- Catalytic study of the copper-based magnetic nanocatalyst on the aerobic oxidation of alcohols in water
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A copper-based magnetic nanocatalyst has been prepared by co-precipitation method and characterized by FESEM, EDS, TEM, XRD, XRF, ICP–OES, FTIR, and BET analysis. This new nanocatalyst displays a good activity toward the aerobic oxidation of a wide range of alcohols in water. Moreover, it is recyclable up to five following runs by simple filtration without any significant loss of its catalytic activity.
- Dehkordi, S. Saeid Saei,Albadi, Jalal,Jafari, Abbas Ali,Samimi, Heshmat Allah
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p. 2527 - 2538
(2021/03/24)
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- Exploring the nitro group reduction in low-solubility oligo-phenylenevinylene systems: Rapid synthesis of amino derivatives
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A small series of amino oligo-phenylenevinylenes (OPVs) were successfully synthesized from their nitro-analogs in a rapid, simple, and highly efficient fashion employing a sodium sulfide/pyridine system as a reducing agent. In this research, classic and sustainable reduction methodologies including NH4HCO2/Zn and a choline chloride/tin (II) chloride deep eutectic solvent (DES) were also evaluated, showing degradation products, incomplete reactivity, and product isolation difficulties in all cases. The straightforward Na2S/pyridine synthetic protocol proved to maintain the E-E stereochemistry of the OPV backbone that has been previously assembled by the Mizoroki–Heck cross-coupling reaction. Also, the optoelectronic properties were determined and discussed, considering the amino group insertion in these conjugated systems as a contribution for future construction of novel materials with applications in supramolecular electronics, light harvesting, and photocatalysis.
- Acelas, Mauricio,Sierra, Andrés Felipe,Sierra, César A.
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supporting information
p. 1335 - 1352
(2020/03/04)
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- Design and Synthesis of Ligand-Tag Exchangeable Photoaffinity Probe Utilizing Nosyl Chemistry
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Construction of a fluorophore or high-sensitive mass tag on target molecules would promise the facile analysis in photoaffinity labeling. A novel 2-nitrobenzenesulfonyl (nosyl; Ns) diazirine, which exhibits bifunctional properties for efficient photoaffinity labeling, was designed. This strategy highlights the simplicity of the chemical probe and its ability to install identification tags via Meisenheimer complex by SNAr after photo-labelling. Herein, in this study, we synthesized new Ns diazirine and demonstrated further studies in terms of photoactivation and SNAr reaction in aqueous condition.
- Saaidin, Aimi Suhaily,Murai, Yuta,Ishikawa, Takuya,Monde, Kenji
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supporting information
p. 7563 - 7567
(2019/12/15)
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- Synthesis and evaluation of antinociceptive and anti-inflammatory effects of nitro-porphyrins
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This manuscript reports the anti-inflammatory and antinociceptive effects of 4 nitrophenyl-porphyrins: 5,10,15,20-tetra-(3-nitrophenyl)-porphyrin (TNPP), 5,10,15,20-tetra-(4-fluoro-3-nitrophenyl)-porphyrin (TpFNPP), 5,10,15,20-tetra-(4-chloro-3-nitrophenyl)-porphyrin (TpClNPP), and 5,10,15,20-tetra-(4-bromo-3-nitrophenyl)-porphyrin (TpBrNPP). The in vivo anti-inflammatory assays were tested on the acute and chronic TPA (12-O-tetradecanoylphorbol 13-acetate) induced ear edema. The in vitro anti-inflammatory assay was carried out using J774A.1 murine macrophages stimulated with LPS. All nitro-porphyrins decreased inflammation significantly in the acute model: 58.55% (TNPP), 67.49% (TpBrNPP), 67.49% (TpClNPP), and 71.32% (TpFNPP). TpFNPP (50 μM/ml) increased the production of the anti-inflammatory cytokine IL-10, and decreased the production of the pro-inflammatory cytokines IL-1β, TNF-α, and IL-6 in macrophages activated with LPS, with similar activity than indomethacin (50 μM/ml). All porphyrins showed antinociceptive activity and lacked visible toxicity in the acute toxicity test. These results open the possibility of further studies to determine mechanisms of action, and study the influence of the structure on the activity of such compounds.
