- Three labdane-type diterpenes from the bark of Juniperus formosana HAY. var. concolor HAY.
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Three new labdane-type diterpenes, (13S)-15-hydroxylabd-8(17)-en-19-oic acid, (13S)-15-acetoxylabd-8(17)-en-19-oic acid, and (13S)-15- octadecanoyloxylabd-8(17)-en-19-oic acid, together with one known compound, enantio-oliveric acid, were found from the hark of Juniperus formosana HAY. var. concolor HAY. Their structures were elucidated on the basis of spectral data and chemical transformation.
- Kuo, Yueh-Hsiung,Yu, Ming-Tsang
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- PHOTOLYSIS OF α-DIAZO CARBONYL COMPOUNDS IN THE PRESENCE OF IMIDAZOLE. A NEW METHOD FOR THE PREPARATION OF NOR OLEFINS AND ITS APPLICATION TO BILE ACID SIDE CHAIN DEGRADATION
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α-Diazomethyl ketones derived from carboxylic acids are photolyzed in the presence of imidazole to give the corresponding nor olefins or, in the case of aryl diazo ketones, the corresponding, stable imidazolides.The application of the method to a novel degradation of bile acid side chain is reported.
- Pellicciari, Roberto,Natalini, Benedetto,Cecchetti, Sergio,Santucci, Sergio
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- Synthesis of 1-oxo-1-(3-pyridazinyl) derivatives - Potent inhibitors of Fatty Acid Amide Hydrolase (FAAH): An improved and optimized procedure
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A greatly improved procedure for the preparation of long-chain α-ketopyridazines, a class of potent inhibitors of fatty acid amide hydrolase (FAAH), is described. This optimization study shows a great dependence of the yields of desired products on the pyrididazinyl lithium/Weinreb amide ratio and offers a general approach to this kind of compound. Georg Thieme Verlag Stuttgart.
- Rosini, Goffredo,Andreotti, Daniele G.,D'Ambrosio, Primiano,Marotta, Emanuela,Tinarelli, Alessandro,Righi, Paolo
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Read Online
- Molecular assembly and photophysical properties of quaternary molecular hybrid materials with chemical bond
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In this paper, two long chain aliphatic carboxylic acids (oleic acid [OLA] and stearic acid [STA]) are modified with cross-linking molecules (N-2-aminoethyl-3-aminopropyl-methyl-dimethoxylsiliane, (AEAPMMS, H 2N(CH2)2HN(CH2)3SiCH 3(OCH3)2 and 3-aminopropyl-methyl- diethoxylsiliane (APMES, H2N(CH2)3SiCH 3(OC2H5)2) resulting in four new kinds of structural molecular bridge OLA (STA)-AEAPMMS (APMES). Subsequently, ternary molecular complex systems with four molecular bridges OLA (STA)-AEAPMMS (APMES) and 2,2-bipyridyl (bipy) of lanthanides (terbium and europium) or zinc ions were assembled, which resulted in four novel kinds of quaternary molecular hybrid materials (named as bipy-Ln (Zn)-OLA (STA)-AEAPMMS (APMES) with strong chemical bonds (N-Ln(Zn)-O coordination bonds and Si-O covalent bonds) after a sol-gel (cohydrolysis and copolycondensation) process of the modified molecular bridges (as structural ligand) with inorganic precursor (tetraethoxysilane, TEOS). And especially bipy behaves as functional ligand to sensitize the luminescence of terbium or europium ions through the effective intramolecular energy transfer process, which gives rise to the characteristic emission of metal ions. The design and assembly from structural and functional ligands can help achieve a candidate technology for molecular hybrids.
- Yan, Bing,Qian, Kai,Lu
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- Inhibitory effect of novel 5-O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response
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We previously found that vitamin K3 (menadione, 2-methyl-1,4-naphthoquinone) inhibits the activity of human mitochondrial DNA polymerase γ (pol γ). In this study, we focused on juglone (5-hydroxy-1,4-naphthoquinone), which is a 1,4-naphthoquinone derivative, and chemically synthesized novel juglones conjugated with C2:0 to C22:6 fatty acid (5-O-acyl juglones). The chemically modified juglones enhanced mammalian pol inhibition and their cytotoxic and anti-inflammatory activities. The juglone conjugated with oleic acid (C18:1-acyl juglone) showed the strongest inhibition of DNA replicative pol α activity and human colon carcinoma (HCT116) cell growth in 10 synthesized 5-O-acyl juglones. C12:0-Acyl juglone was the strongest inhibitor of DNA repair-related pol λ, as well as the strongest suppression of the production of tumor necrosis factor (TNF)-α production induced by lipopolysaccharide (LPS) in the compounds tested. Moreover, this compound caused the greatest reduction in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced acute inflammation in mouse ears. C12:0- and C18:1-Acyl juglones selectively inhibited the activities of mammalian pol species, but did not influence the activities of other pols and DNA metabolic enzymes tested. These data indicate that the novel 5-O-acyl juglones target anti-cancer and/or anti-inflammatory agents based on mammalian pol inhibition. Moreover, the results suggest that acylation of juglone is an effective chemical modification to improve the anti-cancer and anti-inflammation of vitamin K3 derivatives, such as juglone.
- Maruo, Sayako,Kuriyama, Isoko,Kuramochi, Kouji,Tsubaki, Kazunori,Yoshida, Hiromi,Mizushina, Yoshiyuki
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Read Online
- Synthesis and self-assembly of Salen type Schiff based on o-phenylenediamine organogels in response to Zn2+
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Two Salen type Schiff based on o-phenylenediamine were synthesized. The prepared organogelators demonstrated excellent gel properties in some selected solvents, such as n-pentanol, chloroform, and 1,2-dichloroethane. The results for thermal stability showed that under concentrations increasing of the gel molecules and then the gel-to-sol transition temperature value is increased. Through various techniques found that the hydrogen bonding between molecules, the van der Waals force, and the π-π stacking provide multiple driving forces for gel self-assembly. The morphology of the xerogel was investigated by Scanning Electron Microscope (SEM). The metal ions responsiveness experiment is completed by adding the metal ions solution dropwise to the gel surface and confirmed by the UV spectrum.
- Niu, Wei-Ya,Shang, Qi,Xue, Ji-Jun,Yang, Yun-Shang,Zhang, Ying-Peng
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- ABUSE-RESISTANT LONG-ACTING RELEASE OPIOID PRODRUGS
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There are provided, prodrugs of opioid such as levorphanol or morphine, having enhanced physical and chemical stability to resist tampering and to make long- acting release formulations, and pharmaceutically accepted salts and solvates thereof. There are also provided methods of using the disclosed compounds as abuse deterrent products.
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Paragraph 93; 95
(2020/07/31)
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- Catalyst for synthesizing acyl chloride compounds and application thereof
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The invention relates to a catalyst for synthesizing an acyl chloride compound and application of the catalyst. The structural formula is as shown in the specification, and in the formula, R is alkali of which the carbon atom number is 1-12. The catalyst is capable of effectively increasing the product yield, improving the production efficiency and lowering the production cost of acyl chloride, and has wide application prospects. The invention further provides a method for synthesizing acyl chloride with the catalyst.
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Paragraph 0063-0067
(2020/10/20)
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- Sialic acid lipid derivative and preparation method and application thereof
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The invention belongs to the technical field of medicines, and provides a sialic acid lipid derivative which can be used for modifying a particle preparation and a preparation method and application thereof. The structural general formula of the sialic acid lipid derivative is as shown in the specification, wherein R1 is an H atom or C1-C6 alkyl; R2 is H, (CH2) m or C2-C6 alkenyl, and m =1-17; when X is an H atom or an O atom, R3 is (CH2) n or cholesteryl, and n = 1-17; when X is a carbonyl group, R3 is a C12-C24 alkoxy group, a C12-C24 alkyl substituted amino group or cholesteryl; and R4 is -OH, -NHCOCH3 or -NHCOCH2OH. The sialic acid lipid derivative disclosed by the invention can be used for modifying a particle preparation and realizing different treatment or diagnosis purposes according to the properties of the medicine. Especially in the anti-tumor aspect, the sialic acid lipid derivative can endow a particle preparation with excellent tumor targeting ability to improve the tumorinhibition effect.
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Paragraph 0110-0113
(2019/12/29)
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- A new class of pure estrogen alpha receptor antagonists; design, synthesis and in-vitro screening
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Background: In view of the estrogenic receptor inhibitory properties of coumarin nucleus, long chain nature of fatty acid and anti-breast cancer activity of fatty acids, it was proposed to attach long chain fatty acids at 3rd,4th and 7th position of coumarin nucleus and evaluate for their anti-breast cancer activity through suitable in-vitro methods. Methods: The present study focuses a library of fatty acid coumarin conjugates as ligands to the ligand-binding domain of the human estrogen receptor α (PDB ID 2IOG) and their binding affinities using GLIDE module of Schrodinger after ascertaining their drug-likeness with QIKPROP. The compounds LNAC 8, SAC 1 and OAC 5 are the best hits based on their docking scores as well as the Prime MM-GBSA free energy of binding. Based on the in-silico results and synthetic feasibility the compounds SAC 1 PAC 1 and OAC 1 are synthesized, characterized and investigated for their time interval growth inhibitory effect on MCF-7 which is an ER positive breast cancer cell lines. Results: SAC 1, showed better in vitro growth inhibitory effect in sub micromolar range as compared to Tamoxifen, a standard estrogen receptor modulator. Conclusion: Conclusively, in silico molecular docking studies have been very useful in predicting the pharmacokinetic profiles and the binding affinities of new hits before a detailed preclinical and clinical evaluation.
- Jameera Begam, Akbar John,Basheer, Katike Ahamed,Jubie, Selvaraj,Jupudi, Srikanth,Azam, Mohammed Afzal,Dhanabal, Palanisamy
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- Preparation method of acyl chloride
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The invention relates to a preparation method of acyl chloride. The method comprises the following steps that 1, carboxylic acid is added into a reactor, or carboxylic acid is dissolved in organic solvent, a device is connected, and the temperature is raised to 100 DGE C-250 DEG C; 2, phosgene is introduced into the reactor for a reaction, and then the temperature is decreased to room temperature; 3, nitrogen is introduced, residual phosgene and hydrogen chloride are cleaned away, reaction liquid which is reacted without solvent is subjected to decompression distillation and purification directly, and needed acyl chloride is obtained; reaction liquid which is reacted with the solvent is subjected to decompression distillation to remove the solvent, and needed acyl chloride is obtained. According to the preparation method of acyl chloride, no catalyst is added, the risks that in the synthesizing process, due to the fact that the catalyst is dissolved, color of the finial product of acyl chloride is increased, and the catalyst is remained in late products are avoided, after the reaction is finished, high-quality acyl chloride can be obtained through decompression distillation, and the technological process is simple; due to the fact that in the whole technological process, except for absorbable and available phosgene, hydrogen chloride and carbon dioxide, no other three waste is discharged, the preparation method of acyl chloride is environmentally friendly, and the good implement value is achieved.
