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Identification and synthesis of (Z,Z)-8,11-heptadecadienyl formate and (Z)-8-heptadecenyl formate: Unsaturated aliphatic formates found in the unidentified astigmatid mite, Sancassania sp. Sasagawa (Acari: Acaridae)
We identified two aliphatic formates, (Z,Z)-8,11-heptadecadienyl formate and (Z)-8-heptad ecenyl formate in the opisthonotal gland secretions of an unidentified acarid species, namely Sancassania sp. Sasagawa. Both compounds were isolated using silica gel column chromatography and the structures were elucidated by 1H-NMR and GC/FT-IR. Further information on the double bond positions was obtained by GC-MS analysis of the corresponding dimethyl disulfide derivatives. Based on the estimated structures of the two formates and using linoleic and oleic acids as the respective starting materials, a simple four-step synthesis was achieved via Barton decarboxylation as the key step. The aliphatic formates identified in acarids thus far are neryl formate ((Z)-3,7-dimethylocta-2,6-dienyl formate) and lardolure (1,3,5,7-tetramethyldecyl formate), and both have been reported to have pheromone functions. The biological function of the two formates isolated in this study is currently being investigated. Although we can speculate that the two compounds were biosynthesized from linoleic and oleic acid, there is a possibility that the synthetic processes featured a novel chain shortening and formic acid esterification mechanism.
Shimizu, Nobuhiro,Sakata, Daisuke,Miyazaki, Honami,Shimura, Yasuhiro,Kuwahara, Yasumasa
(2016)
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Synthesis of N-functionalized oleamide derivatives
Oleamide is an interesting compound, which shows various pharmacological activities including the inhibitory effect of gap junction formation. Recently, the studies of the gap junction have been some of the hot topics in biology and its inhibitors have become more useful tools [Cravatt, B. F.; Garcia, O. P.; Siuzdak, G.; Gilula, N. B.; Henriksen, S. J.; Boger, D. L.; Lerner, R. A. Science 1995, 268, 1506-1509; Cravatt, B. F.; Lerner, R. A.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 580-590; Guan, X; Cravatt, B. F.; Ehring, G. R.; Hall, J. E.; Boger, D. L.; Lerner, R. A.; Gilula, N. B. J. Cell Biol. 1997, 139, 1785-1792; Boger, D. L.; Patterson, J. E.; Guan, X.; Cravatt, B. F.; Lerner, R. A.; Gilula, N. B. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4810-4815; Ito, A.; Morita, N.; Miura, D.; Koma, Y.; Kataoka, T. R.; Yamasaki, H.; Kitamura, Y.; Kita, Y.; Nojima, H. Carcinogenesis 2004, 25, 2015-2022]. However, many reports suggest that the functionalizations of oleamide to retain its biological activity were difficult [Boger, D. L.; Patterson, J. E.; Guan, X.; Cravatt, B. F.; Lerner, R. A.; Gilula, N. B. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4810-4815; Ito, A.; Morita, N.; Miura, D.; Koma, Y.; Kataoka, T. R.; Yamasaki, H.; Kitamura, Y.; Kita, Y.; Nojima, H. Carcinogenesis 2004, 25, 2015-2022]. The synthesis of the functionalized oleamide derivatives, whose biological activity is not blocked, has become attractive in both the biological and chemical fields. Herein, by linking the fluorophore to the oleamide by alkyl chains, we synthesized the fluorescently tagged oleamide whose biological feature is similar to that of oleamide. Moreover, we also synthesized other bioactive derivatives tagged by other groups such as the sugars and biotin via alkyl chain linkers.
Ohba, Yusuke,Kanao, Yukiko,Takatsuji, Mayuko,Ito, Motoki,Yabuta, Norikazu,Nojima, Hiroshi,Kita, Yasuyuki
p. 3754 - 3761
(2007)
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Set-up and validation of a high throughput screening method for human monoacylglycerol lipase (MAGL) based on a new red fluorescent probe
Monoacylglycerol lipase (MAGL) is a serine hydrolase that has a key regulatory role in controlling the levels of 2-arachidonoylglycerol (2-AG), the main signaling molecule in the endocannabinoid system. Identification of selective modulators of MAGL enables both to provide new tools for investigating pathophysiological roles of 2-AG, and to discover new lead compounds for drug design. The development of sensitive and reliable methods is crucial to evaluate this modulatory activity. In the current study, we report readily synthesized long-wavelength putative fluorogenic substrates with different acylic side chains to find a new probe for MAGL activity. 7-Hydroxyresorufinyl octanoate proved to be the best substrate thanks to the highest rate of hydrolysis and the best Km and Vmax values. In addition, in silico evaluation of substrates interaction with the active site of MAGL confirms octanoate resorufine derivative as the molecule of choice. The well-known MAGL inhibitors URB602 and methyl arachidonylfluorophosphonate (MAFP) were used for the assay validation. The assay was highly reproducible with an overall average Z0 value of 0.86. The fast, sensitive and accurate method described in this study is suitable for low-cost high-throughput screening (HTS) of MAGL modulators and is a powerful new tool for studying MAGL activity.
Miceli, Matteo,Casati, Silvana,Ottria, Roberta,Di Leo, Simone,Eberini, Ivano,Palazzolo, Luca,Parravicini, Chiara,Ciuffreda, Pierangela
(2019)
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Amides of N-Deacetyllappaconitine and Unsaturated Fatty Acids
Amides were prepared from N-deacetyllappaconitine and unsaturated oleic, linoleic, α-linolenic, and γ-linolenic fatty acids.
Gabbasov,Tsyrlina,Yunusova
p. 947 - 950
(2018)
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Unsaturation and Polar Head Effect on Gelation, Bioactive Release, and Cr/Cu Removal Ability of Glycolipids
Designing of multifunctional soft and smart materials from natural sources is a useful strategy for producing safer chemicals having potential applications in biomedical research and pharmaceutical industries. Herein, eight glycolipids with variation in unsaturation of hydrophobic tail and polar headgroup size were designed. The effect of unsaturation in the tail group and headgroup size on gelation ability, and mechanical and thermal stability of glycolipid hydro/organogels was studied to understand structure and property relationship. Glycolipids are functional amphiphilic molecules having potential applications in the field of drug delivery and metal removal. The encapsulation capacity and kinetic release behavior of hydrophobic/hydrophilic bioactives like curcumin/riboflavin from the hydrophobic/hydrophilic pockets of glycolipids hydro/organogels was examined. A significant observation was that the glucamine moiety of the glycolipid headgroup plays a vital role in removal of Cr and Cu from oil/water biphasic systems. Typical functions of the glycolipid hydrogels are metal chelation and enzyme-triggered release behavior, enabled them as promising material for Cr, Cu removal from edible oils and controlled release of water soluble/insoluble bioactives.
