204334-92-9Relevant academic research and scientific papers
β,γ-Diaryl α-methylene-γ-butyrolactones as potent antibacterials against methicillin-resistant Staphylococcus aureus
Abutaleb, Nader S.,Hamann, Henry J.,Pal, Rusha,Ramachandran, P. Veeraraghavan,Seleem, Mohamed N.
, (2020)
A selected series of racemic α-methylene-γ-butyrolactones (AMGBL) synthesized via allylboration or allylindation reactions were screened against methicillin-resistant Staphylococcus aureus (MRSA) USA300. Unlike natural AMGBLs, such as parthenolide, synthe
Factors influencing the cytotoxicity of α-methylene-γ-hydroxy esters against pancreatic cancer
Ramachandran, P. Veeraraghavan,Helppi, Matthew A.,Lehmkuhler, Arlie L.,Marchi, Jennifer M.,Schmidt, C. Max,Yip-Schneider, Michele T.
supporting information, p. 4270 - 4273 (2015/11/03)
A systematic study to identify the factors influencing the cytotoxicity of α-methylene-γ-hydroxy esters against three pancreatic cancer cell lines (Panc-1, MIA-PaCa-2, and BxPC-3) has established that, in addition to Michael acceptor abilities, the possibility to lactonize to α-methylene-γ-butyrolactones is as important. The substitution pattern and the number of carbons between the hydroxy and ester moieties also influence the bio-activity.
A facile indium-mediated synthesis of protected and unprotected [1- (hydroxymethyl)vinyl]alkanols
Moirangthem, Nimalini D.,Thingom, Bhavna,Laitonjam, Warjeet S.
experimental part, p. 455 - 459 (2009/12/24)
Protected and unprotected [l-(hydroxymethyl)vinyl]alkanols (7 and 8) have been synthesized from the homologated y-hydroxy esters 4 which have been prepared by indium-mediated allylation of the rearranged bromides 3 derived from hydroxyl esters 2 in water medium.
Effective 1,4-Asymmetric C-C/C-O Stereoinduction in Indium-Promoted Coupling Reactions of Aldehydes to Protected and Unprotected [1-(Bromomethyl)vinyl] Alkanols. the Status of Intramolecular Chelation within Functionalized Allylindium Reagents
Paquette, Leo A.,Bennett, George D.,Isaac, Methvin B.,Chhatriwalla, Adnan
, p. 1836 - 1845 (2007/10/03)
The stereochemistry of the coupling reactions of oxygen-substituted bromides 8-10 with isobutyraldehyde, benzaldehyde, and cyclohexanecarboxaldehyde in water is described. The examples involving the O-silylated derivatives 8 exhibit moderate anti stereoselectivity. In contrast, rather high (most often in excess of 80:20) syn diastereofacial bias is observed when hydroxy bromides 10 are involved. Consequently, stereocontrolled 1,4-asymmetric induction under aqueous conditions can be realized in either direction on demand. These results are considered to reflect the fact that the siloxy systems enter into C-C bond formation via conventional Felkin-Anh transition state arrangements. The crossover observed for the unprotected analogues is believed to be a consequence of the preferred adoption of chelated transition states, these interactions likely being fundamental to aqueous organometallic chemistry.
