- Design, Synthesis and Herbicidal Activities of Tetrahydroisoindoline-1,3-dione Derivatives Containing Alkoxycarbonyl Substituted 2-Benzoxazolinone
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Several different alkoxycarbonyl-substituted 2-benzoxazolinone moieties have been incorporated into a tetrahydroisoindoline-1,3-dione scaffold to provide 25 compounds (1a-1u and 2a-2d). The structures of these compounds were confirmed by 1H and 13C NMR, HRMS and X-ray single-crystal diffraction. Some of these compounds (1g, 1h, 1j, 1k) exhibited excellent herbicidal activities against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus-galli at a rate of 375 g AI·ha-1. Among them, compounds 1h and 1j displayed the best post-emergence herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 and 5.3 g AI·ha-1, respectively, which are superior to that of the commercial acifluorfen (44.3 g AI·ha-1). Field trials demonstrated that compound 1h exhibited similar herbicidal activity to a high concentration atrazine, and found to be safer for maize than atrazine. The results of this study therefore show that compound 1h could potentially be used as a post-emergence herbicide for maize fields. Two series of tetrahydroisoindoline-1,3-diones containing an alkoxycarbonyl substituted 2-benzoxazolinone moiety were designed and synthesized. Compound 1h displayed excellent herbicidal effect against Abutilon theophrasti with ED50 values of 1.8 g AI·ha-1, and compound 1h could potentially be used as a new post-emergence herbicide for maize fields.
- Zhang, Hao,Liu, Kechang,Liu, Ruiquan,Li, Qibo,Li, Yongqiang,Wang, Qingmin,Liu, Shangzhong
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Read Online
- Method for preparing carbonyl heterocyclic compound
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The invention provides a method for preparing a carbonyl heterocyclic compound, wherein Lewis base and hydrosilane are used as accelerators and can efficiently enable an ortho-substituted aniline compound to react with normal-pressure CO2 to generate corresponding carbonyl heterocyclic compounds containing different functional groups under mild conditions (100 DEG C, digital). According to the method, normal-pressure CO2 is used as an environmentally-friendly non-toxic carbonylation reagent, and cheap Lewis base and PMHS (industrial silicon waste) are used as accelerators, so that the use of CO, high-pressure CO2 and noble metal catalysts is avoided, the intermediate isocyanate does not need to be purified and separated, the pure product can be obtained only through simple suction filtration and separation after the reaction is finished, and the synthetic method is efficient and universal, is suitable for preparing a series of benzimidazolone, benzoxazolone and benzothiazolone compounds and has high industrial application value.
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Paragraph 0036-0040; 0120-0125
(2020/03/25)
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- Synthesis method of 2,6-dichlorobenzooxazole
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The invention relates to the field of organic synthesis, and particularly relates to a synthesis method of 2,6-dichlorobenzooxazole. The synthesis method comprises the following steps: adding benzoxazolone and phosphorus oxychloride in a reaction container, carrying out dissolving by stirring, then adding a chlorination reagent, carrying out a chlorination reaction to obtain the 6-dichlorobenzooxazole, adding a certain amount of a catalyst, carrying out heating for reflux, carrying out a reaction for 6-12 hours, removing the solvent after the reaction is ended, and carrying out reduced pressure distillation to obtain the product 2,6-dichlorobenzooxazole. According to the preparation method of the 2,6-dichlorobenzooxazole, the route is short, the yield is high, operation is simple and convenient, three wastes (waste gas, waste water and industrial residue) generated in a reaction process are few, and the method is suitable for large-scale industrial production. In addition, the phosphorus oxychloride is used for replacing virulent phosgene, diphosgene, solid phosgene or phosphorus pentachloride, the safety coefficient during production is improved, and environment friendliness is achieved.
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Paragraph 0035; 0036; 0038; 0039; 0041; 0042; 0046; 0047
(2019/04/26)
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- Iron-Catalyzed Arene C-H Amidation Using Functionalized Hydroxyl Amines at Room Temperature
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Herein, we report Fe(III)(TPP)Cl as an effective catalyst for promoting arene C-H amidation through intramolecular cyclization of N-tosyloxyarylcarbamate substrates. The reaction proceeds via nitrene (outer sphere pathway) C(sp2)-H i
- Prasanthi,Begum, Samiyara,Srivastava, Hemant Kumar,Tiwari, Sandip Kumar,Singh, Ritesh
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p. 8369 - 8375
(2018/09/06)
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- Visible-Light-Induced Intramolecular C(sp2)-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway
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Catalytic intramolecular C-H amination and aziridination reactions of o-allylphenyl azidoformates have been achieved under visible-light irradiation, providing a mild, clean, and efficient method for the synthesis of useful benzoxazolones and [5.1.0] bicyclic aziridines. Mechanistic studies suggest that a triplet nitrene acts as the reactive intermediate. The chemoselectivity of the reaction, with alkyl olefin aziridination ? electron deficient olefin aziridination ≈ C(sp2)-H amination ? C(sp3)-H amination was observed, which may be instructive in the development of an understanding of visible-light-induced triplet nitrene transformation reactions.
