- Characterization of the molecular packing, thermotropic phase behaviour and critical micellar concentration of a homologous series of N-acyltaurines (n = 9–18). PXRD, DSC and fluorescence spectroscopic studies
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N-acyltaurines (NATs) are amides of fatty acids that can be structurally related to endocannabinoids. They show interesting physiological and pharmacological properties. We have synthesized a homologous series of NATs with saturated acyl chains (n = 9–18) and investigated their supramolecular structure and thermotropic phase transitions by powder X-ray diffraction (PXRD) and differential scanning calorimetry (DSC). The d-spacings obtained from PXRD increase linearly with chain length with an increment of ～0.847 ? per additional CH2 moiety suggesting that NATs adopt a tilted bilayer structure with similar packing in crystal lattice. Results obtained from DSC studies indicate that the endothermic transition temperature (Tt) of NATs showed a gradually increasing trend with increasing acyl chain length. The enthalpy (ΔHt) and entropy (ΔSt) of transition show odd-even alternations with odd-chain compounds having higher values than the even-chain compounds. The critical micellar concentration (CMC) of NATs was determined in water at room temperature by fluorescence spectroscopy by monitoring the spectral changes of 8-anilinonaphthalene-1-sulfonic acid (ANS). The CMCs of NATs were found to decrease with increase in acyl chain length. The present results provide a thermodynamic and structural basis for investigating the interaction of NATs with other membrane lipids and proteins, which in turn can shed light in understanding how they function in vivo (in biological membranes).
- Arul Prakash, Sukanya,Kamlekar, Ravi Kanth
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- 3-Aminobenzenesulfonamides incorporating acylthiourea moieties selectively inhibit the tumor-associated carbonic anhydrase isoform IX over the off-target isoforms I, II and IV
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We describe the synthesis of a series of novel 1-aroyl/acyl-3-(3-aminosulfonylphenyl) thioureas (4a–k) acting as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors. Reaction of alkyl/aryl isothiocyanates with 3-aminobenzenesulfonamide afforded a series of the title compounds incorporating a variety of short as well as highly lipophilic long tails. The newly synthesized sulfonamides were evaluated against 4 physiologically relevant CA isoforms (hCA I, II, IV, and IX). Several compounds showed interesting inhibitory activity. The tumor-associated hCA IX was the most sensitive isoform to inhibition with these compounds, with KIs in the range of 21.5–44.0 nM and selectivity ratios over the major cytosolic isoform hCA II in the range of 3.35–37.3. The sulfonamides incorporating the phenylacetylthioureido and pentadecanoylthioureido moieties were the most hCA IX-selective inhibitors detected in this work, making them of interest for further investigations.
- Fattah, Tanzeela Abdul,Bua, Silvia,Saeed, Aamer,Shabir, Ghulam,Supuran, Claudiu T.
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p. 123 - 128
(2018/10/20)
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- SUGAR FATTY ACID ESTER AND OIL GELLING AGENT
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PROBLEM TO BE SOLVED: To provide a compound that can gel various oils. SOLUTION: The present invention provides a compound containing 1,5-anhydro-D-glucitol fatty acid ester, represented by formula (1), or 1,5-anhydro-D-mannitol fatty acid ester, and a gelling agent containing the compound. (R1 independently represent an acyl group derived from a C10, 11 or 13-22 linear saturated fatty acid). SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0029; 0036; 0048
(2019/07/29)
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- Synthesis, antimicrobial activity and in silico studies on thymol esters
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Derivatisation of parent structure in terpenoids often results in enhancement of biological activity of newly obtained compounds. Thymol, a naturally occurring phenol biosynthesized through the terpene pathway, is a well known biocide with strong antimicrobial attributes and diverse therapeutic activities. We have aimed our study on a single modification of phenolic functionality in thymol in order to obtain a small focused library of twenty thymyl esters, ten of which were new compounds. All compounds were involved in in vitro antimicrobial testing. Another important aspect of current study was implementation of in silico calculation of physico-chemical, pharmacokinetic and toxicological properties, which could be helpful by giving an additional guidance in further research.
