- Synthesis and antibacterial activity of pyridinium-tailored 2,5-substituted-1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives
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By introducing the pyridinium group into 2,5-substituted-1,3,4-oxadiazole, a series of pyridinium-tailored 2,5-substituted-1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives were obtained, and their antibacterial activities were evaluated via turbidimeter test in vitro. The bioassays reveal that most of the target compounds exhibit better inhibition activities against pathogen Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri than positive controls bismerthiazol (CK1) or thiodiazole copper (CK2). Among them, I-8, I-10, I-12, II-10, II-12, III-10, and III-12 exert excellent inhibition activities against the three pathogenic bacteria with the half-maximal effective concentration (EC50) values ranging from 0.54 to 12.14 μg/mL. Our results demonstrate that pyridinium-tailored 1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives can serve as potential alternative bactericides for the management of plant bacterial diseases.
- Wang, Pei-Yi,Zhou, Lei,Zhou, Jian,Wu, Zhi-Bing,Xue, Wei,Song, Bao-An,Yang, Song
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Read Online
- Visible-light-induced selective aerobic oxidation of sp3 C-H bonds catalyzed by a heterogeneous AgI/BiVO4 catalyst
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An efficient oxidation of sp3 C-H bonds to esters and ketones has been developed using AgI/BiVO4 as the photocatalyst and O2 as the oxidant in water. Various substrates can be transformed into the desired esters and ketones in moderate to good yields. The synthetic utility of this approach has been demonstrated by gram-level experiments and consecutive oxidation experiments. A plausible mechanism has been proposed.
- Jiang, Li-Ya,Ming, Jing-Jing,Wang, Lian-Yue,Jiang, Yuan-Yuan,Ren, Lan-Hui,Wang, Zi-Cheng,Cheng, Wen-Chen
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supporting information
p. 1156 - 1163
(2020/03/11)
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- Synthesis, biological evaluation of benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety as potential anti-oxidant and anti-inflammatory agents
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Twenty benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety were synthesized and evaluated for their anti-oxidant and anti-inflammatory activities. Among these compounds, 8h and 8l were appeared to have high radical scavenging efficacies as 0.05 ± 0.02 and 0.07 ± 0.03 mmol/L of IC50 values in ABTS+[rad] bioassay, respectively. In anti-inflammatory tests, compound 8h displayed good activity with 57.35% inhibition after intraperitoneal administration, which was more potent than the reference drug (indomethacin). Molecular modeling studies were performed to investigate the binding mode of the representative compound 8h into COX-2 enzyme. In vitro enzyme study implied that compound 8h exerted its anti-inflammatory activity through COX-2 inhibition.
- Bai, Xue-Qian,Cui, Ming-Yue,Li, Chun-Shi,Liang, Cheng-Wu,Song, Ze-Wen,Wang, Hui-Yan,Zhang, Tian-Yi,Zheng, Xian-Jing
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- Visible light-induced transformation of aldehydes to esters, carboxylic anhydrides and amides
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A transition metal- and organophotocatalyst free synthesis of esters, carboxylic anhydrides and amides from aldehydes induced by visible-light has been reported. The proposed methodology can be carried out by the use of sunlight or artificial visible light as a blue LED source. The methodology has a very broad applicability and the desired products are obtained in very satisfactory yields.
- Gaspa, Silvia,Raposo, Inês,Pereira, Leonor,Mulas, Gabriele,Ricci, Pier Carlo,Porcheddu, Andrea,De Luca, Lidia
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p. 10711 - 10715
(2019/07/15)
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- Synthesis and biological activities of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety
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A series of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety were designed, synthesized and evaluated for their antibacterial, antifungal and antiviral activities. The bioassay results indicated that most of target compounds showed good antiviral activities against tobacco mosaic virus (TMV) and antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs). Especially, the anti-Xoo effect of title compounds 5k (N-(5-methoxybenzo[d]thiazol-2-yl)-2-((5-(2-tolyl)-1,3,4-thiadiazol-2-yl)thio)acetamide) and the anti-Rs effect of title compounds 5a (N-(5-nitrobenzo[d]thiazol-2-yl)-2-((5-(4-(trifluorom ethyl)phenyl)-1,3,4-thiadiazol-2-yl)thio)acetmide) respectively reached 52.4% and 71.6% at 100 μg/mL, which are superior to that of bismerthiazol (32.0% and 52.3%). In addition, the protective and inactivation activities of title compound 5i (N-(5-methoxybenzo [d]thiazol-2-yl)-2-((5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl)thio)acetamide) against TMV were 79.5% and 88.3%, respectively, which are better than that of ningnanmycin (76.4% and 86.8%). The above research showed that benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety may be used as potential molecular templates in searching for highly-efficient antiviral and antibacterial agents.
