- A functional and self-assembling octyl-phosphonium-tagged esculetin as an effective siRNA delivery agent
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Herein, we document a self-assembling octyl-TPP tagged esculetin (Mito-Esc) as functionally active and as a novel small molecule siRNA delivery vector. While Mito-Esc itself induces selective breast cancer cell death, the amphiphilic nature of Mito-Esc delivers therapeutic siRNAs intracellularly without the need for any excipient to exacerbate the anti-proliferative effects.
- Shaikh, Altab,Neeli, Praveen Kumar,Singuru, Gajalakshmi,Panangipalli, Sravya,Banerjee, Rajkumar,Maddi, Sridhar Reddy,Thennati, Rajamannar,Bathula, Surendar Reddy,Kotamraju, Srigiridhar
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supporting information
p. 12329 - 12332
(2021/12/07)
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- Phosphonium-based ionic liquids: Economic and efficient catalysts for the solvent-free cycloaddition of CO2 to epoxidized soybean vegetable oil to obtain potential bio-based polymers precursors
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A series of phosphonium-based ionic liquids have been prepared in one step in a simple way from inexpensive feedstocks. The prepared ionic liquids have been successfully tested as catalysts in the solvent-free cycloaddition reaction of CO2 to an epoxidized soybean oil to obtain carbonated soybean oil that can be potentially employed as bio-monomer in the synthesis for bio-based polymers. The catalytic performance of these ionic liquids was compared to the widely used and benchmark catalyst in CO2 cycloaddition to epoxides reaction, namely tetrabutylammonium bromide at different reaction conditions. The influence of some reaction parameters such as temperature, CO2 pressure, reaction time and catalyst amount was studied. It has been found that the solubility of the prepared ionic liquids in the reaction media (epoxidized soybean oil) is a key factor that limits the catalytic performance of some of the synthesized ionic liquids. All prepared ionic liquids have shown higher thermal stability that the benchmark catalyst and three of them have shown superior catalytic performance. The best results in terms of conversion and selectivity have been obtained with dodecyltriphenylphosphonium bromide (5) achieving almost full conversion (99.8%) and excellent selectivity (84.0%) after 5 h reaction at 160 oC and 40 bar of CO2. Outstanding results compared to those reported in the literature with similar catalysts in the solvent-free CO2 cycloaddtion to an epoxidized soybean oil to obtain the corresponding carbonated oil have been achieved. Considering the facile synthesis of catalyst 5, the large availability and non-expensive of the feedstocks and its catalytic performance it can be considered a valuable and green alternative for CO2 fixation to epoxidized vegetable oil.
- Centeno-Pedrazo, A.,Freixa, Z.,Garcia-Suarez, E. J.,Perez-Arce, J.,Prieto-Fernandez, S.
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- Antiferroptotic Activity of Phenothiazine Analogues: A Novel Therapeutic Strategy for Oxidative Stress Related Disease
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Ferroptosis is an iron-catalyzed, nonapoptotic form of regulated necrosis that has been implicated in the pathological cell death associated with various disorders including neurodegenerative diseases (e.g., Friedreich's ataxia (FRDA), Alzheimer's disease, and Parkinson's disease), stroke, and traumatic brain injury. Recently, we showed that lipophilic methylene blue (MB) and methylene violet (MV) analogues both promoted increased frataxin levels and mitochondrial biogenesis, in addition to their antioxidant activity in cultured FRDA cells. Presently, we report the synthesis of series of lipophilic phenothiazine analogues that potently inhibit ferroptosis. The most promising compounds (1b-5b) exhibited an improved protection compared to the parent phenothiazine against erastin- and RSL3-induced ferroptotic cell death. These analogues have equivalent or better potency than ferrostatin-1 (Fer-1) and liproxstatin-1 (Lip-1), that are among the most potent inhibitors of this regulated cell death described so far. They represent novel lead compounds with therapeutic potential in relevant ferroptosis-driven disease models such as FRDA.
- Liu, Jun,Bandyopadhyay, Indrajit,Zheng, Lei,Khdour, Omar M.,Hecht, Sidney M.
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supporting information
p. 2165 - 2173
(2020/12/17)
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- NOVEL GLYCINE TRANSPORT INHIBITORS FOR THE TREATMENT OF PAIN
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The present invention relates to novel glycine transport inhibitor compounds and their use for treating pain.
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Page/Page column 51; 52
(2018/08/12)
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- COMPOUNDS HAVING AGONISTIC EFFECT AGAINST GPR84, PREPARATION METHOD FOR COMPOUNDS AND USE OF COMPOUNDS
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The present invention relates to a class of compounds represented by the formula I, or pharmaceutically acceptable salts thereof, methods for their preparation, and application as small molecule tools that function as GPR84 agonists, and their use in preparing a medicament for the treatment of septicemia.
