- Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action
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In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.
- Lei, Kang,Li, Pan,Yang, Xue-Fang,Wang, Shi-Ben,Wang, Xue-Kun,Hua, Xue-Wen,Sun, Bin,Ji, Lu-Sha,Xu, Xiao-Hua
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p. 10489 - 10497
(2019/10/02)
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- New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C?H Amination
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1,4-Benzoxazin-3-ones are important structural motifs in natural products and bioactive compounds. Usually, the synthesis of benzoxazinones requires transition-metal catalysts and pre-functionalized substrates such as aryl halides. However, the anodic C?H
- Wesenberg, Lars Julian,Herold, Sebastian,Shimizu, Akihiro,Yoshida, Jun-Ichi,Waldvogel, Siegfried R.
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supporting information
p. 12096 - 12099
(2017/09/13)
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- Synthesis and molecular structures of 1-hydroxyethyl-2-(p-substituted) phenoxymethyl benzimidazoles
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Five novel 1-hydroxyethyl-2-(p-substituted) phenoxymethyl benzimidazoles were synthesized by a three-step route. Under microwave irradiation, the p-substituted phenols were firstly O-carboxymethylated to prepare the corresponding p-substituted phenoxymethyl acids, which then reacted with o-phenylendiamine to get the key intermediates 2-(p-substituted) phenoxymethyl benzimidazole. Finally, the solid-liquid phase transfer catalysis method, where tetrabutyl ammonium bromide (TBAB) was used as the catalyst, was applied to synthesize the target compounds c1-c5 by the N-hydroxyethylation reaction with 2-chloroethyl alcohol. The structures of the obtained compounds were well characterized and confirmed by elemental analysis, MS, IR, 1H NMR, 13C NMR and single-crystal X-ray diffraction analysis.
- Wu, Jiacheng,Zhao, Li,Zhao, Changqing,Wang, Zhiyuan,Gu, Haibin,Chen, Wuyong
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p. 974 - 980
(2016/11/22)
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- PPARG MODULATORS FOR TREATMENT OF OSTEOPOROSIS
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The invention provides methods of treatment of a progressive bone disease, such as osteoporosis, Paget's Disease, multiple myeloma, or hyperparathyroidism, comprising administration of an effective amount of a non-agonist PPARG modulator to a patient afflicted with the disease.
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Page/Page column 130
(2015/11/09)
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- Catalyst-free photoredox addition-cyclisations: Exploitation of natural synergy between aryl acetic acids and maleimide
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Suitably functionalised carboxylic acids undergo a previously unknown photoredox reaction when irradiated with UVA in the presence of maleimide. Maleimide was found to synergistically act as a radical generating photoxidant and as a radical acceptor, negating the need for an extrinsic photoredox catalyst. Modest to excellent yields of the product chromenopyrroledione, thiochromenopyrroledione and pyrroloquinolinedione derivatives were obtained in thirteen preparative photolyses. In situ NMR spectroscopy was used to study each reaction. Reactant decay and product build-up were monitored, enabling reaction profiles to be plotted. A plausible mechanism, whereby photo-excited maleimide acts as an oxidant to generate a radical ion pair, has been postulated and is supported by UV/Vis. spectroscopy and DFT computations. The radical-cation reactive intermediates were also characterised in solution by EPR spectroscopy. UVA photolyses of aryloxy-, arylthio- and arylamino-acetic acids with maleimide yield oxa-, thia- and aza-tricyclo pyrroledione derivatives in the absence of a photoredox catalyst (see scheme). An intriguing mechanism has been proposed and has been supported and supplemented by NMR monitoring experiments, DFT computations and UV/Vis and EPR spectroscopy.
- Manley, David W.,Mills, Andrew,O'Rourke, Christopher,Slawin, Alexandra M. Z.,Walton, John C.
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supporting information
p. 5492 - 5500
(2014/05/20)
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- N-BENZYLINDOLE MODULATORS OF PPARG
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The invention provides molecular entities that bind with high affinity to PPARG (PPARγ), and inhibit kinase-mediated (e.g., cdk5-mediated) phosphorylation of PPARG, but do not exert an agonistic effect on PPARG. Compounds of the invention can be used for treatment of conditions in patients wherein PPARG plays a role, such as diabetes, insulin resistance, impaired glucose tolerance, pre-diabetes, hyperglycemia, hyperinsulinemia, obesity, or inflammation. Side effects such as significant weight gain, edema, impairment of bone growth or formation, or cardiac hypertrophy, or any combination thereof, can be avoided in the mammal receiving the compound. Methods of preparation of the compounds, bioassay methods for evaluating compounds of the invention as non-agonistic PPARG binding compounds, and pharmaceutical compositions are also provided.
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Page/Page column 61
(2012/12/14)
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- Aza-Michael addition of acrylonitrile with 2-aryloxymethylbenzimidazole derivatives under microwave irradiation
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A simple, rapid, and highly efficient method has been developed for the aza-Michael addition of acrylonitrile to 2-aryl-oxymethylbenzimidazole derivatives in the presence of anhydrous potassium carbonate under microwave irradiation. A series novel of 1-cyanoethyl-2-aryloxymethylbenzimidazole derivatives have been prepared and characterised by 1H NMR, 13C NMR, IR spectra and elemental analysis.
- Wei, Tai-Bao,Hua, Mao-Tang,Shi, Hai-Xiong,Liu, Yong,Zhang, You-Ming
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scheme or table
p. 452 - 454
(2010/12/24)
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- A rapid and high-yield synthesis of aryloxyacetic acid in one pot under microwave irradiation and phase transfer catalysis conditions
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A series of aryloxyacetic acid 3a-h has been synthesized in one pot under microwave irradiation and phase transfer catalysis conditions. By the optimization of the reaction condition, a rapid, high-yield and efficient method for the preparation of aryloxyacetic acid is reported.
