Synthesis of novel mono- and bis-Schiff bases of morpholine derivatives and the investigation of their antimalarial and antiproliferative activities

Jarrahpour, Aliasghar; Shirvani, Pouria; Sharghi, Hashem; Aberi, Mahdi; Sinou, Véronique; Latour, Christine; Brunel, Jean Michel

doi:10.1007/s00044-015-1455-0

Cited by 17 publications

(16 citation statements)

References 20 publications

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“…The antiproliferative activity of the morpholine-, thiazole-, and pyrrole-condensed derivatives and their precursors were evaluated initially against A2780 ovarian and WM35 melanoma cancer cell lines at 50 μM concentration by monitoring at 24 and 72 h ( Figures S262 and S263 ). While morpholine and pyrrole units are common structural elements in cytotoxic compounds of synthetic or natural origin [ 35 , 36 , 37 , 38 , 39 ], there are fewer reports available on cytotoxic condensed thiazole derivatives [ 40 , 41 ]. The N -chloroacetyl-3-amino-flavan-4-ol derivatives rac - 19a - g and 22a-g exhibited strong antiproliferative activity regardless the stereochemistry against both cell lines at 50 μM concentration, while the related N -acetyl derivatives rac-cis - 24a - e , g or rac-trans - 24a - g were inactive or they had much weaker activity.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

et al. 2020

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Racemic chiral O,N-heterocycles containing 2-arylchroman or 2-aryl-2H-chromene subunit condensed with morpholine, thiazole, or pyrrole moieties at the C-3-C-4 bond were synthesized with various substitution patterns of the aryl group by the cyclization of cis- or trans-3-aminoflavanone analogues. The 3-aminoflavanone precursors were obtained in a Neber rearrangement of oxime tosylates of flavanones, which provided the trans diastereomer as the major product and enabled the isolation of both the cis- and trans-diastereomers. The cis- and trans-aminoflavanones were utilized to prepare three diastereomers of 5-aryl-chromeno[4,3-b][1,4]oxazines. Antiproliferative activity of the condensed heterocycles and precursors was evaluated against A2780 and WM35 cancer cell lines. For a 3-(N-chloroacetylamino)-flavan-4-ol derivative, showing structural analogy with acyclic acid ceramidase inhibitors, 0.15 μM, 3.50 μM, and 6.06 μM IC50 values were measured against A2780, WM35, and HaCat cell lines, and apoptotic mechanism was confirmed. Low micromolar IC50 values down to 2.14 μM were identified for the thiazole- and pyrrole-condensed 2H-chromene derivatives. Enantiomers of the condensed heterocycles were separated by HPLC using chiral stationary phase, HPLC-ECD spectra were recorded and TDDFT-ECD calculations were performed to determine the absolute configuration and solution conformation. Characteristic ECD transitions of the separated enantiomers were correlated with the absolute configuration and effect of substitution pattern on the HPLC elution order was determined.

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Section: Resultsmentioning

confidence: 99%

Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

et al. 2020

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“…Jarrahpour et al [64] reported the synthesis and biological application of novel Schiff bases bearing morpholine scaffold. The compounds were prepared in hot ethanol as a mixture of 2hydroxy-3-(morpholinomethyl) benzaldehyde with some mono and bis-aromatic amines.…”

Section: Antifungal Activitymentioning

confidence: 99%

Microbial activity of some heterocyclic Schiff bases and metal complexes: A review

Fonkui¹,

Ikhile²,

Ndinteh³

et al. 2019

Trop. J. Pharm Res

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Microbial resistance to current drugs associated with food spoilage and complications in diseases' treatment have resulted in increased mortality rate globally. Schiff bases are an important versatile class of organic compounds with notable pharmacological properties for various industrial applications. They are usually synthesized from a condensation reaction between a primary amine and a carbonyl. They have a wide range of activities against microbes and demonstrate good antimicrobial activity against fungi, bacteria, parasites, and viruses. The antimicrobial activity of Schiff base ligands is usually better upon metal complexation as a result of their chelating behaviour. The synthesis of Schiff bases and their metal complexes are well-documented. Therefore, it is important to categorize and compile them according to their biological significance. In this review, the antibacterial, antifungal, antiparasitic and antiviral activity of some selected heterocyclic Schiff bases and their metal complexes are discussed.

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“…The chemistry of Schiff bases has played an important role as chelating ligands in main group and transition metal coordination chemistry due to their stability in a variety of oxidative and reductive conditions like imine ligands are borderline between hard and soft Lewis base [6,7]. The bases of Schiff are typified by the MUNA ABASS HADI, AND IBTIHAL KADHIM KAREEM -N=CH-(azomethine group) which are typically created from the prime amines condensation and effective carbonyl group [8,9]. Schiff bases form some imperative kinds of biological compounds since they have different donor atoms and are capable of changing reaction based on the initial reagent.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Some Transition Metal Complexes with New Azo- Schiff Base Ligand 3,4-bis(((1E,2E)-2-((2-((4-((Z)-(3-Hydroxyphenyl)Diazenyl)Naphthalen-1-yl)amino)ethyl)imino)-1,2-Diphenylethylidene)Amino)Phenyl)(phenyl)Methanone

Kareem

Hadi

2020

Egypt. J. Chem.

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A NEW Azo-Schiff base derivative (3,4-bis(((1E,2E)-2-((2-((4-((Z)-(3-hydroxyphenyl) diazenyl)naphthalen-1-yl)amino)ethyl)imino)-1,2-diphenylethylidene)amino)phenyl) (phenyl)methanone (HANPH) and its metal complexes which include Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Pt(II), and Au(III) metal ions were synthesized. The structure of these compounds has been investigated by using elemental analysis, FT-IR, UV-Vis spectrometric methods, 1 H-NMR, mass spectra, atomic absorption, molar conductivity and magnetic susceptibility of metal complexes. The spectroscopic data of the complexes suggest that their (1:1) (metal: ligand) is mole ratio. Also, the analytical studies for all new complexes have shown octahedral geometries, except for Pt (II) and Au (III) complexes which suggested square planar geometries also its conductivity measurements show electrical properties. These complexes show high conductance value supporting (1:1) electrolytic nature. Furthermore, the FTIR results show that the coordination site from the ligand to the metal ions were through the nitrogen of azomethine group and the nitrogen of the azo group for all new complexes, except for Pt (II) and Au (III) complexes which were through the nitrogen of imine groups only.

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Synthesis of novel mono- and bis-Schiff bases of morpholine derivatives and the investigation of their antimalarial and antiproliferative activities

Cited by 17 publications

References 20 publications

Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

Synthesis and HPLC-ECD Study of Cytostatic Condensed O,N-Heterocycles Obtained from 3-Aminoflavanones

Microbial activity of some heterocyclic Schiff bases and metal complexes: A review

Synthesis and Characterization of Some Transition Metal Complexes with New Azo- Schiff Base Ligand 3,4-bis(((1E,2E)-2-((2-((4-((Z)-(3-Hydroxyphenyl)Diazenyl)Naphthalen-1-yl)amino)ethyl)imino)-1,2-Diphenylethylidene)Amino)Phenyl)(phenyl)Methanone

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