- Tang, Xu,Wang, Zhongbo,Zhong, Xinmin,Wang, Xiaobin,Chen, Lijuan,He, Ming,Xue, Wei
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p. 241 - 248
(2019/01/04)
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- Synthesis of Thiazolium-Labeled 1,3,4-Oxadiazole Thioethers as Prospective Antimicrobials: In Vitro and in Vivo Bioactivity and Mechanism of Action
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In this study, a type of thiazolium-labeled 1,3,4-oxadiazole thioether bridged by diverse alkyl chain lengths was constructed. The antimicrobial activity of the fabricated thioether toward plant pathogenic bacteria and fungi was then screened. Antibacterial evaluation indicated that title compounds possess specific characteristics that enable them to severely attack three phytopathogens, namely, Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri with minimal EC50 values of 0.10, 3.27, and 3.50 μg/mL, respectively. Three-dimensional quantitative structure-activity relationship models were established to direct the following excogitation for exploring higher active drugs. The in vivo study against plant bacterial diseases further identified the prospective application of title compounds as alternative antibacterial agents. The proteomic technique, scanning electron microscopy patterns, and fluorescence spectrometry were exploited to investigate the antibacterial mechanism. Additionally, some target compounds performed superior inhibitory actions against three tested fungal strains. In view of their simple molecular architecture and highly efficient bioactivity, these substrates could be further explored as promising surrogates for fighting against plant microbial infections.
- Wang, Ming-Wei,Zhu, Huai-He,Wang, Pei-Yi,Zeng, Dan,Wu, Yuan-Yuan,Liu, Li-Wei,Wu, Zhi-Bing,Li, Zhong,Yang, Song
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p. 12696 - 12708
(2019/11/19)
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- Rational Optimization and Action Mechanism of Novel Imidazole (or Imidazolium)-Labeled 1,3,4-Oxadiazole Thioethers as Promising Antibacterial Agents against Plant Bacterial Diseases
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The emergence and widespread occurrence of plant bacterial diseases that cause global production constraints have become major challenges to agriculture worldwide. To promote the discovery and development of new bactericides, imidazole-labeled 1,3,4-oxadiazole thioethers were first fabricated by integrating the crucially bioactive scaffolds of the imidazole motif and 1,3,4-oxadiazole skeleton in a single molecular architecture. Subsequently, a superior antibacterial compound A6 was gradually discovered possessing excellent competence against plant pathogens Xanthomonas oryzae pv oryzae and Xanthomonas axonopodis pv citri with EC50 values of 0.734 and 1.79 μg/mL, respectively. These values were better than those of commercial agents bismerthiazol (92.6 μg/mL) and thiodiazole copper (77.0 μg/mL). Further modifying the imidazole moiety into the imidazolium scaffold led to the discovery of an array of potent antibacterial compounds providing the corresponding minimum EC50 values of 0.295 and 0.607 μg/mL against the two strains. Moreover, a plausible action mechanism for attacking pathogens was proposed based on the concentration dependence of scanning electron microscopy, transmission electron microscopy, and fluorescence microscopy images. Given the simple molecular structures, easy synthetic procedure, and highly efficient bioactivity, imidazole (or imidazolium)-labeled 1,3,4-oxadiazole thioethers can be further explored and developed as promising indicators for the development of commercial drugs.
- Wang, Pei-Yi,Wang, Ming-Wei,Zeng, Dan,Xiang, Meng,Rao, Jia-Rui,Liu, Qing-Qing,Liu, Li-Wei,Wu, Zhi-Bing,Li, Zhong,Song, Bao-An,Yang, Song
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p. 3535 - 3545
(2019/03/26)
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- 5-Aryl-1,3,4-oxadiazol-2-ylthioalkanoic Acids: A Highly Potent New Class of Inhibitors of Rho/Myocardin-Related Transcription Factor (MRTF)/Serum Response Factor (SRF)-Mediated Gene Transcription as Potential Antifibrotic Agents for Scleroderma
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Through a phenotypic high-throughput screen using a serum response element luciferase promoter, we identified a novel 5-aryl-1,3,4-oxadiazol-2-ylthiopropionic acid lead inhibitor of Rho/myocardin-related transcription factor (MRTF)/serum response factor (SRF)-mediated gene transcription with good potency (IC50 = 180 nM). We were able to rapidly improve the cellular potency by 5 orders of magnitude guided by sharply defined and synergistic SAR. The remarkable potency and depth of the SAR, as well as the relatively low molecular weight of the series, suggests, but does not prove, that binding to the unknown molecular target may be occurring through a covalent mechanism. The series nevertheless has no observable cytotoxicity up to 100 μM. Ensuing pharmacokinetic optimization resulted in the development of two potent and orally bioavailable anti-fibrotic agents that were capable of dose-dependently reducing connective tissue growth factor gene expression in vitro as well as significantly reducing the development of bleomycin-induced dermal fibrosis in mice in vivo.
