- Synthesis, antimicrobial study, and molecular docking simulation of 3,4-dimethoxy-β-nitrostyrene derivatives as candidate ptp1b inhibitor
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A derivative series of 3,4-dimethoxy-β-nitrostyrene was synthesized through nitroaldol reaction, including a new compound of 3,4-ethylenedioxy-β-bromo-β-nitrostyrene. The antimicrobial activity effect of 3,4-alkyloxy modification of β-nitrostyrene was investigated. A molecular docking study was also performed to obtain information about their interactions with protein tyrosine phosphatase 1B (PTP1B). The active residues of cysteine-215 and arginine-221 of PTP1B play a key role in signaling pathways that regulate various microorganism cell functions. It also acts as a negative regulator in signaling pathways of insulin that are involved in type 2 diabetes and other metabolic diseases. These derivatives exhibited potential antifungal activity. The studied compounds were also had potential as fragments to be PTP1B inhibitors by interacting with serine-216 and arginine-221 residues, according to their molecular docking. 3,4-Ethylenedioxy-β-methyl-β-nitrostyrene was the most successful potential candidate as a PTP1B inhibitor. However, further research is needed to investigate their potential for medicinal use.
- Alfarisi, Salman,Santoso, Mardi,Kristanti, Alfinda Novi,Siswanto, Imam,Puspaningsih, Ni Nyoman Tri
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- Copper-Catalyzed Propargylation of Nitroalkanes
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Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α-functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N-heterocycles such as pyrroles and 2-pyrrolines.
- Kim, Raphael S.,Dinh-Nguyen, Linh V.,Shimkin, Kirk W.,Watson, Donald A.
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supporting information
p. 8106 - 8110
(2020/11/02)
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- Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation
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ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.
- Kim, Hun Young,Oh, Kyungsoo,Si, Tengda
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p. 9216 - 9221
(2019/10/08)
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- Inhibition of LDL oxidation and inflammasome assembly by nitroaliphatic derivatives. Potential use as anti-inflammatory and anti-atherogenic agents
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We have previously shown the antioxidant and anti-inflammatory properties of several para-substituted arylnitroalkenes. Since oxidative stress and inflammation are key processes that drive the initiation and progression of atherosclerosis, in the present work the antioxidant, anti-inflammatory and anti-atherogenic properties of an extended library of aryl-nitroaliphatic derivatives, including several newly designed nitroalkanes, was explored. The antioxidant capacity of the nitroaliphatic compounds, measured using the oxygen radical absorbance capacity assay (ORAC) showed that the p-methylthiophenyl-derivatives were about three times more effective than Trolox to prevent fluorescein oxidation, independently of the presence or the absence of the double bond next to the nitro group. The peroxyl radical scavenger capacity of the p-dimethylaminophenyl-derivatives was even higher, being the reduced form of these compounds even more active. In fact, while the antioxidant capacity of 1-dimethylamino-4-(2-nitro-1Z-ethenyl)benzene and 1-dimethylamino-4-(2-nitro-1Z-propenyl)benzene was 4.2 ± 0.1 and 5.4 ± 0.1 Trolox Eq/mol, respectively; ORAC values obtained with the ethyl and the propyl derivatives were 10 ± 1 and 13 ± 2 Trolox Eq/mol, respectively. The p-dimethylamino-derivatives, especially the nitroalkanes, were also able to prevent LDL oxidation mediated by peroxyl radicals. Oxygen consumption due to the oxidation of fatty acids was delayed in the presence of the dimethylamino substituted compounds, only the alkanes interrupted the chain of lipid oxidations decreasing the rate of oxygen consumption. Although the formation of foam cells in the presence of oxidized-LDL (oxLDL) remained unaffected, the molecules containing the dimethylamino moiety were able to decrease the expression of IL-1β in LPS/INF-γ challenged macrophages.
- Cataldo, Nicolás,Musetti, Bruno,Celano, Laura,Carabio, Claudio,Cassina, Adriana,Cerecetto, Hugo,González, Mercedes,Thomson, Leonor
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p. 178 - 186
(2018/10/15)
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- ANTIMICROBIAL AND RADIOPROTECTIVE COMPOUNDS
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The present invention relates to a method of treatment and/or prophylaxis of a microbial infection, comprising the step of administering an effective amount of a compound of formula (I), in which X and Y are either the same or different and selected from a heteroatom; is a double or single bond depending on the heteroatoms X and Y; R1 to R5 are either the same or different and selected from hydrogen or a non-deleterious substituent; and R6 and R7 are either the same or different and selected from hydrogen and a non-deleterious substituent or one of R6 and R7 are absent when there is a double bond present, pharmaceutically acceptable salts or derivatives, pro-drugs, tautomers and/or isomers thereof. The present invention also relates to a method for protecting a subject from radiation damage, a method of cancer radiotherapy and use as an antimicrobial or radioprotective agent of the compound of formula (I) defined above. Some of the compounds of formula (I) are novel and are also described in the present invention, together with pharmaceutical or veterinary compositions containing them.
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Paragraph 0115-0116
(2015/11/09)
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- Arylnitroalkenes as scavengers of macrophage-generated oxidants
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Oxygen and nitrogen derived molecules mediated oxidation and nitration have been involved in several pathological conditions. Conversely, nitric oxide and hydrogen peroxide are important signalization intermediates, whose concentrations are tightly regula
- Celano, Laura,Carabio, Claudio,Frache, Renata,Cataldo, Nicolás,Cerecetto, Hugo,González, Mercedes,Thomson, Leonor
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- One-pot solid phase synthesis of (E)-nitroalkenes
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An efficient one-pot protocol for the synthesis of (E)-nitroalkenes by reaction of aldehydes and nitroalkanes in the presence of polymer-bound triphenylphosphine, iodine and imidazole is described. Although the reaction works with similar efficiency with triphenylphosphine and its polymer-bound version, easy removal of the unwanted polymer-bound triphenylphosphine oxide and its recovery as triphenylphosphine provide the edge for practical application of the method.
- Rokhum, Lalthazuala,Bez, Ghanashyam
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p. 5500 - 5504
(2013/09/23)
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- METHOD OF TREATING SCEDOSPORIUM SPP. INFECTION
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The present invention provides a method of treatment of Scedosporium spp. infection in an animal comprising the step of administering to the infected animal an effective amount of a compound of formula I or a pharmaceutically-acceptable salt thereof
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Page/Page column 15
(2014/01/07)
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- Palladium-catalyzed synthesis of substituted nitroolefins
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A one-pot protocol toward several substituted nitroolefins 4 and 6 starting with substituted acetones 2 and 5 was described. A facile process was carried out for the triflation of substituted acetones 2 and 5 with triflic anhydride (Tf2O) under the basic condition (Cs2CO3) and then palladium-catalyzed cross-coupling of enol triflates 3 with NaNO 2 and BINAP in the presence of phase-transfer reagents (n-Bu 4NBr) under the refluxing 1,2-dimethoxyethane (DME) in acceptable yields.
- Chang, Meng-Yang,Lin, Chung-Han,Tai, Hang-Yi
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supporting information
p. 3194 - 3198
(2013/06/26)
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- Ethylenediamine: A highly effective catalyst for one-pot synthesis of aryl nitroalkenes via henry reaction and dehydration
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Ethylenediamine (H2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1%-2% (mol%) of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various arylnitroalkenes 1a-1y in 85%-97% yields. Ethylenediamine (H 2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1-2 mol% of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various aryl nitroalkenes 1a-1y in 85%-97% yields. Copyright
- Yang, Jianxin,Dong, Jing,Lue, Xia,Zhang, Qiang,Ding, Wei,Shi, Xiaoxin
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p. 2827 - 2833
(2013/08/23)
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- Exploring nitrostyrene as a scaffold for a new class a of monoamine oxidase inhibitors
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With the ultimate purpose of finding out the structural features that are relevant for MAO inhibitory activity and selectivity towards MAO-B isoform, a series of compounds encompassing a β-nitrostyrene moiety was designed and the in vitro inhibitory activity was evaluated. In the present work, we report the synthesis and the pharmacological evaluation of a series of functionalized derivatives of β-methyl-β-nitrostyrene with distinct substitution patterns in the phenyl ring, namely hydroxyl, methoxy, benzyloxy and methylenedioxy. All the studied compounds were substituted in meta and para positions of the phenyl ring related to the nitrovinyl side chain. The synthesized compounds were evaluated towards both human MAO isoforms, displaying some of them activities in the low micromolar range. Particularly compound 6 (a methylenedioxy derivative) exhibits high potency and selectivity towards MAO-B.
- Reis, Joana,Oliveira, Catarina,Milhazes, Nuno,Vi?a, Dolores,Borges, Fernanda
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p. 958 - 961
(2013/02/23)
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- UV-absorbers for ophthalmic lens materials
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UV absorbing monomers that are particularly useful in ophthalmic devices are disclosed.
