- Cytoprotective activities of kinetin purine isosteres
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Kinetin (N6-furfuryladenine), a plant growth substance of the cytokinin family, has been shown to modulate aging and various age-related conditions in animal models. Here we report the synthesis of kinetin isosteres with the purine ring replace
- Maková, Barbara,Mik, Václav,Li?ková, Barbora,Gonzalez, Gabriel,Vítek, Dominik,Medvedíková, Martina,Monfort, Beata,Ru?ilová, Veronika,Kadlecová, Alena,Khirsariya, Prashant,Gándara Barreiro, Zoila,Havlí?ek, Libor,Zatloukal, Marek,Soural, Miroslav,Paruch, Kamil,D'Autréaux, Benoit,Hajdúch, Marián,Strnad, Miroslav,Voller, Ji?í
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- Discovery of novel triazole compounds as selective IL-1β releasement inhibitors
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Inflammation and immunity are closely related to the occurrence and development of a variety of immune diseases. Although IL-1β has been identified as a key cytokine in many immune diseases, safe and specific small molecular IL-1β releasement inhibitors a
- Chen, Leyuan,Gou, Wenfeng,Hou, Wenbin,Li, Yiliang,Mu, Ruixu,Wei, Huiqiang,Ye, Caiying,Yu, Jingcheng,Zhou, Yongting,Zhu, Lei
-
supporting information
(2021/10/27)
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- Water/Alkali-Catalyzed Reactions of Azides with 2-Cyanothioacetamides. Eco-Friendly Synthesis of Monocyclic and Bicyclic 1,2,3-Thiadiazole-4-carbimidamides and 5-Amino-1,2,3-triazole-4-carbothioamides
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The reactions of thioamides with azides in water were studied. It was reliably shown that the reaction of 2-cyanothioacetamides 1 with various types of azides 2 in water in the presence of alkali presents an efficient, general, one-step, atom-economic, and eco-friendly method for the synthesis of 1,2,3-thiadiazol-4-carbimidamides 5 and 1,2,3-triazole-4-carbothioamides 4. This method can be extended to the one-pot reaction of sulfonyl chlorides and 6-chloropyrimidines 2′o with sodium azide, leading to final products in higher yields, that is, avoiding the isolation of unsafe sulfonyl azides. The method was furthermore applied to the reaction of N,N′-bis-(2-cyanothiocarbonyl)pyrazine 1h with sulfonyl azides to afford bicyclic 1,2,3-thiadiazoles 8 and 1,2,3-triazoles 9 connected via a 1,1′-piperazinyl linker. 2-Cyanothioacetamides 1 were also shown to react with aromatic azides in water in the presence of alkali to afford 1-aryl-5-amino-1,2,3-triazole-4-carbothioamides 11. In contrast to aromatic azides and similarly to sulfonyl azides, 6-azidopyrimidine-2,4-diones 2o-q react with cyanothioacetamides to form N-pyrimidin-6-yl-5-dialkylamino-1,2,3-thiadiazole-4-N-l-carbimidamides 12. A mechanism was proposed to rationalize the role of water in changing the reactivity of azides toward 2-cyanothioacetamides.
- Filimonov, Valeriy O.,Dianova, Lidia N.,Beryozkina, Tetyana V.,Mazur, Dmitrii,Beliaev, Nikolai A.,Volkova, Natalia N.,Ilkin, Vladimir G.,Dehaen, Wim,Lebedev, Albert T.,Bakulev, Vasiliy A.
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p. 13430 - 13446
(2019/10/16)
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- NEW TRPA1 ANTAGONISTS
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The present invention relates to bicyclic heterocyclic derivatives of Forrmula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by TRPA1 channel inhibition or antagonism.
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Page/Page column 37; 38
(2017/05/02)
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- NEW TRPA1 ANTAGONISTS
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The present invention relates to compounds of Formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by TRPA1 channel inhibition or antagonism.
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Page/Page column 58; 59
(2017/08/01)
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- IRAK INHIBITORS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same for inhibiting one or more interleukin-1 receptor-associated kinases ("IRAK").
