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This review is devoted to the chemistry of fluoroalkyl-substituted 1,2,3-triazoles: their synthesis and chemical properties. Synthesis of C-fluoroalkyl-substituted 1,2,3-triazoles and N-fluoroalkyl-substituted 1,2,3-triazoles is c...
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This review is devoted to the chemistry of fluoroalkyl-substituted 1,2,3-triazoles: their synthesis and chemical properties. Synthesis of C-fluoroalkyl-substituted 1,2,3-triazoles and N-fluoroalkyl-substituted 1,2,3-triazoles is considered. C-Fluoroalkyl-substituted 1,2,3-triazoles can be prepared via 1,3-dipolar cycloaddition, cyclizations of R-F-vinyl azides, deoxyfluorination of alcohols, transformation of CO into CF2H, transformation of CO2H into CF3, electrophilic alpha-fluorination of 4/5-alkyl-1,2,3-triazoles, and using other methods. N-Fluoroalkyl-substituted 1,2,3-triazoles can be prepared via N-difluoromethylation of 1,2,3-triazoles, their N-trifluoromethylation with Togni's reagent, N-fluoroalkylation with haloethylenes, using 1,3-dipolar cycloaddition and other methods. Fluoroalkyl-substituted 1,2,3-triazoles are chemically reactive substances, and they can be used as building-blocks for the preparation of medicinally and biologically beneficial compounds.
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摘要 :The compound 4-amino-3-butyl-1,2,4-triazole-5-thione [crystal data: C6H12N4S, triclinic, P $ \bar 1$ , Z = 2, a = 7.546(2), b = 11.217(3), c = 5.681(1) Å, α = 103.12(2), β = 91.33(2), γ = 72.41(2)°, V = 445.9(2) Å3] contains...
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The compound 4-amino-3-butyl-1,2,4-triazole-5-thione [crystal data: C6H12N4S, triclinic, P $ \bar 1$ , Z = 2, a = 7.546(2), b = 11.217(3), c = 5.681(1) Å, α = 103.12(2), β = 91.33(2), γ = 72.41(2)°, V = 445.9(2) Å3] contains an essentially planar triazole ring with the butyl group rotated out of the plane by approximately 104°. The molecules form hydrogen-bonded dimers through intermolecular N–H $ \cdots $ S interactions involving the thione sulfur atom and the protonated nitrogen atom on the ring. These units are then linked into columns through N–H $ \cdots $ N hydrogen bonds between the amine group and the unsubstituted ring N atom of adjacent molecules. The structural features of this compound are compared with those of the corresponding triazoles with H, methyl, ethyl and propyl groups on the 3-carbon.
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Alkylation of 3-acylamino-, 5-amino-1-phenyl-3-tosylamino-1,2,4-triazoles and 3,5-diacetylamino-1-phenyl-1,2,4-triazole in the presence of an equimolar amount of sodium methylate in DMSO occurs regioselectively at the amide (sulfa...
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Alkylation of 3-acylamino-, 5-amino-1-phenyl-3-tosylamino-1,2,4-triazoles and 3,5-diacetylamino-1-phenyl-1,2,4-triazole in the presence of an equimolar amount of sodium methylate in DMSO occurs regioselectively at the amide (sulfamide) group nitrogen atom. The benzylation of 3-acetylamino-5-amino-1-phenyl-1,2,4-triazole with excess base and benzyl chloride also alkylates the amino group at position 5. Alkylamino-1-R-1,2,4-triazoles can be conveniently prepared by alkylation of the corresponding acetylamino-1,2,4-triazoles in the presence of base and subsequent acid hydrolysis of the N-acetyl-N-alkyl derivatives.
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The reaction of 4-phenyl-1,2,4-triazolin-5-one [Ia] and 3,4-diphenyl-1,2,4-triazolin-5-one [Ib] with 1-bromo-3-chloropropane was carried out. The obtained compounds [IIa, b] were subjected to the reaction with secondary amines and...
