Antiproliferative activity and mode of action analysis of novel amino and amido substituted phenantrene and naphtho[2,1-b]thiophene derivatives

Perin, Nataša; Rep, Valentina; Sović, Irena; Juričić, Štefica; Selgrad, Danijel; Klobučar, Marko; Pržulj, Nataša; Gupta, Chhedi Lal; Malod-Dognin, Noël; Pavelić, Sandra Kraljević; Hranjec, Marijana

doi:10.1016/j.ejmech.2019.111833

Cited by 17 publications

(7 citation statements)

References 100 publications

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“…Heterocyclic compounds are abundantly present in nature and play a significant role in various metabolic processes. Their structural subunits are found in numerous natural products, including antibiotics, vitamins, hormones, alkaloids, agrochemicals, and dyes [1][2][3][4]. Thiophene and its derivatives hold substantial importance in the pharmaceutical field due to their diverse range of biological and clinical applications [5].…”

Section: Introductionmentioning

confidence: 99%

Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

Almatari,

Saeed,

Abdel‐Ghani

et al. 2024

Journal of Heterocyclic Chem

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The objective of this study is to synthesize novel heterocyclic scaffolds containing a thiophene moiety using easily accessible acetoacetamide as a key synthon. The reaction of acetoacetamide with diazonium salts resulted in the formation of the corresponding thiophene derivatives 4a–c. Additionally, the reaction of acetoacetamide derivative 3 with malononitrile, ethyl cyanoacetate, or 2‐cyanoacetamide, along with elemental sulfur, under refluxing in dioxane containing triethylamine afforded thiophene‐containing derivatives 5a–c. Furthermore, compound 3 reacted with phenyl isothiocyanate in dry dimethylformamide and K2CO3 to yield compound 7. In situ alkylation of the non‐isolable salt 6 was achieved by the addition of methyl iodide, resulting in the formation of methylthio‐thiophene‐2‐carboxamide 8. Compound 7 was employed with numerous alpha‐halogenated reagents in ethanol, affording thiazole derivative 9 and thiophene derivatives 10a and 10b, respectively. Moreover, compound 8 was reacted with hydrazine to produce the 1H‐pyrazole‐4‐carboxamide derivative 11. Additionally, refluxing acetoacetamide derivative 3 with malononitrile and/or ethyl cyanoacetate in dioxane, in the presence of catalytic amount of triethylamine afforded 4‐imino‐3,7‐dimethyl‐4H‐pyrido[1,2‐a]thieno[3,2‐e]pyrimidin‐9(5H)‐one derivatives 12a and 12b. Furthermore, the reactivity of acetoacetamide derivative 3 with 2‐cyanoacetohydrazide was investigated through refluxing the reactants in dioxane, which subsequently yielded the corresponding cyanoacetamide derivative 13. The chemical identity of the newly synthesized compounds was determined by employing infrared spectroscopy (IR), 1H NMR, and 13C NMR techniques. Newly synthesized heterocycles incorporating thiophenes were evaluated for their antioxidant and antimicrobial potentials. Notably, thiophene scaffolds 5a, 10b, 11, and 13 displayed notable antioxidant and antimicrobial activities.

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Section: Introductionmentioning

confidence: 99%

Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

Almatari,

Saeed,

Abdel‐Ghani

et al. 2024

Journal of Heterocyclic Chem

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“…In this experiment, phenylacetonitrile was reacted with different aryl aldehydes in the presence of a catalytic base at room temperature. The Knoevenagel condensation 4 produced α-cyanostilbenes as solid compounds in high yields. Product characterizations were performed by thin layer chromatography (TLC), Fourier transform infrared (FTIR) spectroscopy, ultraviolet−visible (UV−vis) spectroscopy, and gas chromatography−mass spectrometry (GC-MS).…”

Section: ■ Introductionmentioning

confidence: 99%

Intrusive Learning Accompanying Knowledge Transfer During Organic Chemistry Laboratory Experiment: Synthesis, Characterization, and Photoisomerization of α-Cyanostilbenes

Kumar,

Maji

2023

J. Chem. Educ.

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Discussion-based outcomes of organic chemistry laboratory experiments form a powerful tool to create a learning environment, facilitate teamwork, and build scientific skills and analytical ability for undergraduate science students. A Knoevenageltype condensation reaction was selected to demonstrate these results by taking phenylacetonitrile and four different aldehydes as reactants to form α-cyanostilbenes. The reactions were performed under almost neat conditions open to air at room temperature. The short duration (2−20 min) and visual solid product formation also make the experiment attractive. Melting points, TLC, FTIR, UV−vis, and GC− MS were utilized to characterize and check the purity of the products. Photoisomerization studies were performed in sunlight. Substituent effects in the IR stretching frequency, UV−vis spectra, and photoisomerization behavior create a platform for group discussion and knowledge transfer.

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“…A couple of reactions have been developed for the synthesis of pharmaceuticals and functional materials. For example, phenanthrene-9-carbonitrile and its derivatives, a kind of anticancer drugs, were synthesized by the reaction of 4-substituted benzaldehydes with phenylacetonitrile in MeOH under alkaline conditions, followed by the coupling reaction for forming the C Ar -C Ar bond ( Scheme 1A ) ( Perin et al, 2020 ). (2Z, 2′Z)-3,3'-[4-(dimethylamino)-1,3-phenylene]bis[2-(4-aminophenyl)acrylonitrile] (DPAA), a stimuli-responsive organic fluorescent material, was obtained by the condensation of 4-(dimethylamino)isophthalaldehyde with p -nitrophenylacetonitrile in EtOH with the reduction of the nitro groups to the amine groups ( Scheme 1B ) ( Fang et al, 2018 ).…”

Section: Introductionmentioning

confidence: 99%

Copper(II)-Catalyzed Selective CAr-H Bond Formylation: Synthesis of Dialdehyde Aniline

Guo

Fan

et al. 2022

Front. Chem.

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A simple and efficient method for the synthesis of dialdehyde aniline in good yields (up to 83%) is explored using Cu(OTf)2 as the catalyst, Selectfluor as the radical initiator, and DMSO as both the carbon and oxygen sources. Experimental studies indicate that the reaction is achieved by the formylation of two CAr-H bonds, first at the para-position and then at the ortho-position. A possible mechanism is proposed, including the thermal homolysis of Selectfluor, the Cu(II)-facilitated formylation of the CAr-H bonds, and the hydrolysis of the amide under alkaline conditions in air atmosphere.

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Antiproliferative activity and mode of action analysis of novel amino and amido substituted phenantrene and naphtho[2,1-b]thiophene derivatives

Cited by 17 publications

References 100 publications

Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

Intrusive Learning Accompanying Knowledge Transfer During Organic Chemistry Laboratory Experiment: Synthesis, Characterization, and Photoisomerization of α-Cyanostilbenes

Copper(II)-Catalyzed Selective CAr-H Bond Formylation: Synthesis of Dialdehyde Aniline

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