Bojja, Sreedhar,Holey, Snehal Ashokrao,Nayak, Rati Ranjan,Sekhar, Kanaparedu P. C.,Swain, Deepak Kumar
p. 3080 - 3088
(2020)
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Oleoyl alanine (HU595): a stable monomethylated oleoyl glycine interferes with acute naloxone precipitated morphine withdrawal in male rats
Rationale: Oleoyl glycine, a little studied fatty acid amide similar in structure to anandamide, interferes with nicotine addiction in mice and acute naloxone-precipitated morphine withdrawal (MWD) in rats. Because endogenous oleoyl glycine is subject to rapid enzymatic deactivation, we evaluated the potential of more stable analogs to interfere with opiate withdrawal. Objectives: The potential of monomethylated oleoyl glycine (oleoyl alanine, HU595) to interfere with somatic and aversive effects of acute naloxone-precipitated MWD, its duration, and mechanism of action was assessed in male Sprague Dawley rats. The potential of dimethylated oleoyl glycine (HU596) to interfere with the aversive effects of naloxone-precipitated MWD was also investigated. Results: Oleoyl alanine (HU595) interfered with somatic and aversive effects produced by naloxone-precipitated MWD at equivalent doses (1 and 5?mg/kg, i.p.) as we have reported for oleoyl glycine; however, oleoyl alanine produced a longer lasting (60?min) interference, yet did not produce rewarding or aversive effects on its own and did not modify locomotor activity. HU596 was not effective. The interference with aversive effects of naloxone-precipitated MWD by oleoyl alanine was prevented by both a PPARα antagonist and a CB1 receptor antagonist. Accordingly, the compound was found to inhibit FAAH and activate PPARα in vitro. Finally, oleoyl alanine also reduced acute naloxone-precipitated MWD anhedonia, as measured by decreased saccharin preference. Conclusions: Oleoyl alanine (also an endogenous fatty acid) may be a more stable and effective treatment for opiate withdrawal than oleoyl glycine.
Ayoub, Samantha M.,Smoum, Reem,Farag, Mathew,Atwal, Harkirat,Collins, Stephen A.,Rock, Erin M.,Limebeer, Cheryl L.,Piscitelli, Fabiana,Iannotti, Fabio Arturo,Lichtman, Aron H.,Leri, Francesco,Di Marzo, Vincenzo,Mechoulam, Raphael,Parker, Linda A.
p. 2753 - 2765
(2020)
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Development of lipoprotein-drug conjugates for targeted drug delivery
Tumour targeting approaches used in cancer chemotherapy offers prolonged, localized, and protected drug interaction with the diseased tissue with minimal side effects and systemic toxicity, which are accountable for the failure of chemotherapy using conventional delivery systems. The purpose of the present study is to develop an anticancer targeted drug delivery system using synthesized lipoproteins with the integration of quality by design approach. Lipoprotein structures were designed, and quality by design approach was implemented to select variables for optimization. Further, the lipoproteins were synthesized and characterized by physicochemical properties. Physical composites of synthesized lipoproteins with the drug (tablets) were prepared and evaluated for post-compression parameters. Moreover, drug-lipoprotein chemical conjugates were synthesized and characterized for physicochemical properties, including cellular drug uptake and cytotoxicity study on HaCaT cancer cells. Synthesized lipoproteins showed good swelling capacity but poor flowability. Nuclear magnetic resonance and infrared spectroscopy of conjugates showed characteristic peaks. Tablets from all batches extended the drug release up to 12 h. All synthesized conjugates showed improved cellular drug uptake (up to 86.1%) and inhibition (87.39%) of HaCat cancer cells. These findings explored the possible use of synthesized lipoproteins in the development of anti-cancer drug formulation against HaCat cancer cells. Communicated by Ramaswamy H. Sarma.
Bhatia, Manish S.,Choudhari, Sujata P.,Dhavale, Rakesh P.,Gaikwad, Vinod L.
p. 6955 - 6973
(2021)
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Modulation of GABA(A) receptors and inhibitory synaptic currents by the endogenous CNS sleep regulator cis-9,10-octadecenoamide (cOA)
1. Cis-9,10-octadecenoamide (cOA) accumulates in the CSF of sleep-deprived cats and may represent a novel signalling molecule. Synthetic cOA has been shown to induce physiological sleep when injected into laboratory rats. Here we assess the cellular mode of action of cOA in vitro. 2. In all rat cultured cortical neurones (pyramidal cells) examined, the synthetic brain lipid (3.2-64 μM) enhanced the responses to subsaturating GABA concentrations (up to circa 2x) in a concentration-dependent manner (EC50, circa 15 μM). 3. (20 μM) cOA significantly enhanced the affinity of exogenous GABA for its receptor without changing the Hill slope or the maximal response. These effects were not voltage-dependent or secondary to shifts in E(Cl). 4. In the absence of GABA, cOA directly evoked small inhibitory currents in a subpopulation (2 subunit was co-expressed with α1β2: the cOA response was not sensitive to the specific benzodiazepine antagonist flumazenil (1 μM). 8. cOA may represent an endogenous ligand for allosteric modulatory sites on isoforms of GABA(A) receptors which are crucial for the regulation of arousal and have recently been implicated in the circadian control of physiological sleep.
Lees, George,Edwards, Michelle D.,Hassoni, Abdul A.,Ganellin, C. Robin,Galanakis, Dimitrious
p. 873 - 882
(1998)
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Nonionic diethanolamide amphiphiles with unsaturated C18 hydrocarbon chains: Thermotropic and lyotropic liquid crystalline phase behavior