- Wei, Tai-Bao,Liu, Hong,Li, Man-Lin,Zhang, You-Ming
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p. 1312 - 1314
(2007/10/03)
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- A rapid and high-yield synthesis of aryloxyacetyl hydrazides under microwave irradiation and with phase transfer catalysis
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A series of aryloxyacetyl hydrazides 4a-l were synthesised under microwave irradiation and phase transfer catalysis conditions. By the optimisation of the reaction conditions, a rapid, high-yield and efficient method for the preparation of aryloxyacety hydrazide was given.
- Wei, Tai-Bao,Liu, Hong,Li, Man-Lin,Zhang, You-Ming
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p. 432 - 433
(2007/10/03)
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- Synthesis of Aryloxyacetic Acids, Esters, and Hydrazides Assisted by Microwave Irradiation
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Under microwave irradiation on clay a series of transformations of a number of phenols into their aryloxyacetic acids 3 and then their methyl esters 4 and hydrazides 5 has been achieved efficiently in good yields.
- Hamid, Hamida M. Abdel,Ramadan, El Sayed,Hagar, Mohamed,El Ashry, El Sayed H.
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p. 377 - 382
(2007/10/03)
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- Structure-activity relationship of small-sized HIV protease inhibitors containing allophenylnorstatine
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We designed and synthesized a new class of peptidomimetic human immunodeficiency virus (HIV) protease inhibitors containing a unique unnatural amino acid, allophenylnorstatine [Apns; (2S,3S)-3-amino-2-hydroxy- 4-phenylbutyric acid], with a hydroxymethylcarbonyl (HMC) isostere as the active moiety. A systematic evaluation of structure - activity relationships for HIV protease inhibition, anti-HIV activities, and pharmacokinetic profiles has led to the delineation of a set of structural characteristics that appear to afford an orally available HIV protease inhibitor. Optimum structures, exemplified by 21f (JE-2147), incorporated 3-hydroxy-2- methylbenzoyl groups as the P2 ligand, (R)-5,5-dimethyl-1,3-thiazolidine-4- carbonyl (Dmt) residue at the P1' site, and 2-methylbenzylcarboxamide group as the P2' ligand. The present study demonstrated that JE-2147 has potent antiviral activities in vitro and exhibits good oral bioavailability and plasma pharmacokinetic profiles in two species of laboratory animals.
- Mimoto, Tsutomu,Kato, Ryohei,Takaku, Haruo,Nojima, Satoshi,Terashima, Keisuke,Misawa, Satoru,Fukazawa, Tominaga,Ueno, Takamasa,Sato, Hideharu,Shintani, Makoto,Kiso, Yoshiaki,Hayashi, Hideya
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p. 1789 - 1802
(2007/10/03)
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- Use of Anion Exchange Resin in Synthesis of Aryloxyacetic Acid Esters
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Insoluble polymer-supported nucleophilic reagent has been prepared by treatment of sodium salt of aryloxyacetic acid with Amberlite IRA-400 (Cl-).This reagent has been used for the synthesis of aryloxyacetic acid esters in high yields by reaction with alkyl halides.In addition to ease and simplicity of the method and regeneration of the polymeric by-product, the polymeric reagent seems to increase the nucleophilicity of the anions.In addition to this, transesterification is observed when alcohol is used as the solvent.
- Bandgar, B. P.,Jagdale, M. H.,Mane, R. B.,Salunkhe, M. M.
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p. 421 - 422
(2007/10/02)
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- Le polyphosphate d'ethyle, un reactif de choix pour la synthese de derives du benzofuranne dicarboxylate-2,3 de methyle
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The aim of this work is to develop a fast and effective method for the synthesis of methylated derivatives of dimethylbenzofuran-2,3-dicarboxylate.With this end in view, we can suggest significant improvements to the Koelsch and Whitney method, especially by using ethyl polyphosphate.This reagent is indeed well adapted to the cyclodehydration of the methyl 2-aryloxy-3-hydroxymaleate intermediates into benzofuran compounds, since the yield is often better than 80percent.
- Belleney, Joel,Vebrel, Joel,Cerutti, Ernest
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p. 1431 - 1435
(2007/10/02)
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- Applicability of Hammett Equation to the Kinetics of Acid-catalysed Esterification of meta- and para-Substituted Phenoxyacetic Acids by Methanol
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Rate constants have been determined for the acid-catalysed esterification of meta- and para-substituted phenoxyacetic acids by methanol, with hydrogen chloride as catalyst.The applicability of the Hammett equation to the rate data has been examined.The para-substituted benzoic acids react slower than the corresponding para-substituted phenoxyacetic acids.The probable cause of this behaviour is discussed.
- Baliah, V.,Gurumurthy, R.
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p. 629 - 631
(2007/10/02)
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- Influence of meta- and para-Substituents on the Kinetics of Esterification of Phenoxyacetic Acids by Methanol
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The influence of meta- and para- substituents on the kinetics of acid-catalysed esterification of phenoxyacetic acids is discussed.In the case of para Cl, Br and I substituents, d-orbital resonance is suggested to explain the observed behaviour.The possibility of protonation of the methoxy oxygen in the acid medium employed is indicated to explain the slower rate of reaction of m- and p-methoxyphenoxyacetic acids.
- Baliah, V.,Gurumurthy, R.
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p. 1082 - 1083
(2007/10/02)
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