- A NEW ALKAMIDE FROM PIPER SYLVATICUM
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Sylvamide, a new amide derivative, has been isolated from the petrol extract of the seeds of Piper sylvaticum (Roxb.).From spectral and chemical studies its structure has been elucidated as N-isobutyl-4,5-dihydroxy-2(E)-decenamide. - Key Word Index: Piper sylvaticum; Piperaceae; seeds; sylvamide; N-isobutyl-4,5-dihydroxy-2(E)-decenamide.
- Banerji, Avijit,Pal, Sudhir Chandra
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- Synthesis and Surface-Active Properties of a Homologous Series of Star-Like Triple-Chain Anionic Surfactants Derived from 1,1,1-Tris(hydroxymethyl)ethane
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A novel homologous series of trimeric anionic surfactants, 3C n TE3CNa (where n is a fatty acid chain length of 7, 10, or 12), with three hydrocarbon chains and three carboxylate heads connected via tri-etheric bonds were synthesized from long-chain α-bromo fatty acids and a triol, 1,1,1-tris(hydroxymethyl)ethane. The obtained trimeric carboxylic acids were esterified and purified by silica gel column chromatography, then hydrolyzed with dilute sodium hydroxide solution to form a series of trimeric carboxylate surfactant products. All prepared compounds were analyzed by IR, 1H NMR, and 13C NMR spectroscopy to confirm their chemical structures. Their surface-active properties were investigated. The critical micelle concentrations (cmc) of 3C n TE3CNa were in the range of 0.12-0.71 mmol/L, and the surface tensions at the cmc (γ cmc) were 29.3-34.8 mN/m.
- Li, Xu,Xing, Fenglan,Xu, Qun,Sun, Xiaolong,Wang, Yuping,Wang, Liyan,Wang, Pinglang
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p. 129 - 135
(2016/01/09)
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- 1, 1, 1-tri (hydroxymethyl) ethane as coupling includes sub-surfactant and method of preparing the same
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The invenetion relates to a preparation method of a ternary surface active agent adopting 1,1,1-tri(hydroxymethyl) ethane as a link group. A structural formula of the ternary surface active agent is as follows (described in specifications). The synthesis method includes a synthesis step of alpha-bromo-carboxylic acid, an esterification reaction step of the link group 1,1,1-tri(hydroxymethyl) ethane and an esterolysis reaction step. The synthesis process condition of the ternary surface active agent is as follows: 30% NaOH and tetrahydrofuran are used as a solvent to be subjected to reflux reaction for 5 to 7 hours.
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- Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators
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Novel N-α-haloacylated homoserine lactones, in which a halogen atom was introduced at the α-position of the carbonyl function of the N - acyl chain, have been studied as quorum sensing (QS) modulators and compared with a library of natural N - acylated homoserine lactones (AHLs). The series of novel analogues consists of α-chloro, α-bromo and α-iodo AHL analogues. Furthermore, the biological QS activity of the synthetic AHL analogues compared to the natural AHLs was evaluated. Halogenated analogues demonstrated a reduced activity in the Escherichia coli JB523 bioassay, with the α-iodo lactones being the less active ones and the α-chloro AHLs the most potent QS agonists. Most of the α-haloacylated analogues did not exhibit a significant reduction when tested in the QS inhibition test. Therefore, these novel analogues could be utilized as chemical probes for QS structure-activity studies.
- Syrpas, Michail,Ruysbergh, Ewout,Stevens, Christian V.,De Kimpe, Norbert,Mangelinckx, Sven
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p. 2539 - 2549
(2015/02/19)
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- Synthesis and characterization of novel phosphonocarboxylate inhibitors of RGGT
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Phosphonocarboxylate (PC) analogs of the anti-osteoporotic drugs, bisphosphonates, represent the first class of selective inhibitors of Rab geranylgeranyl transferase (RabGGTase, RGGT), an enzyme implicated in several diseases including ovarian, breast and skin cancer. Here we present the synthesis and biological characterization of an extended set of this class of compounds, including lipophilic derivatives of the known RGGT inhibitors. From this new panel of PCs, we have identified an inhibitor of RGGT that is of similar potency as the most active published phosphonocarboxylate, but of higher selectivity towards prenyl pyrophosphate synthases. New insights into structural requirements are also presented, showing that only PC analogs of the most potent 3rd generation bisphosphonates inhibit RGGT. In addition, the first phosphonocarboxylate-derived GGPPS weak inhibitor is reported.