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Paragraph 0046; 0047
(2016/11/28)
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- Investigation of fatty acid conjugates of 3,5-bisarylmethylene-4-piperidone derivatives as antitumor agents and human topoisomerase-IIα inhibitors
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A series of five 3,5-bisarylidene-4-piperidones designed as analogs of curcumin and their twenty five fatty acid conjugates were synthesized as candidate anticancer agents. The fatty acid conjugates were designed for efficient delivery of these compounds at the targeted cancer sites. The cytostatic potential of these compounds was evaluated against three representative cancer cell lines namely murine leukemic L1210 cells, and human T-lymphocyte CEM cells and cervical HeLa cells. Most compounds were found to exhibit significant anti-cancer activity in vitro. QSAR studies indicated electrophilicity of these compounds towards cellular nucleophiles may have a key role to play in their cytostatic activity. Representative compounds were also tested for topoisomerase IIα inhibitory potential, which indicated strong catalytic inhibition of the enzyme in vitro. The data showed that the fatty acid conjugates also possessed robust antioxidant activity in multiple analyses. This study also indicated that these compounds prompted significantly lower cellular damage in human fibroblasts than a currently used cancer drug sorafenib in vitro. The wide spectrum of anticancer action, supplemented with antioxidant potential along with non-toxic manifestations, certainly augment the anticancer candidacy of the novel fatty acid conjugates.
- Potter, Elizabeth,Jha, Mamta,Bhullar, Khushwant S.,Rupasinghe, H.P. Vasantha,Balzarini, Jan,Jha, Amitabh
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p. 411 - 421
(2015/01/30)
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- Preparation and properties of a novel form-stable phase change material based on a gelator
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A series of gelators (Gm, m is the length of the alkyl tails, m = 2, 4, 6, 8, 10, 12, 14, 16 and 18) containing 4,4′-diaminodiphenylmethane moieties were synthesized. The chemical structures of Gm were confirmed by 1H NMR and MS. The form-stable phase change materials (FSPCMs) were prepared by introducing Gm into paraffin. The minimum gelation concentration (MGC) and gel-to-sol transition temperature (TGS) properties were tested by the "tube-testing method". It found that Gm (m = 2, 4, 6) was insoluble in paraffin, while the MGC and TGS of Gm (m = 8, 10, 12, 14, 16, 18) increased with the increase of alkyl chain. The structure and morphology of the PCMs were systematically investigated by FT-IR, POM, 1D WXAD and SEM. Experimental results revealed that paraffin was restricted because the gelators could self-assemble into three-dimensional netted structures, leading to form the shape-stable PCMs without leakage even above their melting point. The thermal properties were studied by DSC. The research showed that the G18/paraffin FSPCMs exhibited excellent thermal stability and high heat storage density. The shape stability of G18/paraffin was investigated by rheological measurements, indicating that solid hard gel soft gel liquid was observed with the increase of temperature. This work is useful in the comprehensive academic research and industrial application of PCMs.
- Wu, Dang,Wen, Wen,Chen, Sheng,Zhang, Hailiang
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supporting information
p. 2589 - 2600
(2015/02/19)
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- Acylative Suzuki coupling of amides: Acyl-nitrogen activation via synergy of independently modifiable activating groups
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A highly efficient palladium-catalyzed acylative cross-coupling of carboxylic amides with arylboronic acids has been achieved via synergistic activation of the Cacyl-N bond by independently modifiable activating groups. Coupling of amides features not only good functional group tolerance but also modifiable reactivities to overcome steric hindrance. This journal is
- Li, Xijing,Zou, Gang
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supporting information
p. 5089 - 5092
(2015/03/30)
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- Palladium-catalyzed acylative cross-coupling of amides with diarylborinic acids and sodium tetraarylborates
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Abstract A general and efficient acylative Suzuki coupling of active amides with diarylborinic acids has been achieved by using 1 mol% Pd(PCy3)2Cl2/0.6 mol% PCy3 as catalyst system taking advantage of modifiable reactivities of acyl-nitrogen bonds of amides. Both electronic and steric influences from either aryl or acyl counterparts on the coupling proved to be negligible or small. A variety of aryl ketones including sterically hindered ones could be synthesized by the coupling of diarylborinic acids in good to excellent yields. Sodium tetraarylborates could also be used as high atom-economy aryl source in the palladium-catalyzed cross-coupling with active amides.
- Li, Xijing,Zou, Gang
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p. 136 - 145
(2015/07/27)
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- Divergent Approach to a Family of Tyrosine-Derived Ru-Alkylidene Olefin Metathesis Catalysts
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A simple and generic approach to access a new family of Ru-alkylidene olefin metathesis catalysts with specialized properties is reported. This strategy utilizes a late stage, utilitarian Hoveyda-type ligand derived from tyrosine, which can be accessed via a multigram-scale synthesis. Further functionalization allows the catalyst properties to be tuned, giving access to modified second-generation Hoveyda-Grubbs-type catalysts. This divergent synthetic approach can be used to access solid-supported catalysts and catalysts that function under solvent-free and aqueous conditions.
- Gleeson, Ellen C.,Wang, Zhen J.,Jackson, W. Roy,Robinson, Andrea J.
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p. 7205 - 7211
(2015/07/28)
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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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- Synthesis of pyrazoles based on functionalized allenoates
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Regiospecific synthesis of pyrazole-3-carboxylate derivatives by 1,3-dipolar cycloaddition of diazomethane with allenoates in presence of triethylamine is demonstrated. Reaction of allenoates with stearic acid moiety containing diazoketone is explored under ultrasonic conditions. Novel derivatives of pyrazole were achieved in excellent yields.
- Sakhautdinov, Ilshat M.,Gumerov, Aynur M.,Batyrshin, Ilnur R.,Fatykhov, Akhnaf A.,Suponitsky, Kyrill Yu.,Yunusov, Marat S.
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p. 641 - 651
(2014/04/03)
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- Synthesis, characterization and biological evaluation of novel diesters of 4,4'-dihydroxy azoxy benzene with long chain carboxylic acids
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Synthesis of novel symmetrical azoxy diesters have been prepared by the reaction of 4,4'-dihydroxyazoxy benzene with aliphatic acid halides of varying chain lengths. The synthesized compounds have been characterized by spectral and analytical data. These symmetrical azoxy diesters exhibit good antifungal activity against six fungal strains (Mucor species, Aspergillus niger, Aspergillus flavus, Alternaria solani, Fusarium solani and Aspergillus fumigatus) and antitumor activities while no significant antibacterial activity has been observed. These synthesized compounds are also potent free radical scavengers.
- Shehzadi, Sumaira,Siddiqi, Humaira Masood,Qasim, Malik Muhammed,Fawad, Musfirah,Manan, Abdul,Khan, Naeema,Saleem, Samreen,Bashir, Farah,Mirza, Bushra
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p. 462 - 472
(2014/08/05)
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- Fabrication of organogels achieved by prodrug-based organogelators of ketoprofen
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The treatment strategy of curing diseases using prodrugs of an anti-inflammatory drug is widespread. In the present study, we report on the synthesis of prodrugs of ketoprofen, consisting of a derivatization of ketoprofen and long hydrocarbon chain of fat
- Mahire, Rahul R.,Agrawal, Deepika S.,Patil, Devanand K.,More, Dhananjay H.
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p. 33286 - 33291
(2014/08/18)
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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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- Synthesis, characterization and photophysics of new photoactive esipt lipophilic dyes. partition experiments with different composed liposomes
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New lipophilic dyes were synthesized from a fluorescent precursor and used to produce photoactive liposomes and ethosomes made of different phospholipids. The lipophilic dyes absorbed in the ultraviolet region due to π-π* transitions and had a dual fluorescence emission in the violet-yellow regions, depending on solvent polarity. The long alkyl chain lipophilic dyes had a narrow emission band with a very regular shape, and their photophysical behaviour indicates that these dyes were inserted into the lipid bilayer. The dye with short alkyl chain appeared to be in a polar environment, which indicated this fluorophore experienced a more hydrophobic environment. Fluorescence titration experiments were also performed with this compound and the partition coefficient was determined, which showed higher values than those found in the literature for similar intramolecular proton transfer dyes, likely due to better interaction between this dye and the phospholipids, due to the alkyl chain present in the dyes.
- Coelho, Felipe Lange,Rodembusch, Fabiano Severo,Campo, Leandra Franciscato
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p. 134 - 142
(2014/08/18)
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- Design, synthesis and biological evaluation of novel aliphatic amido/sulfonamido-quaternary ammonium salts as antitumor agents
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RhoB, one of the upstream signaling proteins of the phosphatidylinositol-3- kinase (PI3K)/Akt pathway, is frequently mutated in human cancer. Based on a piperazine alkyl derivative that induced apoptosis via up-regulation of RhoB, we synthesized novel aliphatic amido/sulfonamido-quaternary ammonium salts and evaluated their biological activities using an in vitro growth inhibition assay and RhoB promoter assay in human cancer cells. Compound 3a was the most promising anticancer agent in the series, based upon its potent growth inhibition via RhoB-mediated signaling. These novel aliphatic amido/sulfonamido-quaternary ammonium salts may be useful as a platform for development of anticancer chemotherapeutic agents.
- Song, Doona,Yang, Jee Sun,Kim, Seo Joong,Kim, Bo-Kyung,Park, Song-Kyu,Won, Misun,Kim, Hwan Mook,Choi, Kang-Yell,Lee, Kyeong,Lee, Kiho,Han, Gyoonhee
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p. 788 - 794
(2013/02/23)
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- Anti-influenza active and low toxic N-phenyl-substituted β-amidoamidines structurally related to natural antibiotic amidinomycin
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A set of racemic N-phenyl-substituted β-amidoamidines hydrochlorides 4, which are structurally related to natural antiviral agent amidinomycin (1), was synthesized in four steps starting from methacryloyl anilide (5). In the final step of the synthetic route, an uncommon monoacylation of β-aminoamidine 8 at the less reactive β-phenylamino-group took place. To rationalize this result, a mechanism which involves initial acylation at the more active amidine-function followed by intramolecular acyl-group transfer to β-phenylamino-group was suggested. All three β-amidoamidines 4d-f bearing long linear aliphatic chain (from n-C8H17 to n-C12H25) revealed significant in vitro activity against influenza A virus (H3N2) and modest cytotoxicity. The in vitro antiviral potency of 4d,e is 6-20 times greater than that of commercial rimantadine with lower EC50 values and higher therapeutic index. The non-toxic in vivo compounds 4d-f showed a beneficial protective effect in influenza A (H3N2) infected mice.