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Paragraph 00349
(2017/01/26)
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- Energetic derivatives of 5-(5-amino-2H-1,2,3-triazol-4-yl)-1H-tetrazole
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This study presents the preparation of the novel nitrogen-rich compound 5-(5-amino-2H-1,2,3-triazol-4-yl)-1H-tetrazole (5) from commercially available chemicals in a five step synthesis. The more energetic derivatives with azido (6) and nitro (7) groups, as well as a diazene bridge (8) were also successfully prepared. The energetic compounds were comprehensively characterized by various means, including vibrational (IR, Raman) and multinuclear (1H, 13C, 14N, 15N) NMR spectroscopy, mass spectrometry and differential thermal analysis. The sensitivities towards important outer stimuli (impact, friction, electrostatic discharge) were determined according to BAM standards. The enthalpies of formation were calculated on the CBS-4M level of theory, revealing highly endothermic values, and were utilized to calculate the detonation parameters using EPXLO5 (6.02).
- Izsák, Dániel,Klap?tke, Thomas M.,Pflüger, Carolin
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p. 17054 - 17063
(2015/10/12)
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- [1, 2, 3] TRIAZOLO [4, 5 -D] PYRIMIDINE DERIVATIVES AS AGONISTS OF THE CANNABINOID RECEPTOR 2
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The invention relates to a compound of formula (I), wherein A, R1 and R2 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament as agonists of the cannabinoid receptor 2.
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- NOVEL [1,2,3]TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES
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The invention relates to a compound of formula (I) wherein A, R1 and R2 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.
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- 8-Azapurines as new inhibitors of cyclin-dependent kinases
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Purine inhibitors of cyclin-dependent kinases (CDK) seem to be a potential anticancer drug candidate as one of the first representatives, roscovitine, is passing Phase II clinical trials for cancer and glomerulonephritis. In this article, we describe a no
- Havlicek, Libor,Fuksova, Kveta,Krystof, Vladimir,Orsag, Martin,Vojtesek, Borivoj,Strnad, Miroslav
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p. 5399 - 5407
(2007/10/03)
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- 2,9-Disubstituted-N6-(arylcarbamoyl)-8-azaadenines as new selective A3 adenosine receptor antagonists: Synthesis, biochemical and molecular modelling studies
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A number of N6-(N-arylcarbamoyl)-2-substituted-9-benzyl-8- azaadenines, obtained by a modification of the synthetic scheme used to prepare selective A1 ligands, by only three or two steps, are described. At first we prepared a series
- Biagi, Giuliana,Bianucci, Anna Maria,Coi, Alessio,Costa, Barbara,Fabbrini, Laura,Giorgi, Irene,Livi, Oreste,Micco, Iolanda,Pacchini, Federica,Santini, Edoardo,Leonardi, Michele,Nofal, Fatena Ahmad,Salerni, Oreste LeRoy,Scartoni, Valerio
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p. 4679 - 4693
(2007/10/03)
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- Synthesis of 6-mono- and 5,6-disubstituted 1,2,3-triazolo[4,5-d]pyrimidin- 7-ones
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The reactions of N-substituted 4-amino-3-benzyl-1,2,3-triazole-5- carboxamides with phosphorus oxochloride and dimethylformamide at 80°C or with triethyl orthoacetate and acetic anhydride at 160°C afforded 6-mono- or 5,6-disubstituted 1,2,3-triazolo[4.5-d
- Kislyi,Danilova,Semenov
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p. 1770 - 1776
(2007/10/03)
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- Regioselective synthesis of 9-substituted-8-azaguanines (5-amino-3-substituted-3,6-dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7 -one)
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By modifying previously described methods for the synthesis of 9-substituted-guanines from imidazoles, we have developed a new procedure for the regioselective synthesis of 9-substituted-8-azaguanines (5-amino-3-substituted-3,6-dihydro-7H- 1,2,3-triazolo[4,5-d]pyrimidin-7-one) from triazoles in high yields. The method seems suitable for the introduction of a variety of substituents including sugars, carbocyclic, acyclic and carboacyclic chains.
- Sznaidman,Beauchamp
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p. 1605 - 1610
(2007/10/03)
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- An Improved Procedure for the Preparation of 1-Benzyl-1H-1,2,3-triazoles from Benzyl Azides.
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A procedure for the preparation of substituted 1-benzyl-1H-1,2,3-triazoles from benzyl azides under very mild conditions is described.The method provides improved yields and extends the scope of the Dimroth Reaction to other types of active methylene compound to those previously used.Benzyl azides react with active methylene compounds in dimethyl sulphoxide catalysed by potassium carbonate at 35-40 deg C to give 1H-1,2,3-triazoles usually in good yield.Acetonitrile derivatives gave 5-amino-1H-1,2,3-triazoles whereas diethyl malonate gave 5-hydroxy-1H-1,2,3-triazoles. 1H-1,2,3-Triazole-4-carboxylate esters and 1H-1,2,3-triazole-4-ketones were obtained from ethyl acetoacetate and β-diketones respectively.Benzyl methyl ketone reacted to give 5-methyl-4-phenyl-1H-1,2,3-triazole, but acetone and acetophenone failed to react.Other active methylene compounds which did not react under these reaction conditions included ethyl cyanoacetate, ethyl fluoroacetate and ethyl nitroacetate.