The neat and lyotropic liquid crystalline phase behavior of three nonionic diethanolamide amphiphiles with C18 hydrocarbon chains containing one, two or three unsaturated bonds has been examined. This has allowed the effect of degree of unsaturation on the phase behavior of diethanolamide amphiphiles to be investigated. Neat linoleoyl and linolenoyl diethanolamide undergo a transition from a glassy liquid crystal to a liquid crystal at ～-85 °C, while neat oleoyl diethanolamide undergoes a transition at ～-60 °C to a liquid crystalline material before re-crystallizing at -34 °C. Oleoyl diethanolamide then undergoes a third transition from a crystalline phase to a smectic liquid crystalline phase at ～5 °C. In the absence of water, the transition temperature from a smectic liquid crystal to an isotropic liquid decreases with increasing unsaturation. The addition of water results in the formation of a lamellar phase (Lα) for all three amphiphiles. The lamellar phase is stable under excess water conditions up to temperatures of at least 70 °C. Approximate partial binary amphiphile-water phase diagrams generated for the three unsaturated C18 amphiphiles indicate that the excess water point for each amphiphile occurs at ～60% (w/w) amphiphile. the Owner Societies 2011.
Sagnella, Sharon M.,Conn, Charlotte E.,Krodkiewska, Irena,Drummond, Calum J.
p. 13370 - 13381
(2011)
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Jackson et al.
p. 290
(1944)
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Chemical synthesis of 9(Z)-octadecenamide and its hypolipidemic effect: A bioactive agent found in the essential oil of mountain celery seeds
The unusual hypolipidemic activity of the methanolic fractionate of the essential oil (EOM) obtained from the mountain celery seed was previously reported. The most enriched 9(Z)-octadecenamide (oleamide) was speculated to be responsible for the relevant bioactivity. Chemically syntheized oleamide (CSO) yielded 85.1% with a purity of 98.6% when identified by RP-HPLC, FTIR, HREIMS, 1H NMR, and 13C NMR. CSO was tested for its antioxidative and hypolipidemic bioactivities. Results indicated CSO was potently hypolipidemic with regard to serum TG, TC, LDL-C, LDL-C/HDL-C, and hepatic TG (p 0.05), but not for serum HDL-C and hepatic TC. In addition, CSO exhibited only poor antioxidative activity, implicating the possibility that the hypolipidemic and antioxidative bioactivity of original EOM was due to another coexisting constituent, probably y-selinene. Conclusively, oleamide is a potent hypolipidemic agent as regarding its effects on decreasing serum TG, TC, LDL-C and hepatic TG.
Cheng, Ming-Ching,Ker, Yaw-Bee,Yu, Tung-Hsi,Lin, L.I.-Yun,Peng, Robert Y.,Peng, Chiung-Huei
p. 1502 - 1508
(2010)
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Original polyols based on organosolv lignin and fatty acids: New bio-based building blocks for segmented polyurethane synthesis
A macropolyol was successfully prepared by combining two different biomolecules from biomass, i.e. lignin and oleic acid, using a solvent-free and catalyst-free method. The chemical structures of this original lignin-fatty acid based polyol and its intermediates were determined by 1H NMR and FT-IR analyses. A series of polyurethanes (PUs) were then prepared by a two-step procedure. Three linear isocyanate prepolymers were first synthesized from 4,4′-methylenebis(phenyl isocyanate) and poly(propylene)glycol of different molecular weights (PPG-425, 1000 and 2000 g mol-1). These intermediates were used to obtain different PU macromolecular architectures by varying reaction parameters in the presence of the lignin-fatty acid based macropolyol. The final lignin-based polyurethanes were thoroughly chemically characterized by FT-IR studies, whereas the properties of these polymers were assessed by DSC, TGA, DMTA, and tensile test experiments. All these were performed in order to evaluate the influence of the NCO : OH molar ratio (from 0.2 to 1.0) as well as the influence of the PPG chain length. These new polymers with controlled architectures presented advanced properties. Their high biobased content (until 89%) depicts an important output for the valorisation of lignin and they may be an optimal alternative to conventional PUs. This journal is the Partner Organisations 2014.
Laurichesse, Stephanie,Huillet, Cedric,Averous, Luc
p. 3958 - 3970
(2014)
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Fabrication of microspheres via solvent volatization induced aggregation of self-assembled nanomicellar structures and their use as a pH-dependent drug release system
A series of oleamide derivatives, (C18H34NO) 2(CH2)n [n = 2 (1a), 3 (1b), 4 (1c), or 6 (1d); C18H34NO = oleic amide fragment] and (C 18H34NO)(CH2)6NH2 (2), have been synthesized and their self-assembly is investigated in ethanol/water media. Self-assembly of 1a and 1b in ethanol/water (1/0.1 v/v) solution (5 mg mL-1) yields microspheres (MSs) with the average diameter ～10 μm via a gradual temperature reduction and solvent volatilization process. Under the same self-assembly conditions, microrods (average diameter ～6 μm and several tens of micrometers in length), micronecklace-like, and shape-irregular microparticles are formed from the self-assembly of 1c, 1d, and 2, respectively. The kinetics of evolution for their self-assemblies by dynamic light scattering technique and in situ observation by optical microscopy reveals that the microstructures formation is from a well-behaved aggregation of nanoscale micelles induced by solvent volatilization. The FT-IR and temperature-dependent 1H-NMR spectra demonstrate the hydrogen bonding force and π-π stacking, which drove the self-assembly of all oleamide derivatives in ethanol/water. Among the fabricated microstructures, the MSs from 1a exhibit the best dispersity, which thus have been used as a scaffold for the in vitro release of doxorubicin. The results demonstrate a pH-sensitive release process, enhanced release specifically at low pH 5.2.
Zhang, Lidong,Jeong, Young-Il,Zheng, Sudan,Suh, Hongsuk,Kang, Dae Hwan,Kim, Il
p. 65 - 74
(2013)
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Main-chain functionalization of poly(L -lactide) with pendant unsaturations
Main-chain-functionalized poly(L-lactide) (PLLA) with pendant unsaturations was synthesized through a one-pot postpolymerization procedure with the PLLA homopolymer as the starting material. The material was functionalized through α-hydrogen abstraction by a sterically hindered strong base, lithium diisopropylamide, followed by the addition of an acid chloride. Two different acid chlorides were examined, lauroyl chloride as a concept electrophile and oleoyl chloride to provide the pendant unsaturations. The semisolvated system, together with branching reactions from the alpha position of the acid chloride, yielded a high molar amount of the incorporated reactant in the material. The unsaturations were preserved under the chosen conditions and the material exhibited surfactant-like properties in blends with oleic acid and PLLA.
Olsen, Peter,Odelius, Karin,Albertsson, Ann-Christine