- Lazarevi?, Jelena,Kolarevi?, Ana,Dordevi?, Aleksandra,Stojanovi?, Gordana,?melcerovi?, Andrija,Ciuffreda, Pierangela,Santaniello, Enzo
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p. 603 - 612
(2017/09/11)
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- Structure, supramolecular organization and phase behavior of N-acyl-β-alanines: Structural homologues of mammalian brain constituents N-acylglycine and N-acyl-GABA
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N-Acyl-β-alanines (NABAs) are structural homologues of N-acylglycines (NAGs) and N-acyl-γ-aminobutyric acids (NAGABAs), and achiral isomers of N-acylalanines, which are all present in mammalian brain and other tissues and modulate activity of biological receptors with various functions. In the present study, we synthesized and characterized a homologous series of NABAs bearing saturated acyl chains (n = 8-20) and investigated their supramolecular organization and thermotropic phase behavior. In differential scanning calorimetric (DSC) studies, most of the NABAs gave one or two minor transitions before the main chain-melting phase transition in the dry state as well as upon hydration with water, but gave only a single transition when hydrated with buffer (pH 7.6). Transition enthalpies (ΔHt) and entropies (ΔSt), obtained from the DSC studies showed linear dependence on the chain length in the dry state and upon hydration with buffer, whereas odd-even alteration was observed when hydrated with water. The crystal structures of N-lauroyl-β-alanine (NLBA) and N-myristoyl-β-alanine (NMBA) were solved in monoclinic system in the P21/c space group. Both NLBA and NMBA were packed in tilted bilayers with head-to-head (and tail-to-tail) arrangement with tilt angles of 33.28° and 34.42°, respectively. Strong hydrogen bonding interactions between [sbnd]COOH groups of the molecules from opposite leaflets as well as N[sbnd]H?O hydrogen bonds between the amide groups from adjacent molecules in the same leaflet as well as dispersion interactions between the acyl chains stabilize the bilayer structure. The d-spacings calculated from powder X-ray diffraction studies showed odd-even alteration with odd-chain length compounds exhibiting higher values as compared to the even-chain length ones and the tilt angles calculated from the PXRD data are higher for the even chain NABAs. These observations are relevant to developing structure-activity relationships for these amphiphiles and understand how NABAs differ from their homologues and isomers, namely NAGs, NAGABAs, and N-acylalanines.
- Sivaramakrishna,Swamy, Musti J.
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- Analysis of Intact Cholesteryl Esters of Furan Fatty Acids in Cod Liver
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Furan fatty acids (F-acids) are a class of natural antioxidants with a furan moiety in the acyl chain. These minor fatty acids have been reported to occur with high proportions in the cholesteryl ester fraction of fish livers. Here we present a method for the direct analysis of intact cholesteryl esters with F-acids and other fatty acids in cod liver lipids. For this purpose, the cholesteryl ester fraction was isolated by solid phase extraction (SPE) and subsequently analyzed by gas chromatography with mass spectrometry (GC/MS) using a cool-on-column inlet. Pentadecanoic acid esterified with cholesterol was used as an internal standard. GC/MS spectra of F-acid cholesteryl esters featured the molecular ion along with characteristic fragment ions for both the cholesterol and the F-acid moiety. All investigated cod liver samples (n = 8) showed cholesteryl esters of F-acids and, to a lower degree, of conventional fatty acids. By means of GC/MS-SIM up to ten F-acid cholesteryl esters could be determined in the samples. The concentrations of cholesteryl esters with conventional fatty acids amounted to 78-140 mg/100 g lipids (mean 97 mg/100 g lipids), while F-acid cholesteryl esters were present at 47-270 mg/100 g lipids (mean 130 mg/100 g lipids).
- Hammann, Simon,Wendlinger, Christine,Vetter, Walter
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p. 611 - 620
(2015/06/08)
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- An LC-MS/MS method to quantify acylcarnitine species including isomeric and odd-numbered forms in plasma and tissues
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Acylcarnitines are intermediates of fatty acid and amino acid oxidation found in tissues and body fluids. They are important diagnostic markers for inherited diseases of peroxisomal and mitochondrial oxidation processes and were recently described as biomarkers of complex diseases like the metabolic syndrome. Quantification of acylcarnitine species can become challenging because various species occur as isomers and/or have very low concentrations. Here we describe a new LC-MS/MS method for quantification of 56 acylcarnitine species with acyl-chain lengths from C2 to C18. Our method includes amino acid-derived positional isomers, like methacrylyl-carnitine (2-M-C3:1-CN) and crotonyl-carnitine (C4:1-CN), and odd-numbered carbon species, like pentadecanoyl-carnitine (C15:0-CN) and heptadecanoyl-carnitine (C17:0-CN), occurring at very low concentrations in plasma and tissues. Method validation in plasma and liver samples showed high sensitivity and excellent accuracy and precision. In an application to samples from streptozotocin-treated diabetic mice, we identified significantly increased concentrations of acylcarnitines derived from branched-chain amino acid degradation and of odd-numbered straight-chain species, recently proposed as potential biomarkers for the metabolic syndrome. In conclusion, the LC-MS/MS method presented here allows robust quantification of isomeric acylcarnitine species and extends the palette of acylcarnitines with diagnostic potential derived from fatty acid and amino acid metabolism.
