Synthesis, structure combined with conformational analysis, biological activities and docking studies of bis benzylidene cyclohexanone derivatives

Lotfy, Gehad; Said, Mohamed M.; Ashry, El Sayed H. El; Tamany, El Sayed H. El; Aziz, Yasmine M. Abdel; Soliman, Saied M.; Barakat, Assem

doi:10.1016/j.jscs.2017.04.002

Cited by 10 publications

(5 citation statements)

References 25 publications

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“…The compounds DBC and BCC were prepared according to the general procedure reported in the literature. 19 According to the procedure, a mixture of cyclohexanone, 6 and 12 mmol of the appropriate aromatic aldehyde (benzaldehyde in the case of DBC and 4-chlorobenzaldehyde in the case of BCC ) in ethanol (20 mL) was stirred at room temperature until both reagents were dissolved. To this reaction mixture, a solution of NaOH (14 mmol) in 20 mL of the water–ethanol mixture (1:1) was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Structural, and Intriguing Electronic Properties of Symmetrical Bis-Aryl-α,β-Unsaturated Ketone Derivatives

et al. 2022

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Three symmetrical bis-aryl-α,β-unsaturated ketone derivatives, 2,6-di((E)-benzylidene)-cyclohexan-1-one (DBC), 2,6bis((E)-4-chlorobenzylidene)cyclohexan-1-one (BCC), and (1E,1′E,4E,4′E)-5,5′-(1,4-phenylene)bis(2-methyl-1-phenylpenta-1,4-dien-3-one) (PBMP), have been prepared using the aldol condensation approach toward ketones having two enolizable sites. The structures of DBC, BCC, and PBMP have been resolved via spectrometric methods. Moreover, the crystal structure of PBMP is determined by the single-crystal X-ray diffraction (SC-XRD) technique, which revealed that the PBMP molecular assembly is stabilized by the intermolecular C−H•••O bonding and C− O•••π and weak T-shaped offset π•••π stacking interactions. The Hirshfeld surface analysis (HSA) of the PBMP crystal structure was performed as well, and the results were compared with the results of DBC and BCC. The density functional theory (DFT) study results revealed that the longer conjugated molecule of PBMP has smaller but still quite significant HOMO−LUMO gaps compared to the smaller molecules of BCC and DBC.The natural population analysis (NPA) and natural bonding orbital (NBO) analysis were performed. Accordingly, the hydrogen bonding and dipole−dipole interactions stabilize the crystal structures of these compounds. Additionally, the NBO analysis showed numerous high-energy stabilizing interactions for the PBMP compound due to the presence of numerous delocalized and relatively easily polarizable π-electrons, thus implying its significant thermodynamic stability. According to the global reactivity parameter (GRP) analysis, the compounds BCC and DBC are relatively stable in redox processes and have high thermodynamic stability and relatively lower reactivity in general. The molecular electrostatic potential (MEP) analysis results imply potential formation of the intermolecular hydrogen bonding and dispersion interactions, which stabilizes the crystal structures of these compounds.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Structural, and Intriguing Electronic Properties of Symmetrical Bis-Aryl-α,β-Unsaturated Ketone Derivatives

et al. 2022

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“…In‐silico studies, including Docking and Molecular dynamic simulation unequivocally affirmed the in‐vitro investigations. The antidiabetic activity of some relevant Benzylidene‐Cyclohexanone derivatives has been reported elsewhere, suggesting the hypothesis for its anti‐diabetic application [39] . The hydrophobic nature and the inability to make adequate hydrogen bonding interactions of bare BBC constrain its utility in aqueous environments.…”

Section: Introductionmentioning

confidence: 92%

“…The antidiabetic activity of some relevant Benzylidene-Cyclohexanone derivatives has been reported elsewhere, suggesting the hypothesis for its anti-diabetic application. [39] The hydrophobic nature and the inability to make adequate hydrogen bonding interactions of bare BBC constrain its utility in aqueous environments. Nevertheless, the ongoing efforts persist in scrutinizing various parameters meticulously to assess the viability of its application in antidiabetic contexts.…”

