- A Convenient One-Pot Synthesis of 1,5-Disubstituted Tetrazoles Containing an Amino or a Carboxy Group
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Abstract: A convenient method is proposed for constructing the tetrazole ring by a one-pot reaction of amides with phosphorus oxychloride and sodium azide. A series of 1,5-disubstituted tetrazoles containing an amino or a carboxy group, which present interest as buildings blocks for the synthesis of biologically active substances, were obtained.
- Obushak, M. D.,Pokhodylo, N. T.,Shyyka, O. Ya.
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p. 802 - 812
(2020/07/03)
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- A meclofenoxate hydrochloride preparation method
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The invention discloses a meclofenoxate hydrochloride of the preparation method, comprises the following steps: (A) will acid with thionyl chloride in chlorobenzene acyl chloride reaction, to obtain the chlorophenoxy acetyl chloride; (B) step (A) to get chlorophenoxy acetyl chloride and dimethyl amino ethanol by condensation reaction to obtain the meclofenoxate free alkali; (C) step (B) to obtain the free base of the salt-forming acid salt, thermal insulation and filtering to obtain the hydrochloride. The invention easy availability of raw materials, the reaction temperature is low, the operation is convenient, the crude product of high purity, stable quality, the present invention provides a more easy operation, more environmentally friendly, more economic meclofenoxate hydrochloride synthetic pathway.
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-
Paragraph 0035-0040; 0041; 0044
(2019/03/25)
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- 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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- Esterquat herbicidal ionic liquids (HILs) with two different herbicides: Evaluation of activity and phytotoxicity
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Herbicidal ionic liquids (HILs) constitute a new concept in crop protection products. Their main advantage is the potential to combine the efficiency of traditional herbicides with low vapour pressure and adjustable water solubility which leads to improved environmental safety in the agricultural sector. Among many strategies to obtain new HILs, esterquats seem to be well suited for modification since both the cation and anion may be constituents of herbicides. In the framework of this study 16 new esterquat HILs were synthetized based on standard herbicides: 2,4-D, MCPA, MCPP, 4-CPA, Clopyralid and Dicamba. Germination tests performed on agricultural soil using cornflower indicated the best two HILs. Furthermore, analysis of the toxicological effects of HILs on wheat plants revealed an additional advantage of the two selected HILs. The glutathione (GSH) content and glutathione S-transferase (GST) activity showed a lower oxidative stress level in wheat plants treated with examined HILs, respectively, in comparison to a mixture of reference compounds. Finally the Ames test was applied in order to analyse the mutagenic activity of the two selected HILs.
- Syguda, Anna,Gielnik, Anna,Borkowski, Andrzej,Wo?niak-Karczewska, Marta,Parus, Anna,Piechalak, Aneta,Olejnik, Anna,Marecik, Roman,?awniczak, ?ukasz,Chrzanowski, ?ukasz
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supporting information
p. 9819 - 9827
(2018/06/18)
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- Structure-based design, synthesis and evaluation of 2,4-diaminopyrimidine derivatives as novel caspase-1 inhibitors
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Interleukin-1β converting enzyme contributes in various inflammatory and autoimmune diseases by maturing pro-inflammatory cytokines IL-1β, IL-18 and IL-33. Therefore, inhibition caspase-1 may provide a potential therapeutic strategy for the treatment of chronic inflammatory diseases. Here we have reported structure-based design, synthesis and biological evaluation of 2,4-diaminopyrimidine derivatives (6a-6w) as potential caspase-1 inhibitors. Six compounds 6m, 6n, 6o, 6p, 6q and 6r showed significant enzymatic inhibition with IC5 0 ranging from 0.022 to 0.078 μM. These compounds also displayed excellent cellular potency at sub-micromolar concentration. Moreover, molecular docking studies provided the useful binding insights specific for caspase-1 inhibition. All these results indicated that compounds 6m, 6n and 6o could be potential leads for the development of newer caspase-1 inhibitors as anti-inflammatory agents.
