0000000000291257
AUTHOR
Jamal Lasri
Synthesis, molecular structure and stability of fused bicyclic Δ4-1,2,4-oxadiazoline Pt(II) complexes
Abstract The reaction of trans -[PtCl 2 (NCR) 2 ] (R 1 = CH 2 CO 2 Me ( 1a ), R 2 = CH 2 Cl ( 1b )) with pyrroline N -oxide − O + N CHCH 2 CH 2 C Me 2 ( 4 ), at room temperature for 15 min, furnishes via [3+2] cycloaddition the fused bicyclic Δ 4 -1,2,4-oxadiazoline Pt(II) complexes trans- [PtCl 2 { N C(R)O N C(H)CH 2 CH 2 C Me 2 } 2 ] (R 1 = CH 2 CO 2 Me ( 5a ), R 2 = CH 2 Cl ( 5b )). Compounds 5a and 5b were refluxed in CH 2 Cl 2 for 1 week to afford the derived ketoimine Pt(II) complexes trans- [PtCl 2 {N(C( O)(R)) C CH 2 CH 2 C(Me 2 ) N H} 2 ] (R 1 = CH 2 CO 2 Me ( 6a ), R 2 = CH 2 Cl ( 6b )), respectively, as a result of the N–O bond cleavage of the oxadiazoline ring in 5 . The c…
Synthesis, crystal structure, DFT and biological activity of E-pyrene-1-carbaldehyde oxime and E-2-naphthaldehyde oxime
Abstract The aldoximes E-pyrene-1-carbaldehyde oxime 1 and E-2-naphthaldehyde oxime 2 were synthesized, in ca. 90% yield, by treatment of pyrene-1-carbaldehyde or 2-naphthaldehyde, respectively, with hydroxylamine hydrochloride and sodium carbonate in MeOH. Compounds 1 and 2 were characterized by IR, 1H and 13C{1H} NMR spectroscopies, elemental analyses and single crystal X-ray diffraction (in the case of 1). The studied system (compound 1) showed significant amounts of H⋯H (44.4%), C⋯H (25.4%) and C⋯C (13.3%) intermolecular interactions in addition to the short N⋯H (5.9%) and O⋯H (6.2%) intermolecular interactions. These interactions affect the molecular packing of the studied system in th…
PtII versus PdII-assisted [2+3] cycloadditions of nitriles and nitrone. Synthesis of nitrile-derived arylamido platinum(II) and Δ4-1,2,4-oxadiazoline palladium(II) complexes
Abstract The reactions of bis(organonitrile) platinum(II) complexes trans-[PtCl2(N CR)2] (R = C6H4(p-HC O), CH2C6H4(p-CH3)) with pyrroline N-oxide −O+N CHCH2CH2CMe2 afford arylamido platinum(II) complexes trans-[PtCl2{(O CR)N CCH2CH2CMe2NH}2] (R = C6H4(p-HC O) (1), CH2C6H4(p-CH3) (2)). The spectral data of 1 and 2 show that the oxadiazoline rings in both cases have opened by a spontaneous N O bond cleavage to form (Z)-p-formyl-N-(5,5-dimethylpyrrolidin-2-ylidene)benzamide or (Z)-N-(5,5-dimethylpyrrolidin-2-ylidene)-2-p-tolylacetamide ligands, respectively, where the N-atoms of the benzamide or acetamide moieties coordinate to platinum(II) metal centre in trans positions. However, the reacti…
Crystal and molecular structure studies of (Z)-N-methyl-C-4-substituted phenyl nitrones by XRD, DFT, FTIR and NMR methods
Abstract (Z)-N-methyl-C-4-substituted phenyl nitrones –O+N(Me)=C(H)R (Z-2a R = 4-ClC6H4, Z-2b R = 4-NO2C6H4, Z-2c R = 4-CH3OC6H4) were synthesized and characterized by elemental analyses, FTIR, 1H, 13C and DEPT-135 NMR spectroscopy and also by single crystal X-ray diffraction (in the case of Z-2a and Z-2b). The geometries of the nitrone molecules Z-2a, Z-2b and Z-2c and their E-isomers; (E)-N-methyl-C-4-chlorophenyl nitrone E-2a, (E)-N-methyl-C-4-nitrophenyl nitrone E-2b and (E)-N-methyl-C-4-methoxyphenyl nitrone E-2c were optimized using density functional theory (DFT) at the B3LYP/6-311++G(d,p) level of theory. The theoretical vibrational frequencies obtained by DFT calculations are in go…
A Facile Synthesis of New 3-Substituted-2,3- dihydropyrido[3,2-d]pyrimidine-2,4-diones
Abstract Pyrido[3,2-d]pyrimidine-2,4-diones derivatives have been synthesized in good yields by two efficient synthetic routes, the first one through an hetero-cyclization on the ureas derivatives 3a–e under alkaline conditions, the second one by condensation of the isocyanate 2 with various arylalkylamines in pyridine.