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The reaction of 4-phenyl-1,2,4-triazolin-5-one [Ia] and 3,4-diphenyl-1,2,4-triazolin-5-one [Ib] with 1-bromo-3-chloropropane was carried out. The obtained compounds [IIa, b] were subjected to the reaction with secondary amines and ethylenediamine with resulted in 1-(3-aminopropyl)-1,2,4-triazolin-5-one derivatives.
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Introduction: The triazoles represent a class of five-membered heterocyclic compounds of great importance for the preparation of new drugs with diverse biological activities because they may present several structural variations w...
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Introduction: The triazoles represent a class of five-membered heterocyclic compounds of great importance for the preparation of new drugs with diverse biological activities because they may present several structural variations with the same numbers of carbon and nitrogen atoms. Due to the success of various triazoles that entered the pharmaceutical market and are still being used in medicines, many companies and research groups have shown interest in developing new methods of synthesis and biological evaluation of potential uses for these compounds. In this review, the authors explored aspects of patents for the 1H-1,2,3-, 2H-1,2,3-, 1H-1,2,4- and 4H-1,2,4-triazole families, including prototypes being considered in clinical studies between 2008 and 2011. Areas covered: The triazoles have been studied for over a century as an important class of heterocyclic compounds and still attract considerable attention due to their broad range of biological activities. More recently, there has been considerable interest in the development of novel triazoles with anti-inflammatory, antiplatelet, antimicrobial, antimycobacterial, antitumoral and antiviral properties and activity against several neglected diseases. This review emphasizes recent perspective and advances in the therapeutically active 1H-1,2,3-, 2H-1,2,3-, 1H-1,2,4- and 4H-1,2,4-triazole derivative patents between 2008 and 2011, covering the development of new chemical entities and new Pharmaceuticals. Many studies have focused on these compounds as target structures and evaluated them in several biological targets. Expert opinion: The preparation of 1H-1,2,3-, 2H-1,2,3-, 1H-1,2,4- and 4H-1,2,4-triazole derivatives brings to light several issues. There is a need to find new, more efficient preparations for these triazoles that take into consideration current issues in green chemistry, energy saving and sustainability. New diseases are discovered and new viruses and bacteria continue to challenge mankind, so it is imperative to find new prototypes for these new diseases. Of great urgency is finding prototypes against bacteria that continue to increase resistance and for neglected diseases that affect a large part of humanity, especially the poor and vulnerable.
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摘要 :
Triazoles are heterocyclic compounds which have a five-membered ring of two carbon atoms and three nitrogen atoms. These structures have been interest in the development of novel compounds with anticonvulsant, antidepressant, anti...
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Triazoles are heterocyclic compounds which have a five-membered ring of two carbon atoms and three nitrogen atoms. These structures have been interest in the development of novel compounds with anticonvulsant, antidepressant, antioxidant, anti-inflammatory, analgesic, antinociceptive, antibacterial, antimycobacterial, antifungal, antiviral, anticancer, anti-parasitic, anti-urease and other activities. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. This review contains various pharmacological activities of 1,2,4-triazole-3-thiones in one place and it is also the milestone for the new research towards this moiety. (C) 2014 Elsevier Masson SAS. All rights reserved.
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Triazole and triazoles fused with six-membered ring systems are found to possess diverse applications in the fields of medicine, agriculture and industry. The new 1,2,4-triazole and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine derivati...
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Triazole and triazoles fused with six-membered ring systems are found to possess diverse applications in the fields of medicine, agriculture and industry. The new 1,2,4-triazole and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine derivatives were synthesized as novel antimicrobial agents. The reaction of 1H-indol-3-acetic acid with thiocarbohydrazide gave the 4-amino-3-mercapto-5-[(1H-indol-3-yl)methyl]-4H-1,2,4-triazole. The reaction of triazole with arylaldehydes in ethanol gave the 4-arylideneamino-3-mercapto-5-[(1H-indol-3-yl)methyl]-4H-1,2,4-triazoles (I). The 3-[(1H-indol-3-yl)methyl]-6-aryl-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines (II) were obtained by condensing triazole with phenacyl bromides in absolute ethanol . The chemical structures of the compounds were elucidated by IR, (1)H NMR and FAB(+)-MS spectral data. Their antimicrobial activities against Micrococcus luteus (NRLL B-4375), Bacillus cereus (NRRL B-3711), Proteus vulgaris (NRRL B-123), Salmonella typhimurium (NRRL B-4420), Staphylococcusaureus (NRRL B-767), Escherichia coli (NRRL B-3704), Candida albicans and Candida glabrata (isolates obtained from Osmangazi University, Faculty of Medicine) were investigated and significant activity was obtained.