- Patel, Shivani,Modi, Palmi,Ranjan, Vishal,Chhabria, Mahesh
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p. 258 - 268
(2018/04/05)
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- Synthesis and Biological Activity of 4-[(Substituted Phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one
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A series of novel 4-[(substituted phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o were synthesized. Their structures were confirmed by IR,1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 4b, 4c, 4f, 4h, 4i, and 4j possess 90–100% inhibition against the growth of roots of both rape and barnyard grass at 10 mg/L. Moreover, the title compounds 4f, 4g, and 4h possess 75–89% inhibition against Botrytis cinerea at the concentration of 50 mg/L.
- Sheng, Xijun,Zhou, Yuan,Zhang, Shasha,Peng, Hao,He, Hongwu
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p. 165 - 170
(2017/02/03)
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- Synthesis and Antimicrobial Activity of Novel 2-Substituted Phenoxy-N-(4-substituted Phenyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-yl)acetamide Derivatives
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A series of 2-substituted phenoxy-N-(4-substituted phenyl-5-(1H-1,2,4-triazol-1-yl)thiazole-2-yl)acetamide derivatives 8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r, 8s, 8t was synthesized by the reaction of phenoxyacetyl chloride 7 with intermediate 4-substituted phenyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine 5. Their structures were confirmed by 1H NMR, 13C NMR, MS, IR, and elemental analyses. The synthesized compounds were also screened for their antimicrobial activity against three types of plant fungi (Gibberella zeae, Phytophthora infestans, and Paralepetopsis sasakii) and two kinds of bacteria [Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac)] showing promising results. In particular, 8b, 8f, 8g, and 8h exhibited excellent antibacterial activity against Xoo, with 50% effective concentration (EC50) values of 35.2, 80.1, 62.5, and 82.1 μg/mL, respectively, which are superior to the commercial antibacterial agent bismerthiazol (89.9 μg/mL). The preliminary structure–activity relationship studies of these compounds are also briefly described.
- Liao, Guo-Ping,Zhou, Xia,Xiao, Wei,Xie, Yan,Jin, Lin-Hong
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p. 1506 - 1513
(2017/03/27)
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- Discovery and development of a novel class of phenoxyacetyl amides as highly potent TRPM8 agonists for use as cooling agents
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The paper presents the activity trends for a novel series of phenoxyacetyl amides as human TRPM8 receptor agonists. This series encompasses in vitro activity values ranging from the micromolar to the picomolar levels. Sensory evaluation of these molecules highlights their relevance as cooling agents for oral applications. The positive outcome of the complete evaluation of N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide resulted in its approval for Generally Recognized As Safe (GRAS) status by the Flavor & Extract Manufacturer Association (FEMA) as FEMA 4809.
- Noncovich, Alain,Priest, Chad,Ung, Jane,Patron, Andrew P.,Servant, Guy,Brust, Paul,Servant, Nicole,Faber, Nathan,Liu, Hanghui,Gonsalves, Nicole S.,Ditschun, Tanya L.
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p. 3931 - 3938
(2017/07/27)
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- Synthesis of novel 1,2,5-oxadiazoles and evaluation of action against Acinetobacter baumannii
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With multidrug resistant bacteria on the rise, novel antibiotics are becoming highly sought after. In 2008, eleven compounds were identified by high throughput screening as inhibitors of BasE, a key enzyme of the non-ribosomal peptide synthetase pathway found in Acinetobacter baumannii. Herein, we describe the preparation of four structurally similar heterocyclic lead compounds from that study, including one 1,2,5-oxadiazole. A further library of 30 analogues containing the oxadiazole moiety was then generated. All compounds were screened against Acinetobacter baumannii and their minimum inhibitory concentration data is reported, with (E)-3-(2-hydroxyphenyl)-N-(4-methyl-1,2,5-oxadiazol-3-yl)acrylamide 32 found to have an MIC of 0.5 mM. This work provides the foundation for further investigation of 1,2,5-oxadizoles as novel inhibitors of A. baumannii.
- Christoff, Rebecca M.,Murray, Gerald L.,Kostoulias, Xenia P.,Peleg, Anton Y.,Abbott, Belinda M.
