<i>N</i>'-(1-([1,1'-biphenyl]-4-yl)ethylidene)-2-cyanoacetohydrazide as scaffold for the synthesis of diverse heterocyclic compounds as prospective antitumor and antimicrobial activities

Hamed, Nancy; Marzouk, Magda I.; Ismail, Mahmoud F.; Hekal, Mohamed H.

doi:10.1080/00397911.2019.1655578

Cited by 14 publications

(9 citation statements)

References 22 publications

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“…of 87 percent (108-110 M). (14,15) To a solution of (0.02 mol) substituted benzaldehyde in (20ml) of absolute ethanol and then add drops of glacial acetic acid to the mixture, and add (0.02 mol) to it acid hydrazide dissolved in (25ml) absolute ethanol, then refluxed the mixture for 4 hours and cool the solution, and then filter and wash with distilled water and recrystallized the product with absolute ethanol the physical properties of the synthesized compound are given in Table (1). (16,17) The solvent was evaporated by distillation after a combination of (0.01mol) from Shiff base(D2-6) in (20ml) of dry benzene with (0.01mol) of phthalic anhydride was reflexed for (8) hours.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of some new oxazepine compounds derived from cyanoethyl acetate and study their inhibitory activity against some pathogenic bacterial species

Najim

Al-Badrany

Saleh³

2022

ijhs

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Involves synthesis of Schiff bases (hydrazone) by the reaction of acid hydrazide(D1) (which is prepared from the reaction of cyanoethyl acetate with hydrazine hydrate at (85%) with aromatic aldehydes to obtain compounds (D2-6) and by the reaction of compounds (D2-6) with phthalic anhydride Compounds (D7-11) are obtained, the biological activity of the prepared compounds is studied through two types of Gram-positive and Gram-negative bacteria Staph. aureus, Escherichia Coli and Compare it with one type of antibiotic (Gentamycin). The validity of the structures is confirmed by spectroscopic methods (FTIR, 1H-NMR, 13C-NMR, MASS). The disk diffusion assay technique was used to investigate the antibacterial activity in vitro against two types of bacteria: gram-positive and gram harmful bacteria. The minimum inhibitory concentration [MIC] was measured using standard medications. The findings revealed that azetidine derivatives outperformed drugs in inhibiting the growth of both gram-positive and gram-negative bacteria.

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Section: Methodsmentioning

confidence: 99%

Synthesis of some new oxazepine compounds derived from cyanoethyl acetate and study their inhibitory activity against some pathogenic bacterial species

Najim

Al-Badrany

Saleh³

2022

ijhs

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“…Frankly, we worked on cyanoacetohydrazide derivatives previously, [14][15][16][17][18][19][20] but the doubly behavior of cyanoacetamide derivative 3 encouraged us to employ it as scaffold for the construction of novel compounds containing a wide variety of bis-heterocyclic moieties, and to study their insecticidal activities.…”

Section: Chemistrymentioning

confidence: 99%

“…The extrusion of cyanoacetohydrazide moiety and insertion of hydrazone and oxime moieties was observed and interpreted by our research group in a previous publication. [16] It was also explicated on the basis of spectroscopic and elemental analyses. Initially, the carbonyl and cyano functional groups were absent from the IR spectra of compounds 16 and 18.…”

Section: Chemistryselectmentioning

confidence: 99%

“…So that, cyanoacetohydrazide is used as scaffold and a key material for building enormous number of heterocyclic compounds with different ring sizes. [13,14] From the above scenario and in continuation of our previous work, [14][15][16][17][18][19][20] N',N'''-(methylenebis(6-hydroxy-3,1phenylene))bis(methanylylidene))bis(2-cyanoacetohydrazide) (3) was engaged for the synthesis of different bis-heteroaryl/ arylidenes and bis-heterocycles, followed by evaluation of their insecticidal activity against cotton leaf worm (Spodoptera littoralis).…”

Section: Introductionmentioning

confidence: 99%

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Utility of 5,5′‐Methylenebis(2‐hydroxybenzaldehyde) – cyanoacetohydrazide Hybrid as Scaffold for the Synthesis of Bis‐Heterocyclic Moieties and Study of Their Insecticidal Activity

et al. 2023

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The cotton leafworm, Spodoptera littoralis Boisd. is a serious pest attacking a wide range of ornamentals and many field crops. It is well documented that some heterocyclic systems have efficient insecticidal activities. So novel hydrazide‐hydrazone namely, N′,N′′′‐((methylenebis(6‐hydroxy‐3,1‐phenylene))bis(methanylylidene))bis(2‐cyanoacetohydrazide) 3 was exploited as a target to synthesize bis‐heterocyclic moieties such as furan, pyridone, coumarin, thiazole and isoxazole, and also some bis‐heteroarylidenes including heterocycles as indole and pyrazole. The chemical structures of the synthesized compounds were established on the basis of elemental analyses and some spectroscopic tools. All the synthesized compounds were screened for the insecticidal efficacy against the 4th larval instar of Spodoptera littoralis (cotton leafworm). Manifestly, the data showed that compounds 9 and 14 possess remarkable potency but the rest of compounds showed no pronounced activity against cotton leafworm.

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“…On the other hand, cyanoacetohydrazide plays dramatically an important role as a scaffold in the synthesis of different heterocyclic moieties such as iminocoumarin, pyridone, pyrazole and thiazole rings, etc. [40][41][42][43][44][45][46][47][48][49][50][51][52][53] Due to cyanoacetohydrazide scaffold possessing intriguing functional groups; NH and active methylene groups act as nucleophilic centers, and also cyano group act as an electrophilic center during the reactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antioxidant and Antiproliferative Evaluation, Molecular Docking and DFT Studies of Some Novel Coumarin and Fused Coumarin Derivatives

Gouda

Salem

Marzouk

et al. 2023

Chemistry & Biodiversity

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N methylene]-2-cyanoacetohydrazide (3) was synthesized in excellent yield from the condensation of 4-Chloro-2-oxo-2H-chromene-3-carbaldehyde with cyanoacetohydrazide. Compound 3 was utilized as a building block to synthesize novel coumarin and heterocyclefused coumarin derivatives. The chemical structures of all the new coumarin compounds were identified by spectral analyses. Some of the new coumarins compounds were screened in human cancer cell lines (HEPG-2, MCF-7, HCT-116 and PC-3) to learn about their cytotoxic effects in addition to the study of their DNA damage and antioxidant activity. Three of these compounds exhibited remarkable antioxidant and anti-proliferative activities. Moreover, they have the capability to protect DNA from damage induced by bleomycin. Molecular docking, DFT and molecular electrostatic potential studies were performed on the compounds in vitro.[a] M. A.

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N'-(1-([1,1'-biphenyl]-4-yl)ethylidene)-2-cyanoacetohydrazide as scaffold for the synthesis of diverse heterocyclic compounds as prospective antitumor and antimicrobial activities

Cited by 14 publications

References 22 publications

Synthesis of some new oxazepine compounds derived from cyanoethyl acetate and study their inhibitory activity against some pathogenic bacterial species

Synthesis of some new oxazepine compounds derived from cyanoethyl acetate and study their inhibitory activity against some pathogenic bacterial species

Utility of 5,5′‐Methylenebis(2‐hydroxybenzaldehyde) – cyanoacetohydrazide Hybrid as Scaffold for the Synthesis of Bis‐Heterocyclic Moieties and Study of Their Insecticidal Activity

Synthesis, Antioxidant and Antiproliferative Evaluation, Molecular Docking and DFT Studies of Some Novel Coumarin and Fused Coumarin Derivatives

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