- Giesbertz, Pieter,Ecker, Josef,Haag, Alexander,Spanier, Britta,Daniel, Hannelore
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p. 2029 - 2039
(2015/11/17)
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- Differential scanning calorimetric and powder X-ray diffraction studies on a homologous series of N-acyl-L-alanine esters with matched chains (n = 9-18)
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A homologous series of two chain derivatives of L-alanine, namely N-acyl L-alanine alkyl esters (NAAEs), bearing matched, saturated, acyl and alkyl chains (n= 9-18) have been synthesized. The thermotropic phase transitions and supramolecular structure of NAAEs were investigated by differential scanning calorimetry (DSC) and powder X-ray diffraction (PXRD). Results obtained from DSC studies indicate that the transition temperatures (T t), enthalpies (ΔH t) and entropies (ΔS t) exhibit odd-even alternation with compounds bearing odd acyl and alkyl chains showing higher values of T t, ΔH t and ΔS t as compared to NAAEs with even acyl and alkyl chains. However, the transition enthalpies and entropies of the odd- and even chain length series independently exhibit a linear dependence on the chain length. The d-spacings obtained from PXRD increase linearly with chain length with an increment of 1.76 ?/CH 2, suggesting that NAAEs adopt either a tilted bilayer structure or a bent structure. The present results provide a thermodynamic and structural basis for investigating the interaction of NAAEs with other membrane lipids, which in turn can shed light in understanding how they can enhance the transdermal permeability of stratum corneum.
- Sivaramakrishna,Swamy, Musti J.
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p. 1627 - 1635
(2015/12/01)
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- Odd-even effect in a thiazole based organogelator: Understanding the interplay of non-covalent interactions on property and applications
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New series of thiazole based amides, namely, 1e [N-(thiazol-2-yl)pentadecamide] to 1h [N-(thiazol-2-yl)stearamide], 2e [N-(4-methylthiazol-yl)pentadecamide] to 2h [N-(4-methylthiazol-yl)stearamide], 3e [N-(5-methylthiazol-yl)pentadecamide] to 3h [N-(5-methylthiazol-yl)stearamide] were synthesized, characterized and investigated for their gelation properties. Interestingly, out of three series of thiazole amides synthesized, two (1e-1h and 3e-3h) had displayed odd-even effect on gelation property with an increase in the methylene functional group of alkyl chain attached with thiazole moiety. The gelation-non-gelation of solvents was found to be more significant for the series of compounds 1e-1h, whereas a subtle effect was observed in the series of compounds 3e-3h. A single crystal study of non-gelator (2d) highlighted the crucial role of the methyl group and its position on the thiazole moiety in bringing about a change in supramolecular synthon from a robust cyclic N-H...N interaction to the combination of N-H...N and N-H...O interactions. Self-assembly of four molecules of 2d led to the formation of a zero-dimensional (0-D) hydrogen bonded network instead of a one-dimensional hydrogen bonded network observed in gelling compounds mediated by (methyl)C-H...N, C-H...O and van der Waals interaction. Various gelling agents (3e-3h) were used for the synthesis of nearly spherical silver and ZnO nanoparticles using a sol-gel method, through encapsulation and stabilization of nanoparticles in the gel network. Interestingly, the alkyl chain lengths of thiazole amides were found to affect the size of synthesized Ag and ZnO nanoparticles.