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supporting information
p. 6267 - 6272
(2017/10/13)
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- Synthesis and Biological Activity of Ethyl 4-Alkyl-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylate
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(Chemical Equation Presented) A series of novel ethyl 4-(methyl or trifluoromethyl)-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylates 7a, 7b, 7c, 7d, 7e and 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra and elemental analysis. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal activities. Compared with the fluorine free compounds 7a, 7b, and 7e, the compounds bearing fluorine 8g, 8j, and 8q showed higher herbicidal activities with 70-100% inhibition against Capsella bursa-pastoris, Amaranthus restroflexus, and Eclipta prostrata at the dosage of 150 g/ha, which indicated that the trifluoromethyl on the thiazole ring was beneficial for the herbicidal activity. Furthermore, compounds 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were tested for fungicidal activity against Pseudoperonospora cubensis at 500 μg/mL. Compounds 8f and 8q showed the best fungicidal activity with more than 80% inhibition.
- Mo, Wenyan,Shi, Yanxia,He, Junbo,Li, Baoju,Peng, Hao,He, Hongwu
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p. 183 - 187
(2016/02/10)
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- Synthesis and biological evaluation of aryloxyacetamide derivatives as neuroprotective agents
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A series of new aryloxyacetamide derivatives 10a-s and 14a-m are designed and synthesized. Their protective activities against the glutamate-induced cell death were investigated in differentiated rat pheochromocytoma cells (PC12 cells). Most compounds exhibited neuroprotective effects, especially for 10m, 10r, 14b and 14c, which showed potential protection of PC12 cells at three doses (0.1, 1.0, 10 μM). MTT assay, Hoechst 33342/PI double staining, and high content screening (HCS) revealed that pretreatment of the cells with 10m, 10r, 14b and 14c has significantly decreased the extent of cell apoptosis in a dose-dependent manner. The results of western blot analysis demonstrated these compounds suppressed apoptosis of glutamate-induced PC12 cells via caspase-3 pathway. These compounds can be lead compounds for further discovery of neuroprotective agents for treating cerebral ischemic stroke. Basic structure-activity relationships are also presented.
- Zhong, Yan,Xu, Yi,Zhang, Ai-Xia,Li, Xiao-Feng,Xu, Zhao-Ying,Li, Ping,Wu, Bin
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supporting information
p. 2526 - 2530
(2016/07/07)
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- Synthesis and Herbicidal Activities of Sodium Methyl(α-(Substituted Phenoxyacetoxy)Alkyl)Phosphinates
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A series of sodium methyl(α-(substituted phenoxyacetoxy)alkyl)phosphinates was designed and synthesized. Their structures were confirmed by IR, 1H NMR and elemental analysis, and some of them were further confirmed by MS. The results of bioassay showed that most of title compounds exhibited moderate to good herbicidal activities against the root of barnyard grass and rape at 10~100 mg/L.
- Wang, Tao,Gao, Yujiao,Peng, Hao,He, Hongwu
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p. 972 - 977
(2015/08/04)
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- Synthesis and biological activity of 1-(Substituted phenoxyacetoxy)- 1-(pyridin-2-yl or thien-2-yl)methylphosphonates
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A series of novel O,O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates 6a-n and 7a-d were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 6a, 6c, 6l, 6m, and 7d possess 90-100% inhibition against most of the tested plants at the dosage of 1500 g ai/ha, whereas the title compounds 6b, 6g-h and 6n possess 92-100% inhibition against Fusarium oxysporum, Phyricularia grisea, Botrytis cinereapers, Gibberella zeae, Sclerotinia sclerotiorum, and Cercospora beticola at the concentration of 50mg/L.
- Wang, Tao,Wang, Wei,Peng, Hao,He, Hongwu
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p. 173 - 179
(2015/01/30)
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- Synthesis and Biological Activity of O-Methyl Methyl 1-(Substituted Phenoxyacetoxy)-1-(thien-2-yl)methylphosphinates
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A series of novel O-methyl methyl 1-(substituted phenoxyacetoxy)-1-(thien-2-yl)methylphosphinates 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 5c, 5d, and 5g possess 90-100% inhibition against the tested plants at the concentration of 10 mg/L and 100 mg/L, whereas the title compounds 5a, 5b, 5c, and 5h possess 70-94% inhibition against Phyricularia grisea and Sclerotinia sclerotiorum at the concentration of 50 mg/L.
