114812-44-1Relevant articles and documents
N-[(1-cyclopropylmethyl-2-pyrrolidinyl)methyl]-substituted benzamides: Synthesis and dopamine D-2 and D-3 receptor binding affinities
Yang, Zhi-Ying,Mukherjee, Jogeshwar
, p. 1 - 8 (2007/10/03)
In an attempt to develop substituted benzamide antagonists that may be selective for the D-3 receptor, we have investigated the effects of a cyclopropylmethyl group. The compounds differed in the substitutions present in the aromatic ring and the pyrrolidine ring. Binding affinities were carried out by using 3H-spiperone and SF9 cell lines expressing the rat recombinant D-3 dopamine receptor subtype. Type A compounds, containing a 3- fluoropropyl group in the aromatic ring (fallypride and its N- cyclopropylmethyl analog) exhibited high affinities for D-2 compared to D-3 sites (fallypride: 0.023 nM for D-2 and 0.19 nM for D-3; N-cyclopropyl analog: 0.048 nM for D-2 and 0.36 nM for D-3); type B compounds, containing a 5-bromo substituent in the aromatic ring, N-cyclopropyl analog of FLB 457 showed very high potency for D-2 sites (K(i) = 0.003 nM); while type C compounds, ((S)-N-[(1-cyclopropylmethyl-2-pyrrolidinyl)methyl]-5-chloro-4- cyclopropylcarbonylamino-2-methoxybenzamide), was able to show a 17-fold selectivity for D-3 over D-2 receptor subtypes.
Efficient Stereoconservative Syntheses of 1-Substituted (S)- and (R)-2-Aminomethylpyrrolidines
Hoegberg, Thomas,Raemsby, Sten,Stroem, Peter
, p. 660 - 664 (2007/10/02)
Three-step stereoconservative syntheses of chiral 1-substituted 2-aminomethylpyrrolidines with high optical purities from D- or L-proline are described.The key intermediates, 1-substituted prolinamides, were obtained by N,O-dialkylation of proline followed by ammonolysis or by 1-alkylation of prolinamide.Reduction furnished the optically pure (about 99percent e.e.) pyrrolidine derivatives, which are useful as intermediates in the preparation of antipsychotic substituted benzamides.
