600136-28-5Relevant academic research and scientific papers
Molecular structures and ab initio molecular orbital calculations of the optically active derivatives of 1-aminocyclopropane-1-carboxylic acid
D?oli?, Zoran,Cetina, Mario,Kova?ek, Damir,Hergold-Brundi?, Antonija,Mrvo?-Sermek, Draginja,Nagl, Ante,Slade, Neda,Paveli?, Kre?imir,Balzarini, Jan,De Clercq, Erik,Zerbe, Oliver,Folkers, Gerd,Scapozza, Leonardo,Mintas, Mladen
, p. 229 - 241 (2007/10/03)
The novel optically active derivatives of 2,2′-disubstituted-1-aminocyclopropane-1-carboxylic acid (-)-2 and (+)-3 were synthesised from the spiro-azlactone (+)-1. Oxidation of the diol moiety of (+)-3 gave by ring enlargement the racemic mixture of 2,3-dihydrofuran derivative (±)-6. This conversion is explained by stepwise rearrangement of the initially formed tetrasubstituted cyclopropanecarbaldehyde 4 through zwitterionic's reactive intermediate 5. The formation of (±)-6 is preferred energetically as established by ab initio calculations of the ground states and possible intermediates for that rearrangement. The crystal structure and absolute configuration of the compounds (+)-1, (-)-2, (+)-3 and (-)-7 were determined by single-crystal X-ray diffraction method. All four compounds possess Z-configuration of the cyclopropane ring. The dioxolane ring in the structures(+)-1 and (-)-2 adopts half-chair conformation, while the cyclopropane ring and geminally substituted groups in the structures (-)-2, (+)-3 and (-)-7 possess the anticlinal conformation. The molecules of the compound (+)-1 are connected by very weak intermolecular hydrogen bond of C-H?type. In the compounds (-)-2,(+)-3 and (-)-7 inter- and intramolecular hydrogen bonds of N-H?O type were observed. The spiro-compound (+)-1 exhibited a more pronounced inhibitory activity against the proliferation of murine leukemia and human T-lymphocytes cells than other type of tumor cell lines and normal human fibroblast cells.