- Korshin, Edward E.,Zakharova, Lyubov G.,Levin, Yakov A.,Shulaeva, Marina P.,Pozdeev, Oskar K.
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supporting information
p. 2357 - 2361
(2013/05/09)
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- Synthesis and antimycobacterial activity of isoniazid derivatives from renewable fatty acids
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This work describes the synthesis of a series of fatty acid hydrazide derivatives of isoniazid (INH). The compounds were tested against Mycobacterium tuberculosis H37Rv (ATCC 27294) as well as INH-resistant (ATCC 35822 and 1896 HF) and rifampicin-resistant (ATCC 35338) M. tuberculosis strains. The fatty acid derivatives of INH showed high antimycobacterial potency against the studied strains, which is desirable for a pharmaceutical compound, suggesting that the increased lipophilicity of isoniazid plays an important role in its antimycobacterial activity.
- Rodrigues, Marieli O.,Cantos, Jéssica B.,D'Oca, Caroline R. Montes,Soares, Karina L.,Coelho, Tatiane S.,Piovesan, Luciana A.,Russowsky, Dennis,Da Silva, Pedro A.,D'Oca, Marcelo G. Montes
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p. 6910 - 6914
(2013/11/06)
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- OLEFINS AND METHODS FOR MAKING THE SAME
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Provided herein are olefinic feedstocks derived from conjugated hydrocarbon terpenes (e.g., C10-C30 terpenes), methods for making the same, and methods for their use.
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Page/Page column 76
(2012/11/06)
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- LOW MOLECULAR WEIGHT GELATORS FOR CRUDE OIL, PETROLEUM PRODUCT OR CHEMICAL SPILL CONTAINMENT
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Low molecular weight gelators, methods of making such gelators, organogels comprising such gelators and systems and methods of using such gelators for the containment and/or remediation of a release and/or spill of a crude oil, a petroleum product and/or a chemical is described. In exemplary systems and methods, gels and/or emulsions formed from the combination and/or contact of such gelators and at least one of a crude oil, a petroleum product and a chemical from a release and/or spill into the environment can be used to recover these oils or chemicals while allowing the gelators to be recovered and reused to clean up or contain additional crude oil, petroleum products or chemicals.
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Page/Page column 47
(2012/04/23)
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- Synthesis and performance of N-(benzoyl)stearic acid hydrazide
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N-(benzoyl) stearic acid hydrazide was synthesized from benzoyl hydrazine and stearyl chloride which was deprived from stearic acid via acylation.The structure of the compound had been characterized byFT-IR, 1H NMR, at the same time, the structure of N-(benzoyl) stearic acid hydrazide was optimized by the semiempirical method PM3. The influence of the reaction ratio, reaction time and reaction temperature to the yield of N-(benzoyl) stearic acid hydrazidewas investigated by orthogonal experiment, and the optimized reaction condition was molar ratio of benzoyl hydrazine: stearyl chloride 1:1, reaction time 6 h, reaction temperature 70°, and the yield was 92.9%. The TGAthermalanalysisof N-(benzoyl) stearic acid hydrazideshowed that thermal stability of N-(benzoyl) stearic acid hydrazide was affected by heating rate, and the N-(benzoyl) stearic acid hydrazideenhanced the tensile strength, modulus and elongation at break of Poly (L-lactic acid) (PLLA).
- Cai, Yan-Hua,Li, Shun-Jiang
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experimental part
p. 545 - 552
(2012/07/01)
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- Electrospray ionization and collision induced dissociation mass spectrometry of primary fatty acid amides
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Primary fatty acid amides are a group of bioactive lipids that have been linked with a variety of biological processes such as sleep regulation and modulation of monoaminergic systems. As novel forms of these molecules continue to be discovered, more emphasis will be placed on selective, trace detection. Currently, there is no published experimental determination of collision induced dissociation of PFAMs. A select group of PFAM standards, 12 to 22 length carbon chains, were directly infused into an electrospray ionization source Quadrupole Time of Flight Mass Spectrometer. All standards were monitored in positive mode using the [M + H]+ peak. Mass Hunter Qualitative Analysis software was used to calculate empirical formulas of the product ions. All PFAMs showed losses of 14 m/z indicative of an acyl chain, while the monounsaturated group displayed neutral losses corresponding to H2O and NH3. The resulting spectra were used to propose fragmentation mechanisms. Isotopically labeled PFAMs were used to validate the proposed mechanisms. Patterns of saturated versus unsaturated standards were distinctive, allowing for simple differentiation. This determination will allow for fast, qualitative identification of PFAMs. Additionally, it will provide a method development tool for selection of unique product ions when analyzed in multiple reaction monitoring mode.
