- New nitroindazolylacetonitriles: Efficient synthetic access: Via vicarious nucleophilic substitution and tautomeric switching mediated by anions
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New N-Alkyl-nitroindazolylacetonitriles were efficiently obtained via vicarious nucleophilic substitution of N-methyl-nitroindazoles with 4-chlorophenoxyacetonitrile. All compounds were fully characterized by NMR and mass spectroscopy techniques and the structures of some of them were additionally confirmed by X-ray diffraction analysis data. Tautomeric switching was observed in this series of nitroindazolylacetonitriles upon addition of basic anions followed by UV-Vis spectrophotometric and 1H-NMR titrations. The formation of tautomeric species induced by anionic species was endorsed by Density Functional Theory calculations.
- Eddahmi, Mohammed,Moura, Nuno M. M.,Bouissane, Latifa,Gamouh, Ahmed,Faustino, Maria A. F.,Cavaleiro, José A. S.,Paz, Filipe A. A.,Mendes, Ricardo F.,Lodeiro, Carlos,Santos, Sérgio M.,Neves, Maria G. P. M. S.,Rakib, El Mostapha
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p. 14355 - 14367
(2019/09/30)
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- On the mechanism for the photooxidation of aromatic azides containing a secondary N–H bond: A sequence of intramolecular transformations with the formation of heterocyclic oximes
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During the photooxidation of aromatic azides containing a secondary N–H bond at the para-position, a sequence of intramolecular transformations of nitroso oxides led to the formation of heterocyclic oximes along with the corresponding nitroso and nitro co
- Chainikova, Ekaterina,Khursan, Sergey,Yusupova, Alfia,Lobov, Alexander,Abdullin, Marat,Safiullin, Rustam
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supporting information
p. 3267 - 3271
(2018/07/25)
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- N-indazole substituted thiourea derivatives and preparation method and application thereof
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The invention discloses N-indazole substituted thiourea derivatives and a preparation method and application thereof and belongs to the technical field of chemical medicine.The thiourea derivatives are a series of compounds simultaneously containing the 1H-indazole ring structure and the asymmetrical thiourea structure, and the compounds are not reported in the literature.The bioactivity test result analysis of the thiourea derivatives show that the compounds are good in antioxidant activity, the average scavenging rate is above 80%, the scavenging rate of the compound 12b, the compound 12c, and the compound 12d and the compound 12h is higher than 90%, the scavenging activity IC50 of the compound 12h on DPPH is 0.14mg/mL; part of the target compounds has certain inhibition activity on herpes viruses, vaccinia viruses, reoviruses, Coxsackie viruses, Feline coronary herpes viruses, HIV viruses and the like, and the compound 12c and the compound 12n are high in antivirus activity; the synthesized compounds hopefully have new bioactivity which is not expounded, and a certain material basis is provided for the development of new medicine.
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Paragraph 0074; 0075; 0076; 0083; 0084; 0074
(2016/10/09)
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- 2,3-dimethyl-6-urea -2H-indazoles and its preparation method and application
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The invention discloses a 2, 3-dimethyl-6-urea-2H-indazole compound shown by the following general formula (I), medicinal salt or a solvent compound thereof, wherein Ar is substituted or unsubstituted phenyl or aromatic matrix. The invention also discloses a preparation method and application of the compound. The compound can regulate signal transduction of tyrosine kinase, inhibit bad cellular proliferation, and particularly has obvious curative effect for tumors.
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Paragraph 0229-0232
(2016/10/09)
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- Discovery and synthesis of N2,N4-substitued- cycloalkyl[d]pyrimidine-2,4-diamine analogs: The first examples of small-molecular FGFR-1 activator
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A series of novel, cycloalkyl-modified pazopanib analogs 2 and 3 were designed and synthesized. Their kinase modulatory effects on FGFR-1, VEGFR-2, PDGFR-β, and c-KIT were evaluated by the caliper mobility shift assay. Introduction of cycloalkyl into the pyrimidine linker of pazopanib almost abolished the four kinases inhibitory potency of compounds 2 and 3, but surprisingly, resulted in good activation effects on FGFR-1. Compounds 3d and 3g showed double-digit, nanomolar, selective activation effects on FGFR-1, and could be classified as first-generation small molecular activators of FGFR-1 kinase.
- Li, Bao-Li,Xiao, Fang,Lu, Wen-Chao,Sun, Yu-Yun,Zhu, Jin,Li, Jian
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p. 989 - 994
(2014/08/18)
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- Selective synthesis of 1 -functionalized-alkyl-1H-indazoles
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An efficient method for the selective "N1" alkylation of indazoles is described. Use of a-halo esters, lactones, ketones, amides, and bromoacetonitrile provides good to excellent yield of the desired N1 products.
