Synthesis, characterization, analgesic and anti-inflammation activity of new phthalazines and their Cu(II) and Zn(II) complexes

Sherif, Yousery E.; Gouda, Moustafa A.; El‐Asmy, Ahmed A.

doi:10.1007/s00044-015-1427-4

Cited by 14 publications

(10 citation statements)

References 24 publications

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“…Among the different nitrogen containing heterocycles, phthalazines play an important role in medicinal chemistry and subsequently have emerged as a pharmacophore. The phthalazine structural motifs have attracted a great deal of interest because of their ready accessibility, diverse chemical reactivity, and wide gamut of biological activities like antibacterial, antifungal, antitumor, anti‐inflammatory, and anticonvulsant activities. In organic synthesis, N ‐protected amino acids are essential key precursors and have been used in many areas, for example, peptide synthesis, medicinal chemistry, as chiral sources, and polymer materials .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel phthalazine derivatives as pharmacological activities

Wasfy

Aly

Behalo

et al. 2019

Journal of Heterocyclic Chem

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Phthalazine derivatives attached to amino acid derivatives were synthesized with high yields. The reaction of phthalazine derivatives with different phthalyl and tosylamino acids such as glycine, alanine, phenylalanine, valine, serine, and threonine in the presence of N,N-dicyclo hexylcarbodiimide (DCC) as a dehydrating agent reagent yielded high yields of the afforded compounds.Phthalylamino acids derivatives were obtained by deprotection of phthalazine derivatives, with the latter heating with hydrazine hydrate. The chemical structures of all phthalazine derivatives were affirmed by elemental analysis and spectral data (IR, MS, 1 HNMR, and 13 C NMR). Screening out and estimation of the synthesized derivatives for their cytotoxic and antioxidant activity were done, and most of them showed powerful activity in comparison with standard drugs.We got all chemical reagents from Sigma-Aldrich. Solvents were purchased from El-Nasr Chemicals in analytical grade. Also, we did thin-layer chromatography (TLC) on all products by using silica gel polyester sheets (Kieselgel 60 F254, 0.20 mm, Merck). All melting points are in degree centigrade (uncorrected). We recorded IR spectra (KBr) at the Microanalytical Center (Faculty of S C H E M E 1 Synthesis of phthalazinone derivative 2 S C H E M E 2 Synthesis of phthalazines derivative (4,5) WASFY ET AL.

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Section: Introductionmentioning

confidence: 99%

Synthesis of novel phthalazine derivatives as pharmacological activities

Wasfy

Aly

Behalo

et al. 2019

Journal of Heterocyclic Chem

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“…This effect was also noted to be independent of its antidepressant effect [57]. Furthermore, copper complexes showed analgesic effects [58]. These data prompted us to consider the possibility that the combined administration of sertraline and copper in the form of the (SerH 2 ) 2 [CuCl 4 ] compound may have antinociceptive activity.…”

Section: Analgesic Propertiesmentioning

confidence: 99%

Evidence of promising biological-pharmacological activities of the sertraline-based copper complex: (SerH2)2[CuCl4]

Martini

Parente

Toledo³

et al. 2017

Journal of Inorganic Biochemistry

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In the current study the ability of copper complex to exert multiple biological activities is combined with the pharmacological action of sertraline (SerHCl, antidepressant drug). The hydrated and anhydrous forms of the tetrachlorocuprate(II) salts, namely (SerH)[CuCl]·½HO and (SerH)[CuCl], were synthesized and characterized by physicochemical methods. The crystal structures were determined by X-ray diffraction methods. The hydrate complex crystallizes in the monoclinic P2 space group with a=8.0807(2) Å, b=36.2781(8) Å, c=12.6576(3) Å, β=95.665(2)°, and Z=4 molecules per unit cell and the un-hydrate in P2 with a=13.8727(6) Å, b=7.5090(3) Å, c=18.618(1) Å, β=104.563(6)°, and Z=2. It has been suggested that Cu(II) ions might be critical in the development of mood disorders, showed potent biocidal activity, and also acted as analgesic adjuvant. To improve sertraline efficiency, the antidepressant and analgesic activities of the complex have been assessed in rats denoting a marked synergistic effect. Antithyroid and antimicrobial activities were also evaluated. Because depressive disorders and hyperthyroidism diseases led to an oxidative stress state, antioxidant capability has also been tested. The complex behaved as a good superoxide radical scavenger (IC=6.3×10M). The ability of the complex to act as bromoperoxidase mimic was assessed. A pseudo-first order constant of k=0.157±0.007min has been determined. The complex evidences promising biological-pharmacological activities and the albumin binding studies showed a K of 2.90×10M showing an improvement in the uptake of sertraline by albumin at 8h incubation (time required for effective interaction of sertraline with the protein).

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“…The studies on structures and properties of metal complex materials have achieved much attention in the past decades [1][2][3][4][5], because they show attractive applications in many ways such as magnetic properties [6][7][8], fluorescence [9][10][11][12], catalytic activities [13][14][15], pharmacological activities [16][17][18], and so on. However, to best of our knowledge, the structure and property of alkaline earth metal complexes have not been studied extensively comparing to transition metal complex.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure and Catalytic Activity of a Novel Ba(II) Complex with Pyridine-2-Carboxaldehyde-2-Phenylacetic Acid Hydrazone Ligand

et al. 2017

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A novel Ba(II) complex, [BaL 2 Cl 2 ] (1) (L = pyridine-2-carboxaldehyde-2-phenylacetic acid hydrazone), has been synthesized using BaCl 2 , pyridine-2-carboxaldehyde and 2-phenylacetohydrazide as raw materials. The structure of 1 has been determined by elemental analysis and X-ray single-crystal diffraction technique. X-ray structural analysis showed that the Ba(II) complex (1) crystallizes in monoclinic, space group P2 1 /c with cell parameters: a = 12.464(3) Å, b = 13.531(3) Å, c = 8.8035(18) Å, β = 95.06(3) •. In 1, the Ba(II) atom is eight-coordinated in a distorted doubly-capped octahedral geometry through four N atoms and two O atoms from two different pyridine-2-carboxaldehyde-2-phenylacetic acid hydrazone ligands and two Cl −. The complex (1) forms a 3D network structure by the interaction of intermolecular N-H•••Cl hydrogen bonds and π•••π stacking of neighboring pyridine rings and benzene rings. The optimum conditions for the benzyl alcohol oxidation reaction using the Ba(II) complex as catalyst was investigated.

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Synthesis, characterization, analgesic and anti-inflammation activity of new phthalazines and their Cu(II) and Zn(II) complexes

Cited by 14 publications

References 24 publications

Synthesis of novel phthalazine derivatives as pharmacological activities

Synthesis of novel phthalazine derivatives as pharmacological activities

Evidence of promising biological-pharmacological activities of the sertraline-based copper complex: (SerH2)2[CuCl4]

Synthesis, Crystal Structure and Catalytic Activity of a Novel Ba(II) Complex with Pyridine-2-Carboxaldehyde-2-Phenylacetic Acid Hydrazone Ligand

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