- Wang, Tao,Peng, Hao,He, Hongwu
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p. 1260 - 1263
(2015/08/06)
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- Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus
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In this study, 2-arylbenzo[b]furan-containing derivatives moracin C (1) and moracin M (4), the natural products from Artocarpus, have been synthesized in highest overall yield to date (1, 7 steps with an overall yield of 41.9%; 4, 6 steps with an overall yield of 56.3%), and we also report the first total synthesis of artoindonesianin B-1 (2), another member of this family, in the same route (8 steps with an overall yield of 11.3%). This discovery provides a concise route for preparing enough amounts of 1, 2, and 4 as well as 2-arylbenzo[b]furan-containing natural product-like analogs (71-74) to explore the biological potential.
- Wu, Deyan,Mei, Hanbing,Tan, Ping,Lu, Weiqiang,Zhu, Jin,Wang, Wei,Huang, Jin,Li, Jian
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supporting information
p. 4383 - 4387
(2015/06/22)
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- Synthesis, structure and biological activities of novel triazole compounds containing Ester Group
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Novel triazole compounds containing ester group were synthesized. Their structure were confirmed by means of IR, 1H NMR and elemental analysis. The single crystal structure of compound (1H-1,2,4-triazol-1-yl)methyl 3-(2,4-dichlorophenyl)propanoate (compound 3c) was determined via X-ray diffraction. It crystallizes in a monoclinic system with space group P2(1)/c, a = 1.0814(2) nm, b = 0.64514(13) nm, c = 1.8698(4) nm, β = 101.05(3)°, Z = 4, V = 1.2802(5) nm3, Dc = 1.557 Mg/m3, μ = 0.508 mm-1, F(000) = 616 and final R1 = 0.0700. Intermolecular hydrogen-bond and φ-φ stacking interactions exit in the lattice, facilitating the stabilization of crystal structure. The results of the biological test show that these compounds have some fungicidal activity.
- Yang, Shuang-Hua,Zhai, Zhi-Wei,Zhang, Shao-Wen
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p. 883 - 886
(2014/06/09)
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- Synthesis, Structure, and Properties of the 2-[5-(Aryloxyacetyl)-Amino-1,3,4-Thiadiazol-2-Ylthio] Propionate Derivatives
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A series of novel 2-[5-(aryloxyacetyl)-amino-1,3,4-thiadiazol-2-ylthio] propionate derivatives were synthesized in high yield, and their structures were characterized by IR, 1H NMR, 13C NMR, and elemental analysis, coupled with one selected single-crystal X-ray structure determination. The herbicidal activities of target compounds were assessed. The preliminary bioassay results showed that some compounds exhibited moderate to strong herbicidal symptoms in preemergence and postemergence tests. At 150 g/ha, S. tritici. show tolerance, while E. crus-galli L., E. Dahuricus, A. retroflexus, and C. glaucum L. were killed or severely injured. The activity of some compounds was comparable to the commercial herbicide 2,4-D. A suitable electron-withdrawing substituent at the 2-and/or 4-position of the phenyl ring was essential for high herbicidal activity. Moreover, the antifungal activities of the compounds have also been studied. The compounds were found to possess broad-spectrum antifungal activity.
- Hu, Bing,Zhai, Yue-Yuan,Zhang, Ling,Zhang, You-Ming,Wei, Tai-Bao
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p. 1337 - 1345
(2015/10/29)
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- BENZIMIDAZOLE DERIVATIVES AS SELECTIVE BLOCKERS OF PERSISTENT SODIUM CURRENT
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The present invention is directed to a compound of Formula (I) or a pharmaceutically acceptable salt thereof; wherein R, R1, R2, R3, R4, m, and n are as defined herein, to pharmaceutical compositions comprising said compound, and to methods of treating diseases or conditions mediated by elevated persistent sodium current, such as an ocular disorder, multiple sclerosis, seizure disorder, and chronic pain.
