132920-84-4Relevant academic research and scientific papers
Co-ordination chemistry of 3S-aminopyrrolidine and 3S-(methyl-amino)pyrrolidine: Crystallisation of the two diastereomers of dichloro[3S-(R,S-methylamino)pyrrolidine]palladium(II)
Newman, Paul D.,Hursthouse, Michael B.,Malik, K. M. Abdul
, p. 599 - 606 (2007/10/03)
Complexes of divalent Cu, Ni, Pd and Pt with 3S-aminopyrrolidine (S-ap) have been prepared and characterised by a combination of NMR, CD, electronic, IR and microanalytical techniques. The chosen chirality of the stereogenic carbon (S) forces the secondary nitrogen to adopt the R stereochemistry on co-ordination with the conformation of the 5-membered chelate being λ. The planar [M(S-ap)2]2+ complexes exist as a mixture of cis and trans isomers in the solid state and in solution. The trans arrangement is forced upon co-ordination of an axial donor (X = halide, thiocyanate or nitrite) in the five-co-ordinate ions [Cu(S-ap)2X]+. Methylation of the primary amine of S-ap generates another secondary nitrogen centre in the new ligand 3S-(methylamino)pyrrolidine, S-meap. This exocyclic nitrogen is not restricted to a single configuration on co-ordination. The complexes [M(S-meap)Cl2], where M = Pd or Pt, have been prepared and characterised. Both diastereoisomers (R- and S-NMe) of [Pd(S-meap)Cl2] crystallise from aqueous solution as distinct crystal forms which can be separated by mechanical means. The structure of the NMe(R) isomer has been determined by X-ray crystallography.
Fluoronaphthyridines and -quinolines as Antibacterial Agents. 5. Synthesis and Antimicrobial Activity of Chiral 1-tert-Butyl-6-fluoro-7-substituted-naphthyridones
Cesare, P. Di,Bouzard, D.,Essiz, M.,Jacquet, J. P.,Ledoussal, B.,et al.
, p. 4205 - 4213 (2007/10/02)
A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared.These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position.In this paper we report the full details of the asymmetric synthesis of this series of compounds.Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity.Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.
