104029-18-7Relevant academic research and scientific papers
Expedient synthesis of novel β-ketoesters from the Mizoroki-Heck coupling of ethyl 3-ethoxyacrylate with aryl and pyridyl halides
Kohrt, Jeffrey T.,Conn, Ed,Maguire, Robert,Wright, Stephen W.,Singer, Robert
, p. 7065 - 7068 (2013)
It is well known that β-ketoesters are useful intermediates for the synthesis of a range of heterocyclic templates. While there are many useful synthetic methods available to access these intermediates, there are still opportunities for the discovery of useful methodologies for their construction from novel starting materials. In this regard, we report on the discovery of a facile Pd-catalyzed Mizoroki-Heck coupling of ethyl 3-ethoxyacrylate with aryl and heteroaryl halides to form substituted alkoxyacrylates which can be hydrolyzed to form novel aryl and heteroaryl β-ketoesters.
Identification of Novel Coumestan Derivatives as Polyketide Synthase 13 Inhibitors against Mycobacterium tuberculosis
Zhang, Wei,Lun, Shichun,Wang, Shu-Huan,Jiang, Xing-Wu,Yang, Fan,Tang, Jie,Manson, Abigail L.,Earl, Ashlee M.,Gunosewoyo, Hendra,Bishai, William R.,Yu, Li-Fang
, p. 791 - 803 (2018/02/17)
Inhibition of the mycolic acid pathway has proven a viable strategy in antitubercular drug discovery. The AccA3/AccD4/FadD32/Pks13 complex of Mycobacterium tuberculosis constitutes an essential biosynthetic mechanism for mycolic acids. Small molecules targeting the thioesterase domain of Pks13 have been reported, including a benzofuran-based compound whose X-ray cocrystal structure has been very recently solved. Its initial inactivity in a serum inhibition titration (SIT) assay led us to further probe other structurally related benzofurans with the aim to improve their potency and bioavailability. Herein, we report our preliminary structure-activity relationship studies around this scaffold, highlighting a natural product-inspired cyclization strategy to form coumestans that are shown to be active in SIT. Whole genome deep sequencing of the coumestan-resistant mutants confirmed a single nucleotide polymorphism in the pks13 gene responsible for the resistance phenotype, demonstrating the druggability of this target for the development of new antitubercular agents.
Spiro-imidazolidines as aldose reductase inhibitors and their pharmaceutical use
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, (2008/06/13)
Compounds related to 3',4'-dihydrospiro[imidazolidine-4,1'(2'H)-naphthalene]2,3',5-trione, spiro[chroman-4,4'-imidazolidine]2,2',5'-trione and 1',2'-dihydrospiro[imidazolidine-4,4'-(3'H)-quinoline 2,2'5-trione and reduced products thereof as aldose reduct