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Page/Page column 38
(2013/07/19)
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- Oxadiazole-isopropylamides as potent and noncovalent proteasome inhibitors
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Screening of the 50 000 ChemBridge compound library led to the identification of the oxadiazole-isopropylamide 1 (PI-1833) which inhibited chymotrypsin-like (CT-L) activity (IC50 = 0.60 μM) with little effects on the other two major proteasome proteolytic activities, trypsin-like (T-L) and postglutamyl-peptide-hydrolysis-like (PGPH-L). LC-MS/MS and dialysis show that 1 is a noncovalent and rapidly reversible CT-L inhibitor. Focused library synthesis provided 11ad (PI-1840) with CT-L activity (IC50 = 27 nM). Detailed SAR studies indicate that the amide moiety and the two phenyl rings are sensitive toward modifications. Hydrophobic residues, such as propyl or butyl in the para position (not ortho or meta) of the A-ring and a m-pyridyl group as B-ring, significantly improve activity. Compound 11ad (IC50 = 0.37 μM) is more potent than 1 (IC50 = 3.5 μM) at inhibiting CT-L activity in intact MDA-MB-468 human breast cancer cells and inhibiting their survival. The activity of 11ad warrants further preclinical investigation of this class as noncovalent proteasome inhibitors.
- Ozcan, Sevil,Kazi, Aslamuzzaman,Marsilio, Frank,Fang, Bin,Guida, Wayne C.,Koomen, John,Lawrence, Harshani R.,Sebti, Sa?d M.
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supporting information
p. 3783 - 3805
(2013/06/27)
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- PROTEASOME CHYMOTRYPSIN-LIKE INHIBITION USING PI-1833 ANALOGS
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Focused library synthesis and medicinal chemistry on an oxadiazole- isopropylamide core proteasome inhibitor provided the lead compound that strongly inhibits CT-L activity. Structure activity relationship studies indicate the amide moiety and two phenyl rings are sensitive toward synthetic modifications. Only para-substitution in the A-ring was important to maintain potent CT-L inhibitory activity. Hydrophobic residues in the A-ring?s para-position and meta-pyridyl group at the B- ring significantly improved inhibition. The meta-pyridyl moiety improved cell permeability. The length of the aliphatic chain at the para position of the A-ring is critical with propyl yielding the most potent inhibitor, whereas shorter (i.e. ethyl, methyl or hydrogen) or longer (i.e. butyl, propyl and hexyl) chains demonstrating progressively less potency. Introduction of a stereogenic center next to the ether moiety (i.e. substitution of one of the hydrogens by methyl) demonstrated chiral discrimination in proteasome CT-L activity inhibition (the S-enantiomer was 35-40 fold more potent than the R-enantiomer)
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Page/Page column 62
(2012/10/08)
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- Synthesis and biological activity of 2-Aryloxyacetylamino-2-Deoxy-D- Glucoses
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D-Glucosamine possesses extensive bioactivities including antibacterial, insecticidal and plant growth-regulating activities. A series of 2-aryloxyacetylamino-2-deoxy-D-glucoses have been synthesized by acylation of D-glucosamine with aryloxyacetyl chlorides and their plant growth-regulating activities were tested. The results show that these compounds bearing chlorine atom at para position of benzene ring have notable inhibiting activities against cotyledon rootage of cucumber which are comparable with that of 2,4-dichlorophenoxyacetic acid.
- Han, Liang,Zhu, Qiong-Yan,Jia, Jian-Hong,Li, Yu-Jin,Gao, Jian-Rong
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experimental part
p. 1223 - 1226
(2012/09/07)
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- Synthesis and herbicidal activity of 2-(Substituted phenoxyacetoxy)alkyl-5, 5-dimethyl-1,3,2-dioxaphosphinan-2-one
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A series of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2- dioxaphosphinan-2-ones IIa-s were designed and synthesized on the basis of the previous work for the modification of alkylphosphonates I, and their structures were confirmed by 1H NMR, 31P NMR, 13C NMR, IR, MS, and elemental analysis. Their herbicidal activities against seven species of weeds were evaluated in a greenhouse. A part of the title compounds such as IIa-g, IIk, IIo, and IIr exhibited significant postemergence herbicidal activity against Abutilon theophrasti, Brassica juncea, Amaranthus retroflexus, and Eclipta prostrate at a dosage of 150 g ai/ha. Structure-activity relationship analyses indicated that the introduction of a phosphorus-containing heterocyclic ring had a favorable effect on herbicidal activity, and their herbicidal activity could be further increased by a reasonable combination of X, Y, and R in parent structure II. It could be found that the title compounds IIa 2-[(2,4-dichlorophenoxy)acetoxy](methyl)methyl-5,5-dimethyl-1,3, 2-dioxaphosphinan-2-one and IIr 2-[(4-chloro-2-methyl-phenoxy)acetoxy](methyl) methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one possess high activity and a broad spectrum against all of the test broadleaf weeds with 70-100% inhibition effect at a dosage of 75 g ai/ha, and the title compounds IIa and IIr are safe for corn and wheat at a dosage of 150 g ai/ha. Furthermore, the title compound IIa possesses low rat toxicity. These results suggest that the title compounds IIa and IIr could be potential and selective postemergence herbicides for further development.
