- 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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- 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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- Inhibition of the Cysteine Protease Human Cathepsin L by Triazine Nitriles: Amide???Heteroarene π-Stacking Interactions and Chalcogen Bonding in the S3 Pocket
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We report an extensive “heteroarene scan” of triazine nitrile ligands of the cysteine protease human cathepsin L (hCatL) to investigate π-stacking on the peptide amide bond Gly67–Gly68 at the entrance of the S3 pocket. This heteroarene???peptide bond stacking was supported by a co-crystal structure of an imidazopyridine ligand with hCatL. Inhibitory constants (Ki) are strongly influenced by the diverse nature of the heterocycles and specific interactions with the local environment of the S3 pocket. Binding affinities vary by three orders of magnitude. All heteroaromatic ligands feature enhanced binding by comparison with hydrocarbon analogues. Predicted energetic contributions from the orientation of the local dipole moments of heteroarene and peptide bond could not be confirmed. Binding of benzothienyl (Ki=4 nm) and benzothiazolyl (Ki=17 nm) ligands was enhanced by intermolecular C?S???O=C interactions (chalcogen bonding) with the backbone C=O of Asn66 in the S3 pocket. The ligands were also tested for the related enzyme rhodesain.
- Giroud, Maude,Ivkovic, Jakov,Martignoni, Mara,Fleuti, Marianne,Trapp, Nils,Haap, Wolfgang,Kuglstatter, Andreas,Benz, J?rg,Kuhn, Bernd,Schirmeister, Tanja,Diederich, Fran?ois
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supporting information
p. 257 - 270
(2017/02/15)
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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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- a-AMINO ACID DERIVATIVE AND PHARMACEUTICAL COMPRISING THE SAME AS ACTIVE INGREDIENT
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The present invention provides novel α-amino acid derivatives of formula (1): (wherein, R1, R2, R3, R4, X and Y are as defined in the claims) or pharmaceutically acceptable salts, prodrugs or solvates thereof. T
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Page/Page column 47
(2009/04/23)
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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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- A Novel Approach to 1H-Indazoles via Arylazosulfides
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Treatment of variously substituted (o-alkylaryl)azosulfides 1a-n with potassium tert-butoxide in DMSO at room temperature smoothly furnishes 1H-indazoles 2a-n.
- Dell'Erba, Carlo,Novi, Marino,Petrillo, Giovanni,Tavani, Cinzia
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p. 3529 - 3536
(2007/10/02)
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- Phase Transfer Catalyzed Synthesis of Indazoles from o-Alkylbenzenediazonium Tetrafluoroborates
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Reaction of o-methyl- and o-ethylbenzenediazonium tetrafluoroborates with two equivalents of potassium acetate and five mole percent of 18-crown-6 in ethanol-free chloroform produce indazoles in good to excellent yields.Indazoles bearing either electron-withdrawing or electron-donating substituents may be prepared.
- Bartsch, Richard A.,Yang, Il-Woo
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p. 1063 - 1064
(2007/10/02)
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- Aromatic Diazonium Salts, X. - A One-Pot Procedure for the Jacobson Synthesis of Indazole
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Procedures are described for a one-pot synthesis of 1H-indazole and substituted indazoles 3 in good yield (Table 1) from o-toluidines 2, alkyl nitrite or nitrous oxides, potassium acetate, and acetic anhydride in benzene.The spectroscopic properties of substituted indazoles (Tables 2-4) are discussed. - 4-Phenylcinnoline (18) is prepared by the same procedure from o-(α-methylenebenzyl)aniline.
- Ruechardt, Christoph,Hassmann, Volker
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p. 908 - 927
(2007/10/02)
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