase (IC 50 ¼ 30.9-63.1 mM).

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“…For these reasons we have introduced hydrazide and 1,3,4-oxadiazole moieties to the pyridazine ring to enhance the cytotoxic activity. Hydrazides are very useful starting materials for the construction of several heterocyclic compounds such as 1,3,4-oxadiazoles [13], 1,3-thiazoles [14], 1,3,4-thiadiazoles [15], 1,2,4-triazoles [16] [18], pyrroles [19] and pyrazoles [20]. The common practical route for hydrazide synthesis is the treatment of esters with hydrazine hydrate.…”

Section: Introductionmentioning

confidence: 99%

Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

Shaker

Marzouk

2016

Molecules

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A (pyridazinyl)acetate derivative was reacted with thiosemicarbazide and hydrazine hydrate to yield spiropyridazinone and acetohydrazide derivatives, respectively. The acetohydrazide derivative was used as a starting material for synthesizing some new heterocyclic compounds such as oxoindolinylidene, dimethylpyrazolyl, methylpyrazolyl, oxopyrazolyl, cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives. The behavior of the cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives towards nitrogen and carbon nucleophiles was investigated. The assigned structures of the prepared compounds were elucidated by spectral methods (IR, 1 H-NMR 13 C-NMR and mass spectroscopy). Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines, namely hepatocellular carcinoma (liver) HePG-2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity.

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Regioselective role of the hydrazide moiety in the formation of complex pyrrole–pyrazole systems

Cited by 22 publications

References 45 publications

A New and Convenient Synthesis of 1,2-Diamino-3-hetarylpyrrole Derivatives

A New and Convenient Synthesis of 1,2-Diamino-3-hetarylpyrrole Derivatives

Synthesis, cytotoxic, anti-lipoxygenase and anti-acetylcholinesterase capacities of novel derivatives from harmine

Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

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