- Wang, Wei,He, Hong-Wu,Zuo, Na,He, Hai-Feng,Peng, Hao,Tan, Xiao-Song
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experimental part
p. 7581 - 7587
(2012/10/08)
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- Studies of O,O-Dimethyl α-(2,4-Dichlorophenoxyacetoxy) ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex
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On the basis of the previous work for optimization of O,O-diethyl α-(substituted phenoxyacetoxy)alkylphosphonates, further extensive syntheticmodifications were made to the substituents in alkylphosphonate and phenoxymoieties of the title compounds. New O,O-dimethyl α-(substituted phenoxyacetoxy)alkylphosphonates were synthesized as potential inhibitors of pyruvate dehydorogenase complex (PDHc). Their herbicidal activity and efficacy in vitro against PDHc were examined. Some of these compounds exhibited significant herbicidal activity and were demonstrated to be effective inhibitors of PDHc from three different plants. The structure-activity relationships of these compounds including previously reported analogous compoundswere studied by examining their herbicidal activities. Both inhibitory potency against PDHc and herbicidal activity of title compounds could be increased greatly by optimizing substituent groups of the title compounds. O,O-Dimethyl α-(2,4- dichlorophenoxyacetoxy)ethylphosphonate (I-5), which acted as a competitive inhibitor of PDHc with much higher inhibitory potency against PDHc from Pisum sativum and Phaseolus radiatus than from Oryza sativa, was found to be themost effective compound against broadleaf weeds and showed potential utility as herbicide.
- He, Hong-Wu,Yuan, Jun-Lin,Peng, Hao,Chen, Ting,Shen, Ping,Wan, Shu-Qing,Lee, Yanjun,Tan, Hong-Liang,He, Ya-Hui,He, Jun-Bo,Li, Yan
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scheme or table
p. 4801 - 4813
(2011/12/04)
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- Synthesis and biological activity of α-oxo-2-pyridyl methyl phosphinates
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In an attempt to discover novel compounds with high activity and low toxicity, a series of new O,O-dimethyl-α-(substituted phenoxyacetoxy)-2- pyridyl methyl phosphinates, 5a-5h, have been designed and synthesized by the reaction of substituted phenoxyacetic chloride with 1-hydroxy-2-pyridyl methyl phosphinate, The structures of all new compounds were characterized by elementary analysis, IR, 1H NMR, and MS spectroscopies. The results of preliminary bioassay indicate that most of the target compounds have excellent inhibitory activities on barnyard grass and rape. Copyright Taylor & Francis Group, LLC.
- Wang, Tao,He, Hong Wu
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experimental part
p. 1884 - 1891
(2009/09/06)
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- Synthesis of new plant growth regulator: N-(Fatty acid) O-aryloxyacetyl ethanolamine
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N-(Fatty acyl) O-aryloxyacetyl ethanolamines, prepared from N-acylethanolamine (NAE) and aryloxyacetic acid, were tested for plant growth regulating activity. Compared with N-stearoylethanolamine, most compounds exhibit improved plant growth stimulating activity. In particular, those with chlorine on aryl ring show better activity than 2,4-dichlorophenyloxyacetic acid in stimulating hypocotyls elongation of rape which indicates that chlorine on aryl ring appears significant. Moreover, these derivatives display improved solubility.
- Han, Liang,Gao, Jian-Rong,Li, Zheng-Ming,Zhang, Yun,Guo, Wei-Ming
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p. 3231 - 3234
(2008/02/07)
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- An efficient acid- and metal-free one-pot synthesis of benzothiazoles from carboxylic acids
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Carboxylic acids are converted to benzothiazoles in a one-pot reaction with thionyl chloride followed by treatment with 2-aminothiophenol under acid- and catalyst-free conditions. Georg Thieme Verlag Stuttgart.