- Divito, Erin B.,Davic, Andrew P.,Johnson, Mitchell E.,Cascio, Michael
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experimental part
p. 2388 - 2394
(2012/07/27)
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- Alkyl sulfonyl derivatized PAMAM-G2 dendrimers as nonviral gene delivery vectors with improved transfection efficiencies
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Amphiphilic dendrimer-based gene delivery vectors bearing peripheral alkyl sulfonyl hydrophobic tails were constructed using low-generation PAMAM-G2 as the core and functionalized by means of the aza-Michael type addition of its primary amino groups to vinylsulfone derivatives as an efficient tool for surface engineering. While the unmodified PAMAM-G2 was unable to efficiently transfect eukaryotic cells, functionalized PAMAM-G2 dendrimers were able to bind DNA at low N/P ratios, protect DNA from digestion with DNase I and showed high transfection efficiencies and low cytotoxicity. Dendrimers with a C18 alkyl chain produced transfection efficiencies up to 3.1 fold higher than LipofectAMINE 2000 in CHO-k1 cells. The dendriplexes based in functionalized PAMAM-G2 also showed the ability to retain their transfection properties in the presence of serum and the ability to transfect different eukaryotic cell lines such as Neuro-2A and RAW 264.7. Taking advantage of the vinylsulfone chemistry, fluorescent PAMAM-G2 derivatives of these vectors were prepared as molecular probes to determine cellular uptake and internalization through a clathrin-independent mechanism.
- Morales-Sanfrutos, Julia,Megia-Fernandez, Alicia,Hernandez-Mateo, Fernando,Giron-Gonzalez, Ma Dolores,Salto-Gonzalez, Rafael,Santoyo-Gonzalez, Francisco
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experimental part
p. 851 - 864
(2011/03/22)
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- Synthesis and biological evaluation of new flavonoid fatty acid esters with anti-adipogenic and enhancing glucose consumption activities
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Oleoyl Formononetin (OF) has good weight loss activity and hypolipidemic activity, could improve insulin sensitivity and suppress adipogenesis. To acquire better biological activities, three series of flavonoid fatty acid esters were designed and synthesized by optimizing the structure of OF. Their bioactivities were assayed in vitro. Some of these novel compounds could effectively inhibit preadipocyte proliferation and adipogenesis. Moreover, they could enhance glucose consumption in adipocytes notably.
- Zhao, Wei,Sun, Jie,Xiang, Hua,Zeng, Yan-Yan,Li, Xiao-Bo,Xiao, Hong,Chen, De-Ying,Ma, Ren-Ling
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experimental part
p. 3192 - 3203
(2011/06/24)
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- Synthesis and biological evaluation of novel aliphatic amido-quaternary ammonium salts for anticancer chemotherapy: Part i
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We synthesized novel aliphatic amido-quaternary ammonium salts in an effort to discover anticancer agents that increase Ras homolog gene family, member B, (RhoB) levels. These compounds exert anti-proliferative activities against several human cancer cell types. Seventeen compounds, varying in aliphatic carbon chain length and N-substituents, were synthesized and their biological activities were evaluated. Of these 17 compounds, compound 3i emerged as the most promising anticancer compound by promoting apoptosis through the RhoB mediated pathway. Potent biological activities observed for these novel aliphatic amido-quaternary ammonium salt analogues support their potential as anticancer, chemotherapeutic agents.
- Yang, Jee Sun,Song, Doona,Lee, Boah,Ko, Won Jin,Park, Song-Kyu,Won, Misun,Lee, Kiho,Kim, Hwan Mook,Han, Gyoonhee
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experimental part
p. 2861 - 2866
(2011/06/27)
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- Diaryldiazepine Prodrugs for the Treatment of Neurological and Psychological Disorders
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The present invention provides prodrug compounds of diaryldiazepine drug compounds.
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Page/Page column 61
(2011/07/29)
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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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supporting information; experimental part
p. 1364 - 1369
(2011/08/09)
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- Improved LC-MS method for the determination of fatty acids in red blood cells by LC-orbitrap MS
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We report a new method for fast and sensitive analyses of biologically relevant fatty acids (FAs) in red blood cells (RBC) by liquid chromatography mass spectrometry (LC-MS). A new chemical derivatization approach was developed forming picolylamides from FAs in a quantitative reaction. Fourteen derivatized FA standards, including saturated and unsaturated FAs from C14 to C22, were efficiently separated within 15 min. In addition, the use of a recently introduced benchtop orbitrap mass spectrometer under positive electrospray ionization (ESI) full scan mode showed a 2-10-fold improvement in sensitivity compared with a conventional tandem MS method, with a limit of detection in the low femtomole range for saturated and unsaturated FAs. The developed method was applied to determine FA concentrations in RBC with intra- and interday coefficients of variation below 10%.
- Li, Xingnan,Franke, Adrian A.
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experimental part
p. 3192 - 3198
(2011/11/04)
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- Hydrophobic modification of chitosan and its physicochemical evaluation as sustained release tablet formulation
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Chitosan is being investigated widely for use as an excipient in oral and other pharmaceutical formulations. Chitosan is generally regarded as a nontoxic and non-irritant material. It is biocompatible with both healthy and infected skin. Chitosan has been shown to be biodegradable (LD50 (mouse, oral): > 16 g/kg). Unmodified chitosan exhibited a low degree of disorder and a weak tablet crushing strength. In the present work, the hydrophobically modified chitosan were synthesized in order to formulate a system for sustain release of hydrophilic drug (indomethacine prototype drug in present case). The caproyl (C-8), decanoyl (C-10), lauryl (C-12), myristyl (C-14), palmitoyl (C-16) and stearoyl (C-18), fatty acyl derivatives of chitosan were prepared and physicochemically evaluated as excipient in matrix tablet dosage. The best sustained release studies was defined by palmitoyl chitosan and it can able sustain 50-60 % release upto 12 h and in concentration range 10-30 % much less as compared to chitosan ( > 50 %).
