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Pregled bibliografske jedinice broj: 119020

Časopis

Autori: Džolić, Zoran; Cetina, Mario; Kovaček, Damir; Hergold-Brundić, Antonija; Mrvoš-Sermek, Draginja; Nagl, Ante; Slade, Neda; Pavelić, Krešimir; Balzarini, Jan; De Clercq, Erik; Zerbe, Oliver; Folkers, Gerd; Scapozza, Leonardo; Mintas, Mladen
Naslov: Molecular structures and ab initio molecular orbital calculations of the optically active derivatives of 1-aminocyclopropane-1-carboxylic acid
Izvornik: Journal of molecular structure (0022-2860) 655 (2003), 2; 229-241
Vrsta rada: članak
Ključne riječi: 1-Aminocyclopropane-1-carboxylic acid derivatives; Synthesis; Rearrangement; Ab initio MO calculations; Density functional theory; Single crystal X-ray analysis; Cytostatic activities; Antiviral activities
Sažetak:
The novel optically active derivatives of 2, 2'-disubstituted-1-aminocyclopropane-1-carboxylic acid (-)-2 and (+)-3 weresynthesized 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...O 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.
Projekt / tema: 0125003, 0098092, 0098093
Izvorni jezik: ENG
Rad je indeksiran u
bazama podataka:
Current Contents Connect (CCC)
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Temeljne medicinske znanosti,Kliničke medicinske znanosti
URL cjelovitog teksta:
Google Scholar: Molecular structures and ab initio molecular orbital calculations of the optically active derivatives of 1-aminocyclopropane-1-carboxylic acid



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