87116-20-9Relevant academic research and scientific papers
Esterase-Activatable Synthetic M+/Cl? Channel Induces Apoptosis and Disrupts Autophagy in Cancer Cells
Malla, Javid Ahmad,Sharma, Virender Kumar,Lahiri, Mayurika,Talukdar, Pinaki
, p. 11946 - 11949 (2020)
The formation of a supramolecular synthetic M+/Cl? channel in the membrane phospholipid bilayer has been reported upon activation of a methyl pivalate-linked N1,N3-dialkyl-2-hydroxyisophthalamide by esterases. The channel formation induces apoptosis in cancer cells via the intrinsic pathway. Interestingly, the supramolecular channel was also shown to disrupt autophagy in cancer cells by causing alkalization of lysosomes – a feature that has been confirmed at the cellular and protein level.
Reaction of (Acyloxy)alkyl α-Halides with Phenols: Effect of Nucleofugicity and Nucleophilicity on Product Distribution
Sloan, Kenneth B.,Koch, Suzanne A. M.
, p. 3777 - 3783 (2007/10/02)
The product distribution obtained from the reaction of (acyloxy)alkyl α-halides (1 or 5) with phenols was found to depend on the nucleophilicity of the phenol, the nucleofugicity of the leaving group, and the ability of the electrophile to stabilize a carbenium ion.More nucleophilic phenols tended to give more acylation while better leaving groups and more stable incipient carbenium ions in the electrophile tended to favor the formation of alkylated products.In addition, the reaction of methanol with 1a was found to give a mixture of acylated and alkylated products (40 : 60).Thus, a general trend for all the nucleophiles for which information is available suggests that better nucleophiles undergo relatively more acylation and that poorer nucleophiles undergo more alkylation.These results are suggested to be consistent with the observations of Westaway on the effect of leaving group nucleofugicity and nucleophilicity of the nucleophile on bond lengths in the SN2 transition state.Facile rearrangements of acylated to alkylated products and of one alkylated product to another caused by the phenolate anion were also observed in the 3-phenoxy-1(3H)-isobenzofuranone-phenyl 2-formylbenzoate series.