- Kahl, Dylan J.,Hutchings, Kim M.,Lisabeth, Erika Mathes,Haak, Andrew J.,Leipprandt, Jeffrey R.,Dexheimer, Thomas,Khanna, Dinesh,Tsou, Pei-Suen,Campbell, Phillip L.,Fox, David A.,Wen, Bo,Sun, Duxin,Bailie, Marc,Neubig, Richard R.,Larsen, Scott D.
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p. 4350 - 4369
(2019/05/08)
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- Discovery of Allosteric, Potent, Subtype Selective, and Peripherally Restricted TrkA Kinase Inhibitors
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Tropomyosin receptor kinases (TrkA, TrkB, TrkC) are activated by hormones of the neurotrophin family: nerve growth factor (NGF), brain derived neurotrophic factor (BDNF), neurotrophin 3 (NT3), and neurotrophin 4 (NT4). Moreover, the NGF antibody tanezumab has provided clinical proof of concept for inhibition of the TrkA kinase pathway in pain leading to significant interest in the development of small molecule inhibitors of TrkA. However, achieving TrkA subtype selectivity over TrkB and TrkC via a Type I and Type II inhibitor binding mode has proven challenging and Type III or Type IV allosteric inhibitors may present a more promising selectivity design approach. Furthermore, TrkA inhibitors with minimal brain availability are required to deliver an appropriate safety profile. Herein, we describe the discovery of a highly potent, subtype selective, peripherally restricted, efficacious, and well-tolerated series of allosteric TrkA inhibitors that culminated in the delivery of candidate quality compound 23.
- Bagal, Sharan K.,Omoto, Kiyoyuki,Blakemore, David C.,Bungay, Peter J.,Bilsland, James G.,Clarke, Philip J.,Corbett, Matthew S.,Cronin, Ciaran N.,Cui, J. Jean,Dias, Rebecca,Flanagan, Neil J.,Greasley, Samantha E.,Grimley, Rachel,Johnson, Eric,Fengas, David,Kitching, Linda,Kraus, Michelle L.,McAlpine, Indrawan,Nagata, Asako,Waldron, Gareth J.,Warmus, Joseph S.
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p. 247 - 265
(2018/05/07)
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- Direct oxidation of aldehydes to methyl esters with urea hydrogen peroxide and p-toluenesulfonyl chloride
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Combination of urea hydrogen peroxide and p-toluenesulfonyl chloride in methanol was proved to be facile and highly efficient for the oxidative methyl esterification of various aldehydes to the corresponding carboxylic methyl esters.
- Jeong, Deuk Jun,Lee, Su Bin,Lee, Jong Chan
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p. 725 - 728
(2017/12/28)
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- Solvent- and Metal-free Oxidative Esterification of Aromatic Aldehydes Using Urea-2,2-dihydroperoxypropane as a New Solid Oxidant
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Urea-2,2-dihydroperoxypropane as a noble and solid gem-dihydroperoxide derivative was used to transform various aromatic aldehydes to their corresponding benzoate derivatives in the presence of HBr under mild conditions at room temperature in high yields and short reaction times.
- Khosravi, Kaveh,Khalaji, Kobra,Naserifar, Shirin
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p. 303 - 309
(2017/03/27)
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- Development and Application of a Recyclable High-Load Magnetic Co/C Hybrid ROMP-Derived Benzenesulfonyl Chloride Reagent and Utility of Corresponding Analogues
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The development and application of high-load, recyclable magnetic Co/C hybrid ROMP-derived benzenesulfonyl chloride and analogues is reported. The regeneration and utility of these reagents in the methylation/alkylation of various carboxylic acids is demonstrated via efficient retrieval of the magnetic reagent with a neodymium magnet. Additional reactions employing the analogue sulfonic acid and in situ generated magnetic benzenesulfonyl azide are also reported.
- Faisal, Saqib,Zang, Qin,Maity, Pradip K.,Brandhofer, Agnes,Kearney, Patrick C.,Reiser, Oliver,Grass, Robert N.,Stoianova, Diana,Hanson, Paul R.
