• Klíčová slova
• Asparagus officinalis L., chřest lékařský, Asparagus altilis Aschers., A. hortensis Mill., Asparagus (angl.), Asperge (franc.), Spargel (něm.), špargl (čes.),
• MeSH
• asparagin * MeSH
• Asparagus (rostlina) * chemie   škodlivé účinky   MeSH
• flavonoidy * MeSH
• fytoterapie využití   MeSH
• laktace MeSH
• léčivé rostliny * MeSH
• lidé MeSH
• potraviny * MeSH
• spirostany * MeSH
• těhotenství MeSH
• Check Tag
• lidé MeSH
• těhotenství MeSH
• ženské pohlaví MeSH

BF3·Et2O-catalyzed double aldol condensation between acetylated steroid sapogenins and terephtalaldehyde led to acetylated dimeric spirostanols linked through a 1,4-dimethylidenebenzene moiety in moderate to good yields. The E configurations of the introduced double bonds were corroborated by NOE experiments. Saponification of the dimeric steroids led to the corresponding dimeric spirostanols.

• MeSH
• aldehydy chemie   MeSH
• benzen chemie   MeSH
• borany chemie   MeSH
• dimerizace * MeSH
• ether chemie   MeSH
• katalýza MeSH
• kyseliny ftalové chemie   MeSH
• sapogeniny chemie   MeSH
• spirostany chemická syntéza   chemie   MeSH
• stereoizomerie MeSH
• techniky syntetické chemie MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH

Benzylidenespirostanols were prepared by two-step synthesis including BF3·Et2O-catalyzed aldol condensation of several acetylated steroid sapogenins with benzaldehyde followed by saponification. The obtained compounds showed moderate cytotoxicity against three cancer cell lines (T-lymphoblastic leukemia cell line CEM, breast carcinoma cell line MCF7 and cervical carcinoma cell line HeLa) and normal human fibroblasts (BJ). The most active of the five tested substances was 3c (lowest IC50 for MCF7 cells 19.9±0.1µM) without any selectivity towards human cancer and normal cells, respectively.

• MeSH
• fytogenní protinádorové látky chemická syntéza   chemie   farmakologie   MeSH
• lidé MeSH
• MFC-7 buňky MeSH
• nádorové buněčné linie MeSH
• proliferace buněk účinky léků   MeSH
• sapogeniny chemická syntéza   chemie   farmakologie   MeSH
• screeningové testy protinádorových léčiv MeSH
• spirostany chemická syntéza   chemie   farmakologie   MeSH
• steroidy chemická syntéza   chemie   farmakologie   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH

(25R)-3β-Hydroxy-5α-spirostan-12-one (hecogenin) and 11α-hydroxypregn-4-ene-3,20-dione (11α-hydroxyprogesterone) were used as starting materials for the synthesis of a series of 11- and 12-substituted derivatives of 5ξ-pregnanolone (3α-hydroxy-5α-pregnan-20-one and 3α-hydroxy-5β-pregnan-20-one), the principal neurosteroid acting via γ-aminobutyric acid (GABA). These analogues were designed to study the structural requirements of the corresponding GABAA receptor. Their biological activity was measured by in vitro test with [(3)H]flunitrazepam as radioligand in which allopregnanolone and its active analogues stimulated the binding to the GABAA receptor. Analysis of the SAR data suggests dependence of the flunitrazepam binding activity on the hydrophobic-hydrophilic balance of the groups at the C-ring edge rather than on specific interactions between them and the receptor.

• MeSH
• konformace proteinů MeSH
• kvantitativní vztahy mezi strukturou a aktivitou * MeSH
• molekulární modely MeSH
• myši MeSH
• neurony metabolismus   MeSH
• pregnanolon analogy a deriváty   chemická syntéza   metabolismus   MeSH
• receptory GABA-A chemie   metabolismus   MeSH
• techniky syntetické chemie MeSH
• zvířata MeSH
• Check Tag
• myši MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH