362705-52-0Relevant articles and documents
Propargylglycine-based antimicrobial compounds are targets of TolC-dependent efflux systems in Escherichia coli
Roldan, Bec J.,Pajarillo, Andrea O.,Greenberg, Jacob D.,Karlinsey, Joyce E.,Cafiero, Mauricio,Frawley, Elaine R.,Peterson, Larryn W.
supporting information, (2019/12/24)
A library of novel L-propargylglycine-based compounds were designed and synthesized with the goal of inhibiting the growth of Gram-negative bacteria by targeting LpxC, a highly conserved Gram-negative enzyme which performs an essential step in the lipid A biosynthetic pathway. These compounds were designed with and without a nucleoside and had varying tail structures, which modulate their lipophilicity. The synthetic scheme was improved compared to previous methods: a methyl ester intermediate was converted to a hydroxamic acid, which obviated the need for a THP protecting group and improved the yields and purity of the final compounds. Antimicrobial activity was observed for non-nucleoside compounds containing a phenyl propargyl ether tail (5) or a biphenyl tail (6). An MIC of 16 μg/mL was achieved for 6 in Escherichia coli, but inhibition was only possible in the absence of TolC-mediated efflux. Compound 5 had an initial MIC >160 μg/mL in E. coli. Enhancing outer membrane permeability or eliminating efflux reduced the MIC modestly to 100 μg/mL and 80 μg/mL, respectively. These results highlight the importance of hydrophobicity of this class of compounds in developing LpxC inhibitors, as well as the design challenge of avoiding multidrug efflux activity.
Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers
Alonso-Maran, Lorena,Martnez, M. Montserrat,Sarandeses, Luis A.,Sestelo, Jos Prez
, p. 379 - 387 (2015/02/02)
Indium(iii) halides catalyze efficiently the intramolecular hydroarylation (IMHA) of aryl propargyl ethers. The reaction proceeds regioselectively with terminal and internal alkynes bearing electron-rich and electron-deficient substituents in the benzenes
4-ALKOXY-N- (2-HYDROXYCARBAMOYL-2-PIPERIDINYL-ETHYL) -BENZAMIDE COMPOUNDS AS SELECTIVE TACE-INHIBITORS FOR THE TREATMENT OF INFLAMMATORY DISEASES
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Page/Page column 27, (2011/04/19)
The present invention relates to novel benzene- carboxamide compounds having a structure that corresponds to the general formula (I) below: and also to their method of synthesis and to their use in pharmaceutical compositions intended for use in human or