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supporting information
p. 2274 - 2277
(2017/05/12)
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- ARYL AND HETEROARYL ETHER COMPOUNDS AS ROR GAMMA MODULATORS
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Provided are compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein ring A, ring B, L, R 1, R 2, R a, R b, n, x, y and z are as defined herein, which are active as modulators of retinoid-related orphan receptor gamma t (RORyt).
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Page/Page column 33-34
(2017/04/11)
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- Thermolysis of 2-diazo-3-aryl ketoesters: New route to α-aryl malonates and aromatic esters
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Thermochemical excitation enabled efficient α-aryl malonates synthesis from 2-diazo-3-aryl ketoesters and alcohols under transition metal-free reaction conditions. Furthermore, an unusual C[sbnd]C bond cleavage and C[sbnd]O/(N) bond formation occurred whe
- Zhang, Zhao,Tang, Mengyao,Zang, Lei,Zou, Liang-Hua,Li, Jie
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supporting information
p. 5681 - 5684
(2016/11/28)
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- A simple, one-pot oxidative esterification of aryl aldehydes through dialkyl acetal using hydrogen peroxide
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A simple and an efficient one-pot procedure has been developed to synthesize various aryl carboxylic esters directly from aryl aldehydes using hydrogen peroxide without any catalyst. The reaction proceeds smoothly at room temperature. A preliminary investigation suggests the formation of dialkyl acetal as an intermediate during the reaction sequence.
- Devarajan,Vijayakumar,Ramalingam,Vijayaraghavan
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p. 5849 - 5858
(2016/06/01)
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- Synthesis and antiviral activity of novel thioether derivatives containing 1,3,4-oxadiazole/thiadiazole and emodin moieties
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A series of novel thioether derivatives containing 1,3,4-oxadiazole/thiadiazole and emodin moieties were designed and synthesized. The structures of the target compounds were confirmed by 1H NMR, 13C NMR, Infrared, and elemental analysis. The results of bioactivity analysis showed that most of the target compounds exhibited moderate to good antiviral activity against tobacco mosaic virus at a concentration of 500 mg/L. Especially, among the title compounds, Y2, Y8, and Y10 possessed appreciable curative activity in vivo, with inhibition rates of 50.51, 52.08, and 54.62%, respectively, which were similar to that of Ningnanmycin (53.40%).
- Dong, Liangrun,Song, Baojing,Wu, Jian,Wu, Zengxue,Zhu, Yunying,Chen, Xuewen,Hu, Deyu
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p. 904 - 907
(2016/07/06)
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- An efficient nonconventional glycerol-based solid acid catalyzed synthesis and biological evaluation of phosphonate conjugates of 1,2,4-triazole thiones
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A series of diethyl (3-((5-aryl-1H-1,2,4-triazol-3-yl)thio)propyl)phos-phonates (7a-t) has been synthesized in excellent yields by coupling diethyl (3-bromopropyl)phosphonate and 5-aryl-1H- 1,2,4-triazol-3-thiones employing an efficient, green and nonconventional heterogeneous SO3Hcarbon catalyst derived from glycerol. In addition, a facile and green approach for the esterification of carboxylic acids by utilizing glycerol-based solid acid catalyst has been reported. Structures of the synthesized compounds were characterized by IR, NMR and HRMS studies. These triazole derivatives were screened for their in vitro cytotoxicity using the standard MTT (3-(4,5-dimethylthiazol-2- yl)-2,5-diphenyltetra-zolium bromide) assay against a panel of five different human cancer cell lines (HeLa: Cervix, A549: Lung, A375: Skin, MDA-MB-231: Breast and T98G: Brain). The antimicrobial activities of the synthesized compounds were investigated against four bacterial strains: Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and three fungal strains: Aspergillus Niger, Aspergillus terreus, Aspergillus fumigatus. Preliminary results indicate that the compound 7f displayed maximum anticancer activity and the compounds 7d, 7e, 7f, 7m and 7q exhibited moderate antibacterial activity. The compounds 7g, 7h, 7o and 7p showed good antifungal activity with high inhibition zone diameter compared to the standard drug.
- Murty, Madugula S.R.,Katiki, Mohana R.,Rao, Busam R.,Narayanan, Sai S.,Anto, Ruby J.,Buddana, Sudhreer K.,Prakasham, Reddy S.,Devi, Bethala L.A.P.,Prasad, Rachapudi B.N.
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p. 968 - 981
(2016/10/31)
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- Rhodium-Catalyzed Double Alkyl-Oxygen Bond Cleavage: An Alkyl Transfer Reaction from Bis/Tris(o-alkyloxyphenyl)phosphine to Aryl Acids
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An unprecedented rhodium-catalyzed selective cleavage of double alkyl-oxygen bonds of bis/tris(o-alkyloxyphenyl)phosphine has been realized, in which P atom functions as a directing group and simple aryl acids are the methyl group acceptor to provide methyl esters and a quaternary phosphonium salt. The preliminary mechanism was investigated via an 18O labeling experiment and stoichiometric reaction between a Rh-A crystal and an aromatic acid.
