- Copper(ii)-promoted direct conversion of methylarenes into aromatic oximes
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A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
- Yu, Jiatao,Lu, Ming
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- Synthesis of amides and esters containing furan rings under microwave-assisted conditions
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In this work, we present a novel method for the synthesis of ester and amide derivatives containing furan rings (furfural derivatives) under mild synthetic conditions supported by microwave radiation. N-(Furan-2-ylmethyl)furan-2-carboxamide and furan-2-ylmethyl furan-2-carboxylate were produced using 2-furoic acid, furfurylamine, and furfuryl alcohol. The reactions were carried out in a microwave reactor in the presence of effective coupling reagents: DMT/NMM/TsO? or EDC. The reaction time, the solvent, and the amounts of the substrates were optimized. After crystallization or flash chromatography, the final compounds were isolated with good or very good yields. Our method allows for the synthesis of N-blocked amides using N-blocked amino acids (Boc, Cbz, Fmoc) and amine. As well as compounds with a monoamide and ester moiety, products with diamides and diester bonds (N,N-bis(furan-2-ylmethyl) furan-2,5-dicarboxamide, bis(furan-2-ylmethyl) furan-2,5dicarboxylate, and furan-3,4-diylbis(methylene) bis(furan-2-carboxylate)) were synthesized with moderate yields in the presence of DMT/NMM/TsO– or EDC, using 2,5-furan-dicarboxylic acid and 3,4-bis(hydroxymethyl)furan as substrates.
- Janczewski, ?ukasz,Zieliński, Dariusz,Kolesińska, Beata
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- Synthesis of Novel 3-aryl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene Derivatives and Their Biological Evaluation Against Protein Tyrosine Phosphatase 1B
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A series of novel 3-aryl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene derivatives were designed, synthesized, and evaluated as a new class of inhibitors against protein tyrosine phosphatase 1B. Among them, compound 6f displayed moderate inhibitory activity with IC50 of 2.87 ± 0.24 μm and can be used as a novel lead compound for the design of inhibitors of protein tyrosine phosphatase 1B. A series of novel 3-aryl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene derivatives were designed, synthesized, and evaluated as a new class of inhibitors against PTP1B. Among them, compound 6f displayed moderate inhibitory activity with IC50 of 2.87 ± 0.24 μm and can be used as a novel lead compound for the design of inhibitors of PTP1B.
- Wang, Wen-Long,Chen, Xia,Gao, Li-Xin,Sheng, Li,Li, Jing-Ya,Li, Jia,Feng, Bainian
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- High add valued application of turpentine in crop production through structural modification and qsar analysis
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Turpentine is a volatile component of resin, which is an abundant forest resource in Southern China. As one of the most important components, the integrated application of-pinene has been studied. The broad-spectrum evaluation of -pinene and its analogues has, therefore, been necessary. In an attempt to expand the scope of agro-activity trials, the preparation and the evaluation of the herbicidal activity of a series of -pinene analogues against three agricultural herbs were carried out. In accordance with the overall herbicidal activity, it is noteworthy that compounds 6k, 6l, and 6m demonstrated extreme activity with IC50 values of 0.065, 0.065, and 0.052 mol active ingredients/hectare against E. crus-galli. The preliminary structure-activity relationship (SAR) was analyzed and the compounds with the appropriate volatility and substituent type that had beneficial herbicidal activity were analyzed. Simultaneously, the quantitative structure-activity relationship (QSAR) model was built and the most important structural features were indicated, which was, to a certain extent, in line with the SAR study. The study aimed to study the application of the forest resource turpentine in agriculture as a potential and alternative approach for comprehensive utilization.
- Gao, Yanqing,Li, Jingjing,Li, Jian,Song, Zhanqian,Shang, Shibin,Rao, Xiaoping
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- Formation of C-O bond via cross-dehydrogenative coupling between isochroman and oxime under metal-free oxidation conditions
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DDQ-mediated C-O bond formation through cross-dehydrogenative coupling (CDC) reaction without any metal catalyst under mild conditions was developed. Series of isochromans and oximes could be employed as substrates, and the products were obtained in good yields. Georg Thieme Verlag Stuttgart New York.