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Paragraph 0141; 0142
(2018/09/12)
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- Methylene acetal formation from 1,2- and 1,3-diols using an O, S -acetal, 1,3-dibromo-5,5-dimethylhydantoin, and BHT
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A mild and efficient method for formation of methylene acetals from 1,2- and 1,3-diols using methoxymethylphenylsulfide, 1,3-dibromo-5,5- dimethylhydantoin (DBDMH), and dibutylhydroxytoluene (BHT) is described. The use of BHT in this process suppresses side reactions and enables high-yielding formation of methylene acetals of various diols, including carbohydrate-type substrates.
- Maegawa, Tomohiro,Koutani, Yasuyuki,Otake, Kazuki,Fujioka, Hiromichi
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p. 3384 - 3390
(2013/06/26)
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- Synthesis and inhibitory activities against colon cancer cell growth and proteasome of alkylresorcinols
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We have identified alkylresorcinols (ARs) as the major active components in wheat bran against human colon cancer cell growth (HCT-116 and HT-29) using a bioassay-guided approach. To further study the structure-activity relationships, 15 ARs and their intermediates (1-15) were synthesized expediently by the modified Wittig reaction in aqueous media, and six 5-alkylpyrogallols and their analogues (16-21) were prepared by the general Grignard reaction. The synthetic AR analogues were evaluated for activities against the growth of human colon cancer cells HCT-116 and HT-29 and the chymotrypsin-like activity of the human 20S proteasome. Our results found that (1) AR C13:0 and C15:0 (13 and 14) had the greatest inhibitory effects in human colon cancer cells HCT-116 and HT-29, while decreasing or increasing the side chain lengths diminished the activities; (2) two free meta-hydroxyl groups at C-1 and C-3 on the aromatic ring of the AR analogues greatly contributed to their antitumor activity; (3) the introduction of a third hydroxyl group at C-2 (20 and 21) into the aromatic ring of the AR analogues yielded no significant enhancement in activity against HCT-116 cells and decimated the effects against HT-29 cells, but dramatically increased the activity against the chymotrypsin-like activity of the human 20S proteasome; and (4) AR C11:0 (12) was found to have the greatest effect in a series of AR C9:0-C17:0 against the chymotrypsin-like activity of the human 20S proteasome.
- Zhu, Yingdong,Soroka, Dominique N.,Sang, Shengmin
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p. 8624 - 8631
(2012/11/13)
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- Convenient synthesis of D- and L-xylo-1,2,3,4-alkane tetrols from a D-gluco-configured common building block
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D-gluco-Configured building block derived from d-(+)-gluconolactone has served as a common chiral template for the synthesis of enantiopure d- and l-xylo-configured 1,2,3,4-alkane tetrols. This has enabled synthesis of medicinally important guggultetrols and their enantiomers from a common starting point. Wittig and Grignard reactions are the key steps used for the incorporation of lipophilic chain.
- Borkar, Santosh Ramdas,Manjunath, Beedimane Narayana,Balasubramaniam, Sivaraman,Aidhen, Indrapal Singh
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- IONIC LIQUID AND METHOD FOR PRODUCING THE SAME
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A method according to the present invention is a method for producing an ionic liquid from a molten salt solution containing a molten salt constituted by combining the cation portion and the anion portion, the ionic liquid containing the molten salt as a main component, the method comprising: removing water from the molten salt solution, the step of removing the water including adding a compound in the molten salt solution, the compound being represented by General Formula (1): where at least two of R1 to R4 are a C1 to C8 alkoxy group(s), the rest of R1 to R4 are a hydrogen atom(s) or a C1 to C8 alkyl group(s). By this, it is possible to remove water from the molten salt solution regardless of whether the molten salt solution is hydrophilic or hydrophobic. The present invention provides a method of producing an ionic liquid, which method can remove water from any kind of ionic liquid economically, easily, and quickly.
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Page/Page column 24
(2010/04/24)
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- The separation and synthesis of lipidic 1,2- and 1,3-diols from natural phenolic lipids for the complexation and recovery of boron
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A study has been made of the semi-synthesis of 1,3-diols (anacardic alcohols) from natural phenolic lipid resources from Anacardium occidentale and Anacardium giganteum which have given C15 and C11 derivatives, respectively. An isomeric 1,3-diol (isoanacardic alcohol) has been obtained from cardanol separated from technical cashew nut-shell liquid. Homologous1,3-diols have been synthesised from a range of synthetic 2-alkyl-, 3-alkyl- and 4-alkylphenols and from 6-alkylsalicylic acids. The natural 1,2-diol, urushiol, from Rhus vernicifera has been purified. All these lipidic compounds have been studied for their complexation and the potential recovery of boron as boric acid.
- Tyman, John H.P.,Mehet, Satinderjit K.
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p. 177 - 199
(2007/10/03)
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- Enzymatic route to chiral, nonracemic cis-2,6- and cis,cis-2,4,6-substituted piperidines. Synthesis of (+)-dihydropinidine and dendrobate alkaloid (+)-241D
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Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase (ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee ≥ 98%). The general method is used to effect the synthesis of (±)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.
