7076-17-7Relevant articles and documents
Assessment of the trifluoromethyl ketone functionality as an alternative zinc-binding group for selective HDAC6 inhibition
Depetter, Yves,Geurs, Silke,Vanden Bussche, Flore,De Vreese, Rob,Franceus, Jorick,Desmet, Tom,De Wever, Olivier,D'Hooghe, Matthias
, p. 1011 - 1016 (2018)
Recent studies point towards the possible disadvantages of using hydroxamic acid-based zinc-binding groups in HDAC inhibitors due to e.g. mutagenicity issues. In this work, we elaborated on our previously developed Tubathian series, a class of highly sele
Synthesis and SAR assessment of novel Tubathian analogs in the pursuit of potent and selective HDAC6 inhibitors
De Vreese, Rob,Depetter, Yves,Verhaeghe, Tom,Desmet, Tom,Benoy, Veronick,Haeck, Wanda,Van Den Bosch, Ludo,D'Hooghe, Matthias
, p. 2537 - 2549 (2016)
The synthesis of novel isoform-selective HDAC inhibitors is considered to be an important, emerging field in medicinal chemistry. In this paper, the preparation and assessment of thirteen selective HDAC6 inhibitors is disclosed, elaborating on a previously developed thiaheterocyclic Tubathian series. All compounds were evaluated in vitro for their ability to inhibit HDAC6, and a selection of five potent compounds was further screened toward all HDAC isoforms (HDAC1-11). The capability of these Tubathian analogs to inhibit α-tubulin deacetylation was assessed as well, and ADME/Tox data were collected. This thorough SAR evaluation revealed that the oxidized, para-substituted hydroxamic acids can be recognized as valuable lead structures in the pursuit of novel potent and selective HDAC6 inhibitors.
Selective Inhibition of Histone Deacetylase 10: Hydrogen Bonding to the Gatekeeper Residue is Implicated
Géraldy, Magalie,Morgen, Michael,Sehr, Peter,Steimbach, Raphael R.,Moi, Davide,Ridinger, Johannes,Oehme, Ina,Witt, Olaf,Malz, Mona,Nogueira, Mauro S.,Koch, Oliver,Gunkel, Nikolas,Miller, Aubry K.
, p. 4426 - 4443 (2019/05/17)
The discovery of isozyme-selective histone deacetylase (HDAC) inhibitors is critical for understanding the biological functions of individual HDACs and for validating HDACs as drug targets. The isozyme HDAC10 contributes to chemotherapy resistance and has
Asymmetric N-Hydroxyalkylation of Indoles with Ethyl Glyoxalates Catalyzed by a Chiral Phosphoric Acid: Highly Enantioselective Synthesis of Chiral N,O-Aminal Indole Derivatives
Wang, Le,Zhou, Jia,Ding, Tong-Mei,Yan, Zhi-Qiang,Hou, Si-Hua,Zhu, Guo-Dong,Zhang, Shu-Yu
supporting information, p. 2795 - 2799 (2019/04/30)
A method of SPINOL-derived chiral phosphoric acid catalyzed asymmetric intermolecular N-hydroxyalkylation of multisubstituted indoles with ethyl glyoxalates is described in this report. This protocol provides an alternative, convenient, and direct strategy for efficient access to structurally unique α-chiral indole N,O-acyclic aminals with a broad substrate scope and good to excellent enantioselectivities. The synthetic utility of this methodology is illustrated by a gram-scale experiment and the subsequent efficient synthesis of more complex chiral N,O-aminal indole derivatives.
Thiapyran[4,3-b] indole compound and preparing method and application thereof
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Paragraph 0063; 0065-0067; 0068; 0069, (2018/10/19)
The invention discloses a thiapyran[4,3-b] indole compound and a preparing method and application thereof. The structure of the compound is shown in the formula 1, wherein the formula 1 is shown in the description, and R1-R5 are not all hydrogen. The compound has excellent activities of inhibiting mycelial growth, protecting detached leaves, protecting living bodies and treating the living bodiesfor rhizoctonia solani, the effects of the compound are even superior to those of positive control drugs, and the compound has an important application value in preventing and/or treating rice sheathblight.