Synthesis and evaluation of 2-tosylamino and 2-tosyliminopyrimidine derivatives as inhibitors of some leukocyte functions
Abstract We have studied the potential anti-inflammatory effects of 20 2-tosylamino and 2-tosyliminopyrimidine new derivatives in human neutrophils. We have evaluated their interference with some leukocyte functions and 5-lipoxygenase activity. All the compounds reduced neutrophil degranulation process at concentrations in the μM range. Besides, compounds with a phenolic substitution inhibited leukotriene B 4 biosynthesis in neutrophils and decreased the cell-free 5-lipoxygenase activity. This study demonstrates that 2-tosylamino and 2-tosyliminopyrimidine derivatives can reduce the activation of neutrophil cells which may have relevance for the modulation of the inflammatory response.
Efficient synthesis of novel pyrido[3,2-d]pyrimidine-2,4-diones
Abstract A series of pyrido[3,2- d ]pyrimidine-2,4-diones 5a – g have been synthesized through conversion of 2,3-pyridinedicarboxylic anhydride 1 into half-ester 2 , subsequent Curtius rearrangement and further reaction with amino acids.
Crystal structure oftrans-dichloridobis[N-(5,5-dimethyl-4,5-dihydro-3H-pyrrol-2-yl-κN)acetamide]palladium(II) dihydrate
The title complex, [PdCl2(C8H14N2O)2]·2H2O, was obtained by N–O bond cleavage of the oxadiazoline rings of thetrans-[dichlorido-bis(2,5,5-trimethyl-5,6,7,7a-tetrahydropyrrolo[1,2-b][1,2,4]oxadiazole-N1)]palladium(II) complex. The palladium(II) atom exhibits an almost square-planar coordination provided by twotrans-arranged chloride anions and a nitrogen atom from each of the two neutral organic ligands. In the crystal, N—H...O, O—H...O and O—H...Cl hydrogen bonds link complex molecules into double layers parallel to thebcplane.
Synthesis, X-ray structure, Hirshfeld analysis, and DFT studies of a new Pd(II) complex with an anionic s-triazine NNO donor ligand
A new Pd(II) complex, [Pd(Triaz)Cl], with the hydrazono-s-triazine ligand, 2,4-di-tert-butyl-6-((2-(4-morpholino-6-(phenylamino)-1,3,5-triazin-2-yl)hydrazono)methyl)phenol, was synthesized by the reaction of PdCl2 with the organic ligand (1:1) in acetone under isothermal conditions. The molecular structure of the [Pd(Triaz)Cl] complex was determined using FTIR and 1H NMR spectroscopic techniques, and single-crystal X-ray diffraction. Moreover, using Hirshfeld surface analysis, the percentages of the intermolecular interactions were determined. The obtained values were 60.6%, 11.6%, 8.1%, 3.6%, and 5.0% for the H⋯H, C⋯H, O⋯H, N⋯H, and Cl⋯H interactions, respectively. Among them, the O⋯H, C⋯H…
A New Pt(II) Complex with Anionic s-Triazine Based NNO-Donor Ligand: Synthesis, X-ray Structure, Hirshfeld Analysis and DFT Studies
The reaction of PtCl2 with s-triazine-type ligand (HTriaz) (1:1) in acetone under heating afforded a new [Pt(Triaz)Cl] complex. Single-crystal X-ray diffraction analysis showed that the ligand (HTriaz) is an NNO tridentate chelate via two N-atoms from the s-triazine and hydrazone moieties and one oxygen from the deprotonated phenolic OH. The coordination environment of the Pt(II) is completed by one Cl−1 ion trans to the Pt-N(hydrazone). Hirshfeld surface analysis showed that the most dominant interactions are the H···H, H···C and O···H intermolecular contacts. These interactions contributed by 60.9, 11.2 and 8.3% from the…
Intermolecular and Intramolecular Transamidation Reactions
The amide functional group is resonance stabilised and direct reaction with amines is known to be difficult. Facile amide exchange reactions would enable the synthesis of important new amide based molecules, therefore transamidation reactions represent an important step in this direction. In order to ensure a transamidation reaction takes place, special requirements and conditions are required. According to the different structural characteristics of the carbox-amide group and types of activation, the most relevant examples of this reaction will be reviewed.
