116261-43-9Relevant academic research and scientific papers
Effect of Partially Fluorinated N-Alkyl-Substituted Piperidine-2-carboxamides on Pharmacologically Relevant Properties
Vorberg, Raffael,Trapp, Nils,Zimmerli, Daniel,Wagner, Bj?rn,Fischer, Holger,Kratochwil, Nicole A.,Kansy, Manfred,Carreira, Erick M.,Müller, Klaus
, p. 2216 - 2239 (2016/10/19)
The modulation of pharmacologically relevant properties of N-alkyl-piperidine-2-carboxamides was studied by selective introduction of 1–3 fluorine atoms into the n-propyl and n-butyl side chains of the local anesthetics ropivacaine and levobupivacaine. The basicity modulation by nearby fluorine substituents is essentially additive and exhibits an exponential attenuation as a function of topological distance between fluorine and the basic center. The intrinsic lipophilicity of the neutral piperidine derivatives displays the characteristic response noted for partially fluorinated alkyl groups attached to neutral heteroaryl systems. However, basicity decrease by nearby fluorine substituents affects lipophilicities at neutral pH, so that all partially fluorinated derivatives are of similar or higher lipophilicity than their non-fluorinated parents. Aqueous solubilities were found to correlate inversely with lipophilicity with a significant contribution from crystal packing energies, as indicated by variations in melting point temperatures. All fluorinated derivatives were found to be somewhat more readily oxidized in human liver microsomes, the rates of degradation correlating with increasing lipophilicity. Because the piperidine-2-carboxamide core is chiral, pairs with enantiomeric N-alkyl groups are diastereomeric. While little response to such stereoisomerism was observed for basicity or lipophilicity, more pronounced variations were observed for melting point temperatures and oxidative degradation.
Compounds, compositions, and methods for stimulating neuronal growth and elongation
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, (2008/06/13)
The present invention concerns methods, pharmaceutical compounds, and compositions for stimulating neuroite outgrowth in nerve cells leading to nerve regeneration. These methods, compounds and compositions inhibit rotamase enzyme activity associated with binding proteins.
(-)-Sandramycin: Total synthesis and characterization of DNA binding properties
Boger, Dale L.,Chen, Jyun-Hung,Saionz, Kurt W.
, p. 1629 - 1644 (2007/10/03)
Full details of the total synthesis of the potent antitumor antibiotic (-)-sandramycin (1), a cyclic decadepsipeptide possessing a 2-fold axis of symmetry, is described and constitutes the first total synthesis of a member of the growing class of naturall
A Synthesis of C1-C22 Fragment of the Immunosuppressant FK 506. Stereoselective Construction of (E)-Trisubstituted Double Bond (C19-C20) via Ester-enolate Claisen Rearrangement
Morimoto, Yoshiki,Mikami, Atsushi,Kuwabe, Shin-itsu,Shirahama, Haruhisa
, p. 2909 - 2912 (2007/10/02)
An ene-ester 5 prepared from L-malic acid was subjected to the ester-enolate Claisen rearrangement under Ireland's condition to give stereoselectively C16-C22 fragment 11 containing (E)-trisubstituted double bond which was further advanced to C1-C22 fragm