- Singh,Tiwari
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experimental part
p. 2141 - 2150
(2012/02/14)
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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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- Synthesis and biological evaluation of isoflavone fatty acid esters with potential weight loss and hypolipidemic activities
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A series of isoflavone fatty acid esters were designed on the basis of endogenous oleoyl-estrone using estrogen moiety modification strategy. Ten new compounds were synthesized, and their body weight loss and hypolipidemic bioactivities were assayed. Some of these novel compounds could effectively inhibit the differentiation of 3T3-L1 preadipocytes in vitro. The most potent compound 1a significantly decreased the body weight and white adipose tissue weight in a high-fat diet-induced rat model. Also, compound 1a showed good hypolipidemic activity and low toxicity.
- Xiang, Hua,Zhao, Wei,Xiao, Hong,Qian, Lei,Yao, Yao,Li, Xiao-Bo,Liao, Qing-Jiang
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experimental part
p. 3036 - 3042
(2010/07/06)
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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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- Design, synthesis, and cholesterol-lowering efficacy for prodrugs of berberrubine
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In order to enhance oral bioavailability of berberine (BBR) for its cholesterol-lowering efficacy in vivo, a series of ester or ether prodrugs of berberrubine (M1), which is an active metabolite of BBR after first-pass metabolism, were designed, semi-synthesized, and evaluated. Among these M1 prodrugs, compound 5g possessing palmitate at the 9-position showed a moderate Log P value and esterase hydrolysis rate for releasing M1 in blood. Its cholesterol-lowering efficacy in vivo was evaluated in hyperlipidemic SD rats. Compound 5g (100 mg/kg/d) reduced blood CHO and LDL-c by 35.8% and 45.5%, respectively, similar to that by BBR. It also exhibited a good safety in rats with no side-effect on liver and kidney function. Therefore, the design of M1 prodrug appears to be an effective strategy to improve pharmacokinetic feature of BBR for its lipid-lowering efficacy in vivo.
- Li, Ying-Hong,Li, Yi,Yang, Peng,Kong, Wei-Jia,You, Xue-Fu,Ren, Gang,Deng, Hong-Bin,Wang, Yue-Ming,Wang, Yan-Xiang,Jiang, Jian-Dong,Song, Dan-Qing
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experimental part
p. 6422 - 6428
(2010/10/04)
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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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- Pyridinium based amphiphilic hydrogelators as potential antibacterial agents
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The numerous applications of hydrogelators have led to rapid expansion of this field. In the present work we report the facile synthesis of amphiphilic hydrogelators having a quaternary pyridinium unit coupled to a hydrophobic long alkyl chain through an amide bond. Different amphiphiles with various hydrophobic chain length and polar head groups were rationally designed and synthesized to develop a structure-property relation. A judicious combination of hydrophilic and hydrophobic segments led to the development of pyridinium based amphiphilic hydrogelators having a minimum gelation concentration of 1.7%, w/v. Field emission scanning electronic microscopy (FESEM), atomic force microscopy (AFM), photoluminescence, FTIR studies, X-ray diffraction (XRD) and 2D NOESY experiments were carried out to elucidate the different non-covalent interactions responsible for the self-assembled gelation. The formation of three-dimensional supramolecular aggregates originates from the interdigitated bilayer packing of the amphiphile leading to the development of an efficient hydrogel. Interestingly, the presence of the pyridinium scaffold along with the long alkyl chain render these amphiphiles inherently antibacterial. The amphiphilic hydrogelators exhibited high antibacterial activity against both Gram-positive and Gram-negative bacteria with minimum inhibitory concentration (MIC) values as low as 0.4 μg/mL. Cytotoxicity tests using MTT assay showed 50% NIH3T3 cell viability with hydrogelating amphiphile 2 up to 100 μg/mL.
- Brahmachari, Sayanti,Debnath, Sisir,Dutta, Sounak,Das, Prasanta Kumar
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experimental part
p. 859 - 868
(2011/04/12)
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- Synthesis of [14C] acids from their unlabeled counterparts and application toward a novel [14C] labeled hepatitis C virus polymerase inhibitor
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A strategy has been developed for the rapid construction of a [ 14C] acid from either an aromatic or an alkyl acid via a decarboxylation-carboxylation sequence. A [14C] labeled heptatitis C virus polymerase inhibitor was prepared. Other examples and the limitations of this methodology are discussed. Copyright
- Ho, Jonathan Z.,Wallace, Michael A.,Tang, Yui S.,Zhang, Andy S.,Braun, Matthew P.
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scheme or table
p. 251 - 253
(2011/05/02)
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- Fabrication of nanotubules and microspheres from the self-assembly of amphiphilic monochain stearic acid derivatives
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A series of amphiphilic monochain derivatives of stearic acid, CH 3(CH2)16CONH(CH2)nNH 2 (n = 2, 3, 4, 6), CH3(CH2) 16CONH(CH2)2S2(CH2) 2NH2, and [CH3(CH2) 16CONH]2(CH2)2, are synthesized, and their self-assembly behaviors have been investigated in 1,2-dichloroethane (DCE). In addition to the concentration of the compound in DCE, the number of methylene units in hydrophilic segments play a crucial role in determining the final morphology of self-assembling structures from nanotubules with 20 nm inner diameter to microspheres with an average diameter of 20 μm. The external texture of the microsphere is also influenced by the number of methylene units in the hydrophilic segment. The microspheres formed by highly ordered aggregattion of nanobelts show high thermal stability. The particular processes and causations have been expatiated.