p. 3039 - 3045
(2012)
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Selective Modulation of Protein Kinase C α over Protein Kinase C by Curcumin and Its Derivatives in CHO-K1 Cells
Members of the protein kinase C (PKC) family of serine/threonine kinases regulate various cellular functions, including cell growth, differentiation, metabolism, and apoptosis. Modulation of isoform-selective activity of PKC by curcumin (1), the active constituent of Curcuma L., is poorly understood, and the literature data are inconsistent and obscure. The effect of curcumin (1) and its analogues, 4-[(2Z,6E)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-5-oxohepta-2,6-dien-1-yl]-2-methoxyphenyl oleate (2), (9Z,12Z)-4-[(2Z,6E)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-5-oxohepta-2,6-dien-1-yl]-2-methoxyphenyl octadeca-9,12-dienoate (3), (9Z,12Z,15Z)-4-[(2Z,6E)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-5-oxohepta-2,6-dien-1-yl]-2-methoxyphenyl octadeca-9,12,15-trienoate (4), and (1E,6E)-1-[4-(hexadecyloxy)-3-methoxyphenyl]-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (5), and didemethylcurcumin (6) on the membrane translocation of PKCα, a conventional PKC, and PKC, a novel PKC, has been studied in CHO-K1 cells, in which these PKC isoforms are endogenously expressed. Translocation of PKC from the cytosol to the membrane was measured using immunoblotting and confocal microscopy. 1 and 6 inhibited the TPA-induced membrane translocation of PKCα but not of PKC. Modification of the hydroxyl group of curcumin with a long aliphatic chain containing unsaturated double bonds in 2-4 completely abolished this inhibition property. Instead, 2-4 showed significant translocation of PKCα but not of PKC to the membrane. No membrane translocation was observed with 1, 6, or the analogue 5 having a saturated long chain for either PKCα or PKC. 1 and 6 inhibited TPA-induced activation of ERK1/2, and 2-4 activated it. ERK1/2 is the downstream readout of PKC. These results show that the hydroxyl group of curcumin is important for PKC activity and the curcumin template can be useful in developing isoform specific PKC modulators for regulating a particular disease state.
Pany, Satyabrata,Majhi, Anjoy,Das, Joydip
p. 2135 - 2143
(2016)
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A spectrophotometric assay for fatty acid amide hydrolase suitable for high-throughput screening
Signalling via the endocannabinoids anandamide and 2-arachidonylglycerol appears to be terminated largely through the action of the enzyme fatty acid amide hydrolase (FAAH). In this report, we describe a simple spectrophotometric assay to detect FAAH activity in vitro using the ability of the enzyme to hydrolyze oleamide and measuring the resultant production of ammonia with a NADH/NAD+-coupled enzyme reaction. This dual-enzyme assay was used to determine Km and Vmax values of 104 μM and 5.7 nmol/min/mg protein, respectively, for rat liver FAAH-catalyzed oleamide hydrolysis. Inhibitor potency was determined with the resultant rank order of methyl arachidonyl fluorophosphonate > phenylmethylsulphonyl fluoride > anandamide. This assay system was also adapted for use in microtiter plates and its ability to detect a known inhibitor of FAAH demonstrated, highlighting its potential for use in high-throughput screening.
De Bank, Paul A.,Kendall, David A.,Alexander, Stephen P.H.
p. 1187 - 1193
(2005)
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Preparation of Musk-Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination
Macrocyclic musk belongs to a well-known and valued class of the fragrance family. Originally, natural musks were obtained from rectal musk glands which often led to the death of the animals. Recently, a lot of effort was invested to obtain such macrocycles in a synthetic way. This research presents a study on the preparation of macrocyclic lactones with the musk scent by ring-closing metathesis (RCM) using biomass-derived starting materials: oleic and 9-decenoic acid. An experimental rule correlating the C–C double bond substitution pattern in the starting diene and the yield for the RCM macrocyclization was proposed.
Sytniczuk, Adrian,Leszczyńska, Agnieszka,Kajetanowicz, Anna,Grela, Karol
p. 3157 - 3166
(2018)
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Acyl-CoA: Cholesterol acyltransferase inhibitory activities of fatty acid amides isolated from Mylabris phalerate Pallas
Unsaturated fatty acid amides, 9(Z)-octadecenamide (2) and 9(Z),12(Z)-octadecadienamide (4) as inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT) were isolated from the ethyl acetate extracts of the insect, Mylabris phalerate Pallas, and elucidated by their spectroscopic data analysis. Compounds 2 and 4 inhibited rat liver microsomal ACAT, hACAT-1, and hACAT-2 with IC50 values of 170, 85, and 63μM for 2 and of 151, 53, and 45μM for 4, respectively.
Xu, Ming-Zhe,Lee, Woo Song,Kim, Mi Jeong,Park, Doo-Sang,Yu, Hana,Tian, Guan-Rong,Jeong, Tae-Sook,Park, Ho-Yong
p. 4277 - 4280
(2004)
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Synthesis and antibacterial activity of silver nanoparticles capped with a carboxylic acid-terminated generation 1 oleodendrimer
This study investigated the potential of a novel carboxylic acid-terminated generation 1 oleodendrimer (E1A) as a novel biocompatible capping agent for the synthesis of silver nanoparticles (E1A@Ag). Synthesized E1A@Ag particles were spherical with an average size of 9 ± 3 nm and displayed antimicrobial activity against Staphylococcus aureus, methicillin- resistant Staphylococcus aureus, and Escherichia coli. The current study, therefore, establishes E1A as an effective biocompatible material for the synthesis of silver nanoparticles.
Kalhapure, Rahul S.,Akamanchi, Krishnacharya G.,Mocktar, Chunderika,Govender, Thirumala
p. 1110 - 1112
(2014)
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Wood et al.
p. 289
(1944)
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Decarboxylative Borylation of mCPBA-Activated Aliphatic Acids
A decarboxylative borylation of aliphatic acids for the synthesis of a variety of alkylboronates has been developed by mixing m-chloroperoxybenzoic acid (mCPBA)-activated fatty acids with bis(catecholato)diboron in N,N-dimethylformamide (DMF) at room temperature. A radical chain process is involved in the reaction which initiates from the B-B bond homolysis followed by the radical transfer from the boron atom to the carbon atom with subsequent decarboxylation and borylation.
Wei, Dian,Liu, Tu-Ming,Zhou, Bo,Han, Bing
supporting information
p. 234 - 238
(2020/01/02)

