Antiproliferative activity of aroylacrylic acids. Structure-activity study based on molecular interaction fields

Drakulić, Branko J.; Stanojković, Tatjana; Žižak, Željko; Dabović, Milan

doi:10.1016/j.ejmech.2011.04.043

Cited by 19 publications

(10 citation statements)

References 43 publications

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“…It was found that β-Aroylacrylic acids and their derivatives showed effective biological activities including antibacterial activity, 1 -4 anti-ulcer and cytoprotective properties, 5 kynurenine-3-hydroxylase, 6 and antiproliferative activity toward Human cervix carcinoma (HeLa). 7,8 Besides their broad spectrum of biological activity, β-aroylacrylic acids are versatile and convenient precursors which have been extensively utilized in the synthesis of a wide variety of heterocyclic compounds. 9 -12 The α, β-unsaturated carbonyl moiety of these compounds is a favorable unit for addition of different nucleophiles which occurs exclusively at the olefin electrophilic centre of the molecule and usually results in the formation of various nitrogen-containing heterocyclic compounds of different ring sizes with one or more heteroatom.…”

Section: Introductionmentioning

confidence: 99%

Behaviour of 4-[4-methoxy-3-methylphenyl]-4-oxobutenoic acid towards nitrogen-containing nucleophiles

2014

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A series of novel amino acid derivatives has been synthesized by the reaction of 4-[4-methoxy-3-methylphenyl]-4-oxobutenoic acid with primary and secondary amines. The treatment of amino acids with hydrazine afforded pyridazine. Phenylhydrazone was obtained from the reaction of the acid with phenyl hydrazine in ethanol. On the other hand, the acid underwent heterocyclization upon the treatment with 2-aminopyridine, o-phenylenediamine, aryldithiocarbamates and thiourea derivatives to give the corresponding pyridopyrimidine, quinoxalone, 2-thioxo-1,3-thiazole and 4-hydroxy-1,3-thiazole, respectively. The thiazolopyridazine derivatives were obtained from the reaction of 4-hydroxy-1,3-thiazole with hydrazine and phenylhydrazine, respectively. The behaviour of the 4-hydroxy-1,3-thiazole toward acetic anhydride and bromine was also studied. The proposed structures of the products were based on microanalytical and spectroscopic data. Some of the synthesized compounds also exhibited anti-microbial activities.

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Section: Introductionmentioning

confidence: 99%

Behaviour of 4-[4-methoxy-3-methylphenyl]-4-oxobutenoic acid towards nitrogen-containing nucleophiles

2014

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“…Recently, β–aroylacrylic acid derivatives showed high biological activity and exhibited a broad spectrum of physiological (fungicidal, antitumor, hypotensive, hypolipedemic, and antibacterial) activities and in recovery of Alzheimer's disease. Beside that, β‐aroylacrylic acids were considered as inhibitors for phospholipase and they have antiproliferative activity against human cervix carcinoma (Hela cells) . In another side, β‐aroylacrylic esters are important intermediates in field of medical science and agrochemicals .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Heterocyclic Compounds with Expected Antibacterial Activities from 4‐(4‐Bromophenyl)‐4‐oxobut‐2‐enoic Acid

El‐Hashash

Soliman

Bakeer

et al. 2014

Journal of Heterocyclic Chem

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“…It is worth mentioning that methoxy aryl acrylic acids are found to have antiproliferative effects against chronic myelogenous leukemia, cervix carcinoma, and colon tumour cell lines in humans. 27 The marine natural product lamellarin G trimethyl ether was synthesized by Yadav et al in four steps starting from maleic anhydride by using an electron-rich arene (Scheme 17). 28 Lamellarins have cytotoxic activities against various cancer cell lines and are, to greater or lesser degrees, also inhibitors of HIV-1 integrase.…”

Section: Ring Opening Of Anhydridesmentioning

confidence: 99%

Synthetically Important Ring-Opening Acylations of Alkoxybenzenes

Talukdar¹

2020

Synthesis

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Cyclic ketones, anhydrides, lactams and lactones are a particular class of molecules that are often used in synthesis, wherein their electrophilic properties are leveraged to enable facile Friedel–Crafts ring openings through nucleophilic attack at the carbonyl sp2 centre. The use of electron-rich alkoxybenzenes as nucleophiles has also become important since the discovery of the Friedel–Crafts reaction. As a result, various isomeric alkoxybenzenes are used for preparing starting materials in target-oriented syntheses. This review covers the instances of different alkoxybenzenes that are used as nucleophiles in ring-opening acylations with carbonyl-containing cyclic electrophiles, for the construction of important building blocks for multistep transformations. This review summarizes the ring-opening functionalization of three- to seven-membered molecular rings with alkoxybenzenes in a Friedel–Crafts fashion. Sometimes the rings need subtle or considerable activation by the help of Lewis acid(s), followed by nucleophilic attack. This review is aimed to be a summary of the important acylations of electron-rich alkoxybenzenes by nucleophilic ring-opening of cyclic molecules. The works cited employ a wide range of conditions and differently substituted substrates for target-oriented syntheses.1 Introduction and Scope2 Arenes for Acylative Ring Opening2.1 Three-Membered Rings: Ring Opening of Oxirane-2,3-dione2.2 Four-Membered Rings2.2.1 Ring Opening of Cyclobutanones2.2.2 Ring Opening of β-Lactams2.2.3 Ring Opening of β-Lactone2.3 Five-Membered Rings2.3.1 Ring Opening of Phthalimides2.3.2 Ring Opening of γ-Lactones2.3.3 Ring Opening of Anhydrides2.4 Six-Membered Rings2.5 Seven-Membered Rings3 Conclusion

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Antiproliferative activity of aroylacrylic acids. Structure-activity study based on molecular interaction fields

Cited by 19 publications

References 43 publications

Behaviour of 4-[4-methoxy-3-methylphenyl]-4-oxobutenoic acid towards nitrogen-containing nucleophiles

Behaviour of 4-[4-methoxy-3-methylphenyl]-4-oxobutenoic acid towards nitrogen-containing nucleophiles

Synthesis of Novel Heterocyclic Compounds with Expected Antibacterial Activities from 4‐(4‐Bromophenyl)‐4‐oxobut‐2‐enoic Acid

Synthetically Important Ring-Opening Acylations of Alkoxybenzenes

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