- Zhang, Yipin,Dong, Xunqing,Wu, Yanan,Li, Guigen,Lu, Hongjian
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p. 4838 - 4842
(2018/08/24)
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- Method for preparing 2-chlorobenzoxazole and 2,6-dichlorobenzoxazole from o-aminophenol by taking solid triphosgene as chlorinating agent
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The invention provides a method for preparing 2-chlorobenzoxazole and 2,6-dichlorobenzoxazole from o-aminophenol by taking solid triphosgene as a chlorinating agent. The method comprises the followingsteps: step 1, respectively preparing 2-benzoxazolone and 2-mercapto benzoxazole by taking the o-aminophenol as a raw material; step 2, preparing the 2-chlorobenzoxazole by taking the 2-mercapto benzoxazole as a raw material and the solid triphosgene as the chlorinating agent; step 3, preparing 6-chlorobenzoxazolone by taking TCCA and the 2-benzoxazolone as raw materials; step 4, preparing 2-mercapto-6-chlorobenzoxazole; step 5, preparing the 2,6-dichlorobenzoxazole by taking the 2-mercapto-6-chlorobenzoxazole as a raw material and the solid triphosgene as the chlorinating agent. The method provided by the invention is a brand-new preparation method, which has the advantages of less corrosion to equipment, high yield, less reaction time, mild reaction conditions, less by-products and reduced environmental pollution.
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- Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure-Activity Relationship (SAR) Studies
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Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity-stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.
- Bach, Anders,Pizzirani, Daniela,Realini, Natalia,Vozella, Valentina,Russo, Debora,Penna, Ilaria,Melzig, Laurin,Scarpelli, Rita,Piomelli, Daniele
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supporting information
p. 9258 - 9272
(2015/12/23)
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- Development of benzo[d]oxazol-2(3H)-ones derivatives as novel inhibitors of Mycobacterium tuberculosis InhA
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A series of twenty seven substituted 2-(2-oxobenzo[d]oxazol-3(2H)-yl)acetamide derivatives were designed based on our earlier reported Mycobacterium tuberculosis (MTB) enoyl-acyl carrier protein reductase (InhA) lead. Compounds were evaluated for MTB InhA inhibition study, in vitro activity against drug-sensitive and -resistant MTB strains, and cytotoxicity against RAW 264.7 cell line. Among the compounds tested, 2-(6-nitro-2-oxobenzo[d]oxazol-3(2H)-yl)-N-(5-nitrothiazol-2-yl)acetamide (30) was found to be the most promising compound with IC50 of 5.12 ± 0.44 μM against MTB InhA, inhibited drug sensitive MTB with MIC 17.11 μM and was non-cytotoxic at 100 μM. The interaction with protein and enhancement of protein stability in complex with compound 30 was further confirmed biophysically by differential scanning fluorimetry.
- Pedgaonkar, Ganesh S.,Sridevi, Jonnalagadda Padma,Jeankumar, Variam Ullas,Saxena, Shalini,Devi, Parthiban Brindha,Renuka, Janupally,Yogeeswari, Perumal,Sriram, Dharmarajan
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p. 6134 - 6145
(2015/02/19)
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- General and efficient synthesis of benzoxazol-2(3H)-ones: Evolution of their anti-cancer and anti-mycobacterial activities
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A novel class of benzo[d]oxazol-2(3H)-one derivatives has been synthesized and their in vitro cytotoxicity against human pancreatic adenocarcinoma and human non-small cell lung carcinoma cancer cell lines was evaluated. Many of these compounds were found to display excellent to moderate activity. Among them, 6b, 6l, 6n and 6x were identified as lead molecules. In particular, 6l and 6n were found to be potent against the pancreatic adenocarcinoma cell line whereas the 6x was found to be effective against the human non-small cell lung carcinoma cell line. Conversely, the compounds 6l-x were found to be ineffective against Mycobacterium tuberculosis. Of the various molecules, 6h showed promising anti-mycobacterial activity, with an IC50 value equal to that of ciprofloxacin.
