Oxazolone derivative 2 was utilized as a key intermediate for synthesis of some new oxazolone and imidazolone derivatives. Reaction of oxazolone derivative 2 with diamines under different conditions afforded the corre...Oxazolone derivative 2 was utilized as a key intermediate for synthesis of some new oxazolone and imidazolone derivatives. Reaction of oxazolone derivative 2 with diamines under different conditions afforded the corresponding imidazolone derivatives 3-8, respectively. Moreover, oxazolone 2 reacted with some heterocyclic amines in glacial acetic acid giving the corresponding imidazolone derivatives 9-14, respectively. Cyclocondensation of thiosemicarbazide with compound 2 in dry pyridine afforded compound 15. Addition of secondary amines to olefin double bond of compound 2 gave the corresponding addition products 16-19, respectively. Michael addition of compound 2 with some active methylene compounds afforded oxazolone derivatives 20-23, respectively. These prepared products were evaluated as antioxidant and corrosion inhibitors for gasoline lubricating oil and compounds 6a-e, 10 and 15 exhibited the highest antioxidant and anticorrosive activities. The effect of concentration of additives was studied to recommend the optimum concentration to be used. The results showed, for additive 15, 0.1 g for 1 L oil was the more effective concentration. Measurements for thermal analysis and of surface tension of oil after oxidation were also carried out.展开更多
In view of potent antimicrobial and anti-inflammatory activities exhibited by S-substituted imidazolones, a variety of novel imidazolone analogs 3a-I were synthesized by the condensation of different substituted oxazo...In view of potent antimicrobial and anti-inflammatory activities exhibited by S-substituted imidazolones, a variety of novel imidazolone analogs 3a-I were synthesized by the condensation of different substituted oxazolones I with various aromatic amines 2. All the synthesized compounds were screened for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Several analogs produced good or moderate activities particularly against the tested Gram-positive bacteria Micrococcus luteus and Gram-negative bacteria Pseudornonas aeruginosa and, Meanwhile, compounds 3b and 3c displayed marked antifungal activity against C. albicans. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenin-induced paw oedema method in rats. Two of S-substituted imidazo/one derivatives, 3k and 3d show good anti-inflammatory activity. The structures of all the newly svnthesized compounds were elucidated using IR, 1H NMR and 13C NMR.展开更多
We report here the synthesis and in vivo anticonvulsant/neurotoxicity activities of a series of compounds belonging to 2-aryl-4-arylidene-1-phenyl-1H-imidazol-5(4H)-one. The scaffold is based on the commonality of 5-m...We report here the synthesis and in vivo anticonvulsant/neurotoxicity activities of a series of compounds belonging to 2-aryl-4-arylidene-1-phenyl-1H-imidazol-5(4H)-one. The scaffold is based on the commonality of 5-membered lactam ring structures as successful anticonvulsant agents. The present compounds exhibited a range of anticonvulsant activity in pentylenetetrazole (PTZ)-induced seizure test. In particular, the protection was excellent by compounds bearing furylmethylidene on C4, possibly due to good pharmacokinetic properties. It was found that high lipophilicity and/or electron deficient aryl ring substitution at C4 compromised the anticonvulsant activities. For example, chloro analogues were found much less active than unsubstituted phenyl or furyl derivatives. Regarding side effects, active compounds exerted no observable neurotoxic effect at their therapeutic doses in Chimney test.展开更多
Synthesis,characterization(HRMS,NMR,EPR,UV-Vis spectroscopy,and electrochemistry)and in vitro cytotoxic investigation of a series of new ferrocene-containing derivatives,based onω-ferrocene carboxylic acids and 2-alk...Synthesis,characterization(HRMS,NMR,EPR,UV-Vis spectroscopy,and electrochemistry)and in vitro cytotoxic investigation of a series of new ferrocene-containing derivatives,based onω-ferrocene carboxylic acids and 2-alkylthioimidazolin-4-ones as well as their copper coordination compounds,have been reported.A series of ferrocene–imidazolone conjugates with different lengths and donor properties of the linker fragments have been synthesized;all the obtained compounds were studied in complexation reactions with copper(Ⅰ)and copper(Ⅱ)perchlorates.It is shown that the synthesised conjugates rapidly and efficiently convert coordinating copper ions into the Cu(+1)oxidation state,but a change in the length of the linker in ferrocene–imidazolone ligands fundamentally changes the ratio of products formed as a result of iron oxidation/copper reduction and complexation by various mechanisms.After comparing the data on the qualitative and quantitative composition of the reaction mixtures and the kinetic characteristics of the processes occurring in the mixtures of ferrocene–imidazolones with copper(II)perchlorate,a scheme of the ongoing reactions was proposed which may fully explain all the observed processes and products.It has been shown that the obtained bimetallic Cu/Fe coordination compounds are more toxic than cisplatin and induce apoptosis in micromolar concentrations on Hek-293 and MCF-7 cell lines.展开更多