- He, Hua-Feng,Wang, Kai,Xing, Bo,Sheng, Guorong,Ma, Tingxuan,Bao, Weiliang
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- Structural basis for selective inhibition of Cyclooxygenase-1 (COX-1) by diarylisoxazoles mofezolac and 3-(5-chlorofuran-2-yl)-5-methyl-4-phenylisoxazole (P6)
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The diarylisoxazole molecular scaffold is found in several NSAIDs, especially those with high selectivity for COX-1. Here, we have determined the structural basis for COX-1 binding to two diarylisoxazoles: mofezolac, which is polar and ionizable, and 3-(5
- Cingolani, Gino,Panella, Andrea,Perrone, Maria Grazia,Vitale, Paola,Di Mauro, Giuseppe,Fortuna, Cosimo G.,Armen, Roger S.,Ferorelli, Savina,Smith, William L.,Scilimati, Antonio
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- Some furfural derivatives as nitrification inhibitors
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Three series of furfural derivatives, namely N-O-furfural oxime ethers, furfural Schiff bases (furfurylidene anilines), and furfural chalcones, have been synthesized and evaluated for nitrification inhibition activity in laboratory incubation studies in typic Ustocrept soil. Furfural oxime ethers and furfural Schiff bases showed potential activity, but furfural chalcones were only mildly active. N-O-ethyl furfural oxime among the oxime ethers, and furfurylidine-4-chloroaniline among the furfural Schiff bases, performed the best. These two compounds showed more than 50% nitrification inhibition on the 45th day at 5% dose as compared to 73% inhibition by nitrapyrin. Activity of furfural oxime ethers decreased with an increase in carbon atoms in the N-O-alkyl side chain. Introduction of a chlorine atom in the phenyl ring of furfurylidene anilines increased the persistence of their activity. N-O-Ethyl furfural oxime and furfurylidine-4-chloroaniline coated urea performed at par with their application in solution form. Ethyl and N-O-isopropyl oxime, as well as chloro- and nitro-substituted Schiff bases, did not reveal any phytotoxicity (adverse effect on germination) on chickpea seeds (Cicer arietinum) even at the highest dose (40 ppm, soil basis).
- Datta,Walia,Parmar
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- Metal-Free: A novel and efficient aerobic oxidation of primary amines to oximes using N, N', N''-trihydroxyisocyanuric acid and acetaldoxime as catalysts in water
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A general, efficient, and metal-free method for aerobic oxidation of aromatic primary amines to the corresponding oximes catalyzed by N,N',N''-trihydroxyisocyanuric acid and acetaldoxime with water as solvent is described. This practical method can use air as economic and green oxidant, water as green solvent, and tolerates a wide range of substrates, which can afford the target oximes in moderate to good yields. Georg Thieme Verlag Stuttgart. New York.
- Yu, Jiatao,Lu, Ming
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- Novel design of recyclable copper(II) complex supported on magnetic nanoparticles as active catalyst for Beckmann rearrangement in poly(ethylene glycol)
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Copper complex-functionalized magnetic core–shell nanoparticles (Fe3O4@SiO2-Lig-Cu) were prepared and characterized using various techniques. The activity of the new catalyst was tested for the Beckmann rearrangement. The reaction conditions allow for the conversion of a wide variety of aldoximes, including aromatic and heterocyclic ones, to amides in good to excellent yields. High efficiency, mild reaction conditions, easy work-up, use of poly(ethylene glycol) as a green medium and simple purification of products are important advantages of this system. Moreover, the eco-friendly heterogeneous nanocatalyst could be easily recovered from the reaction mixture using an external magnet and reused several times.
- Keyhaniyan, Mahdi,Shiri, Ali,Eshghi, Hossein,Khojastehnezhad, Amir
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- Clean synthesis of furfural oxime through liquid-phase ammoximation of furfural over titanosilicate catalysts
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The clean synthesis of furfural oxime (FO) has been realized through titanosilicate-catalyzed liquid-phase ammoximation of furfural with ammonia and hydrogen peroxide. A detailed investigation of furfural ammoximation over three representative titanosilicates Ti-MOR, TS-1 and Ti-MWW reveals that the reaction involves the hydroxylamine route and the imine route. The hydroxylamine route accounts for the formation of the target product (FO), while the imine route leads to the formation of undesired products such as 2-furylamide and 2-furoic acid. With a high efficiency for hydroxylamine formation, Ti-MOR proves to be superior to TS-1 and Ti-MWW. The catalytic performance of Ti-MOR depends greatly on the operating conditions of the reaction, which is closely related to its activity in catalyzing hydroxylamine decomposition. The decomposition of hydroxylamine and the non-catalytic oxidation of furfural can be effectively suppressed in Ti-MOR-catalyzed ammoximation when employing water as the solvent and adding H2O2 dropwise into the reaction system. Under optimized conditions, Ti-MOR is capable of providing furfural conversion and oxime selectivity both above 97%.