- Yadav, Priyanka,Ballabh, Amar
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p. 721 - 730
(2015/02/19)
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- Structure and thermotropic phase behavior of a homologous series of n -Acylglycines: Neuroactive and antinociceptive constituents of biomembranes
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N-Acylglycines (NAGs) with different acyl chains have been found in the mammalian brain and other tissues. They exhibit significant biological and pharmacological properties and appear to play important roles in communication and signaling pathways within and between cells. In view of this, a homologous series of NAGs have been synthesized and characterized in the present study. Differential scanning calorimetric (DSC) studies show that the transition enthalpies and entropies of dry as well as hydrated NAGs exhibit a linear dependence on the acyl chain length. Most of the NAGs show a minor transition below the chain-melting phase transition, suggesting the presence of polymorphism in the solid state. Structures of N-myristoylglycine (NMG) and N-palmitoylglycine (NPG) were solved in monoclinic system with C2/c and P21 space groups, respectively. Analysis of the crystal structures show that NAGs are organized in a bilayer fashion, with head-to-head (and tail-to-tail) arrangement of molecules. The acyl chains in both structures are essentially perpendicular to the bilayer plane, which is consistent with a lack of odd-even alternation in the thermodynamic properties. The bilayer is stabilized by strong hydrogen bonding interactions between COOH groups of the molecules from opposite leaflets as well as N-H···O hydrogen bonds between the amide groups of adjacent molecules in the same leaflet and dispersion interactions among the acyl chains. Powder X-ray diffraction data show that the d-spacings for the NAGs with different acyl chains (n = 8-20) exhibit a linear dependence on the chain length, suggesting that all the NAGs investigated here adopt a similar packing arrangement in the crystal lattice. These observations are relevant for understanding the role of N-acylglycines in biological membranes.
- Reddy, S. Thirupathi,Krovi, Krishna Prasad,Swamy, Musti J.
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p. 4944 - 4954
(2014/12/10)
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- N-acylated alanine methyl esters (NAMEs) from Roseovarius tolerans, structural analogs of quorum-sensing autoinducers, N-acylhomoserine lactones
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The Roseobacter clade is one of the most important bacteria group living in the ocean. Liquid cultures of Roseovarius tolerans EL 164 were investigated for the production of autoinducers such as N-acylhomoserine lactones (AHLs) and other secondary metabolites. The XAD extracts were analyzed by GC/MS. Two AHLs, Z7-C14: 1-homoserine lactone (HSL) and C15: 1-HSL, were identified. Additionally, the extract contained five compounds with molecular-ion peaks at m/z 104, 145, and 158, thus exhibiting mass spectra similar to those of AHLs with corresponding peaks at m/z 102, 143, and 156. Isolation of the main compound by column chromatography, NMR analysis, dimethyl disulfide derivatization for the determination of the location of the CiC bond and finally synthesis of the compound with the proposed structure confirmed the compound to be (Z)-N-(hexadec-9-enoyl)alanine methyl ester. Four additional minor compounds were identified as C14: 0-, C15: 0-, C16: 0-, and C17: 1-N-acylated alanine methyl esters (NAMEs). All NAMEs have not been described from natural sources before. A BLASTp search showed the presence of AHL-producing luxI genes, but no homologous genes potentially responsible for the structurally closely related NAMEs were found. The involvement of the NAMEs in chemical communication processes of the bacteria is discussed. Copyright
- Bruns, Hilke,Thiel, Verena,Voget, Sonja,Patzelt, Diana,Daniel, Rolf,Wagner-Doebler, Irene,Schulz, Stefan
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p. 1559 - 1573
(2013/10/21)
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- HETEROCYCLIC DERIVATIVES THAT ARE USED IN THE TREATMENT OF NEURODEGENERATIVE DISEASES
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The present invention relates to compounds of Formula (I) below, to their pharmaceutically acceptable salts and to their isomers or mixtures of isomers: HetAr—X—CHR1R2 (I) in which: -HetAr represents a group chosen from: —X represents a linear, saturated or unsaturated, hydrocarbon-based chain comprising from 8 to 22 carbon atoms, optionally interrupted by an —NH— or —NH—CO— group, —R1 represents a hydrogen atom or an —OH, —O(C1-C6)alkyl, —OCO((C1-C6)alkyl), —OSO2((C1-C6)alkyl) or —OSO3H group, and —R2 represents a hydrogen atom or a (C2-C6)alkynyl, (C2-C6)alkenyl or (C3-C6)cycloalkyl group. The present invention also relates to a process for preparing the compounds of Formula (I), and also to the use thereof, especially in the treatment of neurodegenerative diseases.