- Zhou, Hui,Zhang, Jinlong,Yang, Huameng,Xia, Chungu,Jiang, Gaoxi
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supporting information
p. 3406 - 3412
(2016/10/21)
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- Oxygen-Controlled Catalysis by Vitamin B12-TiO2: Formation of Esters and Amides from Trichlorinated Organic Compounds by Photoirradiation
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An oxygen switch in catalysis of the cobalamin derivative (B12)-TiO2 hybrid catalyst for the dechlorination of trichlorinated organic compounds has been developed. The covalently bound B12 on the TiO2 surface transformed trichlorinated organic compounds into an ester and amide by UV light irradiation under mild conditions (in air at room temperature), while dichlorostilbenes (E and Z forms) were formed in nitrogen from benzotrichloride. A benzoyl chloride was formed as an intermediate of the ester and amide, which was detected by GC-MS. The substrate scope of the synthetic strategy is demonstrated with a range of various trichlorinated organic compounds. A photo-duet reaction utilizing the hole and conduction band electron of TiO2 in B12-TiO2 for the amide formation was also developed.
- Shimakoshi, Hisashi,Hisaeda, Yoshio
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supporting information
p. 15439 - 15443
(2016/01/26)
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- N-Heterocyclic Carbene-Mediated Oxidative Electrosynthesis of Esters in a Microflow Cell
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An efficient N-heterocyclic carbene (NHC)-mediated oxidative esterification of aldehydes has been achieved in an undivided microfluidic electrolysis cell at ambient temperature. Productivities of up to 4.3 g h-1 in a single pass are demonstrated, with excellent yields and conversions for 19 examples presented. Notably, the oxidative acylation reactions were shown to proceed with a 1:1 stoichiometry of aldehyde and alcohol (for primary alcohols), with remarkably short residence times in the electrolysis cell (13 s), and without added electrolyte. (Chemical Equation Presented).
- Green, Robert A.,Pletcher, Derek,Leach, Stuart G.,Brown, Richard C. D.
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supporting information
p. 3290 - 3293
(2015/07/15)
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- Synthesis and biological evaluation of new pyrazol-4-ylpyrimidine derivatives as potential ROS1 kinase inhibitors
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With the aim of discovering potent and selective kinase inhibitors targeting ROS1 kinase, we designed, synthesized and screened a series of new pyrazol-4-ylpyrimidine derivatives based on our previously discovered lead compound KIST301072. Compounds 6a-e and 7a-e showed good to excellent activities against ROS1 kinase, and seven out of tested compounds were more potent than KIST301072. Compound 7c was the most potent with IC50 of 24 nM. Moreover, compound 7c showed ROS1 inhibitory selectivity of about 170-fold, relative to that of ALK sharing about 49% amino acid sequence homology with ROS1 kinase in the kinase domain. In silico modeling of 7c at ROS1 active site revealed some essential features for ROS1 inhibitory activity. Based on this study as well as the previous studies, we could build a hypothetical model predicting the required essential features for ROS1 inhibitory activity. The model validity has been tested through a second set of compounds.
- Abdelazem, Ahmed Z.,Al-Sanea, Mohammad M.,Park, Byung Sun,Park, Hye Mi,Yoo, Kyung Ho,Sim, Taebo,Park, Jong Bae,Lee, Seung-Hoon,Lee, So Ha
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p. 195 - 208
(2015/02/05)
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- Antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives
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In this study, a series of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives were synthesized and evaluated for their antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt caused by Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (R. solanacearum) via the turbidimeter test in vitro. Antibacterial bioassays indicated that most compounds demonstrated appreciable antibacterial bioactivities against Xoo and R. solanacearum. Among the title compounds, compound 4i demonstrated the best inhibitory effect against Xoo and R. solanacearum with half-maximal effective concentration (EC50) values of 14.69 and 15.14 μg/mL, respectively, which were even better than those of commercial agents Bismerthiazol and Thiodiazole Copper. In vivo antibacterial activities tests under greenhouse conditions revealed that the control efficiency of compound 4i against rice bacterial leaf blight and tobacco bacterial wilt were better than those of Bismerthiazol and Thiodiazole Copper. Meanwhile, field trials also indicated that compound 4i demonstrated appreciable control efficiency against rice bacterial leaf blight and tomato bacterial wilt.
