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Keywords = 3-aminoindazoles

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29 pages, 17201 KB  
Article
Design and Synthesis of Novel Aminoindazole-pyrrolo[2,3-b]pyridine Inhibitors of IKKα That Selectively Perturb Cellular Non-Canonical NF-κB Signalling
by Christopher Riley, Usama Ammar, Aisha Alsfouk, Nahoum G. Anthony, Jessica Baiget, Giacomo Berretta, David Breen, Judith Huggan, Christopher Lawson, Kathryn McIntosh, Robin Plevin, Colin J. Suckling, Louise C. Young, Andrew Paul and Simon P. Mackay
Molecules 2024, 29(15), 3515; https://doi.org/10.3390/molecules29153515 - 26 Jul 2024
Cited by 7 | Viewed by 2623
Abstract
The inhibitory-kappaB kinases (IKKs) IKKα and IKKβ play central roles in regulating the non-canonical and canonical NF-κB signalling pathways. Whilst the proteins that transduce the signals of each pathway have been extensively characterised, the clear dissection of the functional roles of IKKα-mediated non-canonical [...] Read more.
The inhibitory-kappaB kinases (IKKs) IKKα and IKKβ play central roles in regulating the non-canonical and canonical NF-κB signalling pathways. Whilst the proteins that transduce the signals of each pathway have been extensively characterised, the clear dissection of the functional roles of IKKα-mediated non-canonical NF-κB signalling versus IKKβ-driven canonical signalling remains to be fully elucidated. Progress has relied upon complementary molecular and pharmacological tools; however, the lack of highly potent and selective IKKα inhibitors has limited advances. Herein, we report the development of an aminoindazole-pyrrolo[2,3-b]pyridine scaffold into a novel series of IKKα inhibitors. We demonstrate high potency and selectivity against IKKα over IKKβ in vitro and explain the structure–activity relationships using structure-based molecular modelling. We show selective target engagement with IKKα in the non-canonical NF-κB pathway for both U2OS osteosarcoma and PC-3M prostate cancer cells by employing isoform-related pharmacodynamic markers from both pathways. Two compounds (SU1261 [IKKα Ki = 10 nM; IKKβ Ki = 680 nM] and SU1349 [IKKα Ki = 16 nM; IKKβ Ki = 3352 nM]) represent the first selective and potent pharmacological tools that can be used to interrogate the different signalling functions of IKKα and IKKβ in cells. Our understanding of the regulatory role of IKKα in various inflammatory-based conditions will be advanced using these pharmacological agents. Full article
(This article belongs to the Special Issue Enzyme Inhibitors: Design, Synthesis and Biological Evaluation, 2nd Edition)
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20 pages, 2205 KB  
Article
Synthesis of Trifluoromethylated Pyrimido[1,2-b]indazole Derivatives through the Cyclocondensation of 3-Aminoindazoles with Ketoester and Their Functionalization via Suzuki-Miyaura Cross-Coupling and SNAr Reactions
by Sakina Tellal, Badr Jismy, Djamila Hikem-Oukacha and Mohamed Abarbri
Molecules 2024, 29(1), 44; https://doi.org/10.3390/molecules29010044 - 20 Dec 2023
Cited by 2 | Viewed by 2316
Abstract
A new series of trifluoromethylated pyrimido[1,2-b]indazol-4(1H)-one derivatives was synthesized with good to excellent yields through a simple condensation of 3-aminoindazole derivatives with ethyl 4,4,4-trifluoro 3-oxobutanoate. The functionalization of the corresponding chlorinated fused tricyclic scaffolds via Suzuki-Miyaura and aromatic nucleophilic [...] Read more.
A new series of trifluoromethylated pyrimido[1,2-b]indazol-4(1H)-one derivatives was synthesized with good to excellent yields through a simple condensation of 3-aminoindazole derivatives with ethyl 4,4,4-trifluoro 3-oxobutanoate. The functionalization of the corresponding chlorinated fused tricyclic scaffolds via Suzuki-Miyaura and aromatic nucleophilic substitution reactions led to the synthesis of highly diverse trifluoromethylated pyrimido[1,2-b]indazole derivatives with good yields. Full article
(This article belongs to the Special Issue Synthesis, Functionalization and Applications of Nitrogen-Containing Compounds)
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16 pages, 3994 KB  
Article
Synthesis and Crystallographic Characterisation of Pyridyl- and Indoleninyl-Substituted Pyrimido[1,2-b]Indazoles
by Abdul Qaiyum Ramle, Sang Loon Tan and Edward R. T. Tiekink
Crystals 2022, 12(9), 1283; https://doi.org/10.3390/cryst12091283 - 9 Sep 2022
Cited by 4 | Viewed by 2704
Abstract
Pyridyl- and indoleninyl-substituted pyrimido[1,2-b]indazole were synthesised in good to high yields from the condensation reaction of 1,3-dialdehydes with 3-aminoindazoles. The structural features of the compounds were determined by NMR (1H, 13C and 19F), FT-IR and HR-MS. The [...] Read more.