- Zapata-Morales, Juan Ramón,Pérez-González, Cuauhtémoc,Alonso-Castro, Angel Josabad,Martell-Mendoza, Miguel,Hernández-Munive, Abigail,Pérez-Gutiérrez, Salud
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p. 1782 - 1791
(2018/05/28)
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- Highly Productive Oxidative Biocatalysis in Continuous Flow by Enhancing the Aqueous Equilibrium Solubility of Oxygen
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We report a simple, mild, and synthetically clean approach to accelerate the rate of enzymatic oxidation reactions by a factor of up to 100 when compared to conventional batch gas/liquid systems. Biocatalytic decomposition of H2O2 is used to produce a soluble source of O2 directly in reaction media, thereby enabling the concentration of aqueous O2 to be increased beyond equilibrium solubility under safe and practical conditions. To best exploit this method, a novel flow reactor was developed to maximize productivity (g product L?1 h?1). This scalable benchtop method provides a distinct advantage over conventional bio-oxidation in that no pressurized gas or specialist equipment is employed. The method is general across different oxidase enzymes and compatible with a variety of functional groups. These results culminate in record space-time yields for bio-oxidation.
- Chapman, Michael R.,Cosgrove, Sebastian C.,Turner, Nicholas J.,Kapur, Nikil,Blacker, A. John
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supporting information
p. 10535 - 10539
(2018/08/17)
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- Discovery of phenoxybutanoic acid derivatives as potent endothelin antagonists with antihypertensive activity
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A series of phenoxybutanoic acid derivatives were synthesized and tested for their antagonistic activity on the contraction of the rat thoracic aortic ring induced by endothelin-1. Preliminary screening results showed that 6e and 6g with benzoheterocycles demonstrated significant antagonistic activities when compared to the reference compound BQ123. The results from additional assays for the binding affinity and selectivity for endothelin receptors showed that 6e was a selective ETA antagonist with a nanomolar IC50. Moreover, 6e was effective in relieving hypoxia-induced pulmonary arterial hypertension and right ventricular weight ratio. Therefore, 6e may have potential for further development as a therapeutic agent for the treatment of cardiovascular diseases.
- Cai, Jin,Liu, Ligang,Hong, Kwon Ho,Wang, Peng,Li, Lushen,Cao, Meng,Sun, Chunlong,Wu, Xiaoqing,Zong, Xi,Chen, Junqing,Ji, Min
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p. 657 - 667
(2015/02/19)
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- Structure-activity relationship study of 4EGI-1, small molecule eIF4E/eIF4G protein-protein interaction inhibitors
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Abstract Protein-protein interactions are critical for regulating the activity of translation initiation factors and multitude of other cellular process, and form the largest block of untapped albeit most challenging targets for drug development. 4EGI-1, (E/Z)-2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl) hydrazono)-3-(2-nitrophenyl)propanoic acid, is a hit compound discovered in a screening campaign of small molecule libraries as an inhibitor of translation initiation factors eIF4E and eIF4G protein-protein interaction; it inhibits translation initiation in vitro and in vivo. A series of 4EGI-1-derived thiazol-2-yl hydrazones have been designed and synthesized in order to delineate the structural latitude and improve its binding affinity to eIF4E, and increase its potency in inhibiting the eIF4E/eIF4G interaction. Probing a wide range of substituents on both phenyl rings comprising the 3-phenylpropionic acid and 4-phenylthiazolidine moieties in the context of both E- and Z-isomers of 4EGI-1 led to analogs with enhanced binding affinity and translation initiation inhibitory activities.
- Takrouri, Khuloud,Chen, Ting,Papadopoulos, Evangelos,Sahoo, Rupam,Kabha, Eihab,Chen, Han,Cantel, Sonia,Wagner, Gerhard,Halperin, Jose A.,Aktas, Bertal H.,Chorev, Michael
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p. 361 - 377
(2014/04/17)
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- Vanadium pentoxide as a catalyst for regioselective nitration of organic compounds under conventional and nonconventional conditions
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Vanadium pentoxide is used as an efficient catalyst for regioselective nitration of aromatic compounds under conventional and nonconventional conditions such as ultrasonically assisted (USAR) and microwave-assisted reactions (MWAR). The reactions underwent smoothly and afforded good yields of products with high regioselectivity. Observed longer reaction times (about 8 h) in V2O5 catalyzed reactions reduced to (0.5/30 min) under sonication and (90 s) in the case of MWAR. When ortho position is blocked, para derivatives are obtained as end products while ortho nitro products are obtained when para position is blocked.