- Li, Pei,Shi, Li,Gao, Man-Ni,Yang, Xia,Xue, Wei,Jin, Lin-Hong,Hu, De-Yu,Song, Bao-An
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p. 481 - 484
(2015/02/18)
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- Calcium and magnesium chlorides-catalyzed oxidative esterification of aromatic aldehydes
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An interesting procedure for the oxidative esterification of aromatic aldehydes has been developed. By using catalytic amount of CaCl2 or MgCl2, various methyl benzoates were isolated in good yields with hydrogen peroxide as the terminal oxidant.
- Feng, Jian-Bo,Gong, Jin-Long,Li, Qin,Wu, Xiao-Feng
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p. 1657 - 1659
(2014/03/21)
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- Regio- and chemoselective C-H chlorination/bromination of electron-deficient arenes by weak coordination and study of relative directing-group abilities
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It's all relative: A practical and efficient PdII-catalyzed regio- and chemoselective chlorination/bromination has been developed for the facile synthesis of a broad range of aromatic chlorides. The reaction demonstrates excellent reactivity, good functional-group tolerance, and high yields. A preliminary study was conducted to evaluate relative directing-group abilities of various functionalities. Copyright
- Sun, Xiuyun,Shan, Gang,Sun, Yonghui,Rao, Yu
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supporting information
p. 4440 - 4444
(2013/05/22)
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- Synthesis, antibacterial activities, and 3d-qsar of sulfone derivatives containing 1, 3, 4-oxadiazole moiety
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A series of sulfone derivatives containing 1, 3, 4-oxadiazole moiety were prepared and evaluated for their antibacterial activities by the turbidimeter test. Most compounds inhibited growth of Ralstonia solanacearum (R. solanacearum) from tomato and tobacco bacterial wilt with high potency, among which compounds 5a and 5b exhibited the most potent inhibition against R. solanacearum from tomato and tobacco bacterial wilts with EC50 values of 19.77 and 8.29 μg/mL, respectively. Our results also demonstrated that 5a, 5b, and a number of other compounds were more potent than commercial bactericides Kocide 3000 and Thiodiazole Copper, which inhibited R. solanacearum from tomato bacterial wilt with EC50 values of 93.59 and 99.80 μg/mL and tobacco bacterial wilt with EC50 values of 45.91 and 216.70 μg/mL, respectively. The structure-activity relationship (SAR) of compounds was studied using three-dimensional quantitative structure-activity relationship (3D-QSAR) models created by comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) based on compound bioactivities against tomato and tobacco bacterial wilts. The 3D-QSAR models effectively predicted the correlation between inhibitory activity and steric-electrostatic properties of compounds.
- Li, Pei,Yin, Juan,Xu, Weiming,Wu, Jian,He, Ming,Hu, Deyu,Yang, Song,Song, Baoan
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p. 546 - 556
(2013/11/06)
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- Continuous flow oxidation of alcohols and aldehydes utilizing bleach and catalytic tetrabutylammonium bromide
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We report a method for the oxidation of a range of alcohols and aldehydes utilizing a simple flow system of alcohols in EtOAc with a stream of 12.5% NaOCl and catalytic Bu4NBr. Secondary alcohols are oxidized to ketones, aldehydes are oxidized directly to methyl esters in the presence of methanol, and benzylic alcohols are oxidized to either benzaldehydes or methyl esters, depending on the conditions used. The reaction conditions are mild and generally provide complete conversion in 5-30 min.
- Leduc, Andrew B.,Jamison, Timothy F.
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supporting information; experimental part
p. 1082 - 1089
(2012/08/27)
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- Metal-free chlorodeboronation of organotrifluoroborates
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A mild and metal-free method for the chlorodeboronation of organotrifluoroborates using trichloroisocyanuric acid (TCICA) was developed. Aryl-, heteroaryl-, alkenyl-, alkynyl-, and alkyltrifluoroborates were converted into the corresponding chlorinated products in good yields. This method proved to be tolerant of a broad range of functional groups.
- Molander, Gary A.,Cavalcanti, Livia N.
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experimental part
p. 7195 - 7203
(2011/10/13)
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- Synthesis of some novel 3,5-disubstituted 1,3,4-oxadiazole derivatives and anticancer activity on EAC animal model
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A series of novel 3,5-disubstituted 1,3,4-oxadiazole- 2-thione derivatives (1e, 2e, 3e, 4e, and 5e) have been synthesized from different substituted aromatic acids. The structure determination of these compounds have been made on the basis of IR, 1H NMR, and Elemental analysis. The effect of all the compounds on tumor growth inhibition was evaluated by studying the parameters-tumor volume, percentage of the tumor cell count (viable and nonviable), hematological values, and the mean survival status of the treated animals on eight groups of Swiss albino mice. Compounds were given at the dose of 50 mg/kg body weight intraperitoneally and all exhibited the significant (P0.001) anticancer activity compared to control. 5-Fluorouracil was used as a standard drug (20 mg/kg body weight i.p.) in the study. All the compounds demonstrated a prominent anticancer activity. The study supported the derivatives of oxadiazoles for the development as potent anticancer molecules. Springer Science+Business Media, LLC 2010.
