- Sodium hydrogen exchanger inhibitory activity of benzotriazole derivatives
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Series of benzotriazole derivatives were synthesized and evaluated for their Sodium hydrogen exchanger-1 inhibitory potential. All compounds inhibit Sodium hydrogen exchanger-1 in the in-vitro platelet swelling assay. This is perhaps the first report of NHE-1 inhibitory activity of benzotriazole. The 1-alkyl benzotriazole derivatives were found to be more active than the 2-alkyl isomers. The activity increases with increase in chain length of alkyl moiety. Potency increased from that of benzotriazole (IC50= 192.68 μM) to heptyl derivative (compound 13; IC50= 59.23 μM). Introduction of electronegative oxygen atom further increased potency as shown by the benzoyl (compound 16, IC50= 51.57 μM) and sulfonyl groups (compound 17, IC50= 50.89 μM; compound 18, IC50= 49.95 μM).
- Singh, Dhandeep,Silakari, Om
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p. 183 - 189
(2016/10/25)
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- 1H,6H-Triazolo[4,5-e]benzotriazole-3-oxides and 5,5′-(Z)-diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) derived from chloronitrobenzotriazoles and hydrazine
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Nitration of 5-chlorobenzotriazole (1) and its N1-methyl derivatives (2 and 3) produced 5-chloro-4-nitrobenzotriazole (5), 5-chloro-1-methyl-4-nitrobenzotriazole (6) and 6-chloro-1-methyl-7-nitrobenzotriazole (7) respectively. Nitration of 5-chloro-2-methylbenzotriazole (4) gave either 5-chloro-2-methyl-4-nitrobenzotriazole (8) or 5-chloro-2-methyl-4,6-dinitrobenzotriazole (9). Introduction of the nitro group activated chlorine atom that underwent nucleophilic displacement by hydrazine to give rise to a new tricyclic system 1H,6H-triazolo[4,5-e]benzotriazole-3-oxide compounds (10 and 11) in the case of 5 and 6. From 9 no linear or angular tricyclic triazolobenzotriazole was obtained but instead the 5,5′-(Z)-diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) (18).{A figure is presented}.
- Carta, Antonio,Piras, Sandra,Boatto, Gianpiero,Paglietti, Giuseppe
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p. 2471 - 2481
(2007/10/03)
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- Organic reactions in ionic liquids: An efficient method for the N-alkylation of benzotriazole
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The N-alkylation of benzotriazole with alkyl halides proceeds efficiently in the presence of potassium hydroxide in ionic liquid 1-butyl-3- methylimidazolium tetrafluoroborate ([Bmim][BF4]).
- Le, Zhang-Gao,Chen, Zhen-Chu,Hu, Yi,Zheng, Qin-Guo
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p. 344 - 346
(2007/10/03)
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- Oxidative Alkylation of Azoles. IV. Reaction of N-Halo- and N-Nitrobenzotriazoles with Methyl Iodide
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Reactions of N-chloro-, N-bromo-, N-iodo-, and N-nitrobenzotriazoles with methyl iodide yield products of mono- and dialkylation at the heteroatoms and also unsubstituted benzotriazole.The reaction of N-chlorobenzotriazole with methyl iodide yields also N
- Kurenkov, A. A.,Pevzner, M. S.
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p. 1122 - 1124
(2007/10/03)
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- SELECTIVE ALKYLATIONS OF 1,2,4-TRIAZOLE AND BENZOTRIAZOLE IN THE ABSENCE OF SOLVENT
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Alkylation of 1,2,4-triazole and benzotriazole has been performed either in basic media under solvent free phase transfer catalysis conditions or in the absence of base by conventional and microwave heating.Several parameters affecting the selectivity have been studied.In the case of triazole alkylation, microwave irradiation produces specific (non thermal) effects both on reactivity and selectivity.