- Hunt, Kevin W.,Moreno, David A.,Suiter, Nicole,Clark, Christopher T.,Kim, Ganghyeok
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supporting information; experimental part
p. 5054 - 5057
(2009/12/28)
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- Mild deprotection of tert-butyl carbamates of NH-heteroarenes under basic conditions
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Aqueous methanolic potassium carbonate under reflux has been demonstrated to be a highly effective deprotective agent for the tert -butyl carbamates of indoles, indazoles, carbazole, thiazoloindole, and pyrrole. The method is a mild one and is particularly expeditious for NH-heteroarenes bearing electron-withdrawing groups. Copyright Taylor & Francis Group, LLC.
- Chakrabarty, Manas,Kundu, Taraknath,Harigaya, Yoshihiro
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p. 2069 - 2077
(2007/10/03)
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- Screening for cardiovascular safety: A structure-activity approach for guiding lead selection of melanin concentrating hormone receptor 1 antagonists
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An inactin-anesthetized rat cardiovascular (CV) assay was employed in a screening mode to triage multiple classes of melanin-concentrating hormone receptor 1 (MCHr1) antagonists. Lead identification was based on a compound profile producing high drug concentration in both plasma (>40 μM) and brain (>20 μg/g) with 15% change in cardiovascular endpoints. As a result of these stringent requirements, lead optimization activities on multiple classes of MCHr1 antagonists were terminated. After providing evidence that the cardiovascular liabilities were not a function of MCHr1 antagonism, continued screening identified the chromone-substituted aminopiperidine amides as a class of MCHr1 antagonists that demonstrated a safe cardiovascular profile at high drug concentrations in both plasma and brain. The high incidence of adverse cardiovascular effects associated with an array of MCHr1 antagonists of significant chemical diversity, combined with the stringent safety requirements for antiobesity drugs, highlight the importance of incorporating cardiovascular safety assessment early in the lead selection process.
- Kym, Philip R.,Souers, Andrew J.,Campbell, Thomas J.,Lynch, John K.,Judd, Andrew S.,Iyengar, Rajesh,Vasudevan, Anil,Gao, Ju,Freeman, Jennifer C.,Wodka, Dariusz,Mulhern, Mathew,Zhao, Gang,Wagaw, Seble H.,Napier, James J.,Brodjian, Sevan,Dayton, Brian D.,Reilly, Regina M.,Segreti, Jason A.,Fryer, Ryan M.,Preusser, Lee C.,Reinhart, Glenn A.,Hernandez, Lisa,Marsh, Kennan C.,Sham, Hing L.,Collins, Christine A.,Polakowski, James S.
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p. 2339 - 2352
(2007/10/03)
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- 1H-INDAZOLES, BENZOTHIAZOLES, 1,2-BENZOISOXAZOLES, 1,2-BENZOISOTHIAZOLES, AND CHROMONES AND PREPARATION AND USES THEREOF
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The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nAChR), activation of nAChRs, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds (indazoles and benzothiazoles), which act as ligands for the α7 nAChR subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 69-70
(2008/06/13)
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- Indoles, 1h-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof
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The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds (indazoles and benzothiazoles), which act as ligands for the α7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 38
(2008/06/13)
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- INDOLES, 1H-INDAZOLES, 1,2-BENZISOXAZOLES, AND 1,2-BENZISOTHIAZOLES, AND PREPARATION AND USES THEREOF
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The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nAChR), activation of nAChRs, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds for example, indoles, 1H-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, which act as ligands for the α7 nAChR subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 37
(2008/06/13)
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- INDAZOLES, BENZOTHIAZOLES, BENZOISOTHIAZOLES, BENZISOXAZOLES, AND PREPARATION AND USES THEREOF
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The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds (e.g., indazoles and benzothiazoles), which act as ligands for the α7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 79-80
(2010/02/14)
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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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- Process for the preparation of substituted indazoles
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Substituted indazoles that have the structural formula SPC1 Wherein X represents halogen, trihalomethyl, nitro, -SO2 R, cyano, acoyl, acoylamino, aroylamino, or -COOR'; R represents hydroxyl, halogen, alkyl, haloalkyl, alkylamino, phenyl, or substituted phenyl; R' represents hydrogen, halogen, alkyl, haloalkyl, phenyl, or substituted phenyl; and n represents a number in the range of 1 to 4 are prepared by the direct nitrosation of the corresponding 2-methylacetanilide with an alkali metal nitrite or alkaline earth metal nitrite under conditions of controlled acidity in the presence of a dehydrating agent at a temperature in the range of 50° to 120° C.
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