- Zhang, Lidong,Li, Haiqing,Ha, Chang Sik,Suh, Hongsuk,Kim, Il
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body text
p. 17890 - 17895
(2011/08/22)
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- Styrene-hydroxyethyl methacrylate copolymer-supported porphyrinatomanganese(III) complexes: Synthesis and catalytic cyclohexane hydroxylation with molecular oxygen
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Two new styrene-hydroxyethyl methacrylate copolymers containing immobilized porphyrinatomanganese(III) were prepared and characterized as microspheres by SEM, UV-Vis, FT-IR, and TG-DTG. Their catalytic activities have been investigated for the hydroxylati
- Ye, Yuan-Jian,Huang, Jin-Wang,Cai, Jin-Hua,Yu, Han-Cheng,Wu, Wen-Hai,Zhou, Xian-Tai,Ji, Hong-Bin,Ji, Liang-Nian
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experimental part
p. 627 - 632
(2011/11/12)
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- PROCESS FOR PRODUCING CARBOXYLIC ACID CHLORIDE
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This invention relates to a method for producing a carboxylic acid chloride, which efficiently decomposes a Vilsmeier reagent type compound in a carboxylic acid chloride lacking a thermal stability or a carboxylic acid chloride hardly distilled in practice due to a high boiling point with a simple operation and has no adverse effect on a subsequent step, and more particularly to a method for producing a carboxylic acid chloride, characterized by comprising reacting a carboxylic acid with a chlorinating agent in the presence of a catalyst, removing the excessive chlorinating agent from a reaction system after the reaction, and then further adding 1.0 to 3.0 equivalents of the starting carboxylic acid based on the catalyst to the reaction system to decompose a Vilsmeier reagent type compound remaining in the reaction system.
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Page/Page column 5
(2009/12/23)
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- Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin
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A synthetic route to 3-hydroxy-2-octadecylindole, the putative structure of the novel indole alkaloid fistulosin, starting from 2-nitro-1-iodobenzene was examined. Key steps include formation of a 1-stannylsubstituted 1-methoxy-1-alkene from a Fischer chr
- Clawson Jr., Ronald W.,Dacko, Christopher A.,Deavers III, Robert E.,Akhmedov, Novruz G.,S?derberg, Bj?rn C.G.
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experimental part
p. 8786 - 8793
(2010/01/06)
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- Creatine-fatty acids
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The present invention describes compounds produced from a creatine molecule and a fatty acid molecule. The compounds being in the form of creatine-fatty acid compounds being bound by an anhydride linkage, or mixtures thereof made by reacting creatine or derivatives thereof with an appropriate fatty acid previously reacted with a thionyl halide. The administration of such molecules provides supplemental creatine with enhanced bioavailability and the additional benefits conferred by the specific fatty acid.
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Page/Page column 10
(2008/06/13)
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- CREATINE-FATTY ACIDS
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The present invention describes compounds produced from a creatine molecule and a fatty acid molecule. The compounds being in the form of creatine-fatty acid compounds being bound by an anhydride linkage, or mixtures thereof made by reacting creatine or derivatives thereof with an appropriate fatty acid previously reacted with a thionyl halide. The administration of such molecules provides supplemental creatine with enhanced bioavailability and the additional benefits conferred by the specific fatty acid. Formula (I).
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Page/Page column 11-12
(2008/12/08)
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- Pyrene derived functionalized low molecular weight organic gelators and gels
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Pyrene derived binary functionalized low molecular weight organic gelators (FLMOGs) and gels thereof in selected organic solvents were synthesized and characterized. The functionality refers to a functional group that does not take part in formation of the supramolecular gel network, but remains free and available for other purposes, such as to bind nanoparticles or other molecules into the gel structure. Functional groups were observed to disturb gel formation strongly, if they interact with each other within the same supramolecule due to the formation of competitive structures. Preventing such interactions restored the original gel properties. A gel with weaker supramolecular bonding than the binding between the functional groups was successfully made by separating the functional groups by distance. The π-π-interaction was found to be of negligible significance to the supramolecular binding energy, but probably essential to align the molecules to a one-dimensional chain and bring them into the range of van der Waals forces mainly responsible for the binding in this system. Solvent was observed to increase the binding energy of the supramolecule. All molecules were characterized by spectroscopic techniques and elemental analysis. Selected gels were characterized with rheometry, scanning electron microscopy, UV- and fluorescence spectroscopy. Gelation kinetics and hysteresis were measured by UV-spectroscopy and a fast gelation process was observed for all the gelators studied. The melting enthalpies were measured by DSC and calculated theoretically by PM3 level of theory. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
- Hahma, Arno,Bhat, Shreedhar,Leivo, Kimmo,Linnanto, Juha,Lahtinen, Manu,Rissanen, Kari
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supporting information; body text
p. 1438 - 1448
(2009/02/04)
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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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- New esters of vanillin and vanillal with some alkane- and arenecarboxylic acids
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Previously unknown esters were synthesized by the reaction of vanillin and vanillal with carboxylic acid chlorides. Pleiades Publishing, Inc., 2006.
- Dikusar
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p. 1035 - 1037
(2008/02/05)
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