Synthesis of heterocyclic compounds. LI. Schiff bases of ethyl 2‐aminofurancarboxylates

Ciller, J. A.; Seoane, Carlos; Soto, J. L.; Yruretagoyena, B.

doi:10.1002/jhet.5570230565

Cited by 17 publications

(9 citation statements)

References 9 publications

(1 reference statement)

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“…Mixed ligand complexes also play an important role in the biological field as exemplified by many ways in which enzymes are known to be activated by metal ions . Schiff bases derived from heterocyclic compounds such as furan‐2‐carbaldehyde have attracted an increased interest in the bioinorganic chemistry field . Furfural is an important renewable, non‐petroleum‐based and chemical raw material.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and biological and anticancer studies of mixed ligand complexes with Schiff base and 2,2′‐bipyridine

Omar

El‐Halim

Khalil

2017

Applied Organom Chemis

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New mixed ligand complexes of transition metals were synthesized from a Schiff base (L 1 ) obtained by the condensation reaction of oxamide and furfural as primary ligand and 2,2′-bipyridine (L 2 ) as secondary ligand. The ligands and their metal complexes were studied using various spectroscopic methods. Also thermal analyses were conducted. The mixed ligand complexes were found to have formulae [M(L 1 ) (L 2 )]Cl m ⋅nH 2 O (M = Cr(III) and Fe(III): m = 3, n = 0; M = Cu(II) and Cd(II): m = 2, n = 1; M = Mn(II), Co(II), Ni(II) and Zn(II): m = 2, n = 0). The resultant data revealed that the metal complexes have octahedral structure. Also, the mixed ligand complexes are electrolytic. The biological and anticancer activities of the new compounds were tested against breast cancer (MCF-7) and colon cancer (HCT-116) cell lines. The results showed high activity for the synthesized compounds. KEYWORDS 2,2′-bipyridine, anticancer activity, biological activity, mixed ligand complexes, Schiff base ligand

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and biological and anticancer studies of mixed ligand complexes with Schiff base and 2,2′‐bipyridine

Omar

El‐Halim

Khalil

2017

Applied Organom Chemis

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“…Schiff base complexes derived from heterocyclic compounds have been found interest in the context of bioinorganic chemistry [1][2][3]. Not only they have played a seminal role in the development of modern coordination chemistry, but they can be also a key point in the development of inorganic biochemistry [4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, fluorescence and catalytic activity of some new complexes of unsymmetrical Schiff base of 2-pyridinecarboxaldehyde with 2,6-diaminopyridine

Ali

El‐Medani

Ahmed

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…[18] Briefly, starting from a mixture of E/Z-isomers of ethyl 2-(4-methoxybenzylidene)-3-oxobutanoate (2), [19] and reacting it with…”

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confidence: 99%

“…The detailed investigation of chiral discrimination has enormous importance in medicinal chemistry as a means to better elucidating the mechanisms of interaction and to identify structural features involved in ligand-target recognition.The synthesis of (R/S)-1 was scaled up for this study, but essentially followed the general protocol previously described. [18] Briefly, starting from a mixture of E/Z-isomers of ethyl 2-(4-methoxybenzylidene)-3-oxobutanoate (2), [19] and reacting it with [a] Dr.…”

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confidence: 99%

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Chemical and Pharmacological Studies on Enantiomerically Pure p‐Methoxytacripyrines, Promising Multi‐Target‐Directed Ligands for the Treatment of Alzheimer’s Disease

et al. 2011

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Alzheimer's disease (AD) is an age-related neurodegenerative process characterized by progressive memory loss and other cognitive impairments.[1] Although the etiology of AD is not well known, several factors such as amyloid-b (Ab) [2] deposits, t-protein aggregation, oxidative stress or low levels of acetylcholine [3] are thought to play significant roles in the pathophysiology of the disease.[4] In spite of the continuous efforts of the pharmaceutical industry and academia, an efficient strategy for the treatment of AD is still lacking. This is partially related to the complexity of the pathology, in which multiple factors contribute to the final scenario. The multifactorial nature of AD has given rise to the rational basis for the development of the most current innovative therapeutic approaches based on the "one molecule, multiple targets" paradigm. [5][6][7][8][9] The multitarget approach [10] has been widely explored leading to the development of several multi-target-direct ligands (MTDLs), which include novel tacrine-melatonin hybrids, [11] dual inhibitors of acetylcholinesterase (AChE) and monoamine oxidase, [12] or serotonin transporters, [13] potent cholinesterase inhibitors with antioxidant and neuroprotective properties, [14] gallamine-tacrine hybrids binding at cholinesterases and M 2 muscarinic receptors, [15] or NO-donor-tacrine hybrids as hepatoprotective anti-AD drugs. [16] Based on the multitarget approach, some years ago we designed and synthesized novel multipotent molecules, called tacripyrines (I), by combination of tacrine and nimodipine, as reference agents with a multipotent cholinergic and calcium antagonism profile, respectively, for the treatment of AD. [17,18] Racemic tacripyrines exhibited potent and selective AChE inhibition, high calcium-channel blocking activity, as well as neuroprotective/antioxidant properties, able to cross the bloodbrain barrier.Particularly, (R/S)-p-methoxytacripyrine (ethyl 5-amino-4-(4-methoxyphenyl)-2-methyl-1, 4,6,7,8,9-hexahydrobenzo[b] [1,8] naphthyridine-3-carboxylate; (R/S)-1), one of the most potent cholinergic tacripyrines (IC 50 = 105 AE 15 nm against human AChE), at 100 mm showed 30.7 AE 8.6 % inhibition of the pro-aggregating action of AChE on Ab peptide (230 mm); furthermore, (R/S)-1 was also a moderate inhibitor of b-amyloid selfaggregation (34.9 AE 5.4 % at [I] = 50 mm).[18] Overall, these results prompted us to consider 1 as an appropriate hit compound in this project, and consequently, to undertake the pharmacological analysis of both enantiomers. The detailed investigation of chiral discrimination has enormous importance in medicinal chemistry as a means to better elucidating the mechanisms of interaction and to identify structural features involved in ligand-target recognition.The synthesis of (R/S)-1 was scaled up for this study, but essentially followed the general protocol previously described. [18] Briefly, starting from a mixture of E/Z-isomers of ethyl 2-(4-methoxybenzylidene)-3-oxobutanoate (2), [19] and reacting it with[a] Dr.

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Synthesis of heterocyclic compounds. LI. Schiff bases of ethyl 2‐aminofurancarboxylates

Abstract: Diaryl‐ and Alkylaryl‐substituted 2‐aminofurancarboxylates have been obtained as Schiff bases 5,6 by cyclization of 2‐ethoxycarbonyl‐4‐oxonitriles 3,4; which result from hydrogen cyanide addition to ethyl α‐acylcinnamates 1,2.

Cited by 17 publications

References 9 publications

Synthesis, characterization, and biological and anticancer studies of mixed ligand complexes with Schiff base and 2,2′‐bipyridine

Synthesis, characterization, and biological and anticancer studies of mixed ligand complexes with Schiff base and 2,2′‐bipyridine

Synthesis, characterization, fluorescence and catalytic activity of some new complexes of unsymmetrical Schiff base of 2-pyridinecarboxaldehyde with 2,6-diaminopyridine

Chemical and Pharmacological Studies on Enantiomerically Pure p‐Methoxytacripyrines, Promising Multi‐Target‐Directed Ligands for the Treatment of Alzheimer’s Disease

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