- Rudrawar, Santosh,Kondaskar, Atul,Chakraborti, Asit K.
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p. 2521 - 2526
(2007/10/03)
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- Piperazin-2-one amides as inhibitors of factor xa
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Novel piperazin-2-one containing compounds of general formulae (I) or (II), including their pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivative having activity against mammalian factor Xa arc described. Compositions containing such compounds are also described. The compounds and the compositions are useful in vitro or in vivo for preventing or treating conditions in mammals characterized by undesired thrombosis.
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- Synthesis and antimicrobial activity of some novel 2-(p-substituted-phenyl)-5-substituted-carbonylaminobenzoxazoles.
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A series of 2-(p-substituted-phenyl)-5-substituted-carbonylamino benzoxazole derivatives (5-22) was synthesized and their antimicrobial activities determined in comparison to several control drugs. The synthesized compounds were tested in vitro against Staphylococcus aureus, Streptococcus faecalis and Bacillus subtilis as Gram-positive, Pseudomonas aeruginosa and Escherichia coli as Gram-negative bacteria and the yeast Candida albicans. Microbiological results showed that the compounds possessed a diffuse spectrum of antibacterial activity against these microorganisms. Compound 9 which bears a phenylacetamido moiety at position 5 and a 4-fluorophenyl group at the 2-position of benzoxazole ring was the most active derivative against S. aureus, S. faecalis and P. aeruginosa with a MIC value of 12.5 microg/ml. Compound 11 provided higher potency than the other tested compounds against B. subtilis at a MIC value of 12.5 microg/ml. Compounds 5-22 showed antifungal activity against C. albicans with MIC values between 50 and 12.5 microg/ml.
- Arpaci, Ozlem Temiz,Oren, Ilkay,Altanlar, Nurten
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p. 175 - 181
(2007/10/03)
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- 2-(4-R-Phenoxy/phenylthio)alkanoic esters of l-lupinine
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Considering the great pharmacological interest in phenoxy/phenylthioalkanoic esters of open-chain or cyclic aminoalcohols, a set of ten such esters of lupinine was prepared. Initially, their ability to displace [3H]QNB from rat brain preparation was investigated. With the exception of two, all the prepared esters exhibited good affinity to muscarinic receptors (on a non-selective basis), with pKi in the range 6.67-7.68.
- Sparatore, Anna,Sparatore, Fabio
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p. 169 - 174
(2007/10/03)
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- Design, synthesis and antihistaminic (H1) activity of some condensed 3- aminopyrimidin-4(3H)-ones
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A novel series of condensed 3-amino-2-(substituted)methylpyrimidin- 4(3H)-ones is reported with potential H1 receptor antagonistic activity. The IC50 values for 23 compounds were found to be in the micromolar range. Five lead compounds (10c, e, g, r and t), when evaluated by the in vivo method were found to protect guinea-pigs from the histamine induced asphyxia and antagonized histamine in a competitive and reversible manner. With a pA2 value of 8.7 and protection time of 9.5 min (in vivo test), compound 10g was the most active amongst these five compounds. The isosteric replacement of the side chain -NH- in series 1, by oxygen and -NHSO2- functions, was undertaken to investigate the role of two amino functions in the receptor binding. This isosteric replacement with -O- does not affect the antihistaminic activity and the sedative potential of the series. Preliminary molecular modelling, studies indicate that the compounds with -NHSO2- in the side chain exhibit a closer fit with temelastine than their -O- isosteres. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
- Shishoo, Chamanlal J.,Shirsath, Vikas S.,Rathod, Ishwarsinh S.,Yande, Vikas D.
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p. 351 - 358
(2007/10/03)
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- Synthesis of N- 2-pyrrolidinone as antimicrobial agent
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Several N- 2-pyrrolidinones have been synthesised and screened for their antibacterial and antifungal activities. their structures have been elucidated on the basis of elemental analysis and spectral data.
- Bhatt, P.,Srivastava, S. D.,Mehta, P.