Synthesis, X-ray structure, Hirshfeld analysis, and DFT studies of a new Pd(II) complex with an anionic s-triazine NNO donor ligand
Abstract A new Pd(II) complex, [Pd(Triaz)Cl], with the hydrazono-s-triazine ligand, 2,4-di-tert-butyl-6-((2-(4-morpholino-6-(phenylamino)-1,3,5-triazin-2-yl)hydrazono)methyl)phenol (HTriaz), was synthesized by the reaction of PdCl2 with the organic ligand (1:1) in acetone under isothermal conditions. The molecular structure of the [Pd(Triaz)Cl] complex was determined using FTIR and 1H NMR spectroscopic techniques, and single-crystal X-ray diffraction. Moreover, using Hirshfeld surface analysis, the percentages of the intermolecular interactions were determined. The obtained values were 60.6%, 11.6%, 8.1%, 3.6%, and 5.0% for the H⋯H, C⋯H, O⋯H, N⋯H, and Cl⋯H interactions, respectively. Among …
Unprecedented intermolecular transamidation reaction of N-carbamoylmethyl-N'-tosylguanidines.
[reaction: see text] N-Carbamoylmethyl-N'-tosyl guanidine 2 reacts easily with primary alkylamines to afford substituted carboxamides 3. The reaction proceeds via a five-membered-ring intermediate 5, which could be isolated, and features a rare example of an intermolecular transamidation reaction under mild conditions.
Synthesis ofN-Tosylguanidinesby Ring Cleavage of 1,2-Dihydro-2-tosyliminopyrimidines
The present communication discloses a new synthetic method for the preparation of N-tosylguanidines in high yields by ring cleavage of 1,2-dihydro-2-tosyliminopyrimidines with methyl- amine.
Synthesis and characterization of ferrocene-based Schiff base and ferrocenecarboxaldehyde oxime and their adsorptive removal of methyl blue from aqueous solution
The ferrocene-based Schiff base 3 was synthetized by reaction of ferrocenecarboxaldehyde 1 with 4-aminoantipyrine 2. However, the reaction of 1 with hydroxylamine affords ferrocenecarboxaldehyde oxime 4. Compounds 3 and 4 were fully characterized by IR, 1H, 13C and DEPT-135 NMR spectroscopy, elemental analyses and also by single crystal X-ray diffraction. Compounds 3 and 4 were used to remove anionic methyl blue dye from wastewater. The results established that both compounds have high adsorption capacity towards methyl blue. Langmuir adsorption capacity of compound 4 (464 mmol/g) is much higher than that of compound 3 (193 mmol/g) at 25 °C. The kinetics data was fitted well pseudo-second-o…
Synthesis, structure and in vitro anticancer activity of Pd(II) complexes of mono- and bis-pyrazolyl-s-triazine ligands
Abstract The square planar complexes [Pd(MPT)Cl2] (1) and [Pd(BPT)Cl]ClO4 (2) were synthesized by the reaction of the 4,4′-(6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,3,5-triazine-2,4-diyl)dimorpholine (MPT) and N-methyl-N-phenyl-4,6-di(1H-pyrazol-1-yl)-1,3,5-triazin-2-amine (BPT) ligands with PdCl2 (1:1) in acetone under thermal conditions, respectively. In complex 1, the Pd(II) ion is coordinated with the MPT ligand as a bidentate NN-chelate, augmented with two chloride ligands in cis positions. In complex 2, the Pd(II) ion is coordinated with the BPT ligand as a tridentate N-chelate in a pincer fashion, together with one chloride ligand. Hirshfeld analysis indicated that complex 1 is packed with…
Synthesis, molecular structure, spectroscopic properties and stability of (Z)-N-methyl-C-2,4,6-trimethylphenylnitrone.
