Anomeric effects in Schiff bases of D-glucosamine with aromatic aldehydes

1973 ◽  
Vol 19 (6) ◽  
pp. 1666-1668
Author(s):  
V. P. Panov ◽  
A. K. Trukhmanov ◽  
R. G. Zhbankov
Keyword(s):  
Schiff Bases ◽  
Aromatic Aldehydes ◽  
Anomeric Effects

Synthesis, Characterization, Anti-proliferative Evaluation, and DNA Flow Cytometry Analysis of Some 2-Thiohydantoin Derivatives

2020 ◽  
Vol 20 (18) ◽  
pp. 1929-1941
Author(s):  
Heba A. Elhady ◽  
Hossa F. Al-Shareef
Keyword(s):  
Anticancer Activity ◽  
Schiff Bases ◽  
Anticancer Agents ◽  
Proliferative Activity ◽  
Cancer Cell Line ◽  
Aromatic Aldehydes ◽  
Pharmaceutical Chemistry ◽  
Dna Flow Cytometry ◽  
Quinazoline Derivative ◽  
Reference Drug

Background and Objective: Due to the well-documented anti-proliferative activity of 2-thiohydantoin incorporated with pyrazole, oxadiazole, quinazoline, urea, β-naphthyl carbamate and Schiff bases, they are noteworthy in pharmaceutical chemistry. Methods: An efficient approach for the synthesis of a novel series of 2-thiohydantoin derivatives incorporated with pyrazole and oxadiazole has proceeded via the reaction of the acyl hydrazide with chalcones and/or triethyl orthoformate. Schiff bases were synthesized by the reaction of the acyl hydrazide with different aromatic aldehydes. Moreover, Curtius rearrangement was applied to the acyl azide to obtain the urea derivative, quinazoline derivative, and carbamate derivative. Results: The synthesized compounds structures were discussed and confirmed depending on their spectral data. The anticancer activity of these heterocyclic compounds was evaluated against the breast cancer cell line (MCF-7), where they showed variable activity. Compound 5d found to have a superior anticancer activity, where it has (IC50 = 2.07 ± 0.13 μg/mL) in comparison with the reference drug doxorubicin that has (IC50 = 2.79 ± 0.07 μg / mL). Then compound 5d subjected to further studies such as cell cycle analysis and apoptosis. Apoptosis was confirmed by the upregulation of Bax, downregulation of Bcl-2, and the increase of the caspase 3/7percentage. Conclusion: Insertion of pyrazole, oxadiazole and, quinazoline moieties with 2-thiohydantoin moiety led to the enhancement of its anti-proliferative activity. Hence they can be used as anticancer agents.

scholarly journals Synthesis and Bioinformatic Characterization of New Schiff Bases with Possible Applicability in Brain Disorders

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4160
Author(s):  
Speranta Avram ◽  
Ana Maria Udrea ◽  
Diana Camelia Nuta ◽  
Carmen Limban ◽  
Adrian Cosmin Balea ◽  
...  
Keyword(s):  
Schiff Bases ◽  
Neurodegenerative Disorders ◽  
Aromatic Aldehydes ◽  
Brain Disorders ◽  
Ir And Nmr Spectroscopy ◽  
Bioinformatics Tools ◽  
Ft Ir ◽  
New Treatments ◽  
New Compounds

(1) Background: The research aims to find new treatments for neurodegenerative diseases, in particular, Alzheimer’s disease. (2) Methods: This article presents a bioinformatics and pathology study of new Schiff bases, (EZ)-N′-benzylidene-(2RS)-2-(6-chloro-9H-carbazol-2-yl)propanehydrazide derivatives, and aims to evaluate the drug-like, pharmacokinetic, pharmacodynamic and pharmacogenomic properties, as well as to predict the binding to therapeutic targets by applying bioinformatics, cheminformatics and computational pharmacological methods. (3) Results: We obtained these Schiff bases by condensing (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanehydrazide with aromatic aldehydes, using the advantages of microwave irradiation. The newly synthesized compounds were characterized spectrally, using FT-IR and NMR spectroscopy, which confirmed their structure. Using bioinformatics tools, we noticed that all new compounds are drug-likeness features and may be proposed as potentially neuropsychiatric drugs (4) Conclusions: Using bioinformatics tools, we determined that the new compound 1e had a high potential to be used as a good candidate in neurodegenerative disorders treatment.

