21627-58-7Relevant academic research and scientific papers
Photoswitching of ortho-Aminated Arylazopyrazoles with Red Light
Simke, Julian,B?sking, Tom,Ravoo, Bart Jan
supporting information, p. 7635 - 7639 (2021/10/05)
Bidirectional photoswitching of arylazopyrazoles with visible light is enabled by substitution with pyrrolidine and piperidine in the ortho-position of the phenyl ring. The absorption maxima were red-shifted and the molar absorption coefficients in the vi
CYCLAMINEPHENYLAMINOQUINOLINES AS FUNGICIDES
-
Page/Page column 104, (2021/10/22)
The present disclosure relates to fungicidal active compounds, more specifically to cyclaminephenylaminoquinolines of formula (I), intermediates for their preparation and use thereof as fungicidal active compound, particularly in the form of fungicide com
Optimisation of 2-(N-phenyl carboxamide) triazolopyrimidine antimalarials with moderate to slow acting erythrocytic stage activity
Bailey, Brodie L.,Nguyen, William,Ngo, Anna,Goodman, Christopher D.,Gancheva, Maria R.,Favuzza, Paola,Sanz, Laura M.,Gamo, Francisco-Javier,Lowes, Kym N.,McFadden, Geoffrey I.,Wilson, Danny W.,Laleu, Beno?t,Brand, Stephen,Jackson, Paul F.,Cowman, Alan F.,Sleebs, Brad E.
, (2021/08/30)
Malaria is a devastating parasitic disease caused by parasites from the genus Plasmodium. Therapeutic resistance has been reported against all clinically available antimalarials, threatening our ability to control the disease and therefore there is an ongoing need for the development of novel antimalarials. Towards this goal, we identified the 2-(N-phenyl carboxamide) triazolopyrimidine class from a high throughput screen of the Janssen Jumpstarter library against the asexual stages of the P. falciparum parasite. Here we describe the structure activity relationship of the identified class and the optimisation of asexual stage activity while maintaining selectivity against the human HepG2 cell line. The most potent analogues from this study were shown to exhibit equipotent activity against P. falciparum multidrug resistant strains and P. knowlesi asexual parasites. Asexual stage phenotyping studies determined the triazolopyrimidine class arrests parasites at the trophozoite stage, but it is likely these parasites are still metabolically active until the second asexual cycle, and thus have a moderate to slow onset of action. Non-NADPH dependent degradation of the central carboxamide and low aqueous solubility was observed in in vitro ADME profiling. A significant challenge remains to correct these liabilities for further advancement of the 2-(N-phenyl carboxamide) triazolopyrimidine scaffold as a potential moderate to slow acting partner in a curative or prophylactic antimalarial treatment.
Access to Polycyclic Indole-3,4-Fused Nine-Membered Ring via Cascade 1,6-Hydride Transfer/Cyclization
Yang, Shuo,An, Xiao-De,Qiu, Bin,Liu, Rui-Bin,Xiao, Jian
supporting information, p. 9100 - 9105 (2021/11/24)
A cascade aldimine condensation/1,6-hydride transfer/Mannich-type cyclization of indole-derived phenylenediamine with aldehydes was developed for one-step construction of a polycyclic indole-3,4-fused skeleton. Aldehyde serves as a key to start the whole process, including 1,6-hydride transfer enabled δ-C(sp3)-H activation of the secondary amine. The challenges of construction of medium-sized rings are addressed via hydride transfer chemistry.
Electrochemical Synthesis of Benzo[ d]imidazole via Intramolecular C(sp3)-H Amination
Li, An,Li, Caohui,Li, Lijun,Liu, Yu,Tang, Kewen,Yang, Tao,Yang, Zan,Zhou, Congshan
, (2022/01/03)
An electrochemical dehydrogenative amination for the synthesis of benzimidazoles was developed. This electrosynthesis method could address the limitations of the C(sp3)-H intramolecular amination synthesis reaction and provide novel access to obtain 1,2-disubstituted benzimidazoles without transition metals and oxidants. Under undivided electrolytic conditions, various benzimidazole derivatives could be synthesized, exhibiting functional group tolerance.
