Pharmacological evaluation of some novel synthesized compounds derived from spiro(cyclohexane-1,2′-thiazolidines)

Flefel, Eman M.; Sayed, Hayam H.; Hashem, Ahmed I.; Shalaby, Emad A.; El-Sofany, Walaa I.; Abdel‐Megeid, Farouk M. E.

doi:10.1007/s00044-013-0830-y

Cited by 19 publications

(18 citation statements)

References 18 publications

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“…In addition, a,b-unsaturated ketone (5-ene-2-spirothiazolidine) was used for the synthesis of corresponding oxiranyl derivatives 220 by treatment with hydrogen peroxide in the presence of sodium hydroxide. Also, starting thiazolidinone was treated with ethylcyanoacetate (medium of acetic acid in the presence of sodium acetate) under reflux to afford the corresponding pyrano-thiazolecarbonitrile derivative 221 [462] (Scheme 103).…”

Section: Addition Reactionsmentioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

133

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The presented review is an attempt to summarize a huge volume of data on 5-ene-4-thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-thiazolidinone modification.

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Section: Addition Reactionsmentioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

133

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“…Functionally substituted cyclohexane derivatives possess diverse biological properties. These include anticancer activity (Sharma et al, 2011;Lallo et al, 2014;Flefel et al, 2014;Song et al, 2015), antioxidant activity (Flefel et al, 2014), analgesic activity (Amin et al, 2010) and anti-inflammatory activity (Usegilo et al, 2006). Antimicrobial activities of numerous cyclohexane derivatives have also been reported.…”

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confidence: 99%

Antimicrobial Activity of Novel Functionally Substituted Monocyclic and Spirocyclic Cyclohexane Derivatives

Shoaib¹,

Ismiyev²,

Ganbarov³

et al. 2019

PJZ

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“…The thia-4-azaspiro[4.5]decan compounds 1 – 3 were prepared via a one-pot three-component reaction involving condensation of ketones namely, 4-methylcyclohexanone and cyclohexanone; aromatic amines namely, 4-bromoaniline or 4-fluoroaniline; and mercaptoacetic acid in dry benzene to afford the corresponding substituted aryl-1-thia-4-azaspiro[4.5]decan-3-one compounds 1 – 3 [ 14 ]. The Infra-Red spectra of the resulting spiro-thiazolidine derivatives 1 and 3 showed characteristic peaks at 1682 and 1677 cm −1 corresponding to the thiazolidinone carbonyl function.…”

Section: Resultsmentioning

confidence: 99%

“…Simple spirothiazolidines have been revealed for their inhibition activity of metalloprotease which allows their application in the control of malaria infection [ 13 ]. Spirothiazolidine derivatives were also found to be of good activity as anticancer and antioxidant [ 14 ] agents. Thiazolopyrimidine is an interesting bicyclic system as its derivatives revealed their activity as analgesic and antiparkinsonian agents [ 15 ], Transient Receptor Potential Vanilloid–receptor 1 (TRPV1) modulators [ 16 ], anticancer agents [ 17 , 18 , 19 , 20 ], antioxidants [ 21 ], pesticides [ 22 ], phosphate inhibitors [ 23 , 24 ], acetylcholinesterase inhibitors [ 25 ] and antimicrobial substances [ 26 , 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

“…Thiazolopyrimidine is an interesting bicyclic system as its derivatives revealed their activity as analgesic and antiparkinsonian agents [ 15 ], Transient Receptor Potential Vanilloid–receptor 1 (TRPV1) modulators [ 16 ], anticancer agents [ 17 , 18 , 19 , 20 ], antioxidants [ 21 ], pesticides [ 22 ], phosphate inhibitors [ 23 , 24 ], acetylcholinesterase inhibitors [ 25 ] and antimicrobial substances [ 26 , 27 , 28 ]. Structures A – D ( Figure 1 ) with spiro-thiazolidine, thiazolopyrimidine and 1,3,4-thiadiazole ring systems have been reported with their anticancer activity [ 14 , 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Anticancer Activity of New 1-Thia-4-azaspiro[4.5]decane, Their Derived Thiazolopyrimidine and 1,3,4-Thiadiazole Thioglycosides

et al. 2017

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New 1-thia-azaspiro[4.5]decane derivatives, their derived thiazolopyrimidine and 1,3,4-thiadiazole compounds were synthesized. The thioglycoside derivatives of the synthesized (1,3,4-thiadiazolyl)thiaazaspiro[4.5]decane and thiazolopyrimidinethione compounds were synthesized by glycosylation reactions using acetylated glycosyl bromides. The anticancer activity of synthesized compounds was studied against the cell culture of HepG-2 (human liver hepatocellular carcinoma), PC-3 (human prostate adenocarcinoma) and HCT116 (human colorectal carcinoma) cell lines and a number of compounds showed moderate to high inhibition activities.

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Pharmacological evaluation of some novel synthesized compounds derived from spiro(cyclohexane-1,2′-thiazolidines)

Cited by 19 publications

References 18 publications

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Antimicrobial Activity of Novel Functionally Substituted Monocyclic and Spirocyclic Cyclohexane Derivatives

Synthesis and Anticancer Activity of New 1-Thia-4-azaspiro[4.5]decane, Their Derived Thiazolopyrimidine and 1,3,4-Thiadiazole Thioglycosides

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