5-Lipoxygenase, Leukotrienes Biosynthesis and Potential Antileukotrienic Agents

Jampílek, Josef; Doležal, Martin; Opletalová, Veronika; Hartl, J.

doi:10.2174/092986706775197935

Cited by 45 publications

(30 citation statements)

References 55 publications

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“…A number of them have been clinically used as antifungal, antibacterial and antiprotozoic drugs [1,2] as well as antituberculotic agents [3,4]. Some quinoline based compounds showed also antineoplastics, antiasthmatic and antiplatelet activity [5][6][7][8][9][10]. The acetylcholinesterase inhibitory activity of various quinoline derivatives has been tested for potential treatment of nervous diseases [11].…”

Section: Introductionmentioning

confidence: 99%

RP-HPLC determination of lipophilicity in series of quinoline derivatives

et al. 2009

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Abstract:In the present paper we describe results on the synthesis and lipophilicity determination of a series of biologically active compounds based on their heterocyclic structure. For synthesis of styrylquinoline-based compounds we applied microwave irradiation and solid phase techniques. The correlation between RP-HPLC retention parameter log k (the logarithm of retention factor k) and log P data calculated in various ways is discussed, as well as, the relationships between the lipophilicity and the chemical structure of the studied compounds.© Versita Warsaw and Springer-Verlag Berlin Heidelberg.

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Section: Introductionmentioning

confidence: 99%

RP-HPLC determination of lipophilicity in series of quinoline derivatives

et al. 2009

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“…Catalytically active 5-LOX requires the conversion of Fe(II) to Fe(III), conferred by certain lipid hydroperoxides (LOOH). Most 5-LOX inhibitors act at the catalytic domain by reducing or chelating the active-site iron or by scavenging radical intermediates in the redox cycle of the iron [6,25]. Accordingly, the reduction of ferric ion is a possible mechanism of inhibition of LTB 4 production by 2-SC, since the most effective compounds (1A-1D) also behaved as strong reducers (Fig.…”

Section: Discussionmentioning

confidence: 99%

“…Celecoxib was an offer from Pfizer. Potassium ferricyanide [K 3 Fe(CN) 6 ] and trichloroacetic acid were obtained from Merck (Darmstadt, Germany).…”

Section: Reagentsmentioning

confidence: 99%

“…From the LOXs existent in the mammalian tissues, 5-LOX, which is mainly found in cells of myeloid origin, i.e., polymorphonuclear leukocytes (PMNL), mast cells, macrophages, is the most implicated in inflammatory and allergical disorders [6]. 5-LOX metabolizes arachidonic acid to yield 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid (5-HETE), which is further metabolized to the bioactive 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) by PMNL 5-hydroxyeicosanoid dehydrogenase [7], and various LTs (LTA 4 -LTE 4 ) [8].…”

Section: Introductionmentioning

confidence: 99%

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Anti-inflammatory potential of 2-styrylchromones regarding their interference with arachidonic acid metabolic pathways

Gomes

Fernandes

Silva

et al. 2009

Biochemical Pharmacology

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“…Some indole derivatives are also identified as good inhibitors of 5-lipoxygenase (LOX) (Hutchinson et al, 1995;Yar et al, 2014). LOX is a lipidperoxidizing enzyme, which shows an essential role in leukotriene biosynthesis and mediates the pathophysiology of allergic disorders, inflammatory reactions and neoangiogenesis (Bhattacharjee, 2005;Jampilek et al, 2006;Pommery et al, 2004). Cholinesterases are wellknown enzymes that are present in cholinergic and noncholinergic tissues and in plasma and other body fluids of animals (Ryhanen, 1983).…”

Section: Introductionmentioning

confidence: 99%

Convergent synthesis of new N -substituted 2-{[5-(1H -indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as suitable therapeutic agents

Rubab

Abbasi

Aziz-Ur-Rehman

et al. 2015

Braz. J. Pharm. Sci.

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A series of N-substituted 2-{[5-(1H-indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides (8a-w) was synthesized in three steps. The first step involved the sequential conversion of 2-(1H-indol-3-yl) acetic acid (1) to ester (2) followed by hydrazide (3) formation and finally cyclization in the presence of CS 2 and alcoholic KOH yielded 5-(1H-indole-3-yl-methyl)-1,3,4-oxadiazole-2-thiol (4). In the second step, aryl/aralkyl amines (5a-w) were reacted with 2-bromoacetyl bromide (6) in basic medium to yield 2-bromo-N-substituted acetamides (7a-w). In the third step, these electrophiles (7a-w) were reacted with 4 to afford the target compounds (8a-w). Structural elucidation of all the synthesized derivatives was done by 1 H-NMR, IR and EI-MS spectral techniques. Moreover, they were screened for antibacterial and hemolytic activity. Enzyme inhibition activity was well supported by molecular docking results, for example, compound 8q exhibited better inhibitory potential against α-glucosidase, while 8g and 8b exhibited comparatively better inhibition against butyrylcholinesterase and lipoxygenase, respectively. Similarly, compounds 8b and 8c showed very good antibacterial activity against Salmonella typhi, which was very close to that of ciprofloxacin, a standard antibiotic used in this study. 8c and 8l also showed very good antibacterial activity against Staphylococcus aureus as well. Almost all compounds showed very slight hemolytic activity, where 8p exhibited the least. Therefore, the molecules synthesized may have utility as suitable therapeutic agents.sulfanyl}acetamides/antibacterial activity. N-substituted 2-{[5-(1H-indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl} acetmides/hmolytic activity. α-Glicosidase. Butirylcholinesterase. Lipoxygenase.Uma série de acetamidas 2-{[5-(1H-indol-3-ilmetil)-1,3,4-oxadiazol-2-il]sulfanila} N-substituídas (8a-w) foi sintetizada em três fases. A primeira etapa envolveu a conversão sequencial de ácido 2-(1H-indol-3-il) acético (1) a éster (2), seguido por hidrazida (3) e, finalmente, a e ciclização na presença de CS 2 e KOH alcoólico produziu 5-(1H-indol-3-il-metil)-1,3,4-oxadiazole-2-tiol (4). Na segunda etapa, aminas arílicas/ aralquílicas(5a-w) reagiram com brometo de 2-bromoacetila (6 ), em meio básico, para se obter acetamidas 2-bromo-N-substituídas (7a-w). Na terceira etapa, estes eletrófilos (7a-w) reagiram com 4, para se obter os compostos alvo (8a-w). A elucidação estrutural de todos os derivados sintetizados foi realizada por 1 H-NMR, IR e técnicas de espectrometria de EI-MS. Além disso, eles foram submetidos a triagem de atividade antibacteriana e hemolítica. Análise da inibição enzimática foi bem apoiada pelos resultados de docking molecular. Por exemplo, o composto 8q exibiu melhor potencial inibitório contra α-glicosidase,e os compostos 8g e 8b exibiram, comparativamente, melhor inibição contra butirilcolinesterase (BChE) elipoxigenase (LOX), respectivamente. Do mesmo modo os compostos 8b e 8c mostraram excelente potencial antibacteriano contra SalmonellaTyphi...

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5-Lipoxygenase, Leukotrienes Biosynthesis and Potential Antileukotrienic Agents

Cited by 45 publications

References 55 publications

RP-HPLC determination of lipophilicity in series of quinoline derivatives

RP-HPLC determination of lipophilicity in series of quinoline derivatives

Anti-inflammatory potential of 2-styrylchromones regarding their interference with arachidonic acid metabolic pathways

Convergent synthesis of new N -substituted 2-{[5-(1H -indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as suitable therapeutic agents

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