141-24-2Relevant academic research and scientific papers
Synthesis of halogenated 1-O-alkylglycerols from ricinoleic acid derivatives
Pemha, René,Pegnyemb, Dieudonné Emmanuel,Mosset, Paul
, p. 1656 - 1664 (2020)
Resistance to the existing drugs and increasing numbers of diseases result in identifying new drug candidates with new forms of activity. As marine organisms are well known to provide a wide range of original compounds, Herein, we report the synthesis of new non-natural brominated, iodinated and chlorinated-substituted 1-O-alkylglycerols 5–7, analogs of a prominent 1-O-alkylglycerol (AKG) of the natural shark liver oil (SLO) mixture, namely the AKGs 18:1, n-9.
Synthesis and biological evaluation of four new ricinoleic acid-derived 1-o-alkylglycerols
Pemha, René,Kuete, Victor,Pagès, Jean-Marie,Pegnyemb, Dieudonné Emmanuel,Mosset, Paul
, (2020)
Aseries of novel substituted 1-O-alkylglycerols (AKGs) containing methoxy (8), gem-difluoro (9), azide (10) and hydroxy (11) group at 12 position in the alkyl chain were synthesized from commercially available ricinoleic acid (12). The structures of these new synthesized AKGs were established by NMR experiments as well as from the HRMS and elementary analysis data. The antimicrobial activities of the studied AKGs 8-11 were evaluated, respectively, and all compounds exhibited antimicrobial activity to different extents alone and also when combined with some commonly used antibiotics (gentamicin, tetracycline, ciprofloxacin and ampicillin). AKG 11 was viewed as a lead compound for this series as it exhibited significantly higher antimicrobial activity than compounds 8-10.
Bromotrimethylsilane as a selective reagent for the synthesis of bromohydrins
Giomi, Donatella,Salvini, Antonella,Ceccarelli, Jacopo,Brandi, Alberto
, p. 14453 - 14458 (2021)
Bromotrimethylsilane (TMSBr) is a very efficient reagent in the solvent-free conversion of glycerol into bromohydrins, useful intermediates in the production of fine chemicals. As glycerol is a relevant by-product in biodiesel production, TMSBr has been also tested as a mediator in transesterification in acidic conditions, providing FAME from castor oil in good yields, along with bromohydrins from glycerol. Subsequently the glycerol conversion was optimized and depending on the reaction conditions, glycerol can be selectively converted into α-monobromohydrin (1-MBH) or α,γ-dibromohydrin (1,3-DBH) in very good yields. This journal is
Preparation of functionalized castor oil derivatives with tunable physical properties using heterogeneous acid and base catalysts
Sankaranarayanan, Sivashunmugam,Srinivasan, Kannan
, p. 50289 - 50297 (2015)
Functionalized castor oil derivatives namely ring-opened glyceryl ricinoleates, epoxy alkyl ricinoleates, and ring-opened alkyl ricinoleates were successfully prepared through two reaction chemistry viz., ring opening and transesterification using epoxidized castor oil (ECO) as a raw material. Amberlyst 15, the most active catalyst among several acid catalysts screened, showed a maximum conversion of 82% for ring opening of ECO with methanol. In another chemistry, 91% yield of epoxy methyl ricinoleate was achieved through transesterification of ECO with methanol using CaAl-layered double hydroxide (LDH) derived oxides as base catalyst. The scope is extendable to many nucleophiles and alcohols for both reactions respectively. Ring-opened alkyl ricinoleates were prepared both in two-pot and one-pot reactions using both acid and base catalysts together. The catalysts were recyclable and were successfully scaled at 25 g. The physical properties of these castor-based derivatives bestow the opportunity to design tailor-made materials suiting industrial needs.
Synthesis and antibacterial activity of ricinoleic acid glycosides
Kuppala, Ramakrishna,Govindarajan, Mugunthan,Tambat, Rushikesh,Patel, Neeraj,Nandanwar, Hemraj,Bhutani, Kamlesh K.,Kartha, K. P. Ravindranathan
, p. 3700 - 3713 (2016)
The antibacterial properties of twenty-eight novel ricinoleic acid glycosides synthesized by Koenigs-Knorr glycosylation are reported. Seven of them were found to show promising wide spectrum antibacterial activity against Gram positive bacteria of which two compounds, the mannopyranosyl- and the arabinofuranosyl derivatives, were proven effective against various non-clinical/clinical/NorA-overexpressed/resistant strains of Staphylococcus aureus as well as other Gram +ve bacteria such as Bacillus subtilis ATCC 6051 and Micrococcus luteus MTCC 2470. It was found that both the presence of the sugar and its structure are necessary and important for the compounds to be bioactive. The methyl ester protection of the carboxylic acid moiety of the ricinoleic acid unit was also found to be important for imparting good bioactivity to the molecule. Based on the membrane permeability and cell disintegration studies, these compounds are found to increase the bacterial cell membrane permeability, subsequently causing cell death.