- Venkatesham,Reddy, K. Rajendar,Rajanna,Veerasomaiah
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p. 921 - 926
(2014/04/03)
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- Oxalylchloride/DMF as an efficient reagent for nitration of aromatic compounds and nitro decarboxylation of cinnamic acids in presence of KNO 3 or NaNO2 under conventional and nonconventional conditions
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Nitration of aromatic compounds and cinnamic acids with oxalylchloride/DMF afforded the corresponding nitro derivatives in the presence of KNO3 or NaNO2 under conventional and nonconventional (ultrasonic and microwave) conditions. The present methodology offers several benefits such as excellent yields, simple work-up procedure, and short reaction times. The yields obtained under present methodology are comparable with those obtained from (POCl3/DMF/KNO3 or NaNO2) and (SOCl 2/DMF/KNO3 or NaNO2) systems followed by shorter reaction times. The reaction times of sonication and microwave conditions are very shorter than those of the conventional conditions.
- Kumar, M. Satish,Reddy, K. Rajendar,Rajanna,Venkanna,Krishnaiah
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p. 977 - 983
(2013/06/05)
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- An ion-responsive fluorescent compound based on NO-photoisomerisation styryl derivative linked to monoaza-15-crown-5
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A novel 15-aza-5-crown ether linked to styryl chemosensory 13-(4-((9H-fluoren-9-ylidene)methyl)-2-nitrophenyl)- 1,4,7,10-tetraoxa-13- azacyclopentadecane was designed and synthesised, it would not occur during photoisomerisation under radiation of light but shows special capability of selectively recognising for Sr2+.
- Cao, Jing,Feng, Jun Xiang,Wu, Yong Xiang,Pei, Xue Qun,Yan, Jiao Jiao,Liu, Yang,Qin, Wen Jie,Zhang, Xiao Bin
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experimental part
p. 407 - 410
(2012/05/04)
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- Conversion of oximes to carbonyl compounds with 2-nitro-4,5- dichloropyridazin-3(2H)-one
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(Chemical Equation Presented) Conversion of oximes to the carbonyl compounds has been demonstrated with use of 2-nitro-4,5-dichloropyridazin-3(2H)- one (2) under microwave irradiated conditions. Fourteen aliphatic and aromatic oximes converted to their corresponding aldehydes and ketones in good to excellent yields. It is noteworthy that the reaction is conducted under neutral, mild, and eco-friendly condition.
- Kim, Bo Ram,Lee, Hyung-Geun,Kim, Eun Jung,Lee, Sang-Gyeong,Yoon, Yong-Jin
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supporting information; experimental part
p. 484 - 486
(2010/03/25)
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- AI203/MeS03H (AMA) as a novel heterogeneous system for the nitration of aromatic compounds by magnesium nitrate hexahydrate
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Mg(NO3)2-6H2O was an efficient nitrating agent in the presence of a mixture of AI2O3/MeSO 3H (AMA) as a novel heterogeneous system for the nitration of aromatic compounds without use of any organic solvents and with high selectivity. The reaction proceeds at room temperature for the nitration of highly reactive aromatic compounds such as phenols and anilines.
- Hosseini-Sarvari, Mona,Tavakolian, Mina
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experimental part
p. 722 - 724
(2009/10/02)
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- N-methyl morpholine chlorochromate: An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds
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Instantaneous generation of N-methyl morpholine chlorochromate (NMMCC) is an efficient reagent for oxidation of primary and secondary alcohols to the corresponding carbonyl compounds. The comparison of reaction time and product yield was studied with novel NMMCC and other chlorochromate reagents and shows that the presented method requires less reaction time with good yield at laboratory temperature. The synthesis of reagent, formation of toxic and hazardous chromylchloride have been avoided, and also use of NMMCC under microwave irradiation for oxidation leads to fast reaction time and success of the strategy. Copyright Taylor & Francis Group, LLC.
