120-14-9Relevant articles and documents
Aromatic amide derivatives of 5,6-dimethoxy-2,3-dihydro-1H-inden(-1-yl)acetic acid as anti-inflammatory agents free of ulcerogenic liability
Sharma, Meenakshi,Ray
, p. 6790 - 6796 (2007)
Amide derivatives of 5,6-dimethoxy-2,3-dihydro-1H-inden(-1-yl)acetic acid were synthesized and evaluated for their anti-inflammatory and analgesic activity. Few selected compounds were also screened for their antipyretic, anti-arthritic, and ulcerogenic potential. Most of the compounds exhibited good activity profile and were free of gastrointestinal toxicity of common NSAIDs. However these compounds failed to decrease secondary lesions of adjuvant induced arthritis and also did not inhibit TNF-α in lipopolysaccharide induced pyresis.
Efficient synthesis of α-substituted-α-arylmethyl phosphonates using trichloroacetimidate C–C coupling method
Fathalla, Walid,Pazdera, Pavel,El-Rayes, Samir,Ali, Ibrahim.A.I.
, p. 1681 - 1691 (2018)
A simple convenient protocol for the synthesis of diethyl α,α-diaryl methylphosphonate derivatives 5a-f, 6b-f, 7a-f and 8a-f, diethyl α-alkenyl α-aryl methylphosphonates 9a-d and 10a-d and α-(oxoalkyl) α-aryl methylphosphonate 11a-d and 12a-d is described. Trichloroacetimidates 3a-d were treated with activated arenes, styrene, allyltrimethylsilane or silylenol ethers C-nucleophiles in the presence TMSOTf to afford the desired products in good yields and short reaction time.
Oxidation of alcohols with benzyltriphenylphosphonium peroxymonosulfate under non-aqueous conditions
Hajipour,Mallakpour,Adibi
, p. 71 - 79 (2000)
Oxidation of allylic and benzylic alcohols with benzyltriphenylphosphonium peroxymonosulfate (PhCH2Ph3P+HSO5-) 1 (BTPPMS) in refluxing acetonitrile is reported. The oxidation in the presence of a catalytic amount of bismuth chloride enhances the rate.
Co-Oxidative Transformation of Piperine to Piperonal and 3,4-Methylenedioxycinnamaldehyde by a Lipoxygenase from Pleurotus sapidus
Krahe, Nina-Katharina,Berger, Ralf G.,Kahlert, Lukas,Ersoy, Franziska
, p. 2857 - 2861 (2021)
The valuable aroma compound piperonal with its vanilla-like olfactory properties is of high interest for the fragrance and flavor industry. A lipoxygenase (LOXPsa1) of the basidiomycete Pleurotus sapidus was identified to convert piperine, the abundant pungent principle of black pepper (Piper nigrum), to piperonal and a second volatile product, 3,4-methylenedioxycinnamaldehyde, with a vanilla-like odor through an alkene cleavage. The reaction principle was co-oxidation, as proven by its dependence on the presence of linoleic or α-linolenic acid, common substrates of lipoxygenases. Optimization of the reaction conditions (substrate concentrations, reaction temperature and time) led to a 24-fold and 15-fold increase of the piperonal and 3,4-methylenedioxycinnamaldehyde concentration using the recombinant enzyme. Monokaryotic strains showed different concentrations of and ratios between the two reaction products.
Benzyltriphenylphosphonium peroxymonosulfate: As a novel and efficient reagent for oxidation of alcohols under solvent-free conditions
Hajipour, Abdol Reza,Mallakpour, Shadpour E.,Adibi, Hadi
, p. 460 - 461 (2000)
This paper describes the oxidation of alcohols under solvent-free conditions using benzyltriphenylphosphonium peroxymonosulfate, which has been prepared by mixing an aqueous solution of benzyltriphenylphosphonium chloride with oxone at room temperature. This reagent is stable white powder, which may be stored for months without loss of its activity. This compound is readily soluble in organic solvents such as acetonitrile, chloroform, and dichloromethane and slightly soluble in carbon tetrachloride, ether, and hexane.
Sphingobacterium sp. T2 Manganese Superoxide Dismutase Catalyzes the Oxidative Demethylation of Polymeric Lignin via Generation of Hydroxyl Radical
Rashid, Goran M. M.,Zhang, Xiaoyang,Wilkinson, Rachael C.,Fül?p, Vilmos,Cottyn, Betty,Baumberger, Stéphanie,Bugg, Timothy D. H.
