Synthesis, anti-inflammatory evaluation in vivo and docking studies of some new 5-(benzo[b]furan-2-ylmethyl)-6-methyl-pyridazin- 3(2H) -one derivatives

Boukharsa, Youness; Lakhlili, Wiame; Harti, Jaouad El; Meddah, Bouchra; Tiendrebeogo, Ramata Yvette; Taoufik, Jamal; Faouzi, My El Abbés; Ibrahimi, Azeddine; Ansar, Mʼhammed

doi:10.1016/j.molstruc.2017.09.092

Cited by 14 publications

(10 citation statements)

References 37 publications

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“…Pyridazines are an important family of six-membered aromatic heterocycles containing two nitrogen atoms. Pyridazinone is an important pharmacophore possessing a wide range of biological activities including antitumor (Bouchmaa et al, 2018(Bouchmaa et al, , 2019, anti-inflammatory (Boukharsa et al, 2018), antihypertensive (Siddiqui et al, 2011), antidepressant (Boukharsa et al, 2016), anti-HIV (Livermore et al, 1993), antihistaminic (Tao et al 2012), analgesic (Gö kçe et al, 2009) and anticonvulsant (Partap et al, 2018) and is used in glucan synthase inhibitors (Zhou et al, 2011) and herbicidal agents (Asif et al, 2013). The chemistry of pyridazinones has been an interesting field of study for decades and this nitrogen heterocycle has become a scaffold of choice for the development of potential drug candidates (Dubey et al, 2015;Thakur et al, 2010).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-[(E)-2-phenylethenyl]pyridazin-3(2H)-one

et al. 2021

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The title pyridazinone derivative, C19H14Cl2N2O, an important pharmacophore with a wide variety of biological applications is not planar, the chlorophenyl and pyridazinone rings being almost perpendicular, subtending a dihedral angle of 85.73 (11)°. The phenyl ring of the styryl group is coplanar with the pyridazinone ring [1.47 (12)°]. In the crystal, N—H...O hydrogen bonds form inversion dimers with an R 2 2(8) ring motif and C—H...Cl hydrogen bonds also occur. The roles of the intermolecular interactions in the crystal packing were clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (37.9%), C...H/H...C (18.7%), Cl...H/ H...Cl (16.4%) and Cl...C/C...Cl (6.7%) contacts.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-[(E)-2-phenylethenyl]pyridazin-3(2H)-one

et al. 2021

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“…Pyridazinone derivatives are a class of nitrogenous heterocyclic compounds that have attracted considerable attention because of their prospective pharmacological and medicinal properties as anti-inflammatory (Boukharsa et al, 2018), antitumor (Bouchmaa et al, 2018(Bouchmaa et al, , 2019, antifungal (Rozada et al, 2020), antidepressant (Boukharsa et al, 2016), antitubercular, anticonvulsant (Asif et al, 2020) and antiviral (El-Shanbaky et al, 2021) agents. In addition, pyridazinones demonstrate some interesting physicochemical properties (Daoui et al, 2020a;El Kalai et al, 2021a,b) and some studies have shown that these compounds are good corrosion inhibitors (Chelfi et al, 2020).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one

Daoui¹,

Muwafaq²,

Çınar³

et al. 2022

Acta Cryst E

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The pyridazine ring in the title compound, C20H17ClN2O3, adopts a screw-boat conformation. The whole molecule is flattened, the dihedral angles subtended by the least-squares plane of the central aromatic ring with those of the terminal benzene and pyridazine rings being 15.18 (19) and 11.23 (19)°, respectively. In the crystal, the molecules are linked by pairs of N—H...O bonds into centrosymmetric dimers and by C—H...π contacts into columns. The results of the Hirshfeld surface analysis show that the most prominent interactions are H...H, accounting for 36.5% of overall crystal packing, and H...O/O...H (18.6% contribution) contacts.

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“…Crystal data and refinement details are given in Table 1. Intensity measurements for 1 were measured employing APEX3 [23] at T = 120 K on a Bruker Smart APEX CCD diffractometer equipped using Mo-Kα radiation (λ = 0.71073 Å). Data reduction was performed with SAINT [26] and the absorption correction was conducted with SADABS [26].…”

Section: Single Crystal X-ray Structure Determinationmentioning

confidence: 99%

“…2, in order to ascertain the influence of the methyl group in 1 upon the molecular packing. Further, based on the wide biological interest of pyridazine derivatives, alluded to above, and due to our continuing interests on the synthesis of heterocyclic systems with remarkable anti-inflammatory and anti-diabetic activities [23][24][25], 1 was also evaluated for anti-inflammatory and enzyme inhibitory activities using an α-Glucosidase inhibition assay.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterisation and theoretical studies of a novel pyridazine derivative: Investigations of anti-inflammatory activity and inhibition of α-glucosidase

Zaoui

Ramli

Tan

et al. 2021

Journal of Molecular Structure

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X-ray crystallography on pyridazine 1 (ethyl 2-(3-methyl-4-(4-methylbenzyl)-6-oxopyridazin-1(6H)-yl)acetate) shows the planar pyridazinyl ring to exhibit significant delocalisation of πelectron density over the constituent atoms and to be substituted with oxo, methyl, (4methylphenyl)methyl and N-bound ethylacetate groups. While three of the ring-bound atoms are close to co-planar with the ring, the ethylacetate group is not; the latter exhibits a definitive kink in its conformation. In the molecular packing of 1, helical supramolecular chains along the b-axis are formed through O-and N-methylene-C-H … O(carbonyl) and Omethylene-C-H … π(pyridazinyl) interactions. The chains are connected into a supramolecular layer by π(pyridazinyl) … π(phenyl) interactions. The flat layers stacks along the c-axis 2 without directional interactions between them. The geometry-optimisation of 1 resulted in the straightening of terminal ethylacetate group but no other substantial changes. Computational chemistry shows the most stabilising interactions in the crystal are due to the π(pyridazinyl) … π(phenyl) (-10.7 kcal/mol) followed by O-and N-methylene-C-H … O(carbonyl) (-9.5 and -9.0 kcal/mol, respectively). The most prominent identified interlayer interaction is a weak methylene-C-H•••N(pyridazinyl) contact.Throughout, comparisons are made with the phenyl analogue of 1, namely 2. Most notably, the lattice energy of 1 is approximately 4.1 kcal/mol more stable than that of 2, an observation related to the influence upon the molecular packing exerted by the methyl substituent of 1. Compound 1 exhibits moderate inhibition against α-glucosidase, compared to Acarbose, and weak heatinduced haemolysis inhibition.

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Synthesis, anti-inflammatory evaluation in vivo and docking studies of some new 5-(benzo[b]furan-2-ylmethyl)-6-methyl-pyridazin- 3(2H) -one derivatives

Cited by 14 publications

References 37 publications

Crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-[(E)-2-phenylethenyl]pyridazin-3(2H)-one

Crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-[(E)-2-phenylethenyl]pyridazin-3(2H)-one

Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one

Synthesis, structural characterisation and theoretical studies of a novel pyridazine derivative: Investigations of anti-inflammatory activity and inhibition of α-glucosidase

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