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Urease has a long and distinguished history in the development of enzymology since it was the first enzyme crystallized by Sumner in 1926. The present review article is focused on the urease inhibitory potential of thiazolidinone,...
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Urease has a long and distinguished history in the development of enzymology since it was the first enzyme crystallized by Sumner in 1926. The present review article is focused on the urease inhibitory potential of thiazolidinone, triazole, and benzothiazole-based heterocyclic derivatives. The study begins with the historical developments in the discovery of urease and its substrate, urea, along with the active site architecture of ureases of different origins. The two pathways for the urease-catalyzed hydrolysis of urea are explained in detail. The urease inhibitory potential of the aforementioned heterocyclic deriva- tives is reviewed and arranged systematically. Structure-activity relationships (SARs) study provided the substituents necessary for urease inhibition and will be useful for the researchers working in the field of anti-ulcer agents. To a step further, important binding interactions were identified with the amino acid residues at the active site of the enzyme. The information gathered is anticipated to offer logical direction and an effective method for creating innovative, potent, and efficient urease inhibitors that will have greater practical uses in the future.
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Triazoles and their derivatives have been widely utilized as precursors in the syntheses of biologically active systems such as anticancers, antimicrobials, antifungals and other cytotoxic active agents. In this review, we tried t...
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Triazoles and their derivatives have been widely utilized as precursors in the syntheses of biologically active systems such as anticancers, antimicrobials, antifungals and other cytotoxic active agents. In this review, we tried to highlight the recent advances (2010- 2013) in the syntheses of 1,2,3-triazoles, bis-1,2,3-triazoles and fused triazoles via click reaction. Click reaction provides substances quickly and reliably by combining small units together. Click chemistry can also be applied widely for the syntheses of biologically active compounds. Since the 1,2,3-triazole scaffold is present in many beneficial biologically structures, we hope this review attracts the attentions of synthetic organic chemists to make use of the advantages of click reaction in the total syntheses of natural products containing 1,2,3-triazoles.
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2-Substituted-2H-1,2,3-triazolo-nucleosides with 3-phosphonopropyl, 2-hydroxyethyl, 2-cyanoethyl, carbamoylmethyl, or 1-deoxy-2,5-anhydro-d- mannitol-1-yl on the triazole N-2 nitrogen atom were obtained via the DBU-promoted N-alky...
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2-Substituted-2H-1,2,3-triazolo-nucleosides with 3-phosphonopropyl, 2-hydroxyethyl, 2-cyanoethyl, carbamoylmethyl, or 1-deoxy-2,5-anhydro-d- mannitol-1-yl on the triazole N-2 nitrogen atom were obtained via the DBU-promoted N-alkylation of 3-(pivaloyloxymethyl)-1-[(NH-1,2,3-triazol-4-yl) methyl]thymine with diethyl 3-bromopropylphoshonate, 2-bromoethanol, acrylonitrile, methyl bromoacetate, or 3,4,6-tris(O-benzoyl)-2,5-anhydro-d- mannitol 1-tosylate. The N-2/N-1 regioselectivity of the alkylation varied from 57/43 (methyl bromoacetate) to 97/3 (diethyl 3-bromopropylphoshonate). The 1-substituted-1H-1,2,3-triazoles, when formed in the appreciated amount in the alkylation reaction, were converted into the corresponding 1-substituted-1H-1,2, 3-triazolo-nucleosides. The substitution pattern of 2-substituted-2H-1,2,3- triazolo-nucleosides was confirmed by ~1H-~(15)N HMBC NMR spectra; the triazole nitrogen atoms were identified through their correlations with the triazole exo-cyclic protons.
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