- Lu, Xinqing,Guan, Yejun,Xu, Hao,Wu, Haihong,Wu, Peng
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- Preparation method O - alkyl substituted hydroxylamine salt
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The invention relates to a preparation method of N - alkyl substituted hydroxylamine salt, and belongs to fine chemical engineering. Pesticide or bulk pharmaceutical chemicals technical field. The present invention reacts with the N - alkyl of the oxime with an inorganic salt of hydroxylamine to give N - alkyl-substituted hydroxylamine salt and oxime. The invention provides an efficient and environment-friendly method for preparing N - alkyl substituted hydroxylamine salt, and simultaneously, an N - alkyl substituted hydroxylamine salt is prepared, and the oxime can be re-prepared to form N - alkylate of oxime so as to realize the material circulation. No equivalent acid is used in the reaction process. Alkali neutralization, avoided the current method to use a large amount of acid, alkali and produce inorganic salt solid waste shortcoming, environmental protection more. The preparation method is mild in reaction condition, and the defects of high pollution and high energy consumption of the traditional process are overcome. In-flight R1 , R2 What is R is as claimed in the claims and the description.
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Paragraph 0128-0131
(2021/11/14)
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- Synthesis and Biological Activity of 2-(2-Amino-2-phenylethyl)-5-oxotetrahydrofuran-2-carboxylic Acid: A Microwave-Assisted 1,3-Dipolar Cycloaddition Approach
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The microwave-assisted 1,3-dipolar cycloaddition of furanyl and benzyl oximes and several methyl acrylates effectively provided several isoxazoline when mediated by diacetoxyiodobenzene. The selected isoxazoline, methyl-5-(3-methoxy-3-oxopropyl)-3-phenyl-4,5-dihydro isoxazole-5-carboxylate, was rapidly transformed to the γ-lactone carboxylic acid, 2-(2-amino-2-phenylethyl)-5-oxotetrahydrofuran-2-carboxylic acid, in reasonable yield. The biological activity of this γ-lactone carboxylic acid increased the growth of E. coli organisms by about 44% and has a potential significance in stem cell research.
- Urquilla, Andromeda,Merrer, Dina C.,Sumner, Ryan,Denton, Richard W.
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supporting information
p. 1735 - 1740
(2021/08/27)
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- One-Pot Regioselective Synthesis of 7-Bromo-2H-Benzo[b][1,4]Oxazin-3(4H)-One Linked Isoxazole Hybrids as Anti-Cancer Agents and Their Molecular Docking Studies
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Abstract: Regioselective synthesis of some novel 7-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one linked isoxazole hybrids via copper(I) catalyzed one-pot reaction of various aromatic aldehydes with 7-bromo-4-(prop-2-yn-1-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one was developed. The structures of the compounds that are synthesized are confirmed by 1H NMR, 13C NMR, and mass spectra. All the hybrids have been tested for their in vitro anticancer activity against four human cancer cell lines, including HeLa, MCF-7, A549, and PC3. Three of the compounds exhibited remarkable anticancer activity compared to standard drug etoposide. Molecular docking studies with EGFR also strengthened the in vitro anticancer activity.