scholarly journals Synthesis, Spectral, and Biological Properties of Copper(II) Complexes of Thiosemicarbazones of Schiff Bases Derived from 4-Aminoantipyrine and Aromatic Aldehydes

2006 ◽  
Vol 2006 ◽  
pp. 1-10 ◽  
Author(s):  
Ram K. Agarwal ◽  
Lakshman Singh ◽  
Deepak Kumar Sharma
Keyword(s):  
Schiff Bases ◽  
Room Temperature ◽  
Electrical Conductance ◽  
Aromatic Aldehydes ◽  
Transition Metal Ions ◽  
Biological Properties ◽  
Thermal Stabilities ◽  
Potential Activity ◽  
Antibacterial And Antifungal ◽  
Solid Complexes

We have synthesized a novel series of Schiff bases by condensation of 4-aminoantipyrine and various aromatic aldehydes followed by reaction with thiosemicarbazide. These thiosemicarbazones are potential ligands toward transition metal ions. The reaction of copper(II) salts with 4[N-(benzalidene)amino]antipyrinethiosemicarbazone (BAAPTS), 4[N-(4′-methoxybenzalidene) amino] antipyrinethiosemicarbozone (MBAAPTS), 4[N-(4′-dimethylamino benzalidene) amino] antipyrinethiosemicarbazone (DABAAPTS), and 4[N-(cinnamalidene) amino] antipyrinethiosemicarbazone (CAAPTS) resulted in the formation of solid complexes with the general compositionCuX2⋅(H2O)(L)(X = Cl, Br,NO3, NCS, orCH3COO; L = BAAPTS, MBAAPTS, DABAAPTS, or CAAPTS). These complexes were characterized through elemental analysis, molecular weight, electrical conductance, infrared, electronic spectra, and magnetic susceptibilities at room temperature. Copper(II) complexes with BAAPTS and MBAAPTS were screened for antibacterial and antifungal properties and have exhibited potential activity. Thermal stabilities of two representative complexes were also investigated.

Tribological studies of some SAPS-free Schiff bases derived from 4-aminoantipyrine and aromatic aldehydes and their synergistic interaction with borate ester

2014 ◽  
Vol 2 (27) ◽  
pp. 10424-10434 ◽  
Author(s):  
Vinay Jaiswal ◽  
Kalyani Kalyani ◽  
Rashmi B. Rastogi ◽  
Rajesh Kumar
Keyword(s):  
Schiff Bases ◽  
Aromatic Aldehydes ◽  
Tribological Performance ◽  
Synergistic Interaction ◽  
Metal Free ◽  
Paraffin Oil ◽  
Borate Ester

Tribological performance of sulfur, phosphorous and metal-free Schiff bases and their synergistic formulations with borate ester in paraffin oil has been evaluated using a four-ball tester at optimized concentrations (1% w/v).

scholarly journals Schiff Bases and Triazolothiadiazines Derived from A Thiophene-Substituted 4-Amino-3-Mercapto-1,2,4-Triazole

2019 ◽  
Vol 27 (2) ◽  
pp. 137-154
Author(s):  
Gheorghe Roman
Keyword(s):  
Schiff Base ◽  
Schiff Bases ◽  
Aromatic Aldehydes ◽  
Nmr Analysis ◽  
Phenacyl Bromides

Abstract 4-Amino-5-(thiophen-2-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione was synthesized and converted into the corresponding Schiff bases using several aromatic aldehydes. Reaction of this aminotriazolethione with phenacyl bromides lead to triazolothiadiazines, which were subsequently reduced with NaBH4 to dihydrotriazolothiadiazines. The latter type of fused heterocycle has been also obtained directly by reacting one of the previously obtained Schiff base with phenacyl bromides. NMR analysis confirmed the structures of the synthesized compounds.

scholarly journals SYNTHESIS OF SOME NEW HETEROCYCLIC COMPOUNDS DERIVED FROM N-(Ñ-PHENYL GLYCYL) SACCHARIN AND STUDY THEIR BIOLOGICAL ACTIVITY