Abstract New N-methyl-C-2,4,6-trimethylphenylnitrone 1 has been synthesized starting from N-methylhydroxylamine and mesitaldehyde. The product was fully characterized using different spectroscopic techniques; FTIR, NMR, UV–Vis, high resolution mass spectrometry and X-ray diffraction. The relative stability and percent of population of its two possible isomers (E and Z) were calculated using the B3LYP/6-311++G(d,p) method in gas phase and in solution. In agreement with the X-ray results, it was found that Z-isomer is the most stable one in both gas phase and solution. The molecular geometry, vibrational frequencies, gauge-including atomic orbital (GIAO), and chemical shift values were also c…
Synthesis and characterization of ferrocene-based Schiff base and ferrocenecarboxaldehyde oxime and their adsorptive removal of methyl blue from aqueous solution
Abstract The ferrocene-based Schiff base 3 was synthetized by reaction of ferrocenecarboxaldehyde 1 with 4-aminoantipyrine 2. However, the reaction of 1 with hydroxylamine affords ferrocenecarboxaldehyde oxime 4. Compounds 3 and 4 were fully characterized by IR, 1H, 13C and DEPT-135 NMR spectroscopy, elemental analyses and also by single crystal X-ray diffraction. Compounds 3 and 4 were used to remove anionic methyl blue dye from wastewater. The results established that both compounds have high adsorption capacity towards methyl blue. Langmuir adsorption capacity of compound 4 (464 mmol/g) is much higher than that of compound 3 (193 mmol/g) at 25 °C. The kinetics data was fitted well pseudo…
Pt(II) and Pd(II)-assisted coupling of nitriles and 1,3-diiminoisoindoline : Synthesis and luminescence properties of (1,3,5,7,9-pentaazanona-1,3,6,8-tetraenato)Pt(II) and Pd(II) complexes
Treatment of trans-[PtCl2(NCR)2] 1 (R = Me (1a), Et (1b), o-ClC6H4 (1c), p-ClC6H4 (1d), p-(HCdouble bond; length as m-dashO)C6H4 (1e), p-O2NC6H4CH2 (1f)) with 1,3-diiminoisoindoline HNdouble bond; length as m-dashCC6H4C(NH)double bond; length as m-dashNH 2 gives access to the corresponding (1,3,5,7,9-pentaazanona-1,3,6,8-tetraenato)Pt(II) complexes [PtCl{NHdouble bond; length as m-dashC(R)Ndouble bond; length as m-dashC(C6H4)NCdouble bond; length as m-dashNC(R)double bond; length as m-dashNH}] 3a–f, in good yields (65–70%). The reaction of trans-[PdCl2(NCMe)2] 4a with 2 furnishes (1,3,5,7,9-pentaazanona-1,3,6,8-tetraenato)Pd(II) complex [PdCl{NHdouble bond; length as m-dashC(Me)Ndouble bond…
Synthesis, X-ray Crystal Structure and Antimicrobial Activity of Unexpected Trinuclear Cu(II) Complex from s-Triazine-Based Di-Compartmental Ligand via Self-Assembly