- Chandrappa,Sadashiva,Rangappa
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p. 2638 - 2645
(2008/12/22)
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- Catalytic oxidations of alcohols to carbonyl compounds by oxygen under solvent-free and transition-metal-free conditions
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A green catalytic oxidation of alcohols to carbonyl compounds by oxygen was developed by using catalytic amounts of [bis(acetoxy)iodo]benzene/TEMPO/ KNO2. In addition, the use of a catalytic amount of poly[4-(bis(acetoxy)iodo)]styrene led to yields (up to 99%) comparable to the non-supported hypervalent iodine reagent, while offering the advantage of an efficient recovery and the subsequent recycling of the hypervalent iodine reagent.
- Herrerías, Clara I.,Zhang, Tony Y.,Li, Chao-Jun
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- Deprotection of 1,3-oxathiolanes to carbonyl compounds with montmorillonite K10
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Montmorillonite K10 has been used in the deprotection of different aromatic and aliphatic 1,3-oxathiolanes to the corresponding carbonyl compounds in 73 to 97% yields under mild and environmentally compatible conditions.
- Chauhan,Kumar, Anil,Sahoo
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p. 2635 - 2637
(2007/10/03)
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- Isoquinoline compound melanocortin receptor ligands and methods of using same
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The invention relates to melanocortin receptor ligands and methods of using the ligands to alter or regulate the activity of a melanocortin receptor. The invention further relates to tetrahydroisoquinoline aromatic amines that function as melanocortin receptor ligands and as agents for controlling cytokine-regulated physiologic processes and pathologies, and combinatorial libraries thereof.
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- Benzopyridazinone and pyridopyridazinone compounds
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Benzo or pyridopyridazinones and pyridazinthiones of the formula STR1 wherein: X and Y are nitrogen or carbon, provided that at least one is carbon, and Z is oxygen or sulfur; R1 is hydrogen, lower alkyl, aryl, aralkyl, heterocyclo, heterocyclo lower-alkyl, heteroaryl, or heteroaralkyl; R2, R3, R4, R5 and R6 are independently selected from hydrogen, lower alkyl, halo, carboxy, alkoxycarbonyl, carbamoyl, lower-alkyl carbonyl, halocarbonyl, thiomethyl, trifluoromethyl, cyano or nitro; or a pharmaceutically acceptable ester, ether or salt thereof, have been found to be useful as an anti-inflammatory, antasthmatic, immunosuppressive, anti-allograft rejection, anti-graft-vs-host rejection, autoimmune disease or analgetic agent(s).
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- Structure-Reactivity Effects in the Hydration of Benzaldehydes
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Rate constants have been measured for the approach to hydration equilibrium for seven substituted benzaldehydes .The kinetic method involves the perturbing of the equilibrium position by forming hydrate anion in concentrated sodium hydroxide; addition of acid and buffer results in solutions containing excess hydrate.Hydration equilibrium constants have been calculated by knowing the rate constants in the two directions for the hydroxide ion catalyzed reaction, and a value for the 3,5-(NO2)2 system has been obtained by using a trapping technique.Literature values are also summarized; hydration has a ρ value of +1.7 in the hydration direction.General base catalysis is associated with Broensted β values around 0.4 and ρ values near zero in the dehydration direction.The β values increase with decreased electron withdrawal, while the ρ values decrease with increased base strength (δβ/δ? = -0.06 = δρ/δpKa).A three-dimensional reaction coordinate diagram is used to show that this behavior is consistent with a class n mechanism - in the dehydration direction, equilibrium deprotonation of the hydrate followed by acid-catalyzed expulsion of OH.The water rates fit the general base correlations, although rate constants at the diffusion limit are required in one step.Two distinct Broensted plots are observed for general acids, one for RCOOH and a second for RPO3H(-), including H2PO4(-).The line for the latter is about 1 log unit above that for the former; this is attributed to an electrostatic interaction and not bifunctional catalysis.A significant cross correlation is also found here, with δα/δ? = -0.12 = δρ/-δpKa.This is shown to be consistent with a class e mechanism - in the dehydration direction, equilibrium protonation of the hydrate followed by base-catalyzed expulsion of water.
- McClelland, Robert A.,Coe, Margaret
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p. 2718 - 2725
(2007/10/02)
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