- Coxon, Fraser,Joachimiak, ?ukasz,Najumudeen, Arafath Kaja,Breen, George,Gmach, Joanna,Oetken-Lindholm, Christina,Way, Rebecca,Dunford, James,Abankwa, Daniel,B?azewska, Katarzyna M.
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supporting information
p. 77 - 89
(2014/07/22)
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- Mesoionic 5-alkyl-1,3-dithiolium-4-thiolates: Synthesis and brine shrimp toxicity
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A series of twelve 1,3-dithiolium-4-thiolate mesoionic compounds were synthesized and characterized. The synthetical approach starting from α-bromoalkanoic acids to obtain the corresponding 2-N-morpholino-dithiocarbamoyl-carboxylic acids that by on-pot reaction with carbon disulfide and acetic anhydride in triethylamine formed not isolate intermediates, 1,3-dithiolium-4-olates. After, the 2-N-morpholino-5-alkyl-1,3-dithiolium-4-thiolates were obtained by retro 1,3-dipolar addition reactions. The alkyl moiety linked to C-5 of heterocyclic ring permitted the increase of the hydrophobic character and this effect was evaluated on Artemia salina lethality. The results indicated a bell-shaped relationship between the number of carbon of side chain in mesoionic derivatives and LD50 in brine shrimp toxicity assays.
- De Almeida, Paulo Afonso,Da Silva, Tania Maria Sarmento,Echevarria, Aurea
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p. 593 - 600
(2007/10/03)
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- N-hdroxy-2-(alkyl, aryl, or heteroaryl, sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors
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Matrix metalloproteinases (MMPs) are a group of enzymes that have been implicated in the pathological destruction of connective tissue and basement membranes. These zinc containing endopeptidases consist of several subsets of enzymes including collagenases, stromelysins and gelatinases. TNF-α converting enzyme (TACE), a pro-inflammatory cytokine, catalyzes the formation of TNF-α from membrane bound TNF-α precursor protein. It is expected that small molecule inhibitors of MMPs and TACE therefore have the potential for treating a variety of disease states. The present invention provides low molecular weight, non-peptide inhibitors of matrix metalloproteinases (MMPs) and TNF-α converting enzyme (TACE) for the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection having the formula wherein R2and R3form a heterocyclic ring and A is S, S(O), or S(O)2, and R1and R4are defined herein.
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- SHORT CHAIN 2-HYDROXYCARBOXYLIC ACID-BASED DERIVATIVES OF CERAMIDES
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The present invention relates to active ceramide derivatives. Specifically, the invention relates to 2(alpha)-hydroxycarboxylic acid-based ceramide derivatives. The present invention describes a method for obtaining these compounds. The invention also relates to the use of these compounds in cosmetic compositions.
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- Enantioselective synthesis of α-bromo acid derivatives and bromohydrins from tartrate derived bromoacetals
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Bromination of the acetals 4 derived from aryl alkyl ketones, ArCOR, and (2R,3R)-tartaric acid results in bromoacetals 5 with 78-90% de. Hydrolysis of those compounds with Ar = 4-methoxyphenyl or 3-bromo-4-methoxyphenyl results, after recrystallisation, in α-bromoketones 8 with 66-98% ee which are shown to undergo the Baeyer-Villiger oxidation to α-bromoesters 9 with minimal racemisation, α-Bromoketone 8d is shown to undergo carbonyl reduction to threo-bromohydrin 15 with retention of stereochemistry.
- Boyes, Scott A.,Hewson, Alan T.
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p. 2759 - 2765
(2007/10/03)
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- Syntheses of 2-(2-Hydroxyethylamino) Fatty Acids
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Eight 2-(2-hydroxyethylamino) fatty acids, 2-(2-hydroxyethylamino)decanoic, -undecanoic, -dodecanoic, -tetradecanoic, -hexadecanoic, -octadecanoic, -nonadecanoic, and docosanoic acid, were synthesized by reacting 2-bromo fatty acids with more than 3 mol of 2-aminoethanol.The surface tension and the critical micelle concentration were determined for these compounds.
- Xianxian, Du
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p. 123 - 124
(2007/10/02)
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