The synthesis and X-ray crystal structure of the trinuclear [Cu3(HL)(Cl)2(NO3)(H2O)5](NO3)2 complex of the s-triazine-based di-compartmental ligand, 2-methoxy-4,6-bis(2-(pyridin-2-ylmsethylene)hydrazinyl)-1,3,5-triazine (H2L), are presented. The Cu1 and Cu2 are penta-coordinated with CuN3ClO coordination environment, distorted square pyramidal coordination geometry while Cu3 is hexa-coordinated with CuN2O4 coordination sphere, and distorted octahedral geometry. The complex crystallized in the primitive P-1 triclinic crystal system with two molecular units per unit cell. Its packing is dominated by the O–H (35.5%) and Cl–H (8.8%) hydrogen bonding interactions as well as the π–π stacking (2.3…
CCDC 1970751: Experimental Crystal Structure Determination
Related Article: Jamal Lasri, Saied M. Soliman, Sobhy E. Elsilk, Matti Haukka, Ayman El-Faham|2020|J.Mol.Struct.|1207|127848|doi:10.1016/j.molstruc.2020.127848
CCDC 1835082: Experimental Crystal Structure Determination
Related Article: Jamal Lasri, Ali I. Ismail, Matti Haukka, Saied M. Soliman|2015|Spectrochim.Acta,Part A|136|1857|doi:10.1016/j.saa.2014.10.096
CCDC 1482397: Experimental Crystal Structure Determination
Related Article: Jamal Lasri, Naser Eltaher Eltayeb, Matti Haukka, Yousef Alghamdi|2017|J.Mol.Struct.|1128|70|doi:10.1016/j.molstruc.2016.08.058
CCDC 1482396: Experimental Crystal Structure Determination
Related Article: Jamal Lasri, Naser Eltaher Eltayeb, Matti Haukka, Yousef Alghamdi|2017|J.Mol.Struct.|1128|70|doi:10.1016/j.molstruc.2016.08.058
CCDC 1864425: Experimental Crystal Structure Determination
Related Article: Jamal Lasri, Naser Eltaher Eltayeb, Matti Haukka, Bandar A. Babgi|2019|Polyhedron|158|65|doi:10.1016/j.poly.2018.10.057
CCDC 1812970: Experimental Crystal Structure Determination
Related Article: Jamal Lasri, Abeer S. Elsherbiny, Naser Eltaher Eltayeb, Matti Haukka, Mohamed E. El-Hefnawy|2018|J.Organomet.Chem.|866|21|doi:10.1016/j.jorganchem.2018.04.004
CCDC 1989545: Experimental Crystal Structure Determination
Related Article: Saied M. Soliman, Jamal Lasri, Matti Haukka, Adel Elmarghany, Abdullah Mohammed Al-Majid, Ayman El-Faham, Assem Barakat|2020|J.Mol.Struct.|1217|128463|doi:10.1016/j.molstruc.2020.128463
CCDC 1998456: Experimental Crystal Structure Determination
Related Article: Jamal Lasri, Hessa H. Al-Rasheed, Ayman El-Faham, Matti Haukka, Nael Abutaha, Saied M. Soliman|2020|Polyhedron|187|114665|doi:10.1016/j.poly.2020.114665
CCDC 1518110: Experimental Crystal Structure Determination
Related Article: Jamal Lasri, Bruno Pedras, Matti Haukka, Mário N. Berberan-Santos|2017|Polyhedron|133|195|doi:10.1016/j.poly.2017.05.036
CCDC 1812968: Experimental Crystal Structure Determination
Related Article: Jamal Lasri, Abeer S. Elsherbiny, Naser Eltaher Eltayeb, Matti Haukka, Mohamed E. El-Hefnawy|2018|J.Organomet.Chem.|866|21|doi:10.1016/j.jorganchem.2018.04.004
CCDC 1998457: Experimental Crystal Structure Determination
Related Article: Jamal Lasri, Hessa H. Al-Rasheed, Ayman El-Faham, Matti Haukka, Nael Abutaha, Saied M. Soliman|2020|Polyhedron|187|114665|doi:10.1016/j.poly.2020.114665