- A novel copper-catalyzed, hydrazine-free synthesis of N-1 unsubstituted 1H-indazoles using stable guanylhydrazone salts as substrates
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A CuI-catalyzed, hydrazine-free transformation of 2-(2-bromoarylidene)guanylhydrazone hydrochlorides using Cs2CO3 as a base and DMEDA as a ligand at 120 °C for 5 h delivers substituted 1H-indazoles with yields up to 75%. The C,N double bond configuration of the substrates was determined by NMR experiments and quantum chemical calculations. The reaction mechanism was studied using quantum chemical calculations.
- Rekowski, Szymon P.,Kroener, Bettina K.,Kathuria, Deepika,Wani, Aabid A.,Chourasiya, Sumit S.,Conrad, Jürgen,Bharatam, Prasad V.,Frey, Wolfgang,Beifuss, Uwe
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- Visible-Light-Mediated N-Desulfonylation of N-Heterocycles Using a Heteroleptic Copper(I) Complex as a Photocatalyst
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A photoredox protocol that uses a heteroleptic Cu (I) complex, [Cu(dq)(BINAP)]BF4, has been developed for the photodeprotection of benzenesulfonyl-protected N-heterocycles. A range of substrates was examined, including indazoles, indoles, pyrazoles, and benzimidazole, featuring both electron-rich and electron-deficient substituents, giving good yields of the N-heterocycle products with broad functional group tolerance. This transformation was also found to be amenable to flow reaction conditions.
- Hunter, Cameron J.,Boyd, Michael J.,May, Gregory D.,Fimognari, Robert
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p. 8732 - 8739
(2020/07/16)
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- Synthesis, antifungal activity and qsar of novel pyrazole amides as succinate dehydrogenase inhibitors
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We design and synthesize a series of novel pyrazole amides based on the commercialized fungicides and our previous work. The antifungal activity was tested in vitro by mycelial growth inhibition assay. The results show that all the compounds are of antifungal activities against the tested fungi at different levels. Among them, N-(2-(7-bromo-5-chloro-1H-indazol-1-yl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (Vk) exhibited higher antifungal activity than boscalid against two fungi. Molecular docking study revealed that the carbonyl oxygen atom of Vk forms two hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.
- Du, Shijie,Li, Zhonghao,Tian, Zaimin,Xu, Lu
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- Preparation method of indazole and application of indazole in medicine synthesis
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The invention belongs to the field of chemicals, and relates to a preparation method of indazole and an application of the indazole in medicine synthesis. The invention discloses a preparation method of indazole and an application of the indazole in synthesizing 1H-indazole-3-carboxylic acid, lonidamine, a compound 8, a compound 9, a compound 10, axitinib, YD-3, YC-1 and similar substances thereof.
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Paragraph 0067; 0074; 0075
(2017/04/21)
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- Copper(I) Oxide-Mediated Cyclization of o-Haloaryl N-Tosylhydrazones: Efficient Synthesis of Indazoles
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An efficient synthesis of indazoles from readily accessible E/Z mixtures of o-haloaryl N-tosylhydrazones has been developed. The thermo-induced isomerization of N-tosylhydrazones is discussed. A series of valuable indazole derivatives are prepared in good yields, and the method has been successfully applied to the synthesis of the bioactive compounds, lonidamine, AF-2785, axitinib, YC-1 and YD-3.
- Tang, Meng,Kong, Yuanfang,Chu, Bingjie,Feng, Dan
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supporting information
p. 926 - 939
(2016/04/05)
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- SUBSTITUTED INDAZOLE COMPOUNDS AS IRAK4 INHIBITORS
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The present invention provides substituted indazole compound of formula (I) and pharmaceutically acceptable salts thereof, and their use to inhibit IRAK4 and/or for the treatment of diseases or disorders induced by IRAK4.
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Page/Page column 80
(2016/04/26)
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- A general synthesis of diversely substituted indazoles and hetero-aromatic derivatives from o-halo-(het)arylaldehydes or -phenones
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A set of variously substituted indazoles and hetero-aromatic derivatives were synthesized from o-halo-(het)arylaldehydes using a palladium catalyzed amination followed by cyclization. Starting from phenones, this process was extended to give 3-substituted indazoles. Moreover, N-1-substituted-indazoles can be reached by this strategy using an optional selective N-1-alkylation step during the process. This methodology offers a general and easy route for the synthesis of regioselectively substituted indazoles.
