Synthesis and pharmacological evaluation of aminoacetylenic isoindoline-1,3-dione derivatives as anti-inflammatory agents

Al-Qaisi, Jinan A.; Alhussainy, Tawfik M.; Qinna, Nidal A.; Matalka, Khalid Z.; Al‐Kaissi, Elham; Muhi-Eldeen, Zuhair

doi:10.1016/j.arabjc.2010.12.030

Cited by 23 publications

(24 citation statements)

References 11 publications

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“…When ZM compounds were introduced to LPS-stimulated CD4+ CD25+ve cells, only ZM5 enhanced TGF-β production, whereas ZM2 and ZM4 suppressed such production, suggesting that the structure difference in the ring size and conformational of the cyclic amine ring size, and lipophilicity may be the reasons in different modulations of LPS-TLR-4 TGF-β production signaling pathways. For instance, the azepan ring in ZM5 and the steric factor neighboring the basic nitrogen in ZM4 over ZM3 could be the reasons in activating downstream pathways to inducing anti-inflammatory cytokine TGF-β1 and therefore enhancing the anti-inflammatory activities [9,10].…”

Section: Discussionmentioning

confidence: 99%

“…All tested compounds were given 20 mg/kg orally and either kept with no intervention or followed 1 h later by an intra-peritoneal (i.p.) administration of LPS (2 μg in 0.5 mL of sterile PBS) [9].…”

Section: Effects Of Zm Compounds On Normal and Lps-induced Cytokines mentioning

confidence: 99%

“…1) [9,10]. This unique combination represents a new series anti-inflammatory compounds differ from the generally used drugs on the market with acidic, enolic, sulfonamide or sulfon groups in their structures that showed anti-inflammatory activities, COX-1 and 2 inhibition and less adverse effects [9][10][11].…”

Section: Introductionmentioning

confidence: 97%

“…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%

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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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Section: Discussionmentioning

confidence: 99%

Section: Effects Of Zm Compounds On Normal and Lps-induced Cytokines mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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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“…After cooling to room temperature, the reaction solution was filtered and solvent was removed under vacuum; the residue was purified by a silica-gel column chromatography (pet-acetone system) and then afforded the desired compound, yield 49 % [11].…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of T-OA analogues as the cytotoxic agents

Chu

et al. 2014

Res Chem Intermed

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The lead compound T-OA, 3b-hydroxyolean-12-en-28-oic acid-(3,5,6-trimethylpyrazine-2-yl) methyl ester, which exhibited promising anticancer effects in vitro and in vivo, has previously been reported. According to the structural features, a series of novel T-OA analogues were synthesized via amino condensation reaction. These analogues' cytotoxic activities were evaluated on five cancer cell lines (Bel-7402, HepG-2, HT-29, Hela, BGC-823) and hepatic stellate cell line (HSC-6). Among the candidates, compounds 8 and 16 showed promising effects; 3b-hydroxy-lup-20(29)-ene-28-oic acid-(3,5,6-trimethylpyrazin-2-yl) methyl amine (16) even possessed superior bioactivities to positive drugs (cisplatin and ursolic acid), which was worthy of further study. In addition, structure-activity relationships and Clog P values of T-OA analogues were briefly discussed.

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Design and Synthesis of Aminoacetylenic Indole and Carbazole Hybrid Compounds

et al. 2020

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A novel series of aminoacetylenic indole and carbazole hybrid compounds had been prepared via a three-component reaction system in which a mannich type reaction was used in the coupling of propargylic indole or carbazole with cyclic amines and formaldehyde in the presence of Cu(I) catalyst. A side product of the self-coupling reaction of propargylic indole was also separated and characterized by physicochemical techniques. NMR, single crystal x-ray, High-resolution mass spectra (HRMS) are used in the characterization of the synthesized compounds and intermediates [a]

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Synthesis and pharmacological evaluation of aminoacetylenic isoindoline-1,3-dione derivatives as anti-inflammatory agents

Cited by 23 publications

References 11 publications

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

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

Synthesis and biological evaluation of T-OA analogues as the cytotoxic agents

Design and Synthesis of Aminoacetylenic Indole and Carbazole Hybrid Compounds

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