Pyridyl- and indoleninyl-substituted pyrimido[1,2-b]indazole were synthesised in good to high yields from the condensation reaction of 1,3-dialdehydes with 3-aminoindazoles. The structural features of the compounds were determined by NMR (1H, 13C and 19F), FT-IR and HR-MS. The spectroscopic assignments were confirmed by X-ray crystallography for two derivatives, i.e., 9-Bromo-3-(pyridin-4-yl)pyrimido[1,2-b]indazole (1b) and 10-Methoxy-3-(pyridin-4-yl)pyrimido[1,2-b]indazole (1c), which further provides support for significant delocalisation of π-electron density over the entire fused ring system. The molecular packing was assessed by conventional methods together with Hirshfeld surface analyses. In 1b, the molecular packing features pyrimidyl-N–H···N(pyrimidyl), π(pyrazolyl)···π(pyrimidyl) and Br···N interactions within a two-dimensional array. In 1c, pyrimidyl-C–H···N(pyrazolyl) and pyridyl-C–H···O(methoxy) interactions feature within a three-dimensional architecture. Full article
(This article belongs to the Special Issue Feature Papers in Crystal Engineering in 2022)
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11 pages, 2680 KB  
Article
Experimental and Theoretical Studies on the Corrosion Inhibition of Carbon Steel by Two Indazole Derivatives in HCl Medium
by Shenying Xu, Shengtao Zhang, Lei Guo, Li Feng and Bochuan Tan
Materials 2019, 12(8), 1339; https://doi.org/10.3390/ma12081339 - 24 Apr 2019
Cited by 36 | Viewed by 4454
Abstract
In this work, two indazole derivatives, namely 5-aminoindazole (AIA) and 5-nitroindazole (NIA), were investigated as corrosion inhibitors for carbon steel in 1 M HCl solution by experimental and density functional theory (DFT) methods. The electrochemical results indicate that the inhibition ability follows the [...] Read more.
In this work, two indazole derivatives, namely 5-aminoindazole (AIA) and 5-nitroindazole (NIA), were investigated as corrosion inhibitors for carbon steel in 1 M HCl solution by experimental and density functional theory (DFT) methods. The electrochemical results indicate that the inhibition ability follows the order of AIA > NIA, which is due to the stronger electron-donating effect of –NH2 of the AIA group than the –NO2 group of NIA. Besides, the frontier orbital theory shows that the AIA exhibits higher reaction activity than NIA, and a more negative adsorption energy for AIA was also obtained, which is consistent with the analysis of the electrochemical measurements. We draw the conclusion that the electron-donating effect makes it easier for AIA to donate electrons to iron atoms to form a stronger protective layer than NIA. Full article
(This article belongs to the Special Issue Recent Advances in Corrosion Science)
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13 pages, 2326 KB  
Article
A Metal-Free Regioselective Multicomponent Approach for the Synthesis of Free Radical Scavenging Pyrimido-Fused Indazoles and Their Fluorescence Studies
by Jeyakannu Palaniraja, Selvaraj Mohana Roopan, G Mokesh Rayalu, Naif Abdullah Al-Dhabi and Mariadhas Valan Arasu
Molecules 2016, 21(11), 1571; https://doi.org/10.3390/molecules21111571 - 18 Nov 2016
Cited by 39 | Viewed by 6697
Abstract
This study deals with a new and efficient metal-free regioselective synthesis of pyrimido-fused indazoles with nitrogen ring junction motifs. We have developed a metal-free domino type reaction between 3-aminoindazole, aryl aldehydes and aceotophenones in the presence of KOH/DMF that leads to pyrimido[1,2-b [...] Read more.
This study deals with a new and efficient metal-free regioselective synthesis of pyrimido-fused indazoles with nitrogen ring junction motifs. We have developed a metal-free domino type reaction between 3-aminoindazole, aryl aldehydes and aceotophenones in the presence of KOH/DMF that leads to pyrimido[1,2-b]indazole analogues. Response Surface Methodology (RSM) coupled with a Box-Behnken design (BBD) were utilized for exploring the effect of base used (A), temperature of reaction (B) and (C), reaction time. This approach can allow access to a variety of pyrimidoindazole fluorophores and related compounds. The compound N,N-dimethyl-4-(2-phenylpyrimido[1,2-b]indazol-4-yl)aniline (4e) displays the maximum fluorescence intensity at 518 nm and shows a fluorescence quantum yield of 0.068. The synthesized pyramido-fused indazoles have been evaluated for their free radical scavenging activity and compound 4f showed good antioxidant activity. Full article
(This article belongs to the Collection Heterocyclic Compounds)
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19 pages, 262 KB  
Article
Models for the Prediction of Receptor Tyrosine Kinase Inhibitory Activity of Substituted 3-Aminoindazole Analogues
by Monika GUPTA, Harish DUREJA and Anil Kumar MADAN
Sci. Pharm. 2011, 79(2), 239-258; https://doi.org/10.3797/scipharm.1102-08 - 28 Apr 2011
Cited by 2 | Viewed by 1617
Abstract
The inhibition of tumor angiogenesis has become a compelling approach in the development of anticancer drugs. In the present study, topological models were developed through decision tree and moving average analysis using a data set comprising 42 analogues of 3-aminoindazoles. A total of [...] Read more.
The inhibition of tumor angiogenesis has become a compelling approach in the development of anticancer drugs. In the present study, topological models were developed through decision tree and moving average analysis using a data set comprising 42 analogues of 3-aminoindazoles. A total of 22 descriptors (distance based, adjacency based, pendenticity and distance-cum-adjacency based) were used. The values of all 22 topological indices for each analogue in the dataset were computed using an in-house computer program. A decision tree was constructed for the receptor tyrosine kinase KDR (kinase insert domain receptor) inhibitory activity to determine the importance of topological indices. The decision tree learned the information from the input data with an accuracy of 88%. Three independent topological models were also developed for prediction of receptor tyrosine kinase inhibitory (KDR) activity using moving average analysis. The models developed were also found to be sensitive towards the prediction of other receptor tyrosine kinases i.e. FLT3 (fms-like tyrosine kinase-3) and cKIT inhibitory activity. The accuracy of classification of single index based models using moving average analysis was found to be 88%. The performance of models was assessed by calculating precision, sensitivity, overall accuracy and Mathew’s correlation coefficient (MCC). The significance of the models was also assessed by intercorrelation analysis. Full article
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