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p. 514 - 516
(2007/10/03)
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- Synthesis and microbiological activity of some novel N-(2-hydroxyl-5- substitutedphenyl)benzacetamides, phenoxyacetamides and thiophenoxyacetamides as the possible metabolites of antimicrobial active benzoxazoles
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Synthesis of some novel N-(2-hydroxyl-5- substitutedphenyl)benzacetamides, phenoxyacetamides and thiophenoxyacetamides (5a-k) were described in order to determine their in vitro antimicrobial activity against 3 Gram-positive, 3 Gram-negative bacteria and the fungus Candida albicans comparing with several control drugs. The derivative 5e was found active at a MIC value of 25μg/ml against the whole tested Gram- positive bacteria strains and the Gram-negative microorganism Klebsiella pneumoniae. Moreover, the synthesized compounds 5a-k exhibited significant antibacterial activity against the enterobacter Pseudomonas aureginosae when compared to the control drugs. For the antifungal activity against C. albicans, the compound 5k was found more active than the other synthesized derivatives. On the other hand, the antimicrobial activity of some of these acetamide derivatives (5c, 5d, 5e, 5j and 5k) which are the possible metabolites of benzoxazoles, were also compared with their cyclic analogues 6-10. However, most of the MIC values of the benzoaxazole derivatives provided better activity than the compared acetamides, while some others of the acetamide derivatives possessed either one fold improved (5d, 5e and 5j) or the same potency (5c, 5d, 5e, 5j and 5k) against the tested microorganisms.
- Yalcin,Kaymakcioglu,Oren,Sener,Temiz
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p. 685 - 689
(2007/10/03)
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- Synthesis of some new benzimidazole-5(6)-carboxylic acids
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The title compounds, 1,2-dialkyl-benzimidazole-5(6)-carboxylic acids 34-45 were prepared at four steps; 1) preparation of mono amide derivatives 1-11 by the reaction of methyl 3,4-diaminobenzoate and substituted phenyl or phenoxyacetic acid chlorides; 2) preparation of the methyl benzimidazolecarboxylates 12-22, with zinc chloride and dry hydrogen chloride gas; 3) alkaline hydrolysis of the esters 23-33; and 4) substitution of the imidazole ring with benzyl or p-fluorobenzyl bromide, in alkali medium. 2-Aryl-benzimidazole-5(6)-carboxylic acids 50-53 were prepared via the oxidative condensation of 3,4-diaminobenzoic acid and aromatic aldehydes with cupric ion.
- Goker,Olgen,Ertan,Akgun,Ozbey,Kendi,Topcu
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p. 1767 - 1773
(2007/10/03)
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- NEW AMINOPYRIMIDINONIC DERIVATIVES WITH POTENTIAL BIOLOGICAL ACTIVITY
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In the industrial synthesis of fungicide, ethyrimol (I) (5-butyl-2-ethylamino-6-methyl-4-pyrimidinol), starting from ethylguanidine nitrate and butylacetoacetic ester, a by product (15 percent of the main product) was also formed: the 2-amino-5-butyl-3-ethyl-4-pyrimidinone (II). In order to render valuable this by-product by means of some of its potentially biologic active derivatives, its 2-amino function was used. By acylation with phenoxyacetyl chlorides, tosyl chloride, p-acetylaminobenzenesulfonic chloride, the corresponding amides were obtained. The amino function was also replaced by the hydroxyl and chlorine groups. With phosgene the N,N-disubstituted urea was obtained. The new compounds were characterized by means of 1H-NMR and IR spectra, some of them proving a biological activity.
- Mager, Sorin,Cristea, I.,Craciun, Liliana,Irimie, F.,Diudea, M.
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p. 665 - 670
(2007/10/03)
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- Synthesis of some new 2-(phenoxyacetylthio)-3-aryl-6-bromo- or 6,8-dibromoquinazoline-4(3H)-ones as possible AChE inhibitors
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Sixteen new 2-(phenoxyacetylthio)-3-aryl-6-bromo- or -6,8-dibromoquinazolines were synthesized by condensation of various phenoxyacetyl chlorides with mercaptoquinazolines. Their inhibitory properties towards choline esterase and their bactericidal activities were studied in vitro. Nine of the compounds exhibited (>50%) choline esterase inhibition, whereas the antibacterial screening showed moderate results.
- Hajela Km.,Sengupta,Shanker,Doval
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p. 431 - 434
(2007/10/02)
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