- Dash, Sasmita,Kumar, B. Ashok,Singh, Jagadish,Maiti,Maity
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experimental part
p. 1206 - 1213
(2012/06/04)
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- Oxidative esterification of aldehydes with alcohols and phenols in air
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Nucleophilic carbene-catalysed oxidative esterification of aldehydes with alcohols and phenols without additional oxidant under an air atmosphere has been achieved, which provides a metal-free new methodology for the oxidative esterification of aldehydes.
- Cheng, Shuanghua,Chen, Jiuxi,Gao, Wenxia,Jin, Huile,Ding, Jinchang,Wu, Huayue
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experimental part
p. 130 - 132
(2010/06/19)
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- Electroreduction of organic compounds, 36 [1]. Electroreduction of chlorinated methyl benzoates
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The preparative electroreduction of the three methyl monochlorobenzoates, the six methyl dichlorobenzoates, and methyl 2,3,4-trichlorobenzoate in different solvent-supporting electrolytes (SSE) was studied. The rate of the dechlorination, which is the main reaction, is dependent on the substitution pattern. Pronounced regioselectivity is therefore observed in case of the oligochloro derivatives. Hydrogenation of the benzene ring and reduction of the methoxycarbonyl group with formation of a hydroxymethyl group are observed as side-reactions. Quantum chemical calculations on the reaction mechanism were performed. The theoretical results are in accordance with the experimental observations.
- Gassmann, Joerg,Voss, Juergen
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experimental part
p. 1291 - 1299
(2009/06/19)
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- Carboxylation and esterification of functionalized arylcopper reagents
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Functionalized arylcopper reagents have been produced in good yields at 25 °C from activated copper and the corresponding functionalized aryl iodides without the need of traditional organolithium or Grignard precursors. These organocopper compounds will undergo carboxylation with CO2 to form the corresponding copper benzoates. In turn, these salts can be acidified to produce the functionalized aryl acids or treated with appropriate alkyl halides in the presence of a dipolar aprotic solvent to generate the corresponding aryl esters. This methodology permits the formation of functionalized organic acids and esters that could not be generated by the carboxylation of organomagnesium compounds.
- Ebert, Greg W.,Juda, Wayne L.,Kosakowski, Robert H.,Ma, Bing,Dong, Liming,Cummings, Keith E.,Phelps, Mwita V. B.,Mostafa, Adel E.,Luo, Jianyuan
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p. 4314 - 4317
(2007/10/03)
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- New isoxazole derivatives designed as nicotinic acetylcholine receptor ligand candidates
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In this work we report the synthesis and evaluation of the analgesic properties of new isosteric heterocyclic derivatives, presenting the isoxazole nucleus, designed as nicotinic acetylcholine receptor ligand candidates, analogues to alkaloid epibatidine. Compound 2-(3-methyl-5-isoxazolyl)pyridine (3) presented the best analgesic profile of this series in hot plate test, which was partially prevented by pretreatment with nicotinic receptor antagonist mecamylamine.
- Silva, Nilda M,Tributino, Jorge L.M,Miranda, Ana L.P,Barreiro, Eliezer J,Fraga, Carlos A.M
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p. 163 - 170
(2007/10/03)
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- Triazole derivative and pharmaceutical use thereof
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An agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, an agent for the prophylaxis and treatment of allergic diseases, an agent for the prophylaxis and treatment of eosinophil-related diseases and an eosinophilia inhibitor, comprising, as an active ingredient, a series of triazole derivatives of the following formula (I) STR1 or the following formula (III) STR2 wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. A novel monocyclic or bicyclic triazole derivative. The agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, the agent for the prophylaxis and treatment of allergic diseases, the agent for the prophylaxis and treatment of eosinophil-related diseases, the eosinophilia inhibitor and the novel triazole derivative of the present invention all, have superior eosinophilia-inhibitory action and lymphocyte activation-inhibitory action. They are low toxic and persistent in action. They are particularly effective in the treatment of accumulation and activation of eosinophil and lymphocytes, inflammatory respiratory tract diseases, eosinophil-related diseases such as eosinophilia, and immune-related diseases.