Catalyst for synthesizing acyl chloride compounds and application thereof
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 0068-0072

(2020/10/20)

OLEIC ACID DERIVATIVES, PHARMACEUTICAL COMPOSITION OR FOOD COMPOSITION COMPRISING SAID OLEIC ACID DERIVATIVES, AND THEIR USES
This invention relates to oleic acid derivative comprising a hydrophobic part C17H33 linked to a particular polar head part "A", especially for use as a medicament, for instance, for the treatment of a disorder caused by the GPR120 receptor and/or the CD36 receptor, comprising administering to a subject in need thereof a therapeutically effective amount of said oleic acid derivative or of said pharmaceutical composition. The invention also relates to the use of said oleic acid derivative as a food composition.
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(2019/12/25)

Antiproliferative 3-deoxysphingomyelin analogs: Design, synthesis, biological evaluation and molecular docking of pyrrolidine-based 3-deoxysphingomyelin analogs as anticancer agents
Sphingomyelins and glycerophospholipids are structurally related phospholipids. Nevertheless, glycerophospholipids analogs are known as antitumor agents while sphingomyelin analogs were reported as cytoprotective agents. Herein, we have addressed the development of 3-deoxysphingomyelin analogs as cytotoxic agents possessing modified sphingobases. Thus, pyrrolidine-based 3-deoxysphingomyelin analogs were synthesized and evaluated against a panel of cell lines representing four major types of cancers. Compounds 3d, 4d and 6d elicited better GI50 values than the FDA approved drug miltefosine. Investigation of their impact on Akt phosphorylation as a possible mechanism for the antiproliferative activity of this class of compounds revealed that these compounds might elicit a concentration-dependent mechanism via inhibition of Akt phosphorylation at the lower concentration. Molecular docking predicted their binding modes to Akt to involve polar head binding to the Pleckstrin homology domain and hydrophobic tail extension into a hydrophobic pocket connecting the Pleckstrin homology domain and the kinase domain. As a whole, the described work suggests compounds 3d, 4d and 6d as promising pyrrolidine-based 3-deoxysphingomyelin analogs for development of novel cancer therapies.
Hassan, Ahmed H.E.,Park, Hye Rim,Yoon, Yoon Mi,Kim, Hye In,Yoo, Sung Yeun,Lee, Kun Won,Lee, Yong Sup
p. 444 - 455
(2019/01/03)

Cinnamyl alcohol fatty acid ester derivative and application and preparation method thereof
The invention relates to a derivative and an application and a preparation method thereof, in particular to a cinnamyl alcohol fatty acid ester derivative and an application and a preparation method thereof. As application of a percutaneous absorption penetration enhancer, a percutaneous administration preparation is prepared, so that the percutaneous absorption of a drug is improved, and the cumulative penetration amount of the drug is increased. The cinnamyl alcohol fatty acid ester derivative is prepared into fatty acyl chloride, and the fatty acyl chloride reacts with cinnamyl alcohol to obtain the cinnamyl alcohol fatty acid ester derivative. The compound can be applied to the percutaneous administration preparation to enhance the drug permeability, can further be used as perfume to cover up the bad smell of the preparation, and has wide potential application prospects.
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Paragraph 0060; 0061

(2019/05/08)

Magnetic nano recombinant and preparation method and applications thereof
The invention discloses a magnetic nano recombinant and a preparation method and applications thereof. Specifically, monodisperse superparamagnetic Fe3O4 nanoparticles are used as a magnetic core, anda dioleic acid-lysine-polyethylene glycol polymer is used as a shell drug carrier, so that a novel multifunctional magnetic nano recombinant is obtained by the assembly of core-shell components. Thecarrier realizes multi-targeting effects such as long circulation (anti-passive targeting) and magnetic targeting (physical targeting) while achieving controllable drug loading, provides breakthroughfor efficient targeted therapy of tumors, and reduces the toxicity of anti-tumor drugs.
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Paragraph 0023; 0027; 0028; 0029

(2019/04/26)

Synthesis of 1-methoxyindoles and related analogs of pimprinine, (±)-chelonin A and B, based on 1-hydroxy-indole chemistry
The total synthesis of pimprinine, (±)-chelonin A and B, and their analogs are achieved based on 1-hydroxyindole chemistry.
Aoki, Kazuko,Nagahama, Yoshiyuki,Sugaya, Katsuko,Maeda, Yuki,Sato, Haruhiko,Nakagawa, Kyoko,Somei, Masanori
p. 236 - 270
(2019/08/01)

GEMCITABINE AMPHIPHILE PRODRUGS
The present invention relates to improved prodrugs, and compositions thereof. In particular, it relates to amphiphilic gemcitabine prodrugs or amphiphilic prodrugs of other biologically active molecules with the capacity to make liquid crystalline nanostructured nanoparticles, and uses thereof to treat animals, including humans.
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(2019/11/12)

Cationic lipid molecule, and application thereof in nucleic acid delivery
The present invention discloses a cationic lipid molecule, and an application thereof in nucleic acid delivery. The structural formula of the cationic lipid molecule is represented by formula i. The invention further provides a cationic liposome, a lipid compound, a reagent, a kit, a preparation and a medicinal composition based on the cationic lipid molecule. The cationic lipid molecule has the advantages of simple synthesis process and good stability, and the cationic liposome has a high efficiency (characterized by high transfection efficiency) and a low toxicity, is stable and uniform, is easy to prepare, and can be used for transferring various cell lines. The cationic lipid molecule has excellent transitivity, and can efficiently deliver active substances (such as exemplary siRNA) omto cells (such as exemplary lung cancer cells), tissues and organs to achieve efficient regulation of the active substances. The problem that the toxicity and the transfer efficiency of cationic liposome existing in the prior art are low is solved.
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Page/Page column 18-20; 22-24

(2019/10/08)

Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration
N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.
Lin, Hua,Long, Jonathan Z.,Roche, Alexander M.,Svensson, Katrin J.,Dou, Florence Y.,Chang, Mi Ra,Strutzenberg, Timothy,Ruiz, Claudia,Cameron, Michael D.,Novick, Scott J.,Berdan, Charles A.,Louie, Sharon M.,Nomura, Daniel K.,Spiegelman, Bruce M.,Griffin, Patrick R.,Kamenecka, Theodore M.
supporting information
p. 3224 - 3230
(2018/04/23)

A new class of pure estrogen alpha receptor antagonists; design, synthesis and in-vitro screening
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
p. 66 - 81
(2019/01/04)

Chemical synthesizing method of N-oleoyl ethanolamine
The invention belongs to the technical field of N-oleoyl ethanolamine synthesizing and discloses a chemical synthesizing method of N-oleoyl ethanolamine. The chemical synthesizing method includes thesteps of S1, performing low-temperature stirring; S2, adding a mixed solution and N, N-dimethyl formamide; S3, adding triethylamine; S4, adding into amine mixed liquid, and stirring; S5, washing, extracting and performing vacuum concentration; S6, distilling to remove impurities; S7, silica gel column chromatography purification. The chemical synthesizing method has the advantages that the methodis simple, high in purification rate and applicable to large-batch factory production, and the synthesized pure N-oleoyl ethanolamine is free of impurities.
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Paragraph 0020; 0021; 0029; 0030; 0038; 0039

(2018/05/01)

Preparation method of positive liposome DOTAP (2,3-dioil oxypropyl trimethylammonium chloride)
The invention discloses a preparation method of positive liposome DOTAP (2,3-dioil oxypropyl trimethylammonium chloride). The preparation method of the positive liposome DOTAP comprises preparation methods of (+/-)-DOTAP, (S)-DOTAP and (R)-DOTAP. The DOTAP product is synthesized by taking cheap 3,-chlorine-1,2-propylene glycol a starting material and by a two-step method, and high-purity positiveliposome DOTAP can be obtained through silica gel column purification. The invention provides a preparation method of the DOTAP, which is low in cost and simple in process. The method is low in raw material cost, mild in reaction condition and simple in aftertreatment, does not need an ion exchange process and has economic property, environmental friendliness and high efficiency.
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Paragraph 0027; 0028; 0033; 0034

