- In vitro antioxidant activity of thiazolidinone derivatives of 1,3-thiazole and 1,3,4-thiadiazole
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The initial steps in preclinical drug developing research concern the synthesis of new compounds for specific therapeutic use which needs to be confirmed by in vitro and then in vivo testing. Nine thiazolidinone derivatives (numerically labeled 1–9) classified as follows: 1,3-thiazole-based compounds (1 and 2); 1,3,4-thiadiazole based compounds (3 and 4); substituted 5-benzylideno-2-adamantylthiazol[3,2-b][1,2,4]triazol-6(5H)ones (5–8); and an ethylaminothiazole-based chalcone (9), were tested for antioxidant activity (AOA) by using three in vitro assays: DPPH (1,1-diphenyl-2-picrylhydrazyl scavenging capacity test); FRAP (ferric reducing antioxidant power test); and TBARS (thiobarbituric acid reactive substances test). Compounds 1–4 and 9 in particular are newly synthesized compounds. Also, traditional antioxidants Vitamins E and C and α-lipoic acid (α-LA) were tested. The results of DPPH testing: Vitamin C 94.35%, Vitamin E 2.99% and α-LA 1.57%; compounds: 4 33.98%; 2 18.73%; 1 15.62%; 5 6.59%; 3 4.99%; 6–9 demonstrated almost no AOA. The results of TBARS testing (% of LPO inhibition): Vitamin C 62.32%; Vitamin E 36.29%; α-LA 51.36%; compounds: 1 62.11%; 5 66.71%; 9 60.93%; 4, 6 and 7 demonstrated ～50%; 3 and 8 displayed ～38%; 2 23.51%. By FRAP method, Vitamins E and C showed equal AOA, ～100%, unlike α-LA (no AOA), and AOA of the tested compounds (expressed as a fraction of the AOA of Vitamin C) were: 2 and 4–75%; 8, 3 and 1–45%; 5–7 and 9–27%. Different red-ox reaction principles between these assays dictate different AOA outcomes for a single compound. Vitamin C appeared to be the superior antioxidant out of the traditional antioxidants; and compound 4 was superior to other tested thiazolidinone derivatives. Vitamin C appeared to be the superior antioxidant out of the traditional antioxidants; and compound 4 was superior to other tested thiazolidinone derivatives. Phenyl-functionalized benzylidene, amino-carbonyl functional domains and chelating ligand properties of the thiazolidinone derivatives correlated with AOA.
- Djukic, Mirjana,Fesatidou, Mara,Xenikakis, Iakovos,Geronikaki, Athina,Angelova, Violina T.,Savic, Vladimir,Pasic, Marta,Krilovic, Branislav,Djukic, Dusan,Gobeljic, Borko,Pavlica, Marina,Djuric, Ana,Stanojevic, Ivan,Vojvodic, Danilo,Saso, Luciano
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- Continuous-flow processing of gaseous ammonia using a Teflon AF-2400 tube-in-tube reactor: Synthesis of thioureas and in-line titrations
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A simple tube-in-tube reactor based on the gas-permeable membrane Teflon AF-2400 was used in the continuous flow reaction of gaseous ammonia with isothiocyanates and one isocyanate. A colourimetric in-line titration technique is also reported as a simple method to quantify the amount of ammonia taken up by the solvent in the system. Georg Thieme Verlag Stuttgart · New York.
- Browne, Duncanl.,O'Brien, Matthew,Koos, Peter,Cranwell, Philippa B.,Polyzos, Anastasios,Ley, Steven V.
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scheme or table
p. 1402 - 1406
(2012/07/27)
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- An efficient approach to dispacamide A and its derivatives
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Dispacamide A and new analogs of this marine alkaloid were prepared in seven steps with an overall yield ranging from 12 to 33%. The key step of the strategy was a stereocontrolled Knoevenagel condensation under microwave dielectric heating in the last step. In this condensation, the 2-aminoimidazolin-4-one hydrochloride partners 10a-c were synthesized in three steps with good overall yields (33-79%) via the ring closure of N-guanidino acetic acids 9a-c and the aldehydes 5a,b as the two others building-blocks, in 3 steps with 60-66% overall yields. The six synthetic products have been obtained with a Z geometry about their exocyclic bond on the basis of 13C/1H long-range coupling constants using a gHSQMBC experiment.