- Karthik, B.,Kumar, A. Kannan,Nukala, Satheesh Kumar,Ravinder, M.,Swamy, T. Narasimha
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p. 1269 - 1275
(2021/12/23)
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- Design, synthesis of novel 4,5-dihydroisoxazole-containing benzamide derivatives as highly potent FtsZ inhibitors capable of killing a variety of MDR Staphylococcus aureus
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Antibiotic resistance among clinically significant bacterial pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA) is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. As a part of continuing effort to develop antibacterial agents, we rationally designed and synthesized two series of 4,5-dihydroisoxazol-5-yl and 4,5-dihydroisoxazol-3-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compound A16 possessing the 4,5-dihydroisoxazol-5-yl group showed outstanding antibacterial activity (MIC, ≤0.125–0.5 μg/mL) against various testing strains, including methicillin-resistant, penicillin-resistant and clinical isolated S. aureus strains. Besides, further mouse infection model revealed that A16 could be effective in vivo and non-toxic to Hela cells. Finally, a detailed discussion of structure-activity relationships was conducted, referring to the docking results. It is worth noting that substituting a 4,5-dihydroisoxazole ring for the isoxazole ring not only broadened the antibacterial spectrum but also resulted in a significant increase in antibacterial activity against S. aureus strains. Taken together, these results suggest a promising chemotype for the development of new FtsZ-targeting bactericidal agents.
- Song, Di,Bi, Fangchao,Zhang, Nan,Qin, Yinhui,Liu, Xingbang,Teng, Yuetai,Ma, Shutao
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supporting information
(2020/09/11)
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- Synthesis of 3-furanyl-4,5-dihydroisoxazole derivatives via cycloaddition and their antibacterial evaluation
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Background: Antimicrobial resistance is a major threat to human health. So this manuscript describes the synthesis of five different 3,5-disubstituted 4,5-dihydroisoxazoles with antimicrobial activity. Methods: They were obtained from nitrile oxide cycloaddition derived from 2-furaldehyde and 5-nitro-2-furaldehyde to different dipolarophiles (acrylamide, ethyl acrylate and styrene). All heterocycles were isolated (30-50 %) and characterized by FTIR, MS,1H and13C NMR, as they were also evaluated against Gram-positive and Gram-negative bacteria. Results and Conclusion: All products showed bioactivity against all bacteria, however, the heterocycle 3-(5-nitro-2-furanyl)-5-carboxylamide-4,5-dihydroisoxazole (6b) presented the lowest value for the minimum inhibition concentration (MIC - 14 μg/mL).
- De Andrade Danin Barbosa, Gabriela,De Aguiar, Alcino Palermo,De Carvalho, Erika Martins,Da Rocha Nogueira, Joseli Maria
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p. 364 - 369
(2019/06/20)
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- Formal Aniline Synthesis from Phenols through Deoxygenative N-Centered Radical Substitution
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Phenolic, lignin-derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical-mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N-centered radical source. The applicability of this triethyl phosphite mediated O-atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.
- Lardy, Samuel W.,Luong, Kristine C.,Schmidt, Valerie A.
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supporting information
p. 15267 - 15271
(2019/12/11)
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- SO 2 F 2 -Promoted Dehydration of Aldoximes: A Rapid and Simple Access to Nitriles
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A rapid, simple and mild process for the dehydration of aldoximes to give the corresponding nitriles, which utilizes SO 2 F 2 as an efficient reagent, has been developed. A variety of (hetero)arene, alkene, alkyne and aliphatic aldoximes proceeded with high efficiency to afford nitriles in excellent to quantitative yields with great functional group compatibilities in acetonitrile under ambient conditions. Furthermore, an eco-friendly synthetic protocol to access nitriles from aldehydes with ortho -, meta - and para -nitrile groups was also described in aqueous methanol by using inorganic base Na 2 CO 3, and a one-pot synthetic strategy to generate nitriles from aldehydes was proved to be feasible.
- Ding, Chengrong,Mei, Guangyao,Wang, Haibo,Zhang, Guofu,Zhao, Yiyong
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supporting information
p. 1484 - 1488
(2019/07/15)
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- 7-Oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-Dioxides: Mechanochemical Synthesis by Tandem Michael Addition–1,3-Dipolar Cycloaddition of Aldoximes and Evaluation of Antibacterial Activities
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A solvent-free, green, and efficient mechanochemical method for the synthesis of a series of bridged bicyclo aza-sulfone derivatives, namely 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxides through tandem Michael addition–1,3-dipolar cycloaddition of aldoximes was developed. Mechanochemical grinding/milling facilitates quick formation of aldoximes from corresponding aldehydes and hydroxylamine, which upon reaction with divinyl sulfone in a mixer mill affords 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxide derivatives in good overall yields. The newly synthesized bicyclo aza-sulfone derivatives 4 were screened for antibacterial activities. Mostly bicyclo aza-sulfones derived from electron-rich aromatic aldehydes inhibit the growth of Mycobacterium smegmatis (mc2155) and those from aliphatic aldehydes the growth of Escherichia coli (DH5α) in moderate to good effect. However, butyraldehyde-derived compound 4r was very effective against both M. smegmatis and E. coli. The key advantages of this mechanochemical method are catalyst- and solvent-free conditions, shorter reaction time, and formation of a new series of 7-oxa-4-thia-1-aza-bicyclo[3.2.1]octane 4,4-dioxide derivatives, which are good antibacterial agents against M. smegmatis and E. coli.