2018 ◽  
Vol 11 (10) ◽  
pp. 555
Author(s):  
Esraa M Ali ◽  
Ahmed W. Naser ◽  
Muthanna S. Farhan
Keyword(s):  
Acetic Acid ◽  
Schiff Bases ◽  
Heterocyclic Compounds ◽  
Glacial Acetic Acid ◽  
Cycloaddition Reaction ◽  
Aromatic Aldehydes ◽  
Positive Bacterium ◽  
Thiazole Derivatives ◽  
Gram Positive ◽  
Cyclic Imides

Objective: In the present work, a variety of new heterocyclic compounds namely aza-β- lactam, cyclicimides, 1,3-thiazole, and 1,2,4-triazole.Methods: Procedure includes the synthesis of aza-β- lactam, cyclic imides, 1,3-thiazole, and 1,2,4-triazole. The synthesis was carried out in eleven steps using N-(Ñ-substituted phenylglycyl) saccharin derivatives (1a,b) as a starting material and converted to benzoic acid derivatives (2a,b) and then to ester derivatives (3a,b), which finally convers to benzohydrazide derivatives (4a,b). The cyclization of (4a,b) with carbon disulfide and hydrazine hydrate (80%) in the presence of potassium hydroxide gives 1,2,4-triazole compounds (5a,b), and subsequently (5a,b) derivatives reacted with different aromatic aldehydes in the presence of few drops of glacial acetic acid to give Schiff bases (6a-f). Compounds (7a-b) was prepared by the reaction of compounds (4a,b) with chloroacetyl chloride. 1,3-thiazole derivatives (8a,b) were synthesized through the cyclization of compounds (7a,b) with thiourea. Schiff bases (9a-f) were obtained by condensation of (4a,b) with different aromatic aldehydes in the presence of few drops of glacial acetic acid. Aza-β-lactam compounds (10a-f) were prepared by the cycloaddition of Schiff-bases (9a-f) with phenyl isocyanate through [2+2] cycloaddition reaction. Reaction (4a,b) with various acid anhydrides in presence of acetic acid gave the corresponding cyclic imide (11a-f). The newly prepared.Results: The results showed that compounds (5a) and (10e) have a good activity against Gram-positive bacterium and no activity against Gram-negative bacterium, compared to standard drugs (ciprofloxacin and amoxicillin), while compounds (8a) and (6b) have a high activity against fungi, compared to standard drugs (metronidazole benzoate), and the other tested compounds have low-to-moderate activity.Conclusion: 1,2,4-triazole is a most potent assemblage of Gram-positive bacterium retardants and cyclic imides are a most potent assemblage of fungi retardants.

scholarly journals 4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents

Biomolecules ◽  
2019 ◽  
Vol 10 (1) ◽  
pp. 9 ◽  
Author(s):  
Martin Krátký ◽  
Klára Konečná ◽  
Jiří Janoušek ◽  
Michaela Brablíková ◽  
Ondřej Janďourek ◽  
...  
Keyword(s):  
Schiff Bases ◽  
Biological Activities ◽  
Aromatic Aldehydes ◽  
Antimycobacterial Activity ◽  
Cytotoxic Agents ◽  
Aminobenzoic Acid ◽  
Human Pathogens ◽  
Essential Nutrient ◽  
One Step ◽  
Imine Bond

4-aminobenzoic acid (PABA), an essential nutrient for many human pathogens, but dispensable for humans, and its derivatives have exhibited various biological activities. In this study, we combined two pharmacophores using a molecular hybridization approach: this vitamin-like molecule and various aromatic aldehydes, including salicylaldehydes and 5-nitrofurfural, via imine bond in one-step reaction. Resulting Schiff bases were screened as potential antimicrobial and cytotoxic agents. The simple chemical modification of non-toxic PABA resulted in constitution of antibacterial activity including inhibition of methicillin-resistant Staphylococcus aureus (minimum inhibitory concentrations, MIC, from 15.62 µM), moderate antimycobacterial activity (MIC ≥ 62.5 µM) and potent broad-spectrum antifungal properties (MIC of ≥ 7.81 µM). Some of the Schiff bases also exhibited notable cytotoxicity for cancer HepG2 cell line (IC50 ≥ 15.0 µM). Regarding aldehyde used for the derivatization of PABA, it is possible to tune up the particular activities and obtain derivatives with promising bioactivities.

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