606092-23-3Relevant academic research and scientific papers
Organotin-catalyzed synthesis of hydroxyalkylamides from lactones via a ring-opening process
Liang, Xiayu,Yu, Peng,Fu, Chen,Shen, Yongcun
supporting information, (2021/02/09)
A new strategy for the facile synthesis of hydroxyalkylamides through the ring-opening reaction of lactone with amine promoted by dibutyltin acetate was developed. A series of hydroxyalkylamide compounds were obtained and the method was successfully applied to the synthesis of pharmaceutically active molecules tyrosinase inhibitor V and HDAC inhibitor VI via a three-step synthetic pathway. The broad substrate scope, mild reaction conditions and practical application proved the effectiveness, compatibility and practicality of this method.
Structural Requirements of HDAC Inhibitors: SAHA Analogues Modified at the C2 Position Display HDAC6/8 Selectivity
Negmeldin, Ahmed T.,Padige, Geetha,Bieliauskas, Anton V.,Pflum, Mary Kay H.
supporting information, p. 281 - 286 (2017/03/17)
Histone deacetylase (HDAC) proteins are epigenetic regulators that deacetylate protein substrates, leading to subsequent changes in cell function. HDAC proteins are implicated in cancers, and several HDAC inhibitors have been approved by the FDA as antica
Metal-Free Synthesis of N-Aryl Amides using Organocatalytic Ring-Opening Aminolysis of Lactones
Guo, Wusheng,Gómez, José Enrique,Martínez-Rodríguez, Luis,Bandeira, Nuno A. G.,Bo, Carles,Kleij, Arjan W.
, p. 1969 - 1975 (2017/05/16)
Catalytic ring-opening of bio-sourced non-strained lactones with aromatic amines can offer a straightforward, 100 % atom-economical, and sustainable pathway towards relevant N-aryl amide scaffolds. Herein, the first general, metal-free, and highly efficient N-aryl amide formation is reported from poorly reactive aromatic amines and non-strained lactones under mild operating conditions using an organic bicyclic guanidine catalyst. This protocol has high application potential as exemplified by the formal syntheses of drug-relevant molecules.
Synthesis and biological evaluation of aziridin-1-yl oxime-based vorinostat analogs as anticancer agents
Nikitjuka, Anna,Shestakova, Irina,Romanchikova, Nadezhda,Jirgensons, Aigars
, p. 647 - 657 (2016/01/15)
The suberoyl anilide hydroxamic acid (vorinostat) analogs with the aziridin-1-yl oxime moiety as a possible metal chelating functionality have been synthesized. Their biological activity and stability under physiological conditions have been evaluated. Although some of the synthesized compounds demonstrated high antiproliferative activity against human HT1080 fibrosarcoma (HT1080, IC50 0.3-7.7 μM) comparable to vorinostat (HT1080, IC50 2.4 μM), they showed only weak histone deacetylase inhibition activity in HeLa cell line extracts.
Structural requirements of HDAC inhibitors: SAHA analogs functionalized adjacent to the hydroxamic acid
Bieliauskas, Anton V.,Weerasinghe, Sujith V.W.,Pflum, Mary Kay H.
, p. 2216 - 2219 (2007/10/03)
Inhibitors of histone deacetylase (HDAC) proteins such as suberoylanilide hydroxamic acid (SAHA) have emerged as effective therapeutic anti-cancer agents. To better understand the structural requirements of HDAC inhibitors, a small molecule library with a
Phosphorus-based SAHA analogues as histone deacetylase inhibitors
Kapustin, Galina V.,Fejer, Gyoergy,Gronlund, Jennifer L.,McCafferty, Dewey G.,Seto, Edward,Etzkorn, Felicia A.
, p. 3053 - 3056 (2007/10/03)
(Matrix presented) Three analogues of suberoyl anilide hydroxamic acid (SAHA) with phosphorus metal-chelating functionalities were synthesized as inhibitors of histone deacetylases (HDACs). The compounds showed weak activity for HeLa nuclear extracts (IC50 = 0.57-6.1 mM), HDAC8 (IC 50 = 0.28-0.41 mM), and histone-deacetylase-like protein (HDLP, IC50 = 0.33-1.9 mM), suggesting that the transition state of HDAC is not analogous to zinc proteases. Antiproliferative activity against A2780 cancer cells (IC50 = 0.11-0.12 mM), comparable to SAHA (0.15 mM), was observed.