(2018/07/06)

At Long Last: Olefin Metathesis Macrocyclization at High Concentration
Macrocyclic lactones, ketones, and ethers can be obtained in the High-Concentration Ring-Closing Metathesis (HC-RCM) reaction in high yield and selectivity at concentrations 40 to 380 times higher than those typically used by organic chemists for similar macrocyclizations. The new method consists of using tailored ruthenium catalysts together with applying vacuum to distill off the macrocyclic product as it is formed by the metathetical backbiting of oligomers. Unlike classical RCM, no large quantities of organic solvents are used, but rather inexpensive nonvolatile diluents, such as natural or synthetic paraffin oils. Moreover, use of a protecting atmosphere or a glovebox is not needed, as the new catalysts are perfectly moisture and air stable. In addition, some other cyclic compounds previously reported as unobtainable by RCM in neat conditions, or in high dilutions even, can be formed with the help of the HC-RCM method.
Sytniczuk, Adrian,Dabrowski, Micha?,Banach, ?ukasz,Urban, Mateusz,Czarnocka-?niada?a, Sylwia,Milewski, Mariusz,Kajetanowicz, Anna,Grela, Karol
supporting information
p. 8895 - 8901
(2018/07/05)

Lubricating compositions containing isoprene based components
A lubricating composition comprising a base oil of lubricating viscosity and one or more lubricant additives, wherein the base oil comprises or consists of a base stock which comprises or consists of at least one isoprenoid compound comprising: (i) one or
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Page/Page column 29

(2018/11/30)

FATTY ACID AMIDES AND USES THEREOF IN THE TREATMENT OF ADDICTION DISORDER AND ADDICTION RELATED CONDITIONS
The present invention is directed to a fatty acid amide of an amino acid, including a stereoisomer and a salt thereof for use in the treatment of a patient suffering from any type of addiction disorder, substance abuse disorder, including any condition and symptom associated therewith and including withdrawal syndrome and relapse addiction during and after a rehabilitation treatment of said patient.
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Paragraph 00116-00117

(2018/12/13)

COMPOUNDS, COMPOSITONS AND METHODS RELATED TO ANTIMICROBIAL APPLICATIONS
The present disclosure is in the field of polymers and pharmaceuticals/antimicrobials. The disclosure provides compounds based on SNAP (synthetic novel antimicrobial polymer) technology, compositions and methods of managing microbial infections including surgical site infections (SSIs). The present compounds are used as a management/therapeutic strategy to target microbial infections and have advantages including excellent antimicrobial potency, biofilm disruption ability, broad spectrum activity against various organisms covering both gram negative and gram positive bacteria as well as fungal pathogens, and low toxicity profile to ensure a healthy therapeutic window for use in humans.
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Page/Page column 82-83

(2018/03/25)

COMPOSITIONS AND METHODS FOR DELIVERY OF THERAPEUTIC AGENTS
This disclosure provides improved lipid-based compositions, including lipid nanoparticle compositions, and methods of use thereof for delivering agents in vivo including nucleic acids and proteins. These compositions are not subject to accelerated blood clearance and they have an improved toxicity profile in vivo.
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Page/Page column 331

(2017/07/18)

Synthesis and biological evaluation of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thioglycosides
In the present study, the synthesis of 1, 3, 4-thiadiazole-based thioglycosides were accomplished in good yields with employing a convergent synthetic route. The starting material 5-amino-1, 3, 4-thiadiazole-2-thiol and followed by a series of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thiols (4a–4j) were synthesized with different fatty acid chlorides. The glycosylation of compounds 4a–4j were achieved with trichloroacetimidate methodology. Antimicrobial and cytotoxicity activities of title compounds were evaluated. Among the entire compounds lauric acid and myristic acid derivatives showed good and moderate antimicrobial activity. In case of cytotoxicity results of compounds 8a–8j and 9a–9j, the acetate protected short chain (C6:0, C8:0, C10:0) compounds and the free hydroxyl long chain saturated (C16:0, C18:0) and unsaturated (C18:1, C22:1) compounds exhibited good activity against different cancer cell lines. Further, the free hydroxyl compounds 9a, 9c–9j did not show any toxicity towards normal CHO-K1 cell line whereas acylated compounds 8a–8j exhibited toxicity.
Vudhgiri, Srikanth,Koude, Dhevendar,Veeragoni, Dileep Kumar,Misra, Sunil,Prasad,Jala, Ram Chandra Reddy
supporting information
p. 3370 - 3373
(2017/07/07)

d-menthol fatty acid ester derivative, application thereof and preparation method for d-menthol fatty acid ester derivative
The invention belongs to the technical field of medicines and relates to a d-menthol fatty acid ester derivative, an application thereof and a preparation method for the d-menthol fatty acid ester derivative. The d-terpineol fatty acid ester is prepared through carrying out an esterification reaction on d-menthol and straight-chain fatty acid. The method comprises the steps of firstly, carrying out a reaction on fatty acid and thionyl chloride so as to prepare acyl chloride, and then, subjecting acyl chloride to a reaction with d-menthol, there by preparing the ester. The d-menthol ester is applied to external preparations such as plasters, cataplasm, ointment, gels, sprays and liniment as a penetration enhancer, so that the percutaneous absorption capacity of drugs, particularly, chiral drug enantiomers is increased; and the d-menthol ester is a very good percutaneous absorption penetration enhancer and has a broad application prospect.
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Paragraph 0032

(2017/08/29)

Ceramide compound, a process of preparing the ceramide compound, an intermediate compound and a process of preparing the intermediate compound
The structural properties of naturally occurring ceramide specification disclosure ceramide like compounds are disclosed. Hydroxy fatty acids (ω - hydroxy fatty acid) is provided end (to alcohol) i.e., ω - alkyl group such as hydroxy group is the group which will know various partially defect number [...] disclosure method is the natural ceramide like structure compounds are disclosed. Using the same, and the shortcomings of natural ceramide list price is expensive, and maintains the also obtain, number and sanitary door number can be overcome and purity of product, lactic effective natural ceramide constrictive forces over properties. (by machine translation)
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Paragraph 0196

(2017/10/31)

Design, synthesis and CoMFA studies of OEA derivatives as FAAH inhibitors
A total of 26 novel oleoylethanolamide derivatives were designed, synthesized, and characterized. All synthesized targets compounds were screened for their inhibitory activities against fatty acid amide hydrolase. Among of them, 13 compounds inhibit fatty acid amide hydrolase by 50% at the concentration of 100 μM. Of these compounds, the most active one is compound 9, which inhibit fatty acid amide hydrolase activity 98.35% at the concentration of 100 μM. Comparative molecular field analysis analyzes were performed based on obtained biological activities data and resulted in a statistically reliable comparative molecular field analysis model with high predictive abilities (r2 = 0.978, q2 = 0.613).
Han, Daxiong,Wang, Biyan,Jin, Hui,Wang, Haiyan,Chen, Meimei
p. 2951 - 2966
(2017/10/06)