- Bhutia, Zigmee T.,Das, Avijit,Biswas, Malabika,Chatterjee, Amrita,Banerjee, Mainak
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p. 506 - 514
(2018/02/09)
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- Efficient synthesis of 1,2,4-oxadiazine-5-ones via [3+3] cycloaddition of in situ generated aza-oxyallylic cations with nitrile oxides
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1,2,4-Oxadiazin-5-ones were prepared via [3+3] cycloaddition of in situ generated aza-oxyallylic cations with nitrile oxides in good yields and excellent functional group compatibility. This efficient transformation is metal-free and is promoted by an inorganic base Cs2CO3. In addition, this reaction features simple-operation, mild conditions, and high regioselectivity.
- Wang, Gangqiang,Chen, Rongxing,Zhao, Sen,Yang, Liangfeng,Guo, Haibing,Sun, Shaofa,Wang, Jian,Domena, Justin,Xing, Yalan
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supporting information
p. 2018 - 2020
(2018/04/25)
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- Method for preparing oxime
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The invention discloses a method for preparing oxime. The method is characterized in that catalytic reaction for oxime synthesis is performed by using a titanium silicate molecular sieve of a MSE topological structure as a catalyst and using ketone or aldehyde, ammonia and hydrogen peroxide as a reaction system, wherein in the reaction system, the weight ratio of ketone or aldehyde to the catalystto a solvent is 1:(0.03 to 0.15):(1 to 15); the molar ratio of the ketone or aldehyde to the ammonia is 1:(1 to 4); the catalyst is Ti-MSE or a combination body of Ti-MSE and silicon dioxide or a titanium-containing molecular sieve. Compared with the prior art, the method has the advantages that the selectivity is high; the catalytic activity is high; the aftertreatment is simple and convenient;the conversion rate of reactants of ketone or aldehyde reaches up to 99 percent; the product oxime selectivity reaches up to 99 percent, so that the molecular sieve shows excellent catalytic activityin the specific catalysis field; the application field of the molecular sieve is expanded; a novel and environment-friendly ammoxidation oxime preparation path is provided; certain industrial popularization and application prospects and prominent economic values are realized.
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Paragraph 0037; 0038; 0039
(2018/09/08)
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- Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators
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Antibiotic resistance among clinically significant bacterial pathogens is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. Utilizing computational docking method and structure-based optimization strategy, we rationally designed and synthesized two series of isoxazol-3-yl- and isoxazol-5-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compounds B14 and B16 that possessed the isoxazol-5-yl group showed strong antibacterial activity against various testing strains, including methicillin-resistant Staphylococcus aureus and penicillin-resistant S. aureus. Further molecular biological studies and docking analyses proved that the compound functioned as an effective inhibitor to alter the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which finally terminated the cell division and caused cell death. Taken together, these results could suggest a promising chemotype for development of new FtsZ-targeting bactericidal agent.
- Bi, Fangchao,Song, Di,Zhang, Nan,Liu, Zhiyang,Gu, Xinjie,Hu, Chaoyu,Cai, Xiaokang,Venter, Henrietta,Ma, Shutao
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- Poly(ethylene glycol)–bound sulfonyl chloride as an efficient catalyst for transformation of aldoximes to nitriles
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An operationally simple, efficient, and environmentally benign preparation of nitriles in good to excellent yields from various aldoximes in the presence of recyclable poly(ethylene glycol)–bound sulfonyl chloride is described.