- Abenhaim, David,Diez-Barra, Enrique,Hoz, Antonio de la,Loupy, Andre,Sanchez-Migallon, Ana
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p. 793 - 802
(2007/10/02)
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- A Novel Selective Route to 1-Substituted Benzotriazoles via Lithiation of Simple 1-Alkylbenzotriazoles
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1-Methylbenzotriazole (2a) is lithiated readily with butyllithium or LDA at the methyl group to 4 and the subsequent reaction with various electrophiles provides 1-substituted benzotriazoles 5.Other 1-(n-alkyl)benzotriazoles 2 also undergo lithiation with LDA, the carbanions can be trapped with alkyl halides giving benzotriazoles 6 bearing secondary alkyl groups on the N-1 atom.On standing in the absence of electrophiles, all the lithium derivatives decompose to afford complex mixtures. - Key Words: Benzotriazoles, 1-alkyl / Lithiation / Haloalkanes
- Katritzky, Alan R.,Wu, Jing,Kuzmierkiewicz, Wojciech,Rachwal, Stanislaw
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- Novel Conversions of Benzotriazol-1-ylmethyl Derivatives
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New (benzotriazol-1-yl)methyl derivatives of type BtCH2X (X = Br, I, ONO2) have been investigated.Ethyl (benzotriazol-1-yl)acetate (BtCH2CO2Et) is converted by treatment with butyl nitrite into the oximes BtCH:NOH of which the E isomer is stable but the Z
- Katritzky, Alan R.,Wu, Jing,Wrobel, Leszek,Rachwal, Stanislaw,Steel, Peter J.
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p. 167 - 175
(2007/10/02)
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- STUDIES ON THE THERMAL DECARBOXYLATION OF 1-ALKOXYCARBONYLBENZOTRIAZOLES
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1-Alkoxycarbonylbenzotriazoles on thermolysis lose carbon dioxide; the decarboxylation is accompanied by the formation of a mixture of 1- and 2-alkylbenzotriazoles, with the N-1 isomer predominating over the N-2 isomer in all cases.A cross-over experiment
- Katritzky, Alan R.,Zhang, Gui-Fen,Fan, Wei-Qiang,Wu, Jing,Pernak, Juliusz
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p. 567 - 573
(2007/10/02)
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- N-SULFONYLBENZOTRIAZOLES. PART 2. REACTIONS OF 1,1'-SULFONYLDIBENZOTRIAZOLE AND 1-BENZENESULFONYL-1,2,4-TRIAZOLE WITH ALCOHOLS; A NEW APPROACH TO N-ALKYLBENZOTRIAZOLES AND N-ALKYL-1,2,4-TRIAZOLES
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1,1'-Sulfonyldibenzotriazole (3) reacts with sodium alkoxides to give N-alkylbenzotriazoles.With alkanols, benzotriazolium alkyl sulfates are produced. 1-Benzenesulfonyl-1,2,4-triazole with sodium salts of alcohols gives 1-alkyl-1,2,4-triazoles.The mechanisms of these reactions are discussed.
- Katritzky, Alan R.,Zhang, Gui-Fen,Pernak, Juliuzs,Fan, Wei-Qiang
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p. 1253 - 1262
(2007/10/02)
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- An improved method for the N-alkylation of benzotriazole and 1,2,4-triazole
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The N-alkylation of benzotriazole and 1,2,4-triazole with alkyl halides proceeds efficiently in the presence of sodium hydroxide in N,N-dimethylformamide.
- Katritzky, Alan R.,Kuzmierkiewiecz, Wojciech,Greenhill, John V.
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p. 369 - 373
(2007/10/02)
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- Alkylation with Oxalic Esters. Scope and Mechanism.
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Alkyl oxalates are well suited for use as standard synthetic reagents in N-, O-, or S-alkylations and often display an interesting regioselectivity.The mechanism seems to be a direct alkylation of the substrate anion.
- Bergman, Jan,Norrby, Per-Ola,Sand, Peter
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p. 6113 - 6124
(2007/10/02)
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- A NEW SIMPLE PROCEDURE FOR ALKYLATION OF NITROGEN HETEROCYCLES USING DIALKYL OXALATES AND ALKOXIDES.
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A variety of nitrogen heterocycles are N-alkylated in high yields with dialkyl oxalates and potassium alkoxides in refluxing dimethylformamide.
- Bergman, Jan,Sand, Peter
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p. 1957 - 1960
(2007/10/02)
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- Methylathion of Heterocyclic Compounds Containing NH, SH and/or OH Groups by Means of N,N-Dimethylformamide Dimethyl Acetal
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Methylations of heterocyclic systems, such as benzimidazole, naphthimidazole, imidazopyridine, purine, pyridine, pyrimidine, pyridazine and s-triazolopyridazine, which bore SH, NH and/or OH groups, were carried out with dimethylformamide dimethyl acetal to give the corresponding S-, N- and/or O-methyl derivatives in high yields.Selective methylation of some compounds containing both SH and NH groups took place to give first the S-methyl and subsequently the S,N-dimethyl derivatives.No side reactions, such as C-methylation, were observed.
- Stanovnik, Branko,Tisler, Miha,Hribar, Alenka,Barlin, Gordon B.,Brown, Desmond J.
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p. 1729 - 1738
(2007/10/02)
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