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Page/Page column 11
(2011/06/10)
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- Lizard epidermal gland secretions. II. Chemical characterization of the generation gland secretion of the sungazer, cordylus giganteus
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In lizards, the epidermal glands of the femoral and precloacal regions are involved in the production of semiochemicals. In addition to its femoral glands, the giant girdled lizard, or sungazer, Cordylus giganteus, which is endemic to South Africa, has generation glands as an additional potential source of semiochemicals. These epidermal glands are described as glandular scales that overlay the femoral glands and are included in the normal epidermal profile located in the femoral (thigh) and anterior antebrachial (fore-leg) regions of the male sungazer. GC-MS analysis of the generation gland secretions and the trimethylsilyl derivatives of some of the steroidal constituents was employed to identify 59 constituents, including alkenes, carboxylic acids, alcohols, ketones, aldehydes, esters, amides, nitriles, and steroids. The quantitative differences of the volatile constituents of the fore- and hind-leg generation glands were compared between individuals. This is the first report on the chemical composition of generation glandular material of lizards.
- Louw, Stefan,Burger, Ben V.,Le Roux, Maritha,Van Wyk, Johannes H.
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experimental part
p. 1364 - 1369
(2011/08/09)
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- Chiral propargyl alcohols via the enantioselective addition of terminal Di- and triynes to aldehydes
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The enantioselective addition of di- and triynes to aldehydes is presented, including the first examples of an asymmetric triyne addition. Modification of the Carreira alkynylation protocol shows that addition of diynes and triynes to α-branched aldehydes can be complete in as little as 4 h, and these reactions give good yields and enantioselectivities (up to 98% ee) for di- and triynes tested (aryl, alkyl, and silyl). It is shown for two cases (20 and 24) that products of this asymmetric addition reaction can undergo further manipulation (desilylation and triazole formation) without affecting the enantiopurity.
- Graham, Erin R.,Tykwinski, Rik R.
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experimental part
p. 6574 - 6583
(2011/10/05)
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- Carbohydrate liquid crystals: Synthesis and characterisation of the methyl-6-O-(n-acyl)-α-D-glucopyranosides
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Seven members of the methyl-6-O-(n-acyl)-α-d-glucopyranosides have been synthesised and their transitional properties determined. The undecanoyl and octadecanoyl members do not exhibit liquid crystallinity while the members having chain lengths between dodecanoyl and hexadecanoyl exhibit a monotropic smectic A phase. Variable temperature infrared spectroscopy reveals that the hydrogen bonding within the system shows a marked change at the melting point but apparently no change at the smectic A-isotropic transition. This observation is interpreted in terms of Goodby's model for the smectic A phase in which the carbohydrate moieties are located at the centre of the smectic bilayer and assuming that hydrogen bonded aggregates persist into the isotropic phase. Within this framework, the unusually low values of the entropy change associated with the smectic A-isotropic transition may also be accounted for.
- Cook, Andrew G.,Wardell, James L.,Imrie, Corrie T.
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scheme or table
p. 118 - 124
(2012/03/10)
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- Host marking pheromone (HMP) in the Mexican Fruit Fly Anastrepha ludens
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Host marking pheromones (HMPs) are used by insects to mark hosts (usually a fruit) where they have already laid eggs. The compounds serve as a deterrent to conspecifics avoiding over-infestation of hosts (i.e. repeated egg-laying into an already occupied/used host). If these HMPs are sprayed onto commercially valuable fruit they act as deterrents preventing attack by females interested in laying eggs into the valuable commodity. Having no insecticidal or toxic properties, and being natural products (or close derivatives thereof) they could be used as fruit sprays to replace insecticides, or in combination with other products to improve efficacy. This review discusses the isolation, and synthesis of the HMP of the Mexican fruit fly Anastrepha ludens a feared pest of citrus and mangos in Mexico and Central America. This compound is also recognized by females of other pestiferous species in the same genus Anastrepha distributed from the Southern USA to Northern Argentina, including many Caribbean Islands. The synthetic HMP was shown to exhibit strong electrophysiological activity against A. ludens and excellent interspecies cross recognition with other Anastrepha species. Behavioural tests confirmed the HMP deterring effect of the synthetic natural product. Further studies enabled us to drastically simplify the structure of the HMP and obtain a derivative, which we named Anastrephamide, which shows HMP deterring effects very similar to the natural product in laboratory and field tests. The potential use of such HMP derivatives in a crop protection scenario is briefly discussed. Schweizerische Chemische Gesellschaft.