- Cottrell, Ian F.,Hands, David,Houghton, Peter G.,Humphrey, Guy R.,Wright, Stanley H. B.
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p. 301 - 304
(2007/10/02)
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- Benzylated 1,2,3-triazoles as anticoccidiostats
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Substituted 5-amino-4-carbamoyl-1,2,3-triazoles 3a-w were prepared by two synthetic schemes and evaluated in vivo for anticoccidial activity. Both schemes proceeded by brominating appropriately substituted toluenes 4a-s,v to 5a-s,v. In Scheme I, the brominated benzyl analogues 5 were converted to the corresponding benzyl azides 6, which were treated with cyanoacetamide to yield 1-substituted-5-amino-4-carbamoyl-1,2,3-triazoles 3. In Scheme II, the benzyl halides 5 were employed to alkylate the sodium salt of 5-amino-4-carbamoyl-1,2,3-triazole (7). Preliminary screening data against Eimeria acervulina and E. tenella in chickens suggested structural requirements for maximizing activity. Further evaluation against a relatively resistant series of eight Eimeria field isolates revealed L-651,582 (3a) to be a highly effective coccidiostat. However, unacceptable tissue residues precluded further development. Mechanistic studies on this series of 5-amino-4-carbamoyl-1,2,3-triazoles and, in particular, on L-651,582 (3a) revealed that its mode of action does not involve inhibition of IMP dehydrogenase, but probably interferes with host cell calcium entry. In addition, L-651,582 has been found to have antiproliferative activity in several disease models and was recently reported to possess antimetastatic activity in a model of ovarian cancer progression.
- Bochis,Chabala,Harris,Peterson,Barash,Beattie,Brown,Graham,Waksmunski,Tischler,Joshua,Smith,Colwell,Wyvratt Jr.,Fisher,Tamas,Nicolich,Schleim,Wilks
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p. 2843 - 2852
(2007/10/02)
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- NEW METHOD FOR STUDYING THE REACTIVITIES OF α-DIAZO IMINES. INVESTIGATION OF THE CYCLIZATION OF N-SUBSTITUTED 2-DIAZOACETAMIDINES TO 1,2,3-TRIAZOLES
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N-Substituted diazoacetamidines were generated in the reaction of N-substituted acetamidines with benzenesulfonyl azide.It is shown that their cyclization to isomeric 1,2,3-triazole characterizes the reactivities of α-diazo imines.The synthesis of 5-amino
- Dankova, E. F.,Bakulev, V. A.,Krut'ko, D. P.
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p. 607 - 613
(2007/10/02)
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- Monoazo compounds having a substituted 1,2,3-triazolyl-5 diazo component radical and an unsubstituted or substituted 1,4-phenylene coupling component radical
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Compounds of the formula STR1 in which R1 is hydrogen or an aliphatic or aromatic substituent conventional for diazo component radicals of disperse dyes and which is bound to a N-atom in the 1- or 2-position of the triazole nucleus through a carbon atom, with the proviso that when R1 is in the 1-position, the broken line represents double bonds in the 2,3- and 4,5-positions and when R1 is in the 2-position, the broken line represents double bonds in the 3,4- and 1,5-positions, R2 is an electron withdrawing or inductive group, and K is a coupling component radical of the aniline series, with the proviso that the molecule is free from cationic groups, sulphonic acid groups, metals and metallizable groups, which compounds are useful as disperse dyes for textile substrates consisting of or comprising synthetic or semi-synthetic, hydrophobic, high molecular weight organic materials such as linear aromatic polyesters, cellulose 21/2 acetate, cellulose triacetate and synthetic polyamides.
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- v-Triazolopyrimidines (8-Azapurines). Part 24. The 3-Alkyl Derivatives
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4-Methylamino-1,2,3-triazole-5-carboxamide (2e) and its 3-benzyl derivative (2b) were cyclized with hydrochloric acid and triethyl orthoformate to give 3-methyl-8-azapurin-6(1H)-one (1c) and its 9-benzyl derivative (1b).The reaction mechanism is discussed
- Albert, Adrion
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p. 2344 - 2351
(2007/10/02)
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