Fast, Facile and Convenient Synthesis of <i>α,α</i>‐Bis(substituted‐arylidene) Cycloalkanones: An improved Protocol

Mahdavinia, Gholam Hossein; Mirzazadeh, Maryam

doi:10.1155/2012/390528

Cited by 13 publications

(11 citation statements)

References 13 publications

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“…Bis-chalcones (1)(2)(3) were synthesized following literature procedures by the condensation of cyclohexanone and cyclopentanone with aromatic aldehydes, respectively. [26][27]. Synthesis and spectroscopic details of the compounds are given in these literatures [26][27].…”

Section: Methodsmentioning

confidence: 99%

Density Functional Theory and Single Crystal X-ray Studies on Some Bis-Chalcone Derivatives

Yakalı¹,

Biçer²,

Barut³

et al. 2019

Turkish Computational and Theoretical Chemistry

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The three bis-chalcone compounds, (2E,6E)-2,6-bis(3-chlorobenzylidene)cyclohexanone (1), (2E,6E)-2,6-bis(2,3-dichlorobenzylidene)cyclohexanone (2) and (2E,5E)-2,5-bis(2,6-dichloro benzylidene) cyclopentanone (3), were studied with theoretical and single-crystal X-ray diffraction (XRD) methods. The molecular geometric parameters, frontier molecular orbitals, MEP, normal mode frequencies and the corresponding vibrational assignments, gauge-including atomic orbital (GIAO) 1 H-NMR, 13 C-NMR chemical shift values of the bis-chalcone compounds in the ground state have been calculated using the density functional (B3LYP) methods with 6-311G (d,p) basis set. These molecules demonstrate apparently a long and flat shape. The each molecule adopt an (E) configuration about the central olefinic bonds. The most important feature is stacking mode in the molecules. The calculated results reveal that the optimized geometries can well reproduce the crystal structure. The theoretical vibrational frequencies and 1 H-NMR and 13 C-NMR chemical shift values show good agreement with the experimental data.

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Section: Methodsmentioning

confidence: 99%

Density Functional Theory and Single Crystal X-ray Studies on Some Bis-Chalcone Derivatives

Yakalı¹,

Biçer²,

Barut³

et al. 2019

Turkish Computational and Theoretical Chemistry

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“…The α,ά-bis (substituted-arylidene) cycloalkanones 1a-g (15,16) were synthesized via aldol condensation as described previously (16). General procedure for the preparation of 7-benzylidene-2,3-diphenyl-3,3a,4,5,6,7-hexahydro-2H-indazole derivatives(3a-g) α,ά-bis (substituted-arylidene) cycloalkanone (1a-g), (1 mmol) was stirred at 120°C with phenyl hydrazine (2), (2 mmol) in presence of DABCO (10 mol%).…”

Section: Methodsmentioning

confidence: 99%

A mild, simple, and efficient approach to the synthesis of some novel 7-benzylidene-2,3-diphenyl-3,3a,4,5,6,7-hexahydro-2H-indazole derivatives

Mahdavinia

Mirzazadeh

Karimi-Jaber

2014

Green Chemistry Letters and Reviews

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“…These compounds were prepared according to a known methods [46] and [47], respectively. Mp: 7a -98-99 °C; Lit.…”

Section: (2e6e)-26-bis(benzylidene)-4-methylcyclohexanone (7a) and mentioning

confidence: 99%

A novel cluster of C5-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold

et al. 2019

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A new series (6) of C 5-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with IC 50 values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [IC 50 = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such C 5-curcuminoids.

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Fast, Facile and Convenient Synthesis of α,α‐Bis(substituted‐arylidene) Cycloalkanones: An improved Protocol

Cited by 13 publications

References 13 publications

Density Functional Theory and Single Crystal X-ray Studies on Some Bis-Chalcone Derivatives

Density Functional Theory and Single Crystal X-ray Studies on Some Bis-Chalcone Derivatives

A mild, simple, and efficient approach to the synthesis of some novel 7-benzylidene-2,3-diphenyl-3,3a,4,5,6,7-hexahydro-2H-indazole derivatives

A novel cluster of C5-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold

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