- Edmunds, Andrew J. F.,Aluja, Martin,Diaz-Fleischer, Fransico,Patrian, Bruno,Hagmann, Leonhard
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scheme or table
p. 37 - 42
(2010/09/05)
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- Tryptamine-derived alkaloids from Annonaceae exerting neurotrophin-like properties on primary dopaminergic neurons
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N-fatty acyl tryptamines constitute a scarce group of natural compounds mainly encountered in Annonaceous plants. No biological activity was reported so far for these rare molecules. This study investigated the neurotrophic properties of these natural tryptaminic derivatives on dopaminergic (DA) neurons in primary mesencephalic cultures. A structure-activity relationships study led us to precise the role of a nitrogen atom into the aliphatic chain conferring to the compounds a combined neuroprotective and neuritogenic activity in the nanomolar range. The potent antioxidant activity of these natural products seems to be involved in part of their mechanism of action. This study provides the first description of natural neurotrophin mimetics present in Annonaceae extracts, and led to the biological characterization of compounds, which present a potential interest in neurodegenerative diseases such as Parkinson's disease.
- Schmidt, Fanny,Douaron, Gael Le,Champy, Pierre,Amar, Majid,Seon-Meniel, Blandine,Raisman-Vozari, Rita,Figadere, Bruno
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experimental part
p. 5103 - 5113
(2010/09/11)
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- Synthesis, calorimetric studies, and crystal structures of N, O-diacylethanolamines with matched chains
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Recent studies show that N-, O -diacylethanolamines (DAEs) can be derived by the O -acylation of N-acylethanolamines (NAEs) under physiological conditions. Because the content of NAEs in a variety of organisms increases in response to stress, it is likely that DAEs may also be present in biomembranes. In view of this, a homologous series of DAEs with matched acyl chains (n = 10-20) have been synthesized and characterized. Transition enthalpies and entropies obtained from differential scanning calorimetry show that dry DAEs with even and odd acyl chains independently exhibit linear dependence on the chainlength. Linear least-squares analyses yielded incremental values contributed by each methylene group to the transition enthalpy and entropy and the corresponding end contributions. N-, O-Didecanoylethanolamine (DDEA), N-, O-dilauroylethanolamine (DLEA), and N-, O-dimyristoylethanolamine (DMEA) crystallized in the orthorhombic space group Pbc21 with four symmetry-related molecules in the unit cell. Single-crystal X-ray diffraction studies show that DDEA, DLEA, and DMEA are isostructural and adopt an L-shaped structure with the N-acyl chain and the central ethanolamine moiety being essentially identical to the structure of N-acylethanolamines, whereas the O-acyl chain is linear with all-trans conformation. In all three DAEs, the lipid molecules are organized in a bilayer fashion wherein the N-acyl and O-acyl chains from adjacent layers oppose each other. Copyright
- Kamlekar, Ravi Kanth,Tarafdar, Pradip K.,Swamy, Musti J.
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body text
p. 42 - 52
(2010/11/04)
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- Lipophilic pyrylium salts in the synthesis of efficient pyridinium-based cationic lipids, gemini surfactants, and lipophilic oligomers for gene delivery
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Several new classes of pyridinium cationic lipids were synthesized and tested as gene delivery agents. They were obtained through a procedure that generates simultaneously the heterocyclic ring and the positively charged nitrogen atom, using lipophilic pyrylium salts as key intermediates that react with primary amines, yielding pyridinium salts. The choice of the appropriately substituted primary amine, diamine or polyamine, allows the design of the shape of the final lipids, gemini surfactants, or lipophilic polycations. We report also a comprehensive structure-activity relationship study that identified the most efficient structural variables at the levels of the hydrophobic anchor, linker, and counterion for these classes of pyridinium cationic lipids. This study was also aimed at finding the best liposomal formulation for the new transfection agents.
- Ilies, Marc Antoniu,Seitz, William A.,Johnson, Betty H.,Ezell, Edward L.,Miller, Aaron L.,Thompson, E. Brad,Balaban, Alexandru T.