- Dubost, Emmanuelle,Stiebing, Silvia,Ferrary, Thibault,Cailly, Thomas,Fabis, Frédéric,Collot, Valérie
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p. 8413 - 8418
(2015/03/04)
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- Fluorinated analogues of marsanidine, a highly α2-AR/imidazoline I1 binding site-selective hypotensive agent. Synthesis and biological activities
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The aim of these studies was to establish the influence of fluorination of the indazole ring on the pharmacological properties of two selective α2-adrenoceptor (α2-AR) agonists: 1-[(imidazolidin-2-yl)imino]-1H-indazole (marsanidine,
- Wasilewska, Aleksandra,S?czewski, Franciszek,Hudson, Alan L.,Ferdousi, Mehnaz,Scheinin, Mika,Laurila, Jonne M.,Rybczyńska, Apolonia,Boblewski, Konrad,Lehmann, Artur
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p. 386 - 397
(2015/01/09)
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- Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists
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A series of novel indazole derivatives were synthesized, and their structure-activity relationships examined in order to identify potent and selective 5-HT2C receptor agonists. Among these compounds, (S)-2-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)-1-methylethylamine (YM348) had a good in vitro profile, that is, high agonistic activity to the human 5-HT2C receptor subtype (EC50 = 1.0 nM) and high selectivity over 5-HT2A receptors. This compound was also effective in a rat penile erection model when administered po.
- Shimada, Itsuro,Maeno, Kyoichi,Kazuta, Ken-ichi,Kubota, Hideki,Kimizuka, Tetsuya,Kimura, Yasuharu,Hatanaka, Ken-ichi,Naitou, Yuki,Wanibuchi, Fumikazu,Sakamoto, Shuichi,Tsukamoto, Shin-ichi
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p. 1966 - 1982
(2008/09/21)
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- 4-Substituted indazoles as new inhibitors of neuronal nitric oxide synthase
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A series of halo-1-H-indazoles has been synthesized and evaluated for its inhibitory activity on neuronal nitric oxide synthase. Introduction of bromine at the C4 position of the indazole ring system provided a compound almost as potent as the reference compound, that is, 7-nitroindazole (7-NI). The importance of position 4 is further demonstrated by the synthesis and pharmacological evaluation of the 4-nitroindazole which was also a potent inhibitor of NOS activity. These compounds also exhibited in vivo NOS inhibitory activity, as attested by potent antinociceptive effects following systemic administration.
- Boulouard, Michel,Schumann-Bard, Pascale,Butt-Gueulle, Sabrina,Lohou, Elodie,Stiebing, Silvia,Collot, Valerie,Rault, Sylvain
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p. 3177 - 3180
(2008/02/04)
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- Inhibition of neuronal nitric oxide synthase by 7-methoxyindazole and related substituted indazoles
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The synthesis and pharmacological evaluation of methoxyindazoles as new inhibitors of neuronal nitric oxide synthase are presented. The 7-methoxyindazole, although less potent than 7-NI, is the most active compound of the series in an in vitro enzymatic assay of neuronal nitric oxide synthase activity. This result shows that the nitro-substitution is not indispensable to the biological activity of the indazole ring. 7-Methoxyindazole possesses in vivo NOS inhibitory as well and related antinociceptive properties.
- Schumann, Pascale,Collot, Valerie,Hommet, Yannick,Gsell, Willy,Dauphin, Francois,Sopkova, Jana,MacKenzie, Eric T.,Duval, Dominique,Boulouard, Michel,Rault, Sylvain
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p. 1153 - 1156
(2007/10/03)
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- Azoles. Part 33: 5-Fluoroindazole derivatives
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On treating with nitric acid/acetic anhydride 5-fluoroindazol (2) gives 5-fluoro-1-, 5-fluoro-2- and 5-fluoro-3-nitroindazole (3-5). 4 as well as the crude nitration product of 2 is used for the synthesis of the 3-aminoindazoles 6-8. The compounds 6, 6, 10-13 have been tested for their ability to inhibit the main enzymes of the arachidonic acid cascade.
- Wrzeciono,Majewska,Buge,Kohler,Rickinger,Nuhn
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