- Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2-dicarbonyl compounds using etidronic acid as a “green catalyst”
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Most of the known methods for the synthesis of heterocyclic compounds have disadvantages, such as a long reaction time and aggressive conditions. We have developed a new, rather simple and efficient method for the synthesis of a number of glycoluryls and hydantoins in water using a etidronic acid (HEDP) as “Green catalyst.” So, for the first time, the condensation reaction of ureas with 1, 2-dicarbonyl compounds was carried out in the presence of HEDP. Also based on NMR studies, a chemism of these reactions, which is stepwise, is proposed. It has been established that the optimal conditions for the synthesis of glycoluryls and hydantoins using HEDP are: temperature 80°C-90°C, 40-20 minutes, and the ratio of urea and HEDP is 1:1. In all cases, the remaining aqueous filtrate containing HEDP after the reaction can be reused for other cycles synthesis of glycoluril and other compounds, because HEDP is not converted during the reaction.
- Bakibaev, Abdigali A.,Uhov, Artur,S. Malkov, Victor,Yu. Panshina, Svetlana
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p. 4262 - 4270
(2020/10/02)
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- 2,4-Imidazolinedione heterocyclic derivative, and preparation method and use thereof
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The invention belongs to the field of chemical medicines, and concretely relates to a 2,4-imidazolinedione heterocyclic derivative, and a preparation method and a use thereof. The structure of the 2,4-imidazolinedione heterocyclic derivative is represented by formula I. The invention also provides the preparation method and the use of the 2,4-imidazolinedione heterocyclic derivative. The 2,4-imidazolinedione heterocyclic derivative has a good inhibition effect on Pim-1 protein kinase micro-molecules, and has important exploitation application prospect.
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Paragraph 0081; 0082; 0083
(2017/07/01)
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- IDENTIFICATION AND TREATMENT OF VULNERABLE PLAQUES
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A method of detecting an atherosclerotic plaque vulnerable to rupture in a subject comprises providing to the subject a labelled necrostatin or a derivative thereof, and visualizing the label, wherein a localization of the label in a plaque indicates the plaque is vulnerable to rupture. A method of detecting and treating an atherosclerotic plaque vulnerable to rupture comprises providing to the subject a labelled necrostatin or a derivative thereof, visualizing the label, wherein a localization of the label in a plaque indicates the plaque is vulnerable to rupture; and providing a necroptosis inhibitor or derivative thereof to the subject when the visualizing indicates that the plaque is vulnerable to rupture. The necroptosis inhibitor may comprise a necrostatin, such as Nec-1. The label may be a radiolabel such as 123I. By visualizing plaques vulnerable to rupture, atherosclerotic plaques may be identified and treated in advance of rupture.
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Paragraph 0149
(2016/11/28)
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- NOVEL AMIDE DERIVATIVE AND USE THEREOF AS MEDICINE
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Provided are a novel low-molecular-weight compound that suppresses production of induction type MMPs, particularly MMP-9, rather than production of hemostatic type MMP-2, as well as a prophylactic/therapeutic drug for autoimmune diseases or osteoarthritis. An amide derivative represented by the following formula (I) wherein each symbol is as defined in the specification, or a pharmacologically acceptable salt thereof.
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Paragraph 0780; 0781; 0782
(2013/03/26)
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- AMINOMETHYL BIARYL BENZOTRIAZOLE DERIVATIVES
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The present invention is directed to aminomethyl biaryl benzotriazole derivatives which are potentiators of metabotropic glutamate receptors, particularly the mGluR2 receptor, and which are useful in the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which metabotropic glutamate receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which metabotropic glutamate receptors are involved.
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Page/Page column 29
(2012/11/14)
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- Facile synthesis of hydantoins and thiohydantoins in aqueous solution
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A series of hydantoins and thiohydantoins have been synthesized in water at room temperature from urea (or N-methylurea, or thiourea) and simple aldehydes (as glyoxal, and its simple derivatives) in the presence of phosphoric anhydride. The reaction time is 10 min using an equimolar amount of P 4O10 with respect to the other reagents, but the reaction occurs also, even if with longer reaction times, with very small amounts of P4O10. In addition, this method provides a clean and 'green' approach to hydantoins, compounds of great interest in biological and pharmacological fields.
- Baccolini, Graziano,Boga, Carla,Delpivo, Camilla,Micheletti, Gabriele
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experimental part
p. 1713 - 1717
(2011/05/05)
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- Synthesis of imidazol[1,5-a]indole-1,3-diones from imidazolidene-2,4-diones
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Copper and tributyltin hydride catalysed cyclization, through the N-aryl bond formation, of imidazolidine-2,4-diones (11-16,18) yielded imidazo[1,5-a]indole-1,3-diones (5-10) in high yields (72-100%). The ease of cyclization was found to be consistent with the normal halogen reactivity and the type of substituents. The highly substituted imidazole-2,4-dione 15 gave brominated 19 and tin incorporated heterocycles 20 when treated with copper bromide and tributyltin hydride, respectively.