文摘Oxazolone derivative 2 was utilized as a key intermediate for synthesis of some new oxazolone and imidazolone derivatives. Reaction of oxazolone derivative 2 with diamines under different conditions afforded the corresponding imidazolone derivatives 3-8, respectively. Moreover, oxazolone 2 reacted with some heterocyclic amines in glacial acetic acid giving the corresponding imidazolone derivatives 9-14, respectively. Cyclocondensation of thiosemicarbazide with compound 2 in dry pyridine afforded compound 15. Addition of secondary amines to olefin double bond of compound 2 gave the corresponding addition products 16-19, respectively. Michael addition of compound 2 with some active methylene compounds afforded oxazolone derivatives 20-23, respectively. These prepared products were evaluated as antioxidant and corrosion inhibitors for gasoline lubricating oil and compounds 6a-e, 10 and 15 exhibited the highest antioxidant and anticorrosive activities. The effect of concentration of additives was studied to recommend the optimum concentration to be used. The results showed, for additive 15, 0.1 g for 1 L oil was the more effective concentration. Measurements for thermal analysis and of surface tension of oil after oxidation were also carried out.
文摘In view of potent antimicrobial and anti-inflammatory activities exhibited by S-substituted imidazolones, a variety of novel imidazolone analogs 3a-I were synthesized by the condensation of different substituted oxazolones I with various aromatic amines 2. All the synthesized compounds were screened for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Several analogs produced good or moderate activities particularly against the tested Gram-positive bacteria Micrococcus luteus and Gram-negative bacteria Pseudornonas aeruginosa and, Meanwhile, compounds 3b and 3c displayed marked antifungal activity against C. albicans. In addition, the in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenin-induced paw oedema method in rats. Two of S-substituted imidazo/one derivatives, 3k and 3d show good anti-inflammatory activity. The structures of all the newly svnthesized compounds were elucidated using IR, 1H NMR and 13C NMR.
文摘We report here the synthesis and in vivo anticonvulsant/neurotoxicity activities of a series of compounds belonging to 2-aryl-4-arylidene-1-phenyl-1H-imidazol-5(4H)-one. The scaffold is based on the commonality of 5-membered lactam ring structures as successful anticonvulsant agents. The present compounds exhibited a range of anticonvulsant activity in pentylenetetrazole (PTZ)-induced seizure test. In particular, the protection was excellent by compounds bearing furylmethylidene on C4, possibly due to good pharmacokinetic properties. It was found that high lipophilicity and/or electron deficient aryl ring substitution at C4 compromised the anticonvulsant activities. For example, chloro analogues were found much less active than unsubstituted phenyl or furyl derivatives. Regarding side effects, active compounds exerted no observable neurotoxic effect at their therapeutic doses in Chimney test.
基金the Russian Foundation of Basic Research(Projects No.19-29-08007 and 19-33-90103)for the financial supportsupported by the M.V.Lomonosov Moscow State University Program of Developmentsupported by Russian Science Foundation grant(No.19-79-30062).
文摘Synthesis,characterization(HRMS,NMR,EPR,UV-Vis spectroscopy,and electrochemistry)and in vitro cytotoxic investigation of a series of new ferrocene-containing derivatives,based onω-ferrocene carboxylic acids and 2-alkylthioimidazolin-4-ones as well as their copper coordination compounds,have been reported.A series of ferrocene–imidazolone conjugates with different lengths and donor properties of the linker fragments have been synthesized;all the obtained compounds were studied in complexation reactions with copper(Ⅰ)and copper(Ⅱ)perchlorates.It is shown that the synthesised conjugates rapidly and efficiently convert coordinating copper ions into the Cu(+1)oxidation state,but a change in the length of the linker in ferrocene–imidazolone ligands fundamentally changes the ratio of products formed as a result of iron oxidation/copper reduction and complexation by various mechanisms.After comparing the data on the qualitative and quantitative composition of the reaction mixtures and the kinetic characteristics of the processes occurring in the mixtures of ferrocene–imidazolones with copper(II)perchlorate,a scheme of the ongoing reactions was proposed which may fully explain all the observed processes and products.It has been shown that the obtained bimetallic Cu/Fe coordination compounds are more toxic than cisplatin and induce apoptosis in micromolar concentrations on Hek-293 and MCF-7 cell lines.
