951173-24-3Relevant academic research and scientific papers
BRIDGED COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS
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Paragraph 00124; 00126-00127, (2016/08/23)
Novel bridged compounds are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antibacterial agents. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating bacterial infections and associated diseases and conditions.
Practical syntheses of both enantiomers of the conformationally restricted GABA analogue cis-(2-aminocyclobutyl)acetic acid
Awada, Hawra,Robin, Sylvie,Guillot, Rgis,Yazbeck, Ogaritte,Naoufal, Daoud,Jaber, Nada,Hachem, Ali,Aitken, David J.
, p. 7148 - 7155 (2015/01/09)
Two efficient routes have been established for the preparation of both enantiomers of cis-(2-aminocyclobutyl)acetic acid, a conformationally restricted analogue of GABA. Both procedures converged on the racemic N-tert-butoxycarbonyl derivative of the target compound, which was resolved through chiral derivatization with an oxazolidinone auxiliary, which also allowed determination of the absolute configuration of the new compounds. The first route involved the homologation of cis-2-aminocyclobutanecarboxylic acid, whereas the second route employed an intramolecular photocyclization protocol, which provided an expedient, cisselective access to the lactam form of the target structure.
Solution state conformational preferences of dipeptides derived from N-aminoazetidinecarboxylic acid: An assessment of the hydrazino turn
Altmayer-Henzien, Amandine,Declerck, Valerie,Merlet, Denis,Baltaze, Jean-Pierre,Farjon, Jonathan,Guillot, Regis,Aitken, David J.
, p. 6031 - 6039 (2013/07/26)
Four model compounds and four dipeptides containing N- aminoazetidinecarboxylic acid (AAzC) and a particular stereoisomer of 2-aminocyclobutanecarboxylic acid (ACBC) were studied to establish their solution state conformational preferences, particularly regarding the ability of AAzC to induce a three-center hydrogen-bonded folding feature known as a "hydrazino turn". On the basis of IR and NMR experiments, supported by molecular modeling, the AAzC residue adopted a trans configuration amenable to the formation of a cyclic eight-membered hydrogen bond conformation in solution, in all cases studied. The implication of the heterocyclic nitrogen atom of AAzC in the trans-like structure was demonstrated via a refined 1H- 15N HMBC experiment giving exploitable data at natural 15N isotopic abundance, providing unprecedented evidence for the solution state hydrazino turn conformation. The predominance of this secondary structural feature depended on the configuration of the neighboring ACBC residue in the dipeptides: while the trans-ACBC derivatives prefer the hydrazino turn, the cis-ACBC derivatives may also populate low-energy 10-membered hydrogen-bonded ring structures. X-ray diffraction analysis of three compounds confirmed the presence of a solid state hydrazino turn in two cases, with geometries similar to those deduced from the solution state studies, but in the third compound, no intramolecular hydrogen-bonding feature was in evidence.
Stereoselective synthesis of all stereoisomers of orthogonally protected cyclobutane-1,2-diamine and some chemoselective transformations
Sans, Marta,Illa, Ona,Ortuno, Rosa M.
supporting information; experimental part, p. 2431 - 2433 (2012/07/13)
The four stereoisomers of protected cyclobutane-1,2-diamine have been prepared in an enantio- and diastereocontrolled manner through stereodivergent synthetic routes starting from a half-ester as a common chiral precursor. Orthogonal protection allows the
[2+2] Photocycloadditions with chiral uracil derivatives: Access to all four stereoisomers of 2-aminocyclobutanecarboxylic acid
Fernandes, Carlos,Gauzy, Christine,Yang, Yi,Roy, Olivier,Pereira, Elisabeth,Faure, Sophie,Aitken, David J.
, p. 2222 - 2232 (2008/03/28)
Starting from a single, chiral, bicyclic derivative of uracil, all four stereoisomers of 2-aminocyclobutanecarboxylic acid have been prepared in enantiomerically pure form, using a synthetic sequence which begins with a key photochemical [2+2] cycloaddition reaction and includes a practical cis to trans β-amino acid isomerisation procedure. Georg Thieme Verlag Stuttgart.
(+)- and (-)-2-aminocyclobutane-1-carboxylic acids and their incorporation into highly rigid β-peptides: Stereoselective synthesis and a structural study
Izquierdo, Sandra,Rua, Federico,Sbai, Abdelouahid,Parella, Teodor,Alvarez-Larena, Angel,Branchadell, Vicenc,Ortuno, Rosa M.
, p. 7963 - 7971 (2007/10/03)
Several derivatives of (+)- and (-)-2-aminocyclobutane-1-carboxylic acid, 1, have been prepared through enantiodivergent synthetic sequences. The stereoselective synthesis of free amino acid (+)-1 has been achieved, and this product has been fully charact