- Indrasena Reddy,Aruna,Sudhakar Babu,Vijayakumar,Manisha,Padma Sridevi,Yogeeswari,Sriram
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p. 59594 - 59602
(2015/02/19)
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- Spectrophotometric method for quantification of fenoxaprop-p-ethyl herbicide in commercial formulations and agricultural samples
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A simple spectrophotometric method was developed for determination of fenoxaprop-p-ethyl herbicide in agricultural samples. The method is based on the acid hydrolysis of fenoxaprop-pethyl to form 6-chloro-2,3-dihydrobenzoxazol-2- one (CDHB) and ethyl 2-(4-hydroxyphenoxy) propionate (EHPP). The 6-chloro-2,3- dihydrobenzoxazol-2-one was used as a coupling reagent in diazotization reaction. The absorbance of the azo dye was measured at 430 nm. The reaction conditions were optimized for hydrolysis as well as for the diazotization reaction. The Beer's law was obeyed over the concentration range of 0.2-25 μg mL-1 with molar absorptivity of 1.4 × 104L mol -1 cm-1. The limit of detection (LOD) and limit of quantification (LOQ) were found to be 0.029 and 0.098g μg mL-1, respectively The method has been successfully applied to the determination of fenoxaprop-p-ethyl commercial formulations and various agricultural samples. The % recoveries were found in the range of 95-97%.
- Shah, Jasmin,Jan, Muhammad Rasul,Shehzad, Farhat-Un-Nisa,Muhammad, Mian
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experimental part
p. 537 - 541
(2010/11/05)
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- More toxic and photoresistant products from photodegradation of fenoxaprop-p-ethyl
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The photodegradation pathway of the commonly used herbicide fenoxaprop-p-ethyl (FE) was elucidated, and the effects of the photodegradation on its toxicity evolution were investigated. Under solar irradiation, FE could undergo photodegradation, and aceton
- Lin, Jing,Chen, Jingwen,Wang, Ying,Cai, Xiyun,Wei, Xiaoxuan,Qiao, Xianliang
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experimental part
p. 8226 - 8230
(2010/03/30)
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- Benzimidazolidinone derivatives as muscarinic agents
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Benzimidazolidinone derivative compounds, which increase acetylcholine signaling or effect in the brain, and highly selective muscarinic agonists, particularly for the M1 and/or M4 receptor subtypes, pharmaceutical compositions comprising the same, as well as methods of treating psychosis using these compounds are disclosed.
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Page/Page column 17
(2010/02/06)
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- Reexamination of the Thermolytic Rearrangement of 4-Halophenyl Azides to 2-Aminophenols and other Products
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The halogenation of derivatives of 2-aminophenol with N-chloro- and N-bromosuccinimides at ambient temperatures in acetic acid was studied.With the necessary compounds available, a reexamination of the thermolytic rearrangement of 2-halophenyl azides to 2-aminophenols and other products was undertaken.It is certain that the rearrangement of 4-halophenyl azides to 2-aminophenols occurs but the products identified in this study differ significantly from those reported previously by Suschitzky et al. (1963, 1966). Keywords: Acetylated-2-amino-5-halophenols; 2-Acetamido-5-haloanisoles; 6-Halo-2-methylbenzoxazoles; 6-Halobenzoxazolones; 6-Halotriacetylaminophenols; 1H-NMR spectra; Fungicidal activity.
- Gershon, H.,Clarke, D. D.,Gershon, M.
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p. 367 - 380
(2007/10/02)
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- Analogues of the Cyclic Hydroxamic Acid 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one: Decomposition to Benzoxazolinones and Reaction with β-Mercaptoethanol
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Analogues of the aglucones of naturally occurring cyclic hydroxamic acids (2,4-dihydroxy-1,4-benzoxazin-3-ones) from Gramineae (Poaceae) have been synthesized by the reductive cyclization of the ring-substituted methyl α-(o-nitrophenoxy)-α-methoxyacetates, followed by demethylation of the C-2 methoxy group with BBr3 or BCl3 to reveal the 2-hydroxy group.A structure-activity series was produced by varying the substituent at C-7 on the aromatic ring .The pKa values for the hydroxamic acid and the phenol moieties were determined for each member of the C-7 series.They correlated well with ? in a linear free energy relationship (LFER) yielding values of ρ = 0.71 (with ?p) for pKa1 (the hydroxamic acid) and ρ = 1.6 (with ρm) for pKa2 (the phenol).A LFER also existed between the rate constants for the unimolecular decomposition of these hydroxamic acids to benzoxazolinones and ?+ (ρ = -1.1).The rates of hydroxamic acid reduction to lactams by β-mercaptoethanol were also investigated.It was found that only compounds with electron-rich aromatic rings and specifically an oxa functionality para to the hydroxamic acid nitrogen atom (compounds 1 and 3 - 5) had measurable rates of reduction. 1H NMR spectra recorded during this reaction in D2O buffers (pD 9), however, showed that compounds 1, 2, 6 - 9 (the only ones investigated) formed a hemithioacetal at C-2 even though only 1 has a measurable rate of reduction by the same thiol.The remarkable rate enhancement provided by an oxa functionality suggests that reduction occurs by direct attack of thiolate on the hydroxamic nitrogen of a resonance-stabilized ion pair.
- Atkinson, Jeffrey,Morand, Peter,Arnason, John T.,Niemeyer, Hermann M.,Bravo, Hector R.
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p. 1788 - 1800
(2007/10/02)
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