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

Jozef Csollei; Josef Jampilek; Lukas Placek; Radka Opatrilova; Katerina Brychtova

doi:10.3390/ecsoc-14-00417

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Synthesis of 5-amino-α-D-gluco-hept-6-enfuranose as usefull 1-deoxynojirimycin precursor using [3,3]-sigmatropic aza-Claisen rearrangement

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

Jozef Csollei

¹,

Josef Jampilek

^{1, 2},

Lukas Placek

²,

Radka Opatrilova

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.
² Zentiva a.s., U kabelovny 130, 102 37 Prague 10, Czech Republic

Published: 31 October 2010 by MDPI in The 14th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-14-00417

Abstract: Skin penetration enhancers are used in the formulation of transdermal delivery systems for drugs that are otherwise not sufficiently skin-permeable. The series of seven esters of 6-(2,5-dioxopyrrolidin-1-yl)-2-(2-oxoazepan-1-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

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Jozef Csollei

Josef Jampilek

Lukas Placek

Radka Opatrilova

Katerina Brychtova