Section: Introductionmentioning

confidence: 99%

In‐Vitro Investigation of the α‐Amylase Inhibition Activity of Bare Bis‐Benzylidene‐Cyclohexanone Synthesized by a Highly Selective Solvent‐Free Route

Veigas,

Ravi,

Narasimhaiaha

et al. 2023

ChemistrySelect

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Current work reports the highly selective, solvent‐free synthesis of an endorsed bioactive compound, Bis benzylidine cyclohexanone (BBC) through solid acid catalysed cross aldol condensation route and checks its in‐vitro bio activity. The catalytic support (Multiwalled carbon nanotube) employed was synthesized through the highly sophisticated catalytic chemical vapor deposition (CVD) method and simple mechanical grinding strategy was adopted to decorate sulfonic acid on the support. The C1s X‐ray photoelectron peak of at 290.3 eV confirms the effective interaction of sulfonic acid with MWCNT. The sharp and intense desorption peaks observed at approximately 528.7 °C and 655.15 °C in the TPD analysis unmistakably substantiate the strong acidity of the synthesized system. The alpha amylase inhibition activity of the synthesized compound was calculated to be around 88.5 %, which is in par with the commercial drug as it could inhibit only 96 %. Further, the in‐silico (Docking and Molecular Dynamic Simulation) investigations unveiled a new target site for the compound and this can further be studied in detail to advance the applications in drug design. Detailed scrutiny of various parameters was conducted to validate the bioactivity and pharmaceutical potential of the synthesized compound.

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“…This IC 50 value was found to be comparable to the common antileishmanial agents such as pentamidine and amphotericin B with IC 50 values of 5.09 and 0.29 μg/mL, respectively, and it was suggested that the activity of 43 might be due to its cytotoxic properties. [ 160 ] It was concluded that the p ‐CF 3 in the diarylpentanoids must be much stronger than the other analog, which consist of a p ‐F substituent that presumably has the potential to form more hydrogen bonds with the active site, thus causing its stronger antileishmanial potential.…”

Section: Bioactivity Of Diarylpentanoids: Anti‐infective Propertiesmentioning

confidence: 99%

Diarylpentanoids, the privileged scaffolds in antimalarial and anti‐infectives drug discovery: A review

Ramli,

Mohd Faudzi

2023

Archiv der Pharmazie

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Asia is a hotspot for infectious diseases, including malaria, dengue fever, tuberculosis, and the pandemic COVID‐19. Emerging infectious diseases have taken a heavy toll on public health and the economy and have been recognized as a major cause of morbidity and mortality, particularly in Southeast Asia. Infectious disease control is a major challenge, but many surveillance systems and control strategies have been developed and implemented. These include vector control, combination therapies, vaccine development, and the development of new anti‐infectives. Numerous newly discovered agents with pharmacological anti‐infective potential are being actively and extensively studied for their bioactivity, toxicity, selectivity, and mode of action, but many molecules lose their efficacy over time due to resistance developments. These facts justify the great importance of the search for new, effective, and safe anti‐infectives. Diarylpentanoids, a curcumin derivative, have been developed as an alternative with better bioavailability and metabolism as a therapeutic agent. In this review, the mechanisms of action and potential targets of antimalarial drugs as well as the classes of antimalarial drugs are presented. The bioactivity of diarylpentanoids as a potential scaffold for a new class of anti‐infectives and their structure–activity relationships are also discussed in detail.

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Synthesis, structure combined with conformational analysis, biological activities and docking studies of bis benzylidene cyclohexanone derivatives

Cited by 10 publications

References 25 publications

Synthesis, Structural, and Intriguing Electronic Properties of Symmetrical Bis-Aryl-α,β-Unsaturated Ketone Derivatives

Synthesis, Structural, and Intriguing Electronic Properties of Symmetrical Bis-Aryl-α,β-Unsaturated Ketone Derivatives

In‐Vitro Investigation of the α‐Amylase Inhibition Activity of Bare Bis‐Benzylidene‐Cyclohexanone Synthesized by a Highly Selective Solvent‐Free Route

Diarylpentanoids, the privileged scaffolds in antimalarial and anti‐infectives drug discovery: A review

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