, p. 2920 - 2929 (2018)
Sphingobacterium sp. T2 contains two extracellular manganese superoxide dismutase enzymes which exhibit unprecedented activity for lignin oxidation but via an unknown mechanism. Enzymatic treatment of lignin model compounds gave products whose structures were indicative of aryl-Cα oxidative cleavage and demethylation, as well as alkene dihydroxylation and alcohol oxidation. 18O labeling studies on the SpMnSOD-catalyzed oxidation of lignin model compound guiaiacylglycerol-β-guaiacyl ether indicated that the an oxygen atom inserted by the enzyme is derived from superoxide or peroxide. Analysis of an alkali lignin treated by SpMnSOD1 by quantitative 31P NMR spectroscopy demonstrated 20-40% increases in phenolic and aliphatic OH content, consistent with lignin demethylation and some internal oxidative cleavage reactions. Assay for hydroxyl radical generation using a fluorometric hydroxyphenylfluorescein assay revealed the release of 4.1 molar equivalents of hydroxyl radical by SpMnSOD1. Four amino acid replacements in SpMnSOD1 were investigated, and A31H or Y27H site-directed mutant enzymes were found to show no lignin demethylation activity according to 31P NMR analysis. Structure determination of the A31H and Y27H mutant enzymes reveals the repositioning of an N-terminal protein loop, leading to widening of a solvent channel at the dimer interface, which would provide increased solvent access to the Mn center for hydroxyl radical generation.
Synthesis and biological evaluation of amide derivatives of (5,6-dimethoxy-2,3-dihydro-1H-inden-1-yl)acetic acid as anti-inflammatory agents with reduced gastrointestinal ulcerogenecity
Sharma, Meenakshi,Ray
, p. 2092 - 2102 (2008)
A variety of amide derivatives of (5,6-dimethoxy-2,3-dihydro-1H-inden-1-yl)acetic acid were synthesized and screened for their analgesic and anti-inflammatory activities. The compounds were found to have longer activity profile exceeding that of indomethacin in carrageenan-induced rat paw edema model. Few selected compounds were also screened for their antipyretic, anti-arthritic and ulcerogenecity potential. From these studies it can be concluded that these compounds though have significant antipyretic activity did not act through the inhibition of TNF-α. The test compounds failed to prevent the development of secondary inflammation in adjuvant-induced arthritis assay. However, these compounds showed no ulcer formation at the tested dose level of 100 mg/kg p.o.
Oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers and ethylene acetals with benzyltriphenylphosphonium peroxomonosulfate in the presence of bismuth chloride under non-aqueous conditions
Hajipour,Mallakpour,Mohammadpoor-Baltork,Adibi
, p. 155 - 163 (2000)
Benzyltriphenylphosphonium peroxomonosulfate (BnPh3P+HSO5-) (1) is used as a new reagent for oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers and ethylene acetals to afford carbonyl compounds in refluxing acetonitrile in the presence of bismuth chloride.
The Oxidation of 3-Aryl-1-propenes by Oxidative System of RuCl 3-NaIO4-Phase Transfer Catalyst
Yuasa, Yoshifumi,Shibuya, Shiroshi,Yuasa, Yoko
, p. 3947 - 3952 (2003)
Methyleugenol 1a was oxidized to give 3,4-dimethoxyphenylacetaldehyde by the oxidative system containing the RuCl3-NaIO4-phase transfer catalyst. The yield and spectroscopic properties were obtained from the stable acetaldoxim 3a. Furthermore, this oxidation system could be applied to other arylpropenes, thus, safrole, 4-methoxyallylbenzene, allylbenzene, and the corresponding arylacetaldehyde formed.
Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis
Mu?kinja, Jovana,Burmud?ija, Adrijana,Ratkovi?, Zoran,Rankovi?, Branislav,Kosani?, Marijana,Bogdanovi?, Goran A.,Novakovi?, Sla?ana B.
, p. 1744 - 1753 (2016)
O-alkylated vanillin derivatives 2a–f and acetylferrocene react under Claisen–Schmidt conditions, resulting in good-to-high yields of the corresponding ferrocene chalcones 3a–f. None of the resultant compounds 3b–f has been previously described in the literature. All synthesized compounds were characterized by spectral and physical data, whereas two of them, 1-ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)-prop-2-en-1-one (3b) and 1-ferrocenyl-3-(4-buthoxy-3-methoxy-phenyl)-prop-2-en-1-one (3e), were crystalline substances, suitable for single-crystal X-ray analysis, which confirmed undoubtedly their structures. Chalcones 3a–f were tested for their biological activity and demonstrated relatively good in vitro antimicrobial activity towards different strains of bacteria and fungi. The best antibacterial activity is expressed by compounds 3b and 3c, while compound 3d shows the best antifungal activity.