- Guiheneuf, Solene,Paquin, Ludovic,Carreaux, Francois,Durieu, Emilie,Meijer, Laurent,Bazureau, Jean Pierre
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experimental part
p. 978 - 987
(2012/04/10)
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- Substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one as CB 1 cannabinoid receptor ligands: Synthesis and pharmacological evaluation
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A set of 30 substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one (thiohydantoins) derivatives was synthesized, and their affinity for the human CB1 cannabinoid receptor has been evaluated. These compounds are derived from the previously described cannabinoid ligands 5,5′- diphenylimidazolidine-2,4-dione (hydantoins). The replacement of the oxygen by a sulfur leads to an increase of the affinity while the function-i.e., inverse agonism-determined by [35S]-GTPγS experiments remains unaffected. Finally, to evaluate the molecular parameters that could influence the affinity of the thiohydantoins, molecular electrostatic potential as well as lipophilicity calculations were undertaken on representative thiohydantoins and hydantoins derivatives. In conclusion, 5,5′-bis-(4-iodophenyl)-3-butyl-2- thioxoimidazolidin-4-one (31) and 3-allyl-5,5′-bis(4-bromophenyl)-2- thioxoimidazolidin-4-one (32) possess the highest affinity for the CB 1 cannabinoid receptor described to date for the hydantoin and thiohydantoins series when compared in a same bioassay.
- Muccioli, Giulio G.,Martin, Diana,Scriba, Gerhard K. E.,Poppitz, Wolfgang,Poupaert, Jacques H.,Wouters, Johan,Lambert, Didier M.
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p. 2509 - 2517
(2007/10/03)
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- Thermally induced transformations of 1-substituted-4,4,6-trimethyl-1,4-dihydropyrimidine-2(3H)-thiones
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Intramolecular thermal rearrangement of 1-substituted-4,4,6-trimethyl-1,4-dihydropyrimidine-2(3H)-thiones (1) to 4-substituted-amino-6,6-dimethyl-5,6-dihydropyridine-2(1H)-thiones (2), in molten state, constituting a unique Dimroth type rearrangement is reported.
- Singh, Harjit,Aggarwal, Pawan,Kumar, Subodh
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p. 740 - 743
(2007/10/02)
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- PRODUCTS FROM REACTION OF BENZALDEHYDE THIOSEMICARBAZONE WITH POTASSIUM ETHOXIDE
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When heated with potassium ethoxide, benzaldehyde thiosemicarbazone gives a mixture of 2,4,5-triphenylimidazole, hydrazodithioformamide, benzoic acid, and benzaldehyde oxime.It was shown that these compounds are formed through the intermediate benzaldehyde azine and benzonitrile.
- Marshalkin, M. F.,Yakhontov, L. N.
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p. 2273 - 2276
(2007/10/02)
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- Synthesis of Heterocyclic Compounds via Enamines. Part 8. Acid-catalysed Transformations in 4,4,6-Trimethyl-1,4-Dihydropyrimidine-2(3H)-thione Derivatives and Related Compounds
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1-Substituted 4,4,6-trimethyl-1,4-dihydropyrimidine-2(3H)-thiones (2) on heating in 11M-HCl at 100-110 deg C are converted into the corresponding 2-substituted-amino-4,6,6-trimethyl-6H-1,3-thiazines (4) and/or thioureas.But at 95-100 deg C, Dimroth rearrangement products, e.g. the corresponding 2-substituted-amino-4,4,6-trimethyl-4H-1,3-thiazenes (3) are formed.
- Singh, Harjit,Singh, Paramjit
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p. 1013 - 1018
(2007/10/02)
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