1,2-Disubstituted Benzimidazoles by the Iron Catalyzed Cross-Dehydrogenative Coupling of Isomeric o-Phenylenediamine Substrates
Foss, Frank W.,Palacios, Philip M.,Pierce, Brad S.,Thapa, Pawan,Tran, Tam
, p. 1991 - 2009 (2020/03/13)
Benzimidazoles are common in nature, medicines, and materials. Numerous strategies for preparing 2-arylbenzimidazoles exist. In this work, 1,2-disubstituted benzimidazoles were prepared from various mono- and disubstituted ortho-phenylenediamines (OPD) by iron-catalyzed oxidative coupling. Specifically, O2 and FeCl3·6H2O catalyzed the cross-dehydrogenative coupling and aromatization of diarylmethyl and dialkyl benzimidazole precursors. N,N′-Disubstituted-OPD substrates were significantly more reactive than their N,N-disubstituted isomers, which appears to be relative to their propensity for complexation and charge transfer with Fe3+. The reaction also converted N-monosubstituted OPD substrates to 2-substituted benzimidazoles; however, electron-poor substrates produce 1,2-disubstituted benzimidazoles by intermolecular imino-transfer. Kinetic, reagent, and spectroscopic (UV-vis and EPR) studies suggest a mechanism involving metal-substrate complexation, charge transfer, and aerobic turnover, involving high-valent Fe(IV) intermediates. Overall, comparative strategies for the relatively sustainable and efficient synthesis of 1,2-disubstituted benzimidazoles are demonstrated.
Preparation method of benzimidazole [1, 3] aza-thio compound
-
Paragraph 0055-0057; 0060-0061, (2020/09/12)
The invention discloses a preparation method of a benzimidazole [1, 3] aza-thio compound, and belongs to the field of organic synthesis research. The preparation method provided by the invention comprises the following steps that: with 2-fluoronitrobenzen
Tert-amino effect-promoted rearrangement of aryl isothiocyanate: A versatile approach to benzimidazothiazepines and benzimidazothioethers
Geng, Xinyu,Liu, Siyuan,Qu, Jingping,Wang, Baomin,Wang, Wenyao
, p. 12635 - 12643 (2020/11/09)
A general and practical approach to benzimidazothiazepine and benzimidazothioether derivatives via an intramolecular nucleophilic addition/ring expansion rearrangement of aryl isothiocyanates promoted by the tert-amino effect has been developed. This reaction is catalyzed by low-cost camphorsulfonic acid and tolerates a broad substrate scope with complete atom economy. Structurally intriguing benzimidazothiazepine and benzimidazothioether products could be easily obtained by a simple operation in good to excellent yield (up to 98%).
A Structure–Activity Study of Nickel NNN Pincer Complexes for Alkyl-Alkyl Kumada and Suzuki–Miyaura Coupling Reactions
Di Franco, Thomas,Stojanovic, Marko,Keller, Sébastien Carlos,Scopelliti, Rosario,Hu, Xile
, p. 830 - 847 (2016/11/11)
A new series of Ni NNN pincer complexes were synthesized and characterized. The main difference among these complexes is the substituents on the side arm amino group(s). No major structural difference was found except for the C–N–C angle of the various substituents and the ‘pseudo bite angle’ of the complexes. Four new complexes were efficient for the alkyl-alkyl Kumada reaction of primary alkyl halides, and among them, one complex was also efficient with secondary alkyl halides. The influence of the substituents on the catalytic performance of the Ni complexes in alkyl-alkyl Kumada and Suzuki–Miyaura cross-coupling reactions was systematically investigated. No correlation was found between the catalytic activity and the key structural parameters (C–N–C angle and ‘pseudo bite angle’), redox properties or Lewis acidity of the complexes.
PYRIDAZINONE COMPOUNDS AND USES THEREOF
-
Paragraph 0246, (2015/03/28)
Disclosed herein are pyridazinone compounds, pharmaceutical compositions that include one or more pyridazinone compounds, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a disease and/or a condition, including an orthomyxovirus infection, with a pyridazinone compounds. Examples of an orthomyxovirus viral infection includes an influenza infection.
