Synthesis of 3-benzyl-2-substituted quinoxalines as novel monoamine oxidase A inhibitors

Hassan, Seham Y.; Khattab, Sherine N.; Bekhit, Adnan A.; Amer, Adel

doi:10.1016/j.bmcl.2005.11.088

Cited by 66 publications

(34 citation statements)

References 19 publications

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“…For example, 4-nitro-1,2-phenylenediamine afforded the product in 90 min with 80% yield (entry 4), whereas methyl and methoxy Products were characterized by IR, 1 substituted 1,2-phenylenediamines gave the expected quinoxaline in 15 min with 95 and 97% yield, respectively (entries 2 and 3). Substituted benzil also reacted smoothly with 1,2-phenylenediamines, to give high yielded of the corresponding quinoxalines (Table 3, entries [13][14][15][16][17][18].…”

Section: Resultsmentioning

confidence: 99%

“…14 Based on the significant applications of quinoxaline compounds in both medicinal and industrial fields, several synthetic strategies have been developed for the preparation of substituted quinoxalines by condensation of aryl 1,2-diamines with ketones, α-halo-β-ketoesters, α-hydroxyketones and 1,2-diketones. [15][16][17][18][19] A number of methods have been reported for the generating quinoxaline derivatives using stoichiometric or catalytic Lewis acids such as Ga(OTf) 3 Nevertheless, some of these methods suffer from long reaction time, low product yields, expensive and detrimental metal precursors for preparation of catalyst, using complex or poorly available catalyst and harsh reaction conditions which limit their use.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Quinoxaline Derivatives Using TiO₂Nanoparticles as an Efficient and Recyclable Catalyst

Alinezhad¹,

Tajbakhsh²,

Salehian³

et al. 2011

Bulletin of the Korean Chemical Society

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Quinoxaline Derivatives Using TiO₂Nanoparticles as an Efficient and Recyclable Catalyst

Alinezhad¹,

Tajbakhsh²,

Salehian³

et al. 2011

Bulletin of the Korean Chemical Society

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“…2-morpholinoethylamino, 2-hydroxyethylamino, hydrazino, etc). 8) The rational design of these compounds was based on a hybrid structure of known inhibitors. The aim of the present study was to design MAO-A inhibitors while taking into consideration various factors responsible for selectivity against the A isoform, 9) namely i) the presence of electron-rich aromatic moieties (e.g.…”

Section: Notesmentioning

confidence: 99%

Synthesis of Some Pyridazinylacetic Acid Derivatives as a Novel Class of Monoamine Oxidase-A Inhibitors

Khattab

Bekhit

El‐Faham

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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NotesMonoamic oxidase (MAO) (EC 1.4.3.4) is an integral flavin-containing enzyme of the outer mitochondrial membrane which is responsible for regulation and metabolism of major monoamine neurotransmitters such as serotonin (5-OH tryptamine), noradrenaline and dopamine. It is also involved in the biodegradation of exogenic amines such as benzylamine, tyramine, 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTT), 1-methyl-4-phenyl pyridium (MPP ϩ ), and a Parkinsonian-producing neurotoxin.2) It is found in two different isoforms designated as MAO-A and MAO-B which are encoded by two different genes 3) and distinguished by different substrate specificities and sensitivities to the selective inhibitors. 4)The new generation of MAO inhibitors is characterized by their relative specificities for the MAO subtypes and in some cases by the reversibility of their actions. In spite of considerable progress in our understanding of the interactions of the two enzyme forms with their preferred substrates and inhibitors, no general rules are yet available for the rational design of potent and selective inhibitors of MAO. This is partly due to the fact that the mechanism of interaction of several new drugs with MAOs has not been fully characterized. Therefore, the discovery of several selective MAO inhibitors has relied on serendipity. Preferential MAO-A inhibitors have been recognized as therapeutically useful antidepressants 5) , while MAO-B inhibitors have been found to be beneficial in the treatment of Parkinson's disease and Alzheimer's disease. 6,7)Recently, we have demonstrated a series of 3-benzyl-2-substituted quinoxalines as selective MAO-A inhibitors bearing substituted amino or hydrazino functionalities at position 2 (e.g. 2-morpholinoethylamino, 2-hydroxyethylamino, hydrazino, etc).8) The rational design of these compounds was based on a hybrid structure of known inhibitors. The aim of the present study was to design MAO-A inhibitors while taking into consideration various factors responsible for selectivity against the A isoform, 9) namely i) the presence of electron-rich aromatic moieties (e.g. Bazinaprine 10) ), ii) the presence of hydrazido functionality (e.g. Iproniazid 11) ), iii) the presence of an ethoxycarbonyl methylene group side chain of an aromatic system (e.g. Eugenol analog 12) ); exchanging the ester group with an amido group was also considered, and iv) the benzyl group was retained in the new model compounds in Fig. 1.The new substituted pyridazine-1-yl acetic acid derivatives (2, 3, 5) were designed as selective monoamine oxidase-A inhibitors. The synthesis and biological evaluation of these compounds were described. As a preliminary result of the biological investigation, compound 5d showed the highest MAO-A selectivity and could be the lead compound for designing more potent and selective MAO-A inhibitors.First, the 4-benzyl-2H-pyridazin-3-one derivatives 1 were prepared. The reaction of the 4-benzyl-2H-pyridazin-3-one derivatives 1 with bromo ethyl acetate in dimethyl formamide in the presence...