- Chenevert, Robert,Dickman, Michael
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p. 3332 - 3341
(2007/10/03)
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- Short, enantiospecific synthesese of indolizidines 209B and 209D, and piclavine A from diethyl-L-glutamate
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The 1H-pyrrole derivative obtained from diethyl L-glutamate hydrochloride and tetrahydro-2,5-dimethoxyfuran was cyclized with BBr3 to ethyl (5S)-5,6,7,8-tetrahydro-8-oxoindolizine-5-carboxylate (18). Catalytic hydrogenation of 18 over Pd/C in AcOH gave ethyl (5S,8aR)-octahydroindolizine-5-carboxylate (21), whereas hydrogenation over Rh/Al2O3 in EtOH/AcOH 99:1 afforded mainly ethyl (5S,8S,8aS)-octahydro-8-hydroxyindolizine-5-carboxylate (22). By functional-group interconversions, 21 was transformed into piclavine A (1) and indolizidine 209D (2). Similarly, (5R,8R,8aS)-octahydro-5-pentylindolizine-8-methanol (37), the final relay for indolizidine 209B (3), was obtained from 22.
- Jefford,Sienkiewicz,Thornton
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p. 1511 - 1524
(2007/10/02)
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- Hindered organoboron groups in organic chemistry. 24. The condensation of aliphatic aldehydes with dimesitylboron stabilised carbanions to give ketones
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The condensation of boron stabilised carbanions, MeS2BCHLiR1, (R1≠H) with aliphatic aldehydes, R2CHO, followed by treatment with trifluoroacetic anhydride (TFAA) or N-chlorosuccinimide (NCS) is an unique, broadly applicable redox process that yields ketones, R1CH2COR2, directly and in high yields. The anion MeS2BCH2Li (MeS2BCHLiR1, R1=H) gives high yields of alkenes, R2CH=CH2 in the same conditions.
- Pelter, Andrew,Smith, Keith,Elgendy, Said M. A.,Rowlands, Martin
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p. 7104 - 7118
(2007/10/02)
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- Hindered organoboron groups in organic chemistry. 25. The condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions to give alkenes
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In the presence of protic acids the condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions results in alkenes. In the presence of strong acids such as HCl or CF3SO3H, the products contain > 90% of E-alkenes in all cases tried. When acetic acid is used, the Z-alkenes may result predominantly, particularly in the cases of R(S)CHO and R(t)CHO.
- Pelter,Smith,Elgendy
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p. 7119 - 7132
(2007/10/02)
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- Amphiphilic Carbohydrate-Based Mesogens, VIII. A Facile Synthetic Route to Mesogenic L-ribo-1,2,3,4-Alkanetetrols
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The Wittig olefinations of 2,3-O-isopropylidene-D-ribofuranose (1) with two equivalents of alkylidenetriphenylphosphorane (alkylidene: hexylidene-undecylidene) followed by hydrogenation catalyzed by palladium on carbon and subsequent deprotection yield (2R,3S,4S-("L-ribo")-1,2,3,4-alkanetetrols 5.These amphiphiles form the smectic A mesophase on melting.However, when 1 is heated with one equivalent of the alkylidenetriphenylphosphoranes for longer periods, (2R,3S,4R)-("D-lyxo")-1,2,3,4-alkanetetrol-type products 4 predominate.Key Words: Liquis crystals / Carbohydrates / L-ribo-, D-lyxo-1,2,3,4-Alkanetetrols / Wittig olefination
- Dahlhoff, Wilhelm V.
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p. 109 - 114
(2007/10/02)
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- Studies on the Synthesis of Linear Aliphatic Compounds. Part. 3. The Synthesis of Paraffins with Very Long Chains
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The approach derived in Part 2 has been modified to increase the purity and yield of intermediates.The C12 starting materials have been doubled in chain length five times, and by using components of similar or different chain length in Wittig condensations ω-halogeno-acetals with 12n carbon atoms have been made up with n up to 32.They have been converted into paraffins with 102, 104, 150, 198, 246, 294, and 390 carbon atoms.Those paraffins with 150 or more carbon atoms show chain-folding in the crystalline state; this observation is contributing to the understanding of chain-folding behaviour long known in linear polyethylene but hitherto unknown in essentially pure paraffins.
- Bidd, Ilesh,Holdup, David W.,Whiting, Mark C.
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p. 2455 - 2464
(2007/10/02)
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- Synthetic Studies of Diels-Alder Adduct of Furan. Formal Total Synthesis of (+/-)-Avenaciolide
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The endo-Diels-Alder adduct of furan with methyl acrylate was transformed into a bis-γ-lactone derivative which is a well-known precursor for the synthesis of (+/-)-avenaciolide.The route involves 13 steps and the overall yield was 17.9percent.
- Kotsuki, Hiyoshizo,Ohnishi, Hiroyuki,Akitomo, Yasuhiro,Ochi, Masamitsu
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p. 3881 - 3884
(2007/10/02)
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