124645-64-3Relevant academic research and scientific papers
Tandem homologation-acylation chemistry: Single and double homologation
Henderson, Carley S.,Mazzone, Jennifer R.,Moore, Amanda M.,Zercher, Charles K.
, (2021)
Treatment of β-dicarbonyls with the Furakawa-variant of the Simmons-Smith reagent results in homologation and production of an intermediate zinc enolate. Treatment of the enolate with various acylating agents generate products with both γ-dicarbonyl funct
Diaryl- and triaryl-pyrrole derivatives: Inhibitors of the MDM2-p53 and MDMX-p53 protein-protein interactions
Blackburn, Tim J.,Ahmed, Shafiq,Coxon, Christopher R.,Liu, Junfeng,Lu, Xiaohong,Golding, Bernard T.,Griffin, Roger J.,Hutton, Claire,Newell, David R.,Ojo, Stephen,Watson, Anna F.,Zaytzev, Andrey,Zhao, Yan,Lunec, John,Hardcastle, Ian R.
, p. 1297 - 1304 (2013/09/12)
Screening identified 2-(3-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)- ylidene)methyl)-2,5-dimethyl-1H-pyrrol-1-yl)-4,5,6,7-tetrahydrobenzo[b] thiophene-3-carbonitrile as an MDM2-p53 inhibitor (IC50 = 12.3 μM). MDM2-p53 and MDMX-p53 activity was seen for 5-((1-(4-chlorophenyl)-2,5- diphenyl-1H-pyrrol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (MDM2 IC50 = 0.11 μM; MDMX IC50 = 4.2 μM) and 5-((1-(4-nitrophenyl)-2,5-diphenyl-1H-pyrrol-3-yl)methylene)pyrimidine-2,4,6(1H, 3H,5H)-trione (MDM2 IC50 = 0.15 μM; MDMX IC50 = 4.2 μM), and cellular activity consistent with p53 activation in MDM2 amplified cells. Further SAR studies demonstrated the requirement for the triarylpyrrole moiety for MDMX-p53 activity but not for MDM2-p53 inhibition. The Royal Society of Chemistry.
Microwave-assisted Paal-Knorr reaction - Three-step regiocontrolled synthesis of polysubstituted furans, pyrroles and thiophenes
Minetto, Giacomo,Raveglia, Luca F.,Sega, Alessandro,Taddei, Maurizio
, p. 5277 - 5288 (2007/10/03)
An efficient and highly versatile synthesis of furans, pyrroles and thiophenes is described. Starting from commercially available or easily prepared β-keto esters, functional homologation provides differently substituted 1,4-diketones that can be transfor
New pyrrole-based amino acids for the synthesis of peptidomimetic constrained scaffolds
Alongi, Maddalena,Minetto, Giacomo,Taddei, Maurizio
, p. 7069 - 7072 (2007/10/03)
A new family of pyrrole-based amino acids have been prepared through the microwave assisted Paal-Knorr reaction of 1-4 ketoesters derived from the corresponding β-ketoester with a functional homologation. The carboxylic group is located in position 3 of the pyrrole, whereas the amino group, protected with the Cbz moiety, is present on the side chain in positions 1 or 2. These compounds were used to prepare constrained oligopeptides.
Microwave-Assisted Paal-Knorr Reaction. A Rapid Approach to Substituted Pyrroles and Furans
Minetto, Giacomo,Raveglia, Luca F.,Taddei, Maurizio
, p. 389 - 392 (2007/10/03)
(Equation presented) An array of tetrasubstituted pyrroles (and trisubstituted furans) was obtained using a simple three-step procedure. Functional homologation of a β-ketoester with an aldehyde followed by oxidation gave a series of differently substitut
A TITANOXYCYCLOPROPANE AS INTERMEDIATE IN A HIGHLY STEREOSELECTIVE HOMOALDOL TYPE ADDITION SYNTHESES OF CIS-SUBSTITUTED TETRAHYDROFURAN DERIVATIVES
Reissig, Hans-Ulrich,Holzinger, Hiltrud,Glomsda, Gabriele
, p. 3139 - 3150 (2007/10/02)
Reaction of methyl 2-siloxycyclopropanecarboxylate 4 with TiCl4 provides the unique titanoxycyclopropane 10 whose structure could be elucidated by means of NMR-spectroscopy.Its additions to aldehydes and acetophenone occur with high stereoselectivity to a
