4887-54-1

Usage

InChI:InChI=1/C10H15NO4/c12-8-5-6-9(13)11(8)7-3-1-2-4-10(14)15/h1-7H2,(H,14,15)

Upstream product

• 105-60-2 caprolactam 
• 108-30-5 succinic acid anhydride 
• 60-32-2 6-aminohexanoic acid 

Relevant academic research and scientific papers

Copper catalyzed coupling of α-Bromocarboxylate with ω-Lactam

This paper especially deals with the problem associated with the reaction of α-bromocarboxyl compound and 5- membered ω-lactam ring. Specific heterogeneous copper catalyst was used to achieve the C-N nucleophilic coupling. Synthetic pathway of ethyl-6-(2,

Coupling reactions of α-Bromocarboxylate with Non-aromatic N-heterocycles

The conditions for the C-N bond forming reaction (C-N coupling reaction) between α-bromocarboxylate and nitrogen-containing non-aromatic heterocyclic rings under heterogeneous copper(I) oxide catalysis are investigated in this paper. All the generated com

Synthesis, physico-chemical properties and penetration activity of alkyl-6-(2,5-dioxopyrrolidin-1-yl)-2-(2-oxopyrrolidin-1-yl)hexanoates as potential transdermal penetration enhancers

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 substituted 6-aminohexanoic acid as potential transdermal penetration enhanc

Investigating the activity of 2-substituted alkyl-6-(2,5-dioxopyrrolidin-1- yl)hexanoates as skin penetration enhancers

Skin penetration enhancers are used in the formulation of transdermal delivery systems for drugs that are otherwise not sufficiently skin-permeable. We generated two series of esters by multi-step synthesis with substituted 6-aminohexanoic acid as potential transdermal penetration enhancers by multi-step synthesis. The synthesis of all newly prepared compounds is presented here. Structure confirmation of all generated compounds was accomplished by 1H NMR, 13C NMR, IR and MS spectroscopy. All the prepared compounds were analyzed using RP-HPLC and their lipophilicity (log k) was determined. The hydrophobicity (log P/C log P) of the studied compounds was also calculated using two commercially available programs and 3D structures of the selected compounds were investigated by means of ab initio calculations of geometry and molecular dynamic simulations. All the synthesized esters were tested for their in vitro transdermal penetration-enhancing activity and showed higher enhancement ratios than oleic acid. The highest enhancement ratios were exhibited by compound 5f (C(2) substituted with piperidine-2-one, C11 ester chain) and 5a (C(2) substituted with piperidine-2-one, C6 ester chain). The series with a ω-lactam ring (piperidin-2-one; 5a-g), showed slightly higher activities than those with morpholine (6a-6g). All of the agents showed minimal anti-proliferative activity (IC50 >6.25 μM), indicating they would have low cytotoxicity when administered as chemical penetration enhancers. The relationships between the lipophilicity and the chemical structure of the studied compounds, as well as the correlation between their chemical structure and transdermal penetration-enhancing activity, are discussed.

Investigation of substituted 6-aminohexanoates as skin penetration enhancers

Skin penetration enhancers are compounds used to facilitate the transdermal delivery of drugs that are otherwise not sufficiently permeable. Through a synthetic route implementing two series of esters, we generated transdermal penetration enhancers by a multi-step reaction with substituted 6-aminohexanoic acid. We present the synthesis of all newly prepared compounds here with structural confirmation accomplished by 1H NMR, 13C NMR, IR and mass spectroscopy (MS). The lipophilicity (log k) of all compounds was determined via RP-HPLC and their hydrophobicity (log P/C log P) was also calculated using two commercially available programs. Ab initio calculations of geometry and molecular dynamic simulations were employed to investigate the 3-dimensional structures of selected compounds. The transdermal penetration-enhancing activity of all the synthesized esters were examined in vitro and demonstrated higher enhancement ratios than oleic acid. Compounds 2e (C10 ester chain) and 2f (C11 ester chain) exhibited the highest enhancement ratios. It can be concluded that the series non-substituted at the C(2) position by a ω-lactam ring showed significantly higher activity than those with azepan-2-one. None of the prepared compounds penetrated through the skin. All of the investigated agents demonstrated minimal anti-proliferative activity using the SK-N-MC neuroepithelioma cell line (IC50 >6.25 μM), suggesting these analogs would have a low cytotoxic profile when administered in vivo as chemical penetration enhancers. The correlation between the chemical structure of the studied compounds and their lipophilicity is discussed in regards to transdermal penetration-enhancing activity.

Structure-Activity Relationships of Triple-Action Platinum(IV) Prodrugs with Albumin-Binding Properties and Immunomodulating Ligands

Chemotherapy with platinum complexes is essential for clinical anticancer therapy. However, due to side effects and drug resistance, further drug improvement is urgently needed. Herein, we report on triple-action platinum(IV) prodrugs, which, in addition to tumor targeting via maleimide-mediated albumin binding, release the immunomodulatory ligand 1-methyl-d-tryptophan (1-MDT). Unexpectedly, structure-activity relationship analysis showed that the mode of 1-MDT conjugation distinctly impacts the reducibility and thus activation of the prodrugs. This in turn affected ligand release, pharmacokinetic properties, efficiency of immunomodulation, and the anticancer activity in vitro and in a mouse model in vivo. Moreover, we could demonstrate that the design of albumin-targeted multi-modal prodrugs using platinum(IV) is a promising strategy to enhance the cellular uptake of bioactive ligands with low cell permeability (1-MDT) and to improve their selective delivery into the malignant tissue. This will allow tumor-specific anticancer therapy supported by a favorably tuned immune microenvironment.

Imidoperoxycarboxylic acids, processes for their preparation and their use

Imidopercarboxylic acids or salts thereof of the formula STR1 in which A denotes a group of the formula STR2 n denotes the number 0, 1 or 2, R1 denotes hydrogen, chlorine, bromine, C1 -C20 -alkyl, C2 -C20 -alkenyl, aryl, or alkylaryl, R2 denotes hydrogen, chlorine, bromine or a group of the formula --SO3 M, --CO2 M, CO3 M or OSO3 M. M denotes hydrogen, an alkali metal or ammonium ion or the equivalent of an alkaline earth metal ion and X denotes C3 -C19 -alkylene or arylene, preferably phenylene. These compounds are suitable as stable peroxide compounds in bleaching, oxidizing and cleaning agents.