Steroidal Ribbons from (3 alpha,5 beta,20S)-3-Hycloxy-20-Methyl-Pregnan-21-oic Acid

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F16%3A00471227" target="_blank" >RIV/61389030:_____/16:00471227 - isvavai.cz</a>

Výsledek na webu

<a href="http://www.eurekaselect.com/147510" target="_blank" >http://www.eurekaselect.com/147510</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1174/1570178614666161118161810" target="_blank" >10.1174/1570178614666161118161810</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Steroidal Ribbons from (3 alpha,5 beta,20S)-3-Hycloxy-20-Methyl-Pregnan-21-oic Acid

Popis výsledku v původním jazyce

Background: Steroidal ribbons (or steroid containing ribbons) are being studied for several reasons, firstly, they may be included in the lipid bilayer, especially if they have suitable size (as "extended cholesterol"), and they are interesting in binding to steroidal receptors, gelators, and/or superassembly synthons. Bile acids seem to be very suitable as their components have natural tendency to form supramolecular assemblies. nMethods: Synthesis of ester bonded tetramer of (3 alpha,5 beta,20S)-3-Hycloxy-20-Methyl-Pregnan-2-oic acid was achieved using 2,6-dichlorobenzoyl chloride and DMAP in toluene. To prepare shortened side chain steroid, the oxidative decarboxylation of protected lithocholic acid was used, followed by oxidation of thus formed terminal double bond. Aggregation properties of the prepared steroidal ribbon were studied alone and after binding with copper(II) ions. nResults: There was synthesized 3 alpha-{3 alpha-{3 alpha-[(3 alpha,5(3,20S)-3-hydroxy-pregnane-20-carbonyBoxy] [(5 beta,20S)-pregnane-20-carbonyBoxyll-[(5 beta,20S)-pregnane-20-carbonyBoxyll-(5 beta,20S)pregnane-20carboxylate as a steroidal ribbon derived from bile acid, however, with the shortened side chain. The aggregation of the ribbon prepared in chloroform after binding of Cu(II) ions was monitored by absorption and circular dichroism spectroscopy at different ratios [tetramer]/[Cu(II)]. A positive bisignate band centered at 280 nm emerges; whose intensity increases with the [tetramer]/[Cu(II)] ratio. This result suggests that chiral aggregates are obtained as a consequence of Cu(II) complexation. Time dependent experiments did not show any variation in both UV-Vis and CD spectra. nConclusion: Prepared and documented new type of tetrasteroidal ribbon is unique one for the length of the connecting steroidal side chain. Its construction was done aiming to have more rigid ribbon than the one of lithocholic acid, and on the other hand, less rigid than the one derived from etieni...

Název v anglickém jazyce

Steroidal Ribbons from (3 alpha,5 beta,20S)-3-Hycloxy-20-Methyl-Pregnan-21-oic Acid

Popis výsledku anglicky

Background: Steroidal ribbons (or steroid containing ribbons) are being studied for several reasons, firstly, they may be included in the lipid bilayer, especially if they have suitable size (as "extended cholesterol"), and they are interesting in binding to steroidal receptors, gelators, and/or superassembly synthons. Bile acids seem to be very suitable as their components have natural tendency to form supramolecular assemblies. nMethods: Synthesis of ester bonded tetramer of (3 alpha,5 beta,20S)-3-Hycloxy-20-Methyl-Pregnan-2-oic acid was achieved using 2,6-dichlorobenzoyl chloride and DMAP in toluene. To prepare shortened side chain steroid, the oxidative decarboxylation of protected lithocholic acid was used, followed by oxidation of thus formed terminal double bond. Aggregation properties of the prepared steroidal ribbon were studied alone and after binding with copper(II) ions. nResults: There was synthesized 3 alpha-{3 alpha-{3 alpha-[(3 alpha,5(3,20S)-3-hydroxy-pregnane-20-carbonyBoxy] [(5 beta,20S)-pregnane-20-carbonyBoxyll-[(5 beta,20S)-pregnane-20-carbonyBoxyll-(5 beta,20S)pregnane-20carboxylate as a steroidal ribbon derived from bile acid, however, with the shortened side chain. The aggregation of the ribbon prepared in chloroform after binding of Cu(II) ions was monitored by absorption and circular dichroism spectroscopy at different ratios [tetramer]/[Cu(II)]. A positive bisignate band centered at 280 nm emerges; whose intensity increases with the [tetramer]/[Cu(II)] ratio. This result suggests that chiral aggregates are obtained as a consequence of Cu(II) complexation. Time dependent experiments did not show any variation in both UV-Vis and CD spectra. nConclusion: Prepared and documented new type of tetrasteroidal ribbon is unique one for the length of the connecting steroidal side chain. Its construction was done aiming to have more rigid ribbon than the one of lithocholic acid, and on the other hand, less rigid than the one derived from etieni...

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Letters in Organic Chemistry

ISSN

1570-1786

e-ISSN

—

Svazek periodika

13

Číslo periodika v rámci svazku

10

Stát vydavatele periodika

AE - Spojené arabské emiráty

Počet stran výsledku

7

Strana od-do

711-717

Kód UT WoS článku

000391710500003

EID výsledku v databázi Scopus

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