- Akeng'a,Read
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- Unusual oxidation behaviour of a propargylic alcohol
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Attempts to convert a propargylic alcohol bearing an imidazolone substituent to the corresponding aldehyde under Parikh-Doering conditions gave an α,β-unsaturated-β-methylsulfanyl aldehyde, which cyclised under mildly acidic conditions. Attempts to convert a propargylic alcohol bearing an imidazolone substituent to the corresponding aldehyde under Parikh-Doering conditions gave an α,β-unsaturated-β- methylsulfanyl aldehyde, which cyclised under mildly acidic conditions.
- Porter, Michael J.,White, Nicola J.,Howells, Garnet E.,Laffan, David D.P.
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p. 6541 - 6543
(2007/10/03)
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- Methyl orthocarboxylates as methylating agents of heterocycles
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Methylation reactions occurring between trimethyl orthocarboxylates or N,N-dimethylcarboxamide dimethyl acetals and various hydroxylated heterocycles, involving a lactam-lactim tautomeric equilibrium, were investigated as an alternative to classic methyla
- Janin, Yves L.,Huel, Christiane,Flad, Genevieve,Thirot, Sylvie
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p. 1763 - 1769
(2007/10/03)
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- A New Method of Synthesis of 3-Monosubstituted-2-thiohydantoins and -Hydantoins
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A new method of synthesis of 3-monosubstituted derivatives of 2-thiohydantoin and hydantoin in reaction of isothiocyanate or isocyanate glycin ethyl ester with primary aliphatic and aromatic amines has been described. Crude products were obtained with high yield and purity. The structure of these compounds was confirmed by spectral methods. Key words: 2-thiohydantoin, hydantoin, isothiocyanate glycin ethyl ester, isocyanate glycin ethyl ester
- Ryczek, J.
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p. 2599 - 2604
(2007/10/02)
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- MECHANISM OF BASE-CATALYZED CYCLIZATION OF ETHYL N-(SUBSTITUTED AMINOCARBONYL)GLYCINATES
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The cyclization rate constants have been measured of substituted ethyl N-(phenylaminocarbonyl)-, N-(alkylaminocarbonyl)-, and N-(phenylaminothiocarbonyl)glycinates RNHCXNHCH2CO2C2H5 (X=O,S).Logarithms of these constants increase with decreasing basicity of the amines down to the value of pKa(RNH2) = 5.5.The rate-limiting step of the reaction is formation of the tetrahedral intermediate.With ethyl N-(phenylaminocarbonyl)glycinates (whose pKa(RNH2) values are higher) this dependence, on the contrary, slightly decreases, and the acid-catalyzed splitting off of ethoxy group from the cyclic intermediate becomes rate-li miting.The cyclization rate of a series of ethyl N-(phenylaminothiocarbonyl)glycinates is practically independent of the pKa(RNH2) values, the change in the rate limiting step would take place at pH about 9.
- Mindl, Jaromir,Sterba, Vojeslav
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p. 156 - 161
(2007/10/02)
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- BASE CATALYZED CYCLIZATION OF SUBSTITUTED ESTERS OF HYDANTOIC AND THIOHYDANTOIC ACID
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Base catalyzed cyclization rates have been measured of 22 derivatives of hydantoic and thiohydantoic acid esters in water and methanol.The cyclization of methyl and ethyl esters of hydantoic and 5-methylhydantoic acids is accompanied by hydrolysis of the ester group, whereas with the other derivatives the hydrolysis does not take place.Hydrolysis of the cyclization products (hydantoin and thiohydantoin derivatives) is not significant under the kinetic conditions.The cyclization of methyl ester of 5-phenylhydantoic acid in methanol is reversible; the equilibrium mixture contains 30percent of the starting ester.In all the cases the cyclization is subject to specific base catalysis; exceptions are esters of 5-phenylthiohydantoic and 5-phenyl-2-methylthiohydantoic acids whose cyclizations are subject to general base catalysis.Substituents always accelerate the cyclization.The 3-substituents have the greatest effects, the cyclization rate being considerably increased with bulk of the substituents; similarly large effect of 5-phenyl group consists mainly in its polar effects on the pre-equilibrium.The cyclizations are slower in methanol at the same concentration of the lyate ion: the greatest difference (up to 3 orders of magnitude) is observed with the 5-phenyl derivatives.
- Kavalek, Jaromir,Machacek, Vladimir,Svobodova, Gabriela,Sterba, Vojeslav
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p. 375 - 390
(2007/10/02)
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- Kinetics and Mechanism of Cyclisation of N-(Methylaminocarbonyl)glycine to 3-Methylimidazolidine-2,4-dion
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The dependence of rate coefficients for cyclisation upon acidity, solvent isotope effects, and the kinetics of oxygen exchange of the product, support the view that in the acid catalysed cyclisation there is rate-determining ring closure of the neutral substrate synchronous with protonation of the carboxy oxygen.This is contrary to what current view of the mechanism of acid catalysed amide hydrolysis would lead one to expect; reasons for this are discussed.The kinetics of the uncatalysed cyclisation and of the reverse ring opening reaction in alkali are reported, and a mechanistic scheme for the whole pH range is presented.The equilibrium constant of the title reaction in water at 25 degC is shown to lie between 1E3 and 1E6; the slowness of the reaction at central values of pH prevents a closer estimate.
- Gueler, Faruk,Moodie, Roy B.
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p. 1752 - 1756
(2007/10/02)
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