6222-16-8

Usage

InChI:InChI=1/C15H32O3S/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-19(2,16)17/h3-15H2,1-2H3

Upstream product

• 112-72-1 1-Tetradecanol 
• 124-63-0 methanesulfonyl chloride 
• 7132-64-1 pentadecanoic acid methyl ester 

Downstream Products

• 1561-06-4 1-myristyl glycerol 
• 75010-38-7 cholesteryl tetradecyl ether 
• 78944-76-0 Tetradecylhydroperoxid 
• 128577-72-0 3-[3-(2-Ethoxycarbonyl-ethyl)-4-tetradecyloxy-benzoyl]-benzoic acid ethyl ester 
• 19218-94-1 1-iodotetradecane 
• 25737-87-5 2-(tetradecylamino)ethan-1-ol 
• 96022-96-7 2-O-Benzyl-3-O-tetradecyl-sn-glycerin 
• 96022-94-5 3-O-Tetradecyl-1-O-trityl-sn-glycerin 
• 96022-70-7 2-O-Benzyl-3-O-tetradecyl-1-O-<2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl>-sn-glycerin 
• 128577-97-9 3-[3-(2-Carboxy-ethyl)-4-tetradecyloxy-benzoyl]-benzoic acid 
• 18924-66-8 N,N-bis(2-hydroxyethyl)tetradecylamine 
• 1345831-68-6 (3R, 4R)-1-benzyl-3,4-bis(tetradecyloxy)pyrrolidine 
• 1192259-45-2 N,N-dibenzyl-3,4-bis(tetradecyloxy)butan-1-amine 

Relevant academic research and scientific papers

Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities

Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.

Synthesis and antileishmanial activity of lipidic amino alcohols

In this work, a number of lipidic amino alcohols wereas synthesized and evaluated in vitro on cultures of Leishmania amazonensis and Leishmania chagasi. Nine amino alcohols showed inhibition of L. chagasi growth, and seven of them showed inhibition of L. amazonensis with IC50 below 10 μm. Compound 11f was more active than the reference drug amphotericin B against L. chagasi promastigote forms.

Preparation and antitubercular activities of alkylated amino alcohols and their glycosylated derivatives

A series of N- and C-alkylated amino alcohols and of their protected galactopyranosyl derivatives was synthesized and evaluated for antitubercular activity. Five of these compounds displayed good activity, with a MIC below 12.5 μg/mL. The presence of the carbohydrate slightly affected the antibacterial activity.

Novel Biodegradable Pyridinium Amphiphiles for Gene Delivery

Biodegradable synthetic cationic pyridinium-based amphiphiles (SAINTs) prove to be promising non-viral carrier systems for delivery of DNA into eukaryotic cells. Six novel SAINTs were synthesised from 3,5-pyridinedicarboxylic acid as starting material, with two ester groups as linkers between the cationic headgroup and the hydrophobic tails. The vesicle-forming properties of the amphiphiles were studied by differential scanning calorimetry and transmission electron microscopy, whereas the hydrolysis of the diesters in water was investigated by NMR spectroscopy. Finally, the transfection potential and cytotoxicity were determined on COS-7 and HepG-2 cells in culture. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Compositions and methods using novel substituted imidazolium lipids

Compounds of the formula: are provided, in which R1 and R2 each independently represent a C8-C24 saturated or unsaturated hydrocarbon chain, which is optionally interrupted by from 1 to 3 heteroatom moieties, such as -O-, -S-, -NH- and -NR-. The symbol X represents -CH2-, -O-, -S-, -NH- or -NR-. The R group for each of the -NR- moieties represents an alkyl group having from 1 to 4 carbon atoms. Finally, the subscript n represents the integer 1 or 2, and A- represents an anion, preferably chloride or citrate.

N-substituted glycerophosphoethanolamines

The present invention relates to novel, therapeutically active fatty alkyl and alkenyl ether glycerophospholipids bearing a 3-(2-imidazolinyl)-2-imidazolinyl or 2-imidazolinyl substituent on the ethanolamine nitrogen, methods of using the compounds and pharmaceutically acceptable salts thereof, and pharmaceutical compositions containing same. The novel, therapeutically active compounds and salts of the invention possess anti-tumor, anti-psoriatic, anti-inflammatory, and anti-asthma activities.

Benzophenone Dicarboxylic Acid Antagonists of Leukotriene B4. 2. Structure-Activity Relationships of the Lipophilic Side Chain

A series of lipophilic benzophenone dicarboxylic acid derivatives were found to inhibit the binding of the potent chemotoxin leukotriene B4 (LTB4) to its receptor on intact human neutrophils.Activity at the LTB4 receptor was determined by using a 3H>LTB4-binding assay.The structure-activity relationship for the lipophilic side chain was systematically investigated.Compounds with n-alkyl side chains of varying lengths were prepared and tested.Best inhibition of 3H>LTB4 binding was observed with the n-decyl derivative.Analogues with alkyl chains terminated with an aromatic ring showed improved activity.The 6-phenylhexyl side chain was optimal.Substitution on the terminal aromatic ring was also evaluated.Methoxyl, methylsulfinyl, and methyl substituents greatly enhanced the activity of the compound.For a given substituent, the para isomer had the best activity.Thus the nature of the lipophilic side chain can greatly influence the ability of the compounds to inhibit the binding of LTB4 to its receptor on intact human neutrophils.The most active compound from this series, 84 (LY223982), bound to the LTB4 receptor with the affinity approaching that of the agonist.

Stereoselective Synthesis of Long-chain 1-O-(β-D-Maltosyl)-3-O-alkyl-sn-glycerols (Alkyl Glyceryl Ether Lysoglycolipids)

The synthesis of long-chain 2-O-benzyl-3-O-alkyl-sn-glycerols 5 was improved, making these compounds easily accessible for glycosylation experiments.Glycosylation with α-acetobromomaltose following a modified Koenings-Knorr procedure after removal of the protective groups yielded the title compound 9 in good yields.These compounds represent examples of alkyl glyceryl ether lysoglycolipids.Some properties of these amphiphilic compounds with a nonionic carbohydrate head-group differ not much (critical micell concentration, hemolytic activity), other properties differ very much (antitumor efficiency) from the properties of the analogous compounds with a zwitterionic phosphorylcholine head-group.