Design, synthesis, characterization, computational study and in-vitro antioxidant and anti-inflammatory activities of few novel 6-aryl substituted pyrimidine azo dyes

Unnisa, Aziz; Abouzied, Amr S.; Anupama, B.; Lakshmi, K.; Hussain, Talib; Kunduru, Rama Devi; Banu, Humera; Fatima, Syeda Bushra; Hussian, Arshad; Selvarajan, Kesavanarayanan Krishnan

doi:10.1016/j.arabjc.2020.09.050

Cited by 34 publications

(19 citation statements)

References 26 publications

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“…In fact, the sec-butyl group contributes 66.77 A 3 and the isopropyl 49.97 A 3 to the macrolactone molecule according to the Molinspiration server calculations. This method for predicting molecular geometries is very robust and relies on the contributions of each group for the calculation of molecular volume [ 92 ]. The efficient molecular docking algorithms used consider the spatial configuration of functional groups, as well as the incidence of molecular interactions by hydrogen bonding, rotation and steric shocks [ [55] , [56] , [57] , [58] , [59] , [60] , [61] ].…”

Section: Resultsmentioning

confidence: 99%

Comparative study of the interaction of ivermectin with proteins of interest associated with SARS-CoV-2: A computational and biophysical approach

González

Hurtado-León

Lossada

et al. 2021

Biophysical Chemistry

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The SARS-CoV-2 pandemic has accelerated the study of existing drugs. The mixture of homologs called ivermectin (avermectin-B1a [HB1a] + avermectin-B1b [HB1b]) has shown antiviral activity against SARS-CoV-2 in vitro . However, there are few reports on the behavior of each homolog. We investigated the interaction of each homolog with promising targets of interest associated with SARS-CoV-2 infection from a biophysical and computational-chemistry perspective using docking and molecular dynamics. We observed a differential behavior for each homolog, with an affinity of HB1b for viral structures, and of HB1a for host structures considered. The induced disturbances were differential and influenced by the hydrophobicity of each homolog and of the binding pockets. We present the first comparative analysis of the potential theoretical inhibitory effect of both avermectins on biomolecules associated with COVID-19, and suggest that ivermectin through its homologs, has a multiobjective behavior.

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Section: Resultsmentioning

confidence: 99%

Comparative study of the interaction of ivermectin with proteins of interest associated with SARS-CoV-2: A computational and biophysical approach

González

Hurtado-León

Lossada

et al. 2021

Biophysical Chemistry

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“…The reactivity of thiazolopyrimidinone 2 towards malononitrile dimmer was investigated. Thus, heating compound 2 with malononitrile dimmer in acetic acid and ammonium acetate yielded [8-acetyl-3-cyano-9-(3-hydroxyphenyl)-7-methyl-4-phenyl-9H-pyrido[2 0 ,3 0 :4,5][1,3]thiazolo[3,2-a] pyrimidin-2 (1H)-ylidene]malononitrile (3). The formation of compound 3 proceeds by Michael addition of the active methylene of malononitrile dimmer on the double bond of benzylidene followed by cyclization and aromatization through intermediates formation of A and B (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…3,4-Dihydropyrimidin-2(1H)-ones are known to have important pharmacological activities, such as anti HIV, 1 antihypertensive, 2 antioxidant, 3 anti-inflammatory, 4 and anticancer. 5 Italian chemist, Pietro Biginelli, introduced a simple method for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives for the first time in 1893.…”

Section: Introductionmentioning

confidence: 99%

Efficient access to some new pyrimidine derivatives and their antimicrobial evaluation

El-mahdy

Farouk

2021

Journal of Heterocyclic Chem

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1-[4-(3-Hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]eth anone (1) was used as a precursor for heterocyclic synthesis. Condensation of compound 1 with monochloroacetic acid and benzaldehyde gave thiazolopyrimidine 2 which in turn underwent cyclization with malononitrile dimmer to afford malononitrile derivative 3. Also, the reaction of compound 1 with benzaldehyde under a basic condition produced chalcone 4. Chalcone 4 can be used as a key intermediate for further preparation of heterocyclic compounds. In addition, compound 1 was allowed to react with malononitrile dimmer and/or ethyl chloroacetate to give pyrimidines 8 and 9, respectively.Alkylation of compound 8 with ethyl chloroacetate afforded S-alkylated product 10 which was treated with hydrazine hydrate to yield the hydrazino derivative 11. Alternative synthesis of compound 10 was taken place through reaction of compound 9 with malononitrile dimmer. The biological activity of the synthesized compounds was investigated. Compounds 1, 4, 5, and 8 recorded high activities against Gram positive bacteria (S. aureus). Structures of the new synthesized compounds were elucidated by elemental analysis and spectral data.

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“…In addition, they have found many applications in different fields such as non-linear optics (Dudek et al, 2020), optical storage (Kovalchuk et al, 2020), photoluminescence (He et al, 2019), chemosensors (Akram et al, 2020) and magnetism (Nandi et al, 2021). They are used not only in physics but also in the biomedical and pharmacological fields as they can offer new therapeutic properties such as antiviral (Chhetri et al, 2021), antimicrobial (Kyei et al, 2020), anti-inflammatory and antioxidant (Unnisa et al, 2020). On the other hand, azo-naphthol derivatives form a widely studied class of azo compounds.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(5-chloro-2-hydroxyphenyl)hydrazin-1-ylidene]naphthalen-2(1H)-one

Bougueria¹,

Chetioui²,

Bensegueni³

et al. 2021

Acta Cryst E

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The title compound, C16H11ClN2O2, was obtained by diazotization of 2-amino-4-chlorophenol followed by a coupling reaction with β-naphthol. There are two molecules (A and B) in the asymmetric unit. The crystal structure features only one type of intermolecular interaction, that is strong hydrogen bonds involving the hydroxyl group. The naphthol and phenol fragments attached to the C=N—N— moiety exhibit an s-trans conformation. In addition, those fragments are almost coplanar, subtending a dihedral angle of 13.11 (2)° in molecule A and 10.35 (2)° in molecule B. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (32.1%), C...H/H...C (23.1%), Cl...H/H...Cl (15.2%), O...H/H...O (12.8%) and C...C (9%) contacts.

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Design, synthesis, characterization, computational study and in-vitro antioxidant and anti-inflammatory activities of few novel 6-aryl substituted pyrimidine azo dyes

Cited by 34 publications

References 26 publications

Comparative study of the interaction of ivermectin with proteins of interest associated with SARS-CoV-2: A computational and biophysical approach

Comparative study of the interaction of ivermectin with proteins of interest associated with SARS-CoV-2: A computational and biophysical approach

Efficient access to some new pyrimidine derivatives and their antimicrobial evaluation

Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(5-chloro-2-hydroxyphenyl)hydrazin-1-ylidene]naphthalen-2(1H)-one

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