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Page/Page column 6
(2011/02/26)
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- Pharmacological characterization of ecstasy synthesis byproducts with recombinant human monoamine transporters
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Ecstasy samples often contain byproducts of the illegal, uncontrolled synthesis of N-methyl-3,4-methylenedioxy-amphetamine or 3,4-methylenedioxy- methamphetamine (MDMA). MDMA and eight chemically defined byproducts of MDMA synthesis were investigated for their interaction with the primary sites of action of MDMA, namely the human plasmalemmal monamine transporters for norepinephrine, serotonin, and dopamine [(norepinephrine transporter (NET), serotonin transporter (SERT), and dopamine transporter (DAT)]. SKN-MC neuroblastoma and human embryonic kidney cells stably transfected with the transporter cDNA were used for uptake and release experiments. Two of the eight compounds, 1,3-bis (3,4-methylenedioxyphenyl)-2-propanamine (12) and N-formyl-1,3-bis (3,4-methylenedioxyphenyl)-prop-2-yl-amine (13) had uptake inhibitory potencies with IC50 values in the low micromolar range similar to MDMA. Compounds with nitro instead of amino groups and a phenylethenyl instead of a phenylethyl structure or a formamide or acetamide modification had IC50 values beyond 100 μM. MDMA, 12, and 13 were examined for induction of carrier-mediated release by superfusion of transporter expressing cells preloaded with the metabolically inert transporter substrate [3H]1-methyl-4-phenylpyridinium. MDMA induced release mediated by NET, SERT, or DAT with EC50 values of 0.64, 1.12, and 3.24 μM, respectively. 12 weakly released from NET- and SERT-expressing cells with maximum effects less than one-tenth of that of MDMA and did not release from DAT cells. 13 had no releasing activity. 12 and 13 inhibited release induced by MDMA, and the concentration dependence of this effect correlated with their uptake inhibitory potency at the various transporters. These results do not support a neurotoxic potential of the examined ecstasy synthesis byproducts and provide interesting structure-activity relationships on the transporters. Copyright
- Pifl, Christian,Nagy, Gabor,Berenyi, Sandor,Kattinger, Alexandra,Reither, Harald,Antus, Sandor
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p. 346 - 354
(2007/10/03)
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- Binding of Phenylalkylamine Derivatives at 5-HT1C and 5-HT2 Serotonin Receptors: Evidence for a Lack of Selectivity
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Certain phenyalkylamine derivatives have been considered to bind selectively at 5-HT2 serotonin receptors.It is now recognized that the most widely used derivatives, i.e., 1-(2,5-dimethoxy-4-X-phenyl)-2-aminopropanes where X = Me (DOM), Br (DOB), and I (DOI) (1-3, respectively) also bind at the more recently identified population of serotonin 5-HT1C receptors.The purpose of the present investigation was to determine whether simple phenylalkylamines bind selectively at one population of receptors over the other.An examination of 34 derivatives reveals (i) similar structure-affinity relationships and (ii) a significant correlation (r = >0.9, n = 25) between 5-HT1C and 5-HT2 affinity.None of the compounds included in the present study displayed more than a 10-fold selectivity for one population of these receptors over the other; the results suggest that these compounds (including the widely used 5-HT2 agonists DOB and DOI) are 5-HT1C/5-HT2 agents.
- Glennon, Richard A.,Raghupathi, Reva,Bartyzel, Piotr,Teitler, Milt,Leonhardt, Sigrun
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p. 734 - 740
(2007/10/02)
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- NITRATION SUBSTITUTED STYRENES WITH NITRYL IODIDE
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Nitration of substituted styrenes by nitryl iodide, followed by treatment of the product with triethylamine, gives β-nitrostyrenes in good yield.
- Sy, Wing-Wah,By, Arnold W.
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p. 1193 - 1196
(2007/10/02)
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- A Convenient & Short Route for the Synthesis of Ayapin & Scoparone
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A short, convenient and general route to synthesise two important intermediates in coumarin synthesis, viz. 2-hydroxy-4,5-methylenedioxybenzaldehyde (4a) and 2-hydroxy-4,5-dimethoxybenzaldehyde (4b), is described.These have been converted by Wittig reaction into the naturally occurring coumarins, ayapin (1a) and scoparone (1b), respectively.
- Kelkar, Shriniwas L.,Phadke, Chetan P.,Marina, Sister
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p. 458 - 459
(2007/10/02)
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- Isocoumarins : Part III - Synthesis of Methyl- and Methylenedioxydihydroisocoumarins and a New Synthesis of (+/-)-5-Methylmellein
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o-Lithio-N-methylbenzamide upon condensation with propylene oxide gives 3-methyldihydroisocoumarin.Similarly o-lithio-N-methyl-p-toluamide upon condensation with ethylene oxide and propylene oxide give 6-methyl- and 3,6-dimethyldihydroisocoumarin.A similar condensation of o-lithio-N-methyl-m-toluamide with ethylene oxide gives 5-methyldihydroisocoumarin but condensation with propylene oxide gives 3,5-dimethyl- and 3,7-dimethyldihydroisocoumarins.The method has been used to synthesize (+/-)-5-methylmellein.The synthesis of 5,6-methylenedioxydihydroisocoumarin from o-lithio-N-methylpiperonylamide is also described. 3-Methyl-6,7-methylenedioxydihydroisocoumarin has been synthesized by an acid-catalyzed cyclization reaction.
- Bhide, Bhaskar H.,Shah, Kashmira K.
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