- Zhang, Xiao-Lan,Liu, Xiao-Ling,Sang, Xiao-Yan,Sheng, Shou-Ri
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p. 232 - 237
(2017/01/22)
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- Iron-catalyzed synthesis of benzoxazoles by oxidative coupling/cyclization of phenol derivatives with benzoyl aldehyde oximes
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An iron-catalyzed oxidative coupling/cyclization reaction for the synthesis of benzoxazoles at room temperature is reported. This reaction was enabled by an inexpensive iron(iii) catalyst by treating readily available phenol derivatives with benzoyl aldehyde oximes. Mechanistic studies show that benzoyl aldehyde oxime is not only used as a substrate, but also serves as an ancillary ligand to support the iron salt in the promotion of the transformation.
- Gao, Sen,Gao, Liming,Meng, Hong,Luo, Meiming,Zeng, Xiaoming
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supporting information
p. 9886 - 9889
(2017/09/11)
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- Iron-Catalyzed Asymmetric Nitro-Mannich Reaction
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The first enantioselective addition of nitroalkanes to imines (nitro-Mannich reaction), mediated by an iron(II) catalyst assembled by a hindered hydroxyethyl-pybox ligand, is described. This valuable carbon-carbon bond-forming reaction proceeds smoothly at room temperature to afford enantioenriched β-nitro amines in good yields and high enantioselectivity, up to 98% with unprecedentedly low iron catalyst loading (5 mol %).
- Dudek, Agata,Mlynarski, Jacek
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p. 11218 - 11224
(2017/10/27)
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- Five-membered azole heterocyclic compound and its preparation method, pharmaceutical composition and use thereof
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The present invention relates to a five-membered azole heterocycle compound represented by the following general formula (I), a preparation method of the five-membered azole heterocycle compound, a drug composition of the five-membered azole heterocycle compound, and a use of the five-membered azole heterocycle compound in preparation of drugs for prevention or treatment of TGR5-mediated diseases. The formula (I) is represented by the instruction.
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Paragraph 0235; 0236; 0310; 0311
(2017/02/28)
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- Monocyclic β-lactam and unexpected oxazinone formation: synthesis, crystal structure, docking studies and antibacterial evaluation
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Novel monocyclic β-lactam derivatives bearing aryl, phenyl and heterocyclic rings were synthesized as possible antibacterial agents. Cyclization of imines (3h, 3t) with phenylacetic acid in the presence of phosphoryl chloride and triethyl amine did not afford the expected β-lactams. Instead, highly substituted 1,3-oxazin-4-ones (4h, 4t) were isolated as the only product and confirmed by single crystal X-ray analysis of 4t. The results of antibacterial activity showed that compound 4l exhibited considerable antibacterial activity with MIC and MBC values of 62.5 μg/mL against Klebsiella pneumoniae. Cytotoxicity assay on Chinese Hamster Ovary (CHO) cell line revealed non-cytotoxic behavior of compounds 4d, 4h, 4k and 4l up to 200 μg/mL conc. Molecular docking was performed for compound 4l with penicillin binding protein-5 to identify the nature of interactions. The results of both in silico and in vitro evaluation provide the basis for compound 4l to be carried as a potential lead molecule in the drug discovery pipeline against bacterial infections.
- Aneja, Babita,Irfan, Mohammad,Hassan, Md. Imtaiyaz,Prakash, Amresh,Yadava, Umesh,Daniliuc, Constantin G.,Zafaryab, Md.,Rizvi, M. Moshahid A.,Azam, Amir,Abid, Mohammad
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p. 834 - 852
(2016/07/07)
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- Nanocrystalline CeO2 as a Highly Active and Selective Catalyst for the Dehydration of Aldoximes to Nitriles and One-Pot Synthesis of Amides and Esters
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The dehydration of aldoximes into nitriles has been performed in the presence of various metal oxides with different acid-base properties (Al2O3, TiO2, CeO2, MgO). The results showed that a nanocrystalline CeO2 was the most active catalyst. An in situ IR spectroscopy study supports a polar elimination mechanism in the dehydration of aldoxime on metal oxide catalysts, in which Lewis acid sites and basic sites are involved. The Lewis acid sites intervene in the adsorption of the oxime on the catalyst surface while surface base sites are responsible for the C1-H bond cleavage. Thus, the acid-base properties of nanocrystalline CeO2 are responsible for the high catalytic activity and selectivity. A variety of aldoximes including alkyl and cycloalkyl aldoximes have been dehydrated into the corresponding nitriles in good yields (80-97%) using nanosized ceria which moreover resulted in a stable and reusable catalyst. Additionally, it has been showed that a variety of pharmacologically important products such as picolinamide and picolinic acid alkyl ester derivatives can be obtained in good yields from 2-pyridinaldoxime in a one-pot process using the nanoceria as catalyst.