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- Natural formation of chlorobenzoic acids (CBA) and distinction between PCB-degraded CBA
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Mono- and dichlorobenzoic acid (CBA) could be found in samples of remote bog pond water and sediment. The 2,4-CBA always had the highest concentrations. In bog water samples the concentrations ranged between 0.11 and 0.48 μg/l. Besides 2,4-CBA most only 2,5-CBA could be found as dichlorobenzoic acid. In all samples we could detect also trichloroacetic acid (TCAA). The TCAA concentrations correlate with the CBA concentrations. As TCAA is known as a naturally produced organohalogen, this correlation can be seen as an indication to a natural formation of CBA. A confirmation of this presumption is our detection CBA in a reaction of benzoic acid with the chlorinating enzyme chloroperoxidase (CPO).
- Niedan,Schoeler
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p. 1233 - 1241
(2007/10/03)
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- Carbophilic reactions of amines or methanol with thioaldehyde-S-oxides
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Correspondence and reprints Reaction of primary aliphatic amines with 7-ethylenic thioaldehyde-S-oxides la,b affords the corresponding imines 2a,b via a carbophilic addition of amine. When treated with sodium methoxide (1 equiv) and an excess of a primary amine, some methyl sulfinates 3 or 6, bearing a benzylic or allylic chain on the sulfur, are converted into imines 4 or 7. Treatment of the methyl sulfinates 3 with methoxide anion in THF or methanol generally affords a mixture of aldehydes 9, the corresponding dimethylacetals 14, a,a'-dimethoxydisulfides 10, esters 11, thionoesters 12 and methyl a-methoxysulfinates 15, whose ratios depend on the conditions. The formation of these compounds is best explained by a deprotonationelimination of the methyl sulfinates into the corresponding thioaldehyde-S-oxides; which then undergo a carbophilic addition of methoxide anion or methanol. Several possible reaction paths from the so-formed a-methoxysulfenate anions IX are discussed for their conversion into the final compounds. unsaturated sulfinic ester / elimination / thioaldehyde-S-oxide / imine / aldehyde / a,a -dimethoxydisulflde / thionoester / methyl u-methoxysulflnate Eisevier,.
- Baudin, Jean-Bernard,Commenil, Marie-Gabrielle,Julia, Sylvestre A.,Lome, Robert,Ruel, Odile
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p. 1127 - 1141
(2007/10/03)
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- Structural modifications of the primary amino group of anticonvulsant aryl semicarbazones
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A number of aryl semicarbazones had been shown previously to possess significant anticonvulsant properties. The principal objective of the present investigation was to determine the importance of the primary amino group in this series of compounds by replacing it with other substituents. The results indicate that the amino group was not essential for anticonvulsant activity. However its replacement by an aryl ring generally abolished activity while a terminal phenylamino function was better tolerated. Thus both the size of the group and its hydrogen bonding capabilities appear to influence bioactivity. Alteration of the oxygen atom of the semicarbazones by isosteres did not enhance anticonvulsant properties.
- Dimmock,Puthucode,Lo,Quail,Yang,Stables
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- Pharmacologically active CNS compounds
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The invention relates to compounds of formula (I) and salts thereof wherein R1 and R2 are the same or different and are each selected from hydroxy, or a group NR9R10 wherein R9 and R10 are each hydrogen, alkyl, aryl, arylalkyl or together with the nitrogen atom to which they are attached form a ring, optionally containing a further heteroatom and optionally further substituted by alkyl, aryl or arylalkyl;, R3 is selected from hydrogen, haloalkyl, alkyl and halo, R4 to R8 are the same or different, and are each selected from hydrogen, halo, nitro, amino, sulphonamido or alkylsulphonylamino;, or R4 and R5 or R5 and R6 may together form a carbocyclic ring;, with the proviso that at least one of R4 to R8 is other than hydrogen. The compounds may be used for the treatment or prophylaxis of a neurodegenerative or other neurological disorder of the CNS, the aetiology of which includes excessive release of the neurotransmitter glutamate.
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- Alkylating agents and method of use thereof
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The present invention comprises a haloacetoxyalkyl ether having the formula: STR1 wherein R is H or a C1 -C4 substituted or unsubstituted alkyl group, R' is H or a C1 -C3 group, and X is chlorine or fluorine; aroyloxymethyl ethers having the formula: wherein the R is p-NO2 C6 H4, halogen substituted C6 H4, or other aromatics; the method of making such ethers and monoquaternary salts; and the method of alkylating amines, pyridines, or acetals or pyridine derivatives with such ethers to form quaternary ammonium salts; particularly HI-6, HGG-12, Toxogonin, and SAS-128.
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