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“…Quinoxalines have extraordinary potential in pharmacological research [1] and practice. These are important components of several pharmacologically active compounds [2][3][4][5][6][7][8] and exhibit special and wider ranges of functions in biologically active compounds [9], electroluminescent materials [10], dyes [11] and anion sensors [12]. Although rarely describe in nature, synthetic quinoxaline derivatives showed variety of pharmaceutical activities encompassed major types of drug target families and effective in many clinical applications such as anti tumor agents [13], kinase inhibitors [14], HIV drugs [15], antibiotics [16], ion channel regulators [17] and anti protozoal agents [18].…”

Section: Introductionmentioning

confidence: 99%

“…A variety of catalysts were tested in these reactions such as acetic acid [29], iodine [30], CuSO 4 .5H 2 O [31], nickel nanoparticles [32], gallium(III)triflate [33], montmorillonite K-10 [34], ionic liquids [35], Nano-TiO 2 [36], sulfated TiO 2 [37], Pd(OAc) 2 [38], RuCl 2 -(PPh 3 ) 3 -2,2,6,6-tetramethylpiperidine 1-oxyl(TEMPO) [38], MnO 2 [38], Al 2 O 3 [39], zirconium(IV)-modified silica gel [40], nanocrystalline CuO [41], cerium(IV) ammonium nitrate [42], iron exchanged molybdophosphoric acid [43], silica-bonded S-sulfonic acid [44], and sulfamic acid/MeOH [45]. Here we report synthesis of novel thiophene thiazole based quinoxaline derivatives by chloro-amine condensation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Thiophenyl Thiazole Based Novel Quinoxaline Derivatives

Kathrotiya

Naliapara

2015

ILCPA

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A new series of thiophenyl thiazole based novel quinoxaline derivatives 4a-4t have been synthesized by base catalysed condensation reaction. In which 6-substituted 2,3-dichloroquinoxaline 1a and 4-(thiophen-2-yl)thiazol-2-amine 2b reacted in basic condition to afford intermediate 3c which reacts with various aromatic amine to form final compounds. Easy experimental procedure, high yield, and selectivity are the imperative features of this method. The identity of all the compounds has been established by 1 H NMR, 13 C NMR, FT-IR, and elemental analysis.

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Synthesis of 3-benzyl-2-substituted quinoxalines as novel monoamine oxidase A inhibitors

Cited by 66 publications

References 19 publications

Synthesis of Quinoxaline Derivatives Using TiO₂Nanoparticles as an Efficient and Recyclable Catalyst

Synthesis of Quinoxaline Derivatives Using TiO₂Nanoparticles as an Efficient and Recyclable Catalyst

Synthesis of Some Pyridazinylacetic Acid Derivatives as a Novel Class of Monoamine Oxidase-A Inhibitors

Synthesis of Thiophenyl Thiazole Based Novel Quinoxaline Derivatives

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Synthesis of 3-benzyl-2-substituted quinoxalines as novel monoamine oxidase A inhibitors

Cited by 66 publications

References 19 publications

Synthesis of Quinoxaline Derivatives Using TiO2Nanoparticles as an Efficient and Recyclable Catalyst

Synthesis of Quinoxaline Derivatives Using TiO2Nanoparticles as an Efficient and Recyclable Catalyst

Synthesis of Some Pyridazinylacetic Acid Derivatives as a Novel Class of Monoamine Oxidase-A Inhibitors

Synthesis of Thiophenyl Thiazole Based Novel Quinoxaline Derivatives

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Synthesis of Quinoxaline Derivatives Using TiO₂Nanoparticles as an Efficient and Recyclable Catalyst

Synthesis of Quinoxaline Derivatives Using TiO₂Nanoparticles as an Efficient and Recyclable Catalyst