Nerol aliphatic ester derivative as well as application and preparation method thereof
The invention belongs to the technical field of medicine, and relates to a nerol aliphatic ester derivative as well as application and a preparation method thereof. The nerol aliphatic ester is obtained by a esterification reaction between nerol and straight-chain fatty acid and is prepared from the following steps: preparing acyl chloride by reaction between fatty acid and sulfoxide chloride; preparing nerol aliphatic ester. by reaction between acyl chloride and nerol. The nerol aliphatic ester can be used as a penetration enhancer to be applied to external preparation, such as a patch, a cataplasm, an ointment, a gelling agent and a spraying agent, so that the percutaneous absorption of medicine is improved. The nerol aliphatic ester is a good percutaneous absorption enhancer and has a wide application prospect.
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Paragraph 0059; 0060

(2017/11/04)

Lavandulol fatty acid ester derivative, application and preparation method thereof
The invention relates to a derivative, application and a preparation method of the derivative, in particular to a lavandulol fatty acid ester derivative, application and a preparation method thereof. The lavandulol fatty acid ester derivative is prepared by preparing fatty acyl chloride and then carrying out reaction with lavandulol. The lavandulol fatty acid ester derivative can be applied as a transdermal absorption penetration enhancer to prepare transdermal drug delivery preparations, and can improve transdermal absorption of drugs and increase the cumulative penetration amount of drugs. The compound provided by the invention can be applied to transdermal drug delivery preparations to strengthen the penetration performance of drugs, and also can be used as lavender alcohol fatty acid ester derivative, and its application and preparation method. Lavender fatty acid ester derivatives are prepared by preparing fatty acyl chloride and then reacting with lavender. As a percutaneous absorption and penetration enhancer, the transdermal drug preparation is prepared to improve the absorption of the drug and increase the cumulative permeation of the drug. The compounds described in the present invention can be used in the percutaneous drug delivery, enhance the permeation ability of the drug, and can also be used as a spice to cover up the objectionable odor of preparations.
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Paragraph 0006; 0007; 0060; 0061

(2017/12/27)

Eugenol fatty acid ester derivative as well as application and preparation method thereof
The invention discloses a eugenol fatty acid ester derivative as well as application and a preparation method thereof. Eugenol fatty acid ester is obtained by an esterification reaction of eugenol and straight-chain fatty acid. The method comprises the following steps: firstly, preparing acyl chlorine by reacting fatty acid with thionyl chloride; mixing eugenol with an equal mole amount of pyridine or triethylamine; then, dropwise adding the prepared acyl chloride under the cooling action of an ice bath to generate the eugenol fatty acid ester. Eugenol ester can be applied to external preparations such as patches, cataplasm, ointments, gels and spray agents as a penetration enhancer in order to increase the transdermal absorption amount of medicaments, is a very good percutaneous absorption penetration enhancer, and has a wide application prospect.
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Paragraph 0062-0063

(2017/11/18)

Linalool fatty acid ester type derivative as well as application and preparation method thereof
The invention belongs to the technical field of medicines and relates to a linalool fatty acid ester type derivative as well as application and a preparation method thereof. A fatty acid ester is obtained by carrying out esterification reaction on linalool and straight-chain fatty acid; the method comprises the following steps: firstly, taking fatty acid and sulfoxide chloride to react to prepare acyl chloride; taking the acyl chloride and the linalool to react to prepare ester. The linalool is used as a penetration enhancer and is applied to external preparations including patches, cataplasm, ointment, gel, spray, liniments and the like, so that the transdermal absorption amount of drugs, especially chiral drug enantiomers, is improved; the linalool fatty acid ester type derivative is a very good transdermal absorption penetration enhancer and has a wide application prospect.
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Paragraph 0055; 0056

(2018/01/03)

A oleoyl ethanolamine derivatives, preparation method and application thereof
The invention discloses oleoylethanolamide derivatives, a preparation method and application thereof. The oleoylethanolamide derivatives have a structure as shown in a formula in the specification; meanwhile, the invention also discloses potential effects of the oleoylethanolamide derivatives in the aspects of reducing serum total cholesterol and triglyceride content, inhibiting activities of fatty acid amide hydrolase (FAAH) and N-acylethanolamine acid amidase (NAAA), etc.
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Paragraph 0051-0053; 0056-0058; 0062; 0063

(2018/11/04)

Synthesis of novel ethyl 1-ethyl-6-fluoro-7-(fatty amido)-1,4-dihydro-4-oxoquinoline-3-carboxylate derivatives and their biological evaluation
A series of novel ethyl 1-ethyl-6-fluoro-7-(fatty amido)-1,4-dihydro-4-oxoquinoline-3-carboxylate derivatives were prepared through multistep synthesis. The key step in the synthesis was to obtain the C-7 fatty amide derivative. The azide was selectively formed at C-7 position using sodium azide at 60 °C. Subsequently, the azide was reduced under mild conditions using zinc and ammonium chloride to form the corresponding amine. The synthesized derivatives were further subjected to biological evaluation studies like cytotoxicity against a panel of cancer cell lines such as DU145, A549, SKOV3, MCF7 and normal lung cells, IMR-90 as well as with antimicrobial and antioxidant activities. It was observed that the carboxylated quinolone derivatives with hexanoic (8a), octanoic (8b), lauric (8d) and myristic (8e) moieties exhibited promising cytotoxicity against all the tested cancer cell lines. The results also suggested that hexanoic acid-based fatty amide carboxylated quinolone derivative (8a) exhibited promising activity against both bacterial and fungal strains and significant antibacterial activity was observed against Staphylococcus aureus MTCC 96 (MIC value of 3.9 μg/mL). The compound 8a also showed excellent anti-biofilm activity against Staphylococcus aureus MTCC 96 and Bacillus subtilis MTCC 121 with MIC values of 2.1 and 4.6 μg/mL, respectively.
Venepally, Vijayendar,Prasad,Poornachandra,Kumar, C. Ganesh,Jala, Ram Chandra Reddy
supporting information
p. 613 - 617
(2016/01/09)

