49826-70-2Relevant academic research and scientific papers
Design, Synthesis, and Biological Evaluation of 1-(Indolizin-3-yl)ethan-1-ones as CBP Bromodomain Inhibitors for the Treatment of Prostate Cancer
Hu, Jiankang,Hu, Qingqing,Kong, Xiangqian,Liu, Jinsong,Luo, Guolong,Shen, Hui,Wang, Chao,Wu, Tianbang,Wu, Xishan,Xiang, Qiuping,Xu, Yong,Zhang, Cheng,Zhang, Yan,Zhuang, Xiaoxi,Zou, Lingjiao
, (2022/01/12)
CREB (cyclic-AMP responsive element binding protein) binding protein (CBP) is a potential target for prostate cancer treatment. Herein, we report the structural optimization of a series of 1-(indolizin-3-yl)ethan-1-one compounds as new selective CBP bromodomain inhibitors, aiming to improve cellular potency and metabolic stability. This process led to compound 9g (Y08284), which possesses good liver microsomal stability and pharmacokinetic properties (F = 25.9%). Furthermore, the compound is able to inhibit CBP bromodomain as well as the proliferation, colony formation, and migration of prostate cancer cells. Additionally, the new inhibitor shows promising antitumor efficacy in a 22Rv1 xenograft model (TGI = 88%). This study provides new lead compounds for further development of drugs for the treatment of prostate cancer.
Catalyst-Free N-Deoxygenation by Photoexcitation of Hantzsch Ester
Cardinale, Luana,Jacobi Von Wangelin, Axel,Konev, Mikhail O.
supporting information, (2020/02/15)
A mild and operationally simple protocol for the deoxygenation of a variety of heteroaryl N-oxides and nitroarenes has been developed. A mixture of substrate and Hantzsch ester is proposed to result in an electron donor-acceptor complex, which upon blue-light irradiation undergoes photoinduced electron transfer between the two reactants to afford the products. N-oxide deoxygenation is demonstrated with 22 examples of functionally diverse substrates, and the chemoselective reduction of nitroarenes to the corresponding hydroxylamines is also shown.
Molybdenum-Catalyzed Deoxygenation of Heteroaromatic N-Oxides and Hydroxides using Pinacol as Reducing Agent
Rubio-Presa, Rubén,Fernández-Rodríguez, Manuel A.,Pedrosa, María R.,Arnáiz, Francisco J.,Sanz, Roberto
supporting information, p. 1752 - 1757 (2017/05/22)
A molybdenum-catalyzed deoxygenation of pyridine N-oxides and N-hydroxybenzotriazoles, as well as other azole N-oxides, has been developed using pinacol as an environmentally friendly oxo-acceptor. The only by-products are acetone and water making the process a convenient alternative to established protocols in terms of waste generation. The reaction is highly chemoselective and a variety of functional groups are tolerated. The processes are usually very clean allowing the isolation of the pure deoxygenated products after a simple extraction in most cases. (Figure presented.).
Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism
Todorov, Aleksandar R.,Wirtanen, Tom,Helaja, Juho
, p. 13756 - 13767 (2017/12/26)
Facile photoreductive protocols have been developed to remove benzyl O-protective groups from oxyarene N-heterocycles at positions capable for 2-/4-O-pyridine-2-/4-pyridone tautomerism. Blue light irradiation, a [Ru] or [Ir] photocatalyst, and ascorbic acid in a water-acetonitrile solution debenzylates a variety of aryl N-heterocycles cleanly and selectively. Ascorbic acid has two functions in the reaction. On the one hand, it protonates the N-heterocycles that reduces their reduction potentials notably and on the other hand it acts as a sacrificial reductant. Reduction potentials and free energy barriers calculated at the CPCM-B3LYP/6-31+G? level can predict the reactivities of the studied substrates.
Choline chloride based deep eutectic solvent as an efficient solvent for the benzylation of phenols
Singh, Abhilash S.,Shendage, Suresh S.,Nagarkar, Jayashree M.
, p. 7243 - 7246 (2015/02/02)
Deep eutectic solvents (such as the combination of urea and choline chloride) are found to be promising solvent and phase-transfer-media for benzylation of phenol. These methods avoided the complexity of multiple alkylations giving selectively O-alkylated aromatic products. Good to excellent yields of the corresponding benzyl phenyl ether were obtained. The non-toxic, biodegradable, inexpensive, and recyclable nature of DES make this protocol green and cost-effective.
INDOLIZINE INHIBITORS OF LEUKOTRIENE PRODUCTION
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Page/Page column 60, (2011/11/13)
The present invention relates to compounds of formula (I): and pharmaceutically acceptable salt thereof, wherein X1 to X4, R1 to R4, A, B, D and m are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.
INDOLIZINE INHIBITORS OF LEUKOTRIENE PRODUCTION
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Paragraph 0070; 0071, (2011/06/26)
The present invention relates to compounds of formula (I): and pharmaceutically acceptable salt thereof, wherein X1 to X4, R1 to R4, A, B, D and m are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.
Deoxygenation of N-oxides with triphenylphosphine, catalyzed by dichlorodioxomolybdenum(VI)
Sanz, Roberto,Escribano, Jaime,Fernández, Yolanda,Aguado, Rafael,Pedrosa, María R.,Arnáiz, Francisco J.
, p. 1389 - 1392 (2007/10/03)
Chemoselective deoxygenation of N-oxides was carried out under mild conditions with common phosphines in the presence of dichlorodioxomolybdenum(VI) . Georg Thieme Verlag Stuttgart.
Synthesis of substituted pyridines by the reactions of halopyridines with sulfur, oxygen and carbon nucleophiles under focused microwave irradiation
Cherng, Yie-Jia
, p. 4931 - 4935 (2007/10/03)
The nucleophilic substitution reactions of halopyridines with sulfur, oxygen and carbon nucleophiles under microwave irradiation was complete within several minutes with yields up to 99%. The method using microwave irradiation is superior to those conducted under conventional heating processes.
Benzimidazole derivatives
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, (2008/06/13)
The invention is directed to substituted benzimidazole compounds which are ligands for dopamine receptor subtypes used in the treatment of the dopamine system.