HDAC6 INHIBITORS AND USES THEREOF
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Page/Page column 17, (2014/10/03)
The present invention relates to Histone deacetylases 6 (HDAC6) inhibitors and compositions containing the same. Methods of treating diseases and conditions wherein inhibition of HDAC6 provides a benefit, like a cell proliferative disease, an autoimmune or inflammatory disorder, a neurodegenerative disease, a viral disease, malaria, or a combination thereof, also are disclosed.
Potent and selective HDAC6 inhibitory activity of N-(4- hydroxycarbamoylbenzyl)-1,2,4,9-tetrahydro-3-thia-9-azafluorenes as novel sulfur analogues of Tubastatin A
De Vreese, Rob,Verhaeghe, Tom,Desmet, Tom,D'Hooghe, Matthias
supporting information, p. 3775 - 3777 (2013/05/22)
Eight N-(4-hydroxycarbamoylbenzyl)-1,2,4,9-tetrahydro-3-thia-9-azafluorenes were efficiently prepared as sulfur analogues of Tubastatin A and thus evaluated as new HDAC6 inhibitors. All compounds exhibited potency against HDAC6, and four of them were active in the nanomolar range (IC50 = 1.9-22 nM). Further analysis revealed that the sulfone derivatives (designated as Tubathians) are superior to their non-oxidized sulfide analogues, and the two most active sulfones showed good to excellent HDAC6 selectivity compared to all other HDAC isoform classes.
Fischer indole synthesis catalyzed by novel SO3H-functionalized ionic liquids in water
Xu, Dan-Qian,Wu, Jian,Luo, Shu-Ping,Zhang, Ji-Xu,Wu, Jia-Yi,Du, Xiao-Hua,Xu, Zhen-Yuan
supporting information; experimental part, p. 1239 - 1246 (2010/04/26)
Novel SO3H-functionalized ionic liquids bearing two alkyl sulfonic acid groups in the imidazolium cations were designed and successfully applied as catalysts for the one-pot Fischer indole synthesis in water medium. The sequence of the catalytic activity observed in the transformation was in good agreement with the Bronsted acidity order determined by the Hammett method. Various types of indoles from single-carbonyl ketones/aldehydes and cyclohexandiones were provided in 68-96% yields using the catalytic system of [(HSO3-p)2im][HSO4]/H2O. The indole products could be conveniently separated from the reaction mixture by filtration and the dissolved catalyst could be regenerated by treatment with a strongly acidic cation exchange resin, which meant the whole process was performed in water without using any organic solvents.
Bismuth nitrate promoted fischer indole synthesis: A simple and convenient approach for the synthesis of alkyl indoles
Sudhakara, Aralihalli,Jayadevappa, Honnali,Kumar, Hosanagara N.H.,Mahadevan, Kittappa M.
scheme or table, p. 159 - 164 (2010/04/23)
A novel one-pot fisher indole synthesis approach has been developed by using bismuth nitrate as a catalyst. Yields around 90-95% were obtained after reaction in methanol at reflux temperature in 20-40 min. Apart from the mild reaction conditions of the process and its excellent results, the simplicity of product isolation and the possibility to recycle the bismuth nitrate offers a significant advantage.
Fischer indole synthesis in bronsted acidic ionic liquids: A green, mild, and regiospecific reaction system
Xu, Dan-Qian,Yang, Wen-Long,Luo, Shu-Ping,Wang, Bing-Tao,Wu, Jian,Xu, Zhen-Yuan
, p. 1007 - 1012 (2008/03/12)
A novel one-pot Fischer indole synthesis approach has been developed by using Bronsted acidic ionic liquids as dual solvent-catalysts. Yields of 83-97 % were obtained after reaction in BMImHSO4 at 70-110°C in 0.5-6 h, and exclusive formation of 2,3-disubstituted indoles was observed in the reaction of alkyl methyl unsymmetrical ketones. The indoles produced could be conveniently separated from the reaction mixture without any volatile organic solvents, and the BMImHSO4 could be readily reused without efficiency loss after simple treatment involving only 1 equiv. of HCl for neutralization followed by filtration. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