Design and synthesis of a castor oil based plasticizer containing THEIC and diethyl phosphate groups for the preparation of flame-retardant PVC materials
Jia, Puyou,Hu, Lihong,Feng, Guodong,Bo, Caiying,Zhou, Jing,Zhang, Meng,Zhou, Yonghong
, p. 897 - 903 (2017)
A fine chemical product based on a castor oil containing THEIC and diethyl phosphate groups (THEIC-MR-phosphate) was designed and synthesized, and it was used as a substitute flame retardant plasticizer to prepare PVC materials instead of the commercial plasticizer dioctyl phthalate (DOP). The performance of the PVC materials plasticized with THEIC-MR-phosphate was investigated with TGA, DSC, cone calorimeter analysis, and tensile tests. The results indicated that the addition of THEIC-MR-phosphate improved the flame retardant properties of the PVC materials. The time to ignition (TI) increased from 10 s to 25 s, the pHRR value decreased from 167.5 kW m-2 to 52.1 kW m-2, the av-HRR value decreased from 44.7 kW m-2 to 21.1 kW m-2, and the t-pHRR value increased from 45.0 s (D-1) to 73.0 s (N-3). These data indicated that the THEIC-MR-phosphate was effective in increasing the PVC material resistance to fire, and it not only decreased the HRR, but also delayed the fire process.
LIPID CONJUGATE PREPARED FROM SCAFFOLD MOIETY
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Page/Page column 54-55, (2020/10/18)
The application relates to a lipid conjugate of formula M-X1-L wherein M is a molecule of interest such as a drug moiety; X1 is a linker group such as ester, ether or carbamate; and L is a lipid scaffold represented by formula (lId): -L1-[L2(H)(X2R)]n-L3-[L4(H)(X2R)]p-L5-L6 and wherein L comprises 5 to 40 carbon atoms and 0 to 2 carbon-carbon double bonds. The lipid conjugate can be formulated in a drug delivery vehicle such as a lipid nanoparticle (LNP).
Fatty acid based biocarbonates: Al-mediated stereoselective preparation of mono-, di- and tricarbonates under mild and solvent-less conditions
Pe?a Carrodeguas,Cristòfol,Fraile,Mayoral,Dorado,Herrerías,Kleij
supporting information, p. 3535 - 3541 (2017/08/15)
A catalytic method for the preparation of a series of fatty acid derived biocarbonates has been developed using a binary Al-complex/PPNCl catalyst. This catalyst system allows conversion of fatty acid derived epoxides under comparatively mild reaction conditions (70-85 °C, 10 bar) while maintaining high levels of diastereospecificity with cis/trans ratios of up to 97:3 in the products. The comparative catalysis data obtained for the reactions catalysed only by the nucleophilic halide based components show that the presence of the Al-complex is crucial for the retention of the original stereochemistry.
Designing, synthesis, and antimicrobial action of oxazoline and thiazoline derivatives of fatty acid esters
Ahmad, Anis,Ahmad, Aiman,Sudhakar, Raja,Varshney, Himani,Subbarao, Naidu,Ansari, Saba,Rauf, Abdul,Khan, Asad U.
, p. 3412 - 3431 (2017/11/16)
In this study, a novel series of oxazoline and thiazoline were designed as inhibitors of cytochrome P450 14 alpha-sterol demethylase (CYP51) from Candida albicans and peptide deformylase (PDF) of Escherichia coli. The long chain dibromo derivative of fatty acid esters on reaction with urea and thiourea gave their corresponding oxazolines and thiazolines, respectively. All the compounds were characterized by their spectral data (IR, 1H NMR, 13C NMR and MS) and tested for antibacterial and antifungal activity by disk diffusion assay and minimum inhibitory concentration by the broth microdilution method against gram-positive and gram-negative strains of bacteria as well as fungus strains. The investigation into antimicrobial screening revealed that all the compounds were found to be potent antimicrobial agents. After calculating likeness drug properties of the compounds by Prediction of Activity Spectra for Substances software, ADMET-related descriptors were computed to predict the pharmacokinetic properties for the active and bioavailable compounds by discovery studio 2.5. Molecular docking studies have been performed on PDF of E. coli and CYP 450-14DM of C. albicans to understand the mode of binding of the molecules in the active site of the receptor. Compounds (2-amino-5-(carbomethoxyoctyl)-1,3-oxazoline, 2-amino-5-(carbomethoxyoctyl)-1,3-thiazoline and 2-amino-4-pentyl-5-[(8’R)-8’ hydroxy (carbomethoxydecyl)-1,3-oxazoline) showed excellent antimicrobial activity nearly equivalent to the control compounds and compounds, 2-amino-4-octyl-5-(carbomethoxyheptyl)-1,3-oxazolin, 2-amino-4-(2’R)(2’-hydroxy octyl)-5-(carbomethoxyheptyl)-1,3-oxazoline and 2-amino-4-pentyl-5-[(8’R)-8’-hydroxy(carbomethoxy decyl)-1,3-oxazolineshowed vasodilation and antihypertensive properties. Furthermore, a computational analysis of physicochemical parameters revealed that the most of the compounds possessed drug-like attributes. Using Bioinformatics approach, we found a correlation between the observed and predicted antimicrobial activities.
[1 + 1]-Condensation of 12-Oxo-Derivatives of Ricinoleic Acid Esters with Hydrazine Hydrate on the Route to Macrocycles
Ishmuratov, G. Yu.,Yakovleva,Vydrina,Rubleva,Ishmuratova,Tolstikov
, p. 231 - 233 (2017/07/05)
The reactivities of the keto analogs of methyl ricinolate and its triglyceride with hydrazine hydrate were studied. The ester was found to be inert, which made it possible to synthesize a macrocyclic azine with a side chain hydrazone moiety from a 12-oxo-derivative.