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p. 3872 - 3887
(2007/10/03)
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- Pyridinium cationic lipids as gene transfer agents
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Pyridinium cationic lipids useful as non-viral gene delivery agents are disclosed. The agents are prepared by reaction of pyrylium salts with primary amines. Also disclosed are methods of trasfectind cells using the pyridinium cationic lipids as gene tran
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Page/Page column 30-31
(2008/06/13)
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- Cosmetics and N-acylamino acid composition
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There are disclosed cosmetics which comprise N-acylamino acids containing acyl groups having specifically numbered carbon atoms, or derivatives thereof and which are well suited for hair growth, skin care and the like; N-acylamino acid compositions which are favorably usable for detergents, dispersants, emulsifying agents, antimicrobial drugs, antiseptics, ultraviolet absorbers and the like. The invention provides cosmetics which comprise N-acylamino acids containing acyl groups having odd-numbered carbon atoms, salts thereof or esters thereof; N-acylamino acid compositions; and further N-acylamino acids containing acyl groups having carbon atoms in an odd number in the range of 13 to 17 along with salts and esters thereof.
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- N-acylamino acids and cosmetics using the same
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Disclosed herein are N-acylamino acids selected from the group consisting of N-pentadecanoylalanine, N-pentadecanoylleucine, N-pentadecanoylmethionine, N-pentadecanoylvaline, N-pentadecanoylisoleucine, N-pentadecanoylphenylalanine and N-pentadecanoyltyros
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- Inhibitors of Acyl-CoA:cholesterol acyltransferase. I. Identification and structure-activity relationships of a novel series of fatty acid anilide hypocholesterolemic agents
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A series of fatty acid anilides was prepared, and compounds were tested for their ability to inhibit the enzyme acyl-CoA:cholesterol acyltransferase (ACAT) in vitro and to lower plasma total cholesterol and elevate high- density lipoprotein cholesterol in cholesterol-fed rats in vivo. The compounds reported were found to fall into two subclasses with different anilide SAR. For nonbranched acyl analogues, inhibitory potency was found to be optimal with bulky 2,6-dialkyl substitution. For α-substituted acyl analogues, there was little dependence of in vitro potency on anilide substitution and 2,4,6-trimethoxy was uniquely preferred. Most of the potent inhibitors (IC50 50 nM) were found to produce significant reductions in plasma total cholesterol in cholesterol-fed rats. Additionally, in vivo activity could be improved significantly by the introduction of α,α- disubstitution into the fatty acid portion of the molecule. A narrow group of α,α-disubstituted trimethoxyanilides, exemplified by 2,2-dimethyl-N-(2,4,6- trimethoxyphenyl)dodecanamide (39), was found to not only lower plasma total cholesterol (-60%) in cholesterol-fed rats but also elevate levels of high- density lipoprotein cholesterol (+94%) in this model at the screening dose of 0.05% in the diet (ca. 50 mg/kg).
- Roth,Blankley,Hoefle,Holmes,Roark,Trivedi,Essenburg,Kieft,Krause,Stanfield
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p. 1609 - 1617
(2007/10/02)
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- Soil fungi inhibiting agent
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Soil fungi-inhibiting agent containing as the active ingredient one or more of the compounds represented by the following general formula STR1 wherein I. WHEN BOTH X and Y are oxygen atoms, Z is hydrogen atom, unsubstituted alkyl group, unsubstituted alkenyl group, STR2 (in this case the compound is p-toluene sulfonate), NH2 CH2 -- (in this case the compound is p-toluene sulfonate), acyl group, ClCH2 CONH--, or alkyl group substituted by substituents such as R1 COO--, CH3 COS--, R2 O--, R2 S--, HO--, HOOC--, CH3 CONH--, acyl group, alkoxyacyl group, where R1 is lower-alkyl group or alkenyl group, R2 is lower-alkyl group or benzyl group; Ii. when X is oxygen and Y is sulfur or --NH--, Z is lower alkyl group; Iii. when X is sulfur and Y is oxygen, Z is lower-alkyl group, acetylmethyl group, methoxymethyl group, 2-methyl-1-propynyl group or nitromethyl group; Iv. when X is sulfur and Y is --NH--, Z is lower-alkyl group.
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- 2-Acyl-3-substituted cyclopentan-1-ones and process for their preparation
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1,3-Dicarbonyl compounds useful as medicines, agricultural chemicals, perfumes, and their intermediates are prepared by reacting a specific α,β-unsaturated carbonyl compound with a specific organic copper lithium compound in the presence of an aprotic inert organic solvent, and then reacting the reaction product with an organic carboxylic acid halide or anhydride. In particular, novel 2-acyl-3-substituted cyclopentan-1-ones and 2-acyl-3-substituted cyclohexan-1-ones having important physiological activities are provided.
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