22979-83-5Relevant articles and documents
A B2(OH)4-Mediated Synthesis of 2-Substituted Indazolone and Its Application in a DNA-Encoded Library
Bao, Yapeng,Deng, Zongfa,Feng, Jing,Zhu, Weiwei,Li, Jin,Wan, Jinqiao,Liu, Guansai
supporting information, p. 6277 - 6282 (2020/08/24)
Indazolone cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. In this report, a mild and efficient approach to 2-substituted indazolones via B2(OH)4-mediated reductive N-N b
One-Pot Synthesis of Seven-Membered Heterocyclic Derivatives of Diazepines Involving Copper-Catalyzed Rearrangement Cascade Allyl-Amination
Chen, Yuepeng,Liu, Xinglei,Shi, Wei,Zheng, Shilong,Wang, Guangdi,He, Ling
, p. 5146 - 5157 (2020/05/19)
A novel and efficient method has been proposed for the synthesis of 1,4-benzodiazepine-5-ones from o-nitrobenzoic N-allylamides by using molybdenyl acetylacetonate and copper(II) trifluoromethanesulfonate as catalysts in the presence of triphenylphosphine. This synthesis process involves nitrene formation, C-H bond insertion, C≠C bond rearrangement, and C-N bond formation cascade reactions via copper- and molybdenum-catalyzed mediation. The method features a wide substrate scope and a moderate to high yield (up to 90%), exhibiting the possibility for practical applications.
Synthesis and thrombin, factor Xa and U46619 inhibitory effects of non-amidino and amidino N2-thiophenecarbonyl- and N2-tosylanthranilamides
Lee, Soo Hyun,Lee, Wonhwa,Nguyen, ThiHa,Um, Il Soo,Bae, Jong-Sup,Ma, Eunsook
, (2017/06/08)
Thrombin (factor IIa) and factor Xa (FXa) are key enzymes at the junction of the intrinsic and extrinsic coagulation pathways and are the most attractive pharmacological targets for the development of novel anticoagulants. Twenty non-amidino N2-thiophencarbonyl- and N2-tosyl anthranilamides 1-20 and six amidino N2-thiophencarbonyl- and N2-tosylanthranilamides 21-26 were synthesized to evaluate their activated partial thromboplastin time (aPTT) and prothrombin time (PT) using human plasma at a concentration of 30 μg/mL in vitro. As a result, compounds 5, 9, and 21-23 were selected to study the further antithrombotic activity. The anticoagulant properties of 5, 9, and 21-23 significantly exhibited a concentration-dependent prolongation of in vitro PT and aPTT, in vivo bleeding time, and ex vivo clotting time. These compounds concentration-dependently inhibited the activities of thrombin and FXa and inhibited the generation of thrombin and FXa in human endothelial cells. In addition, data showed that 5, 9, and 21-23 significantly inhibited thrombin catalyzed fibrin polymerization and mouse platelet aggregation and inhibited platelet aggregation induced by U46619 in vitro and ex vivo. Among the derivatives evaluated, N-(30-amidinophenyl)-2-((thiophen-200-yl)carbonylamino)benzamide (21) was the most active compound.
Scaffold identification of a new class of potent and selective BCRP inhibitors
Marighetti, Federico,Steggemann, Kerstin,Karbaum, Maria,Wiese, Michael
, p. 742 - 751 (2015/04/14)
We recently reported the synthesis and quantitative structure-activity relationships of a new breast cancer resistance protein (BCRP) inhibitor class. In the study presented herein, we investigated the possibility to better define the scaffold of this compound class by removing or modifying the aromatic ring A with various substituents selected on the basis of their electronic and lipophilic properties. The results show that this aromatic ring is important, but not essential, for activity. Many of the selected substituents led to compounds with low activity, but in some cases activity was retained. Among these, a phenolic hydroxy group proved to impart as much potency to the molecule as a hydroxyethyl side chain, initially considered necessary for activity. This derivative is one of the most active compounds in this class, maintaining an inhibitory activity similar to that of the reference compound; it is also selective for BCRP.
Iron-catalyzed one-pot 2,3-diarylquinazolinone formation from 2-nitrobenzamides and alcohols
Wang, Huamin,Cao, Xiangxiang,Xiao, Fuhong,Liu, Saiwen,Deng, Guo-Jun
supporting information, p. 4900 - 4903 (2013/10/08)
A novel approach for the synthesis of 2,3-diarylquinazolinones using iron as catalyst is described. Various 2-nitro-N-arylbenzamides reacted with benzylic alcohols to selectively give the corresponding products in the absence of external oxidant or reduct
QUINAZOLINONE AND FUSED PYRIMIDINONE COMPOUNDS AND THEIR USE IN TREATING SODIUM CHANNEL-MEDIATED DISEASES OR CONDITIONS
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Page/Page column 91, (2008/12/07)
This invention is directed to compounds of formula (I): wherein (A), n, R1, R2 and R3 are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain.
N-LINKED ARYL HETEROARYL INHIBITORS OF LTA4H FOR TREATING INFLAMMATION
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Page/Page column 6-7; 9, (2010/11/27)
The present invention relates to a chemical genus of biaryl nitrogen-attached heterocycles that are inhibitors of LTA4H (leukotriene A4 hydrolase). The compounds have the general formula: They are useful for the treatment and prevention and prophylaxis of
Anthranilamide inhibitors of factor Xa
Mendel, David,Marquart, Angela L.,Joseph, Sajan,Waid, Philip,Yee, Ying K.,Tebbe, Anne Louise,Ratz, Andrew M.,Herron, David K.,Goodson, Theodore,Masters, John J.,Franciskovich, Jeffry B.,Tinsley, Jennifer M.,Wiley, Michael R.,Weir, Leonard C.,Kyle, Jeffrey A.,Klimkowski, Valentine J.,Smith, Gerald F.,Towner, Richard D.,Froelich, Larry L.,Buben, John,Craft, Trelia J.
, p. 4832 - 4836 (2008/02/11)
SAR about the B-ring of a series of N2-aroyl anthranilamide factor Xa (fXa) inhibitors is described. B-ring o-aminoalkylether and B-ring p-amine probes of the S1′ and S4 sites, respectively, afforded picomolar fXa inhibitors that performed well in in vitro anticoagulation assays.
Electrosynthesis and in situ chemical rearrangement of o-nitrosobenzamides
Guilbaud-Criqui, A.,Moinet, C.
, p. 101 - 110 (2007/10/02)
Primary and secondary o-nitrosobenzamides can be prepared in a "redox" cell but are unstable in the solvent used for electrolysis (acetate buffer-alcohol).At room temperature N-aryl-2-nitrosobenzamides give 2-carboxyazobenzenes.N-alkyl-2-nitrosobenzamides decompose thermally into 2-methoxy or 2-ethoxycarbonylphenylhydrazones according to the alcohol used.Similarly, methyl benzoate (or ethyl benzoate) is obtained from 2-nitrosobenzamide.A possible mechanism involves an unstable heterocycle formed by the coupling of the two nitrogen atoms (nitroso and amide) followed by cleavage of the carbonyl-nitrogen bond resulting from nucleophilic attack of the solvent (water or alcohol). Key Words: flow cell electrosynthesis / 2-nitrosobenzamides / 2-carboxyazobenzenes / 2-alkoxycarbonylphenylhydrazones / indazol-3-one
