ChemInform Abstract: SYNTHESIS AND BIOLOGICAL EVALUATION OF N‐(4‐T‐AMINO‐2‐BUTYNYLOXY) AND N‐(4‐T‐AMINO‐2‐BUTYNYL) PHTHALIMIDES

Eldeen, Zuhair Muhi; Shubber, Amjad K.; Musa, Nasreen O.; Ayaz, Muhammad; Khayat, A.; Ghantous, Hanan

doi:10.1002/chin.198024191

Cited by 3 publications

(3 citation statements)

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“…The first step, however, in any drug discovery is to develop inhibitors against the target protein regardless of their selectivity; afterwards attempts should be performed to optimize activity through enhancing selectivity of the obtained hits as well as their potency and pharmacokinetics properties. Recently, new COX inhibitors were tested and introduced as potential anti-inflammatory candidates [13,14]. These COX inhibitors were designed based on the reported pharmacological activities of acetylenic and groups, and promoted our interest to synthesize a novel series of N-[4-(t-amino-yl)-but-2-yn-1-yl] isoindoline-1,3-diones ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Non-Selective Inhibition of Cyclooxygenase Enzymes by Aminoacetylenic Isoindoline 1,3-Diones

Qinna

Muhi-Eldeen²,

Ghattas³

et al. 2012

IADT

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The reported pharmacological activities of acetylenic and phthalimide groups promoted our interest to synthesize a novel series of N-[4-(t-amino-yl)-but-2-yn-1-yl] isoindoline-1,3-diones as anti-inflammatory compounds. The aim of this research is to investigate the selectivity of two compounds, ZM4 and ZM5, on inhibiting cyclooxygenase (COX) in vitro and in silico as well as reducing carrageenan-induced edema in rats. Oral administration of 5-20 mg/kg ZM4 and ZM5 reduced significantly carrageenan-induced edema in dose-and time dependent manner. Furthermore, the IC50 values induced by ZM4 and ZM5 were in the range of 3.0-3.6 μM for COX1 and COX 2 but were higher than those induced by Diclofenac and Celecoxib, respectively. Docking of ZM4 and ZM5 in both COX enzymes, on the other hand, exhibited the conventional binding modes that are usually adopted by different non-steroidal anti-inflammatory drugs (NSAIDs). Furthermore, ZM4 and ZM5 bind to COX enzymes as strongly as Flurbiprofen and Celecoxib. In conclusion, aminoacetylenic isoindoline 1, 3-dione compounds have shown anti-inflammatory activity by inhibiting COX-1 and COX-2 enzymes. Interestingly, the best hits showed inhibition at low micromolar levels although they are not selective at this stage. Further research will be conducted to improve both selectivity and potency.

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Section: Introductionmentioning

confidence: 99%

Non-Selective Inhibition of Cyclooxygenase Enzymes by Aminoacetylenic Isoindoline 1,3-Diones

Qinna

Muhi-Eldeen²,

Ghattas³

et al. 2012

IADT

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“…Due to the anti-inflammatory activity of phthalimide (isoindoline1, 3-dione) [6] and the analgesic and anti-inflammatory properties of oxadiazolo-phthalimides [7], we recently designed series of N-[ 4-(tamino-yl)-but-2-yn-1-yl] isoindoline-1, 3-diones as anti-inflammatory compounds [8,9]. The latter compounds include aminoacetylenic isoindoline-1,3-dione and basic amino group that result in increasing the potency and selectivity toward COX-2 inhibition (Fig.…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory aminoacetylenic isoindoline-1,3-dione derivatives modulate cytokines production from different spleen cell populations

Matalka

Alfarhoud

Qinna

et al. 2012

International Immunopharmacology

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“…These activities may be shown in 0xotremorine antagonists [1,2,3], their effects on behavioral functional changes and central motor effects [4,5]. Aminoacetylenic compound showed Monoaminooxidase inhibitory activity type B as seen with Rasagiline (Azilect®)in treatment of Parkinson's disease [6,7], Clorgyline a drug used in depression treatment through monoaminooxidase A inhibition [8,9,10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and pharmacological evaluation of N-[4-(t-amino)-2- butynyloxy] phthalimides

Muhi-Eldeen¹,

Al‐Kaissi²,

Awad³

et al. 2012

iosrphr

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A series of aminoacetylenicoxyphthalimide namely N-[4-(t-amino)-2-butynyloxy] phthalimides were synthesized from the reaction of N-hydroxyphthalimide with propargyl bromide in sodium ethoxide to generate N-(2-butynyloxy)phthalimide. The desired compounds were prepared through Mannich reaction of N-(2-butynyloxy)phthalimide with formaldehyde, appropriate amine in peroxide-free dioxin and cuprous chloride as catalyst. The N-[4-(t-amino)-2-butynyloxy] phthalimides were investigated for their rectal temperature, motor activity and palpebral pitosis effects in comparison with harmaline, all compounds showed similar activity to harmaline, however compound 4 was more potent than harmaline.

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ChemInform Abstract: SYNTHESIS AND BIOLOGICAL EVALUATION OF N‐(4‐T‐AMINO‐2‐BUTYNYLOXY) AND N‐(4‐T‐AMINO‐2‐BUTYNYL) PHTHALIMIDES

Abstract: Die Aminobutinyloxy‐ (III) bzw. die Aminobutinylphthalimide (V) wurden durch Mannich‐Reaktion der Phthalimide (I) bzw. (IV) mit den cyclischen Aminen (II) und Paraformaldehyd synthetisiert.

Cited by 3 publications

References 0 publications

Non-Selective Inhibition of Cyclooxygenase Enzymes by Aminoacetylenic Isoindoline 1,3-Diones

Non-Selective Inhibition of Cyclooxygenase Enzymes by Aminoacetylenic Isoindoline 1,3-Diones

Anti-inflammatory aminoacetylenic isoindoline-1,3-dione derivatives modulate cytokines production from different spleen cell populations

Synthesis and pharmacological evaluation of N-[4-(t-amino)-2- butynyloxy] phthalimides

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