Synthesis and antioxidant activity of some thiazolidin-4-one derivatives

El‐Nezhawy, Ahmed O. H.; Ramla, Mostafa M.; Khalifa, Nagy M.; Abdulla, Mohamed M.

doi:10.1007/s00706-008-0085-3

Cited by 21 publications

(7 citation statements)

References 18 publications

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“…As agonists of nuclear receptor peroxisome proliferator-activated receptor gamma (PPAR-γ), thiazolidinediones (TZD) reduce insulin resistance in the liver and peripheral tissues; increase the intake of insulin-dependent glucose and decrease withdrawal of glucose from the liver [14,18]. On the other hand, the thiazolidine derivatives have been reported to have antioxidant activities that could be effective in the T2DM therapy [21][22][23].…”

Section: Introductionmentioning

confidence: 99%

The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety

et al. 2013

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Abstract:Starting from theophylline (1,3-dimethylxanthine) new thiazolidin-4-one derivatives 7a 1-7 , 7b 1-7 have been synthesized as potential antidiabetic drugs. The structure of the new derivatives was confirmed using spectral methods (FT-IR, 1 H-NMR, 13 C-NMR). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the ferric reducing power, the total antioxidant activity and the DPPH and ABTS radical scavenging assays. Reactive oxygen species (ROS) and free radicals are considered to be implicated in a variety of pathological events, such as diabetes mellitus and its micro-and macrovascular complications. The results of chemical modulation of the thiazolidin-4-one intermediaries 6a, 6b through condensation with several aromatic aldehydes is the improvement of the antioxidant effect. All benzylidenethiazolidin-4-one derivatives 7a 1-7 , 7b 1-7 are more active than their parent thiazolidin-4-ones. The most active compounds are the ones obtained by reaction of condensation with 4-hydroxybenzaldehyde (compounds 7a 5 , 7a 6 ), 4-dimethylaminobenzaldehyde (compounds 7a 6 , 7b 6 ) and 2-nitrobenzaldehyde (compounds 7a 7 , 7b 7 ).

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Section: Introductionmentioning

confidence: 99%

The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety

et al. 2013

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“…Knoevenagel condensation of 2-iminothiazolidin-4-one ( 3 ) with 2-quinoxalinecarboxaldehyde-1, 4-di- N -oxide ( IV ) in the presence of ammonium acetate and glacial acetic acid provided compound V (Jadav et al, 2015 ; Ghareb et al, 2017 ). Compounds IV were refluxed with thioglycollic acid and ammonium carbonate for 18 h to get compounds VI (El Nezhawy et al, 2009 ). Subsequently, we modified the structure of thiazolidinone to obtain new derivatives.…”

Section: Resultsmentioning

confidence: 99%

“…The mixture was cooled, washed with water, and evaporated under reduced pressure. The oily residue was purified by silica gel column chromatography to get 2- (4'(5H)-thiazolone)-quinoxaline-1, 4-di- N -oxide (VI) (El Nezhawy et al, 2009 ).…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Novel Thiazolidinone-Containing Quinoxaline-1,4-di-N-oxides as Antimycobacterial and Antifungal Agents

Zhang

et al. 2020

Front. Chem.

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Tuberculosis and fungal infections can pose serious threats to human health. In order to find novel antimicrobial agents, 26 novel quinoxaline-1,4-diN oxides containing a thiazolidinone moiety were designed and synthesized, and their antimycobacterial activities were evaluated. Among them, compounds 2t, 2u, 2y, and 2z displayed the most potent antimycobacterial activity against Mycobacterium tuberculosis strain H37Rv (minimal inhibitory concentration [MIC] = 1.56 µg/mL). The antifungal activity of all the compounds was also evaluated against Candida albicans, Candida tropicalis, Aspergillus fumigatus, and Cryptococcus neoformans. Compounds 2t, 2u, 2y, and 2z exhibited potential antifungal activities, with an MIC between 2 and 4 µg/mL. Comparative molecular field analysis (CoMFA: q 2 = 0.914, r 2 = 0.967) and comparative molecular similarity index analysis (CoMSIA: q 2 = 0.918, r 2 = 0.968) models were established to investigate the structure and antimycobacterial activity relationship. The results of contour maps revealed that electronegative and sterically bulky substituents play an important role in the antimycobacterial activity. Electronegative and sterically bulky substituents are preferred at the C7 position of the quinoxaline ring and the C4 position of the phenyl group to increase the antimycobacterial activity. Additionally, more hydrogen bond donor substituents should be considered at the C2 side chain of the quinoxaline ring to improve the activity.

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“…Tetralins (tetrahydronaphthalene derivatives) are of increasing interest since many of these compounds play a vital role in the biological activities because of their biological potentialities, for example, as potent agonists for D2-type receptors (Dutta et al, 2002), a treatment of Alzheimer's disease (Taddei et al, 2002) and as anti-cancer agents (Zaghary et al, 2005). Also, we found that certain substituted tetralin and heterocyclic derivatives show inhibition for cercarial serine protease (Bahgat & Khalifa, 2006), antioxidant (El Nezhawy et al, 2009) and antiinflammatory (Khalifa et al, 2008) activities. Tetralin derivative containing cyanoaceto-hydrazide was prepared as the title compound and its crystal structure is now reported.…”

Section: Data Collectionmentioning

confidence: 98%

“…For background to tetralin, see: Dutta et al (2002); Taddei et al (2002); Zaghary et al (2005); Bahgat & Khalifa (2006);El Nezhawy et al (2009); Khalifa et al (2008). For ring puckering parameters, see: Cremer & Pople (1975).…”

Section: Related Literaturementioning

confidence: 99%

(E)-2-Cyano-N′-(1,2,3,4-tetrahydronaphthalen-1-ylidene)acetohydrazide

Al-Omar¹,

Khalifa²,

Ghabbour³

et al. 2012

Acta Cryst E

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In the title compound, C13H13N3O, the tetrahydrobenzene ring adopts a half-boat (envelope) conformation. The mean plane of the tetrahydronaphthalene ring system forms a dihedral angle of 9.56 (6)° with the mean plane of the cyanoacetohydrazide group. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) loops. The dimers are connected by C—H⋯N hydrogen bonds into a chain propagating along [101]. The crystal packing also features C—H⋯π interactions.

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Synthesis and antioxidant activity of some thiazolidin-4-one derivatives

Cited by 21 publications

References 18 publications

The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety

The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety

Design, Synthesis, and Biological Evaluation of Novel Thiazolidinone-Containing Quinoxaline-1,4-di-N-oxides as Antimycobacterial and Antifungal Agents

(E)-2-Cyano-N′-(1,2,3,4-tetrahydronaphthalen-1-ylidene)acetohydrazide

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