RING CLOSING METATHESIS APPROACH TO PRODUCE PRECURSORS OF NYLON 11, 12, AND 13 FROM OLEIC ACID
Provided herein is a method of producing C11, C12, and C13 nylon precursors from oleic acid or esters of oleic acid, the method involving amide formation, ring-closing metathesis, and hydrogenation. Further provided are the products of the method described. Provided herein is a method for producing a lactam, the method comprising the steps of converting oleic acid or an ester of oleic acid into an amide having a general formula of H3C-(CH2)rCH=CH-(CH2)rCONR-(CH2)n-CH=CH2, wherein n is 1, 2, or 3, and R is either hydrogen or benzyl; subjecting the amide to a ring-closing metathesis reaction to produce an intermediate having a general formula of -(CH2)rCONR-(CH2) n-CH=CH2-, wherein n is 1, 2, or 3, R is either hydrogen or benzyl, and both ends are connected to each other; and hydrogenating the intermediate to produce a saturated lactam. In certain embodiments, the saturated lactam has a formula of -NH-(CH2) 10-CO-.
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Paragraph 0072-0077

(2016/01/25)

Synthesis and biological evaluation of macamides derivatives as potent inhibitors of breast cancer cell MCF-7
A series of macamides (1-4) and their synthetic analogs (5-14) were synthesized and evaluated for in vitro inhibitory activities against breast cancer cell MCF-7. The results of bioactive assay showed that two of the macamides (compound 1 and 4) and one synthetic analog (compound 5) displayed comparable inhibitory activities against MCF-7 cell line, with IC50 values of 29.6, 36.2 and 27.2 μM, respectively.
Liang, Xiao Xia,Xiong, Cheng,He, Min,He, Changliang,Yin, Zhongqiong
p. 489 - 494
(2016/07/19)

Α-terpineol fatty acid ester derivatives and use
The invention belongs to the technical field of medicine and discloses alpha-terpineol aliphatic ester and a preparation with the compound. The alpha-terpineol aliphatic ester is formed by alpha-terpineol and fatty acid after esterification reaction. According to a method, first, fatty acid and thionyl chloride react to prepare acyl chloride, and then acyl chloride and alpha-terpineol react to prepare the alpha-terpineol aliphatic ester. The alpha-terpineol ester can be used as penetration enhancers to be used for external preparations of patching agents, Cataplasm, ointment agents, gel agents and the like, accordingly, the percutaneous absorptive amount of medicine is improved, and the alpha-terpineol aliphatic ester is good percutaneous absorptive penetration enhancers and has wide application prospect.
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Paragraph 0061; 0062

(2017/03/18)

Transdermal Penetration Enhancer and Their Uses
The present invention relates to a transdermal penetrating enhancer comprising an amino sugar-fatty acid conjugate. The conjugate included in the transdermal penetrating enhancer of the present invention can be industrially used in a cosmetic industry pursuing skin health and aesthetic enhancement of skin, and as well as used as a key material for a formulation of a transdermal drug delivery system. The transdermal penetrating enhancer of the present invention has effect of increasing permeability of a bioactive material or a drug into skin. Also, in some cases, the transdermal penetrating enhancer of the present invention can be applied as a single preparation for the therapeutic purpose by preparing a conjugate including a certain drug. Moreover, since the transdermal penetrating enhancer of the present invention uses a conjugate including a material in which skin safety is ensured, the transdermal penetrating enhancer can be applied to various fields besides a cosmetic or medicinal field.
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Paragraph 0091; 0092

(2019/08/07)

Synthesis and evaluation of fatty acid amides on the N-oleoylethanolamide-like activation of peroxisome proliferator activated receptor α
A series of fatty acid amides were synthesized and their peroxisome proliferator-activated receptor α (PPAR-α) agonistic activities were evaluated in a normal rat liver cell line, clone 9. The mRNAs of the PPAR-α downstream genes, carnitine-palmitoyltransferase-1 and mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase, were determined by real-time reverse transcription-polymerase chain reaction (RT-PCR) as PPAR-α agonistic activities. We prepared nine oleic acid amides. Their PPAR-α agonistic activities were, in decreasing order, N-oleoylhistamine (OLHA), N-oleoylglycine, Oleamide, N-oleoyltyramine, N-oleoylsertonin, and Olvanil. The highest activity was found with OLHA. We prepared and evaluated nine N-acylhistamines (N-acyl-HAs). Of these, OLHA, C16:0-HA, and C18:1Δ9-trans-HA showed similar activity. Activity due to the different chain length of the saturated fatty acid peaked at C16:0-HA. The PPAR-α antagonist, GW6471, inhibited the induction of the PPAR-α downstream genes by OLHA and N-oleoylethanolamide (OEA). These data suggest that N-acyl-HAs could be considered new PPAR-α agonists.
Takao, Koichi,Noguchi, Kaori,Hashimoto, Yosuke,Shirahata, Akira,Sugita, Yoshiaki
p. 278 - 285
(2015/04/22)

Investigation of fatty acid conjugates of 3,5-bisarylmethylene-4-piperidone derivatives as antitumor agents and human topoisomerase-IIα inhibitors
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
p. 411 - 421
(2015/01/30)

Analysis of Intact Cholesteryl Esters of Furan Fatty Acids in Cod Liver
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
p. 611 - 620
(2015/06/08)

PRODRUG COMPOUNDS AND THEIR USES
Provided herein are prodrug compounds, their preparation and their uses, such as treating liver diseases or nonliver diseases via intervening in molecular pathways in the liver. Novel prodrug compounds of acid/alcohol derivatives such as phosphates, phosp
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Paragraph 0444; 0445

(2015/09/22)

Esterification catalysis by pyridinium p -toluenesulfonate revisited - Modification with a lipid chain for improved activities and selectivities
The lipid analogs of pyridinium p-toluenesulfonate (PPTS) were examined for catalysis of the condensation of an equimolar mixture of carboxylic acids and alcohols under mild conditions without removal of water. Although PPTS is a poor catalyst, the introduction of a lipid chain and nitro group significantly improved the activity of PPTS and led to selectivity at suppressing the elimination side reactions of alcohols. 2-Oleamido-5-nitro-pyridinium p-toluenesulfonate (6) is a lead catalyst that promoted various esterification reactions with yields up to 99%.
Wang, Wei,Liu, Huimin,Xu, Shaoyi,Gao, Yong
supporting information
p. 2906 - 2912
(2013/09/02)

Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition
Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50 = 10-17 μM). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50 = 0.153 μM).
Wu, Hui,Kelley, Charles J.,Pino-Figueroa, Alejandro,Vu, Huyen D.,Maher, Timothy J.
p. 5188 - 5197
(2013/09/02)

Synthesis, molecular characterization and preliminary antioxidant activity evaluation of quercetin fatty esters
Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2-diphenyl-1-picryl-hydrazyl method and by 2,2-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) assay.
Mainini, Francesca,Contini, Alessandro,Nava, Donatella,Corsetto, Paola Antonia,Rizzo, Angela Maria,Agradi, Elisabetta,Pini, Elena
p. 1751 - 1759
(2013/11/19)