Synthesis of Esters of 6-(2,5-Dioxopyrrolidin-1-yl)-2- (morpholin-4-yl)hexanoic Acid as Potential Transdermal Penetration Enhancers

Jozef Csollei; Josef Jampilek; Radka Opatrilova; Lukas Placek; Barbora Slaba; Sylva Dittrichova; Katerina Brychtova

doi:10.3390/ecsoc-13-00210

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ORGANOCATALYTIC APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE 1,2,3-TRISUBSTITUTED AZETIDINES

Synthesis of Esters of 6-(2,5-Dioxopyrrolidin-1-yl)-2- (morpholin-4-yl)hexanoic Acid as Potential Transdermal Penetration Enhancers

Jozef Csollei

¹,

Josef Jampilek

^{1, 2},

Radka Opatrilova

¹,

Lukas Placek

^{1, 2},

Barbora Slaba

^{1, 2},

Sylva Dittrichova

¹,

Katerina Brychtova

^{*

1}

¹ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic; e-mail: brychtovak@vfu.cz, tel: +420-5-41562924
² Zentiva a.s., U kabelovny 130, 102 37 Prague 10, Czech Republic

Published: 01 November 2009 by MDPI in The 13th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic Chemistry and Natural Products

https://doi.org/10.3390/ecsoc-13-00210

Abstract: Skin penetration enhancers are used to allow formulation of transdermal delivery systems for drugs that are otherwise insufficiently skin-permeable. The series of seven esters of 6-(2,5-dioxopyrrolidin-1-yl)-2-(morpholin-4-yl)hexanoic acid as potential transdermal penetration enhancers was formed by multistep synthesis. The general synthetic approach of all newly synthesized compounds is presented. Structure confirmation of all generated compounds was accomplished by IR, 1H, 13C NMR and HR-MS spectroscopy. All the prepared compounds were analyzed using RP-HPLC method for the lipophilicity measurement and their lipophilicity (log k) was determined.

Keywords: Transdermal penetration enhancers; 6-Aminohexanoic acid derivatives; Lipophilicity

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Jozef Csollei

Josef Jampilek

Radka Opatrilova

Lukas Placek

Barbora Slaba

Sylva Dittrichova

Katerina Brychtova