- Rapeyko, Anastasia,Climent, Maria J.,Corma, Avelino,Concepción, Patricia,Iborra, Sara
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p. 4564 - 4575
(2016/07/12)
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- Design, synthesis, biological evaluation and molecular docking studies of phenylpropanoid derivatives as potent anti-hepatitis B virus agents
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A series of phenylpropanoid derivatives were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Most of the synthesized derivatives showed effective anti-HBV activity. Of these compounds, compound 4c-1 showed the most potent anti-HBV activity, demonstrating potent inhibitory effect not only on the secretion of HBsAg (IC50 = 14.18 μM, SI = 17.85) and HBeAg (IC50 = 6.20 μM, SI = 40.82) secretion but also HBV DNA replication (IC50 = 23.43 μM, SI = 10.80). The structureeactivity relationships (SARs) of phenylpropanoid derivatives had been discussed, which were useful for phenylpropanoid derivatives to be explored and developed as novel anti-HBV agents. Moreover, the docking study of all synthesized compounds inside the HLA-A protein (PDB ID: 3OX8) active site were carried out to explore the molecular interactions and a molecular target for activity of phenylpropanoid derivatives with the protein using a moe-docking technique. This study identified a new class of potent anti-HBV agents.
- Liu, Sheng,Wei, Wanxing,Li, Yubin,Liu, Xu,Cao, Xiaoji,Lei, Kechan,Zhou, Min
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p. 473 - 482
(2015/04/14)
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- An efficient comparison of methods involving conventional, grinding and ultrasound conditions for the synthesis of fulleroisoxazolines
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In this research, an efficient comparison between conventional, grinding and sonication methods for the synthesis of fulleroisoxazolines was investigated. Compared to the conventional methods, ultrasound procedure showed several advantages including mild reaction conditions, high yields, short reaction times and environmental friendliness.
- Safaei-Ghomi, Javad,Masoomi, Reihaneh
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p. 212 - 218
(2015/02/19)
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- APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT
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PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0109
(2018/10/27)
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- Copper(II)-promoted direct conversion of methylarenes into aromatic oximes
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A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
- Yu, Jiatao,Lu, Ming
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supporting information
p. 7397 - 7401
(2015/11/27)
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- Dual nature of polyethylene glycol under microwave irradiation for the clean synthesis of oximes
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Polyethylene glycol (PEG-400 and PEG-600) is an efficient, inexpensive, and recyclable homogeneous medium and catalyst (dual nature) for the clean synthesis of oximes (and aldoximes) under microwave irradiation in the absence of acid and base catalysts. Both aliphatic and aromatic aldehydes/ketones give satisfactory results under microwave irradiation within a short time. Graphical abstract: [Figure not available: see fulltext.]
- Dutta, Papia,Dutta, Arup Kumar,Sarma, Parishmita,Borah, Ruli
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p. 505 - 508
(2014/03/21)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Paragraph 0137
(2013/03/26)
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- Synthetic communications reviews: Synthesis of primary amines by one-pot reductive amination of aldehydes
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We report here a novel, one-pot, two-step reductive amination of aldehydes for the atom-economical synthesis of primary amines. The amination step has been carried out with hydroxylammonium chloride and does not require the use of a base. In the subsequent reduction step, a metal zinc/hydrochloride acid system has been used. This method is applicable to both aliphatic and aromatic aldehydes. The operational simplicity, the short reaction times, and the mild reaction conditions add to the value of this method as a practical alternative to the reductive amination of aldehydes. Copyright
- Ayedi, Mohamed Ali,Le Bigot, Yves,Ammar, Houcine,Abid, Souhir,Gharbi, Rachid El,Delmas, Michel
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p. 2127 - 2133
(2013/07/25)
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- Oximation of carbonyl compounds by basic alumina supported amberlite IRA 400 under microwave energy and pestle/mortar
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An efficient and novel method for the preparation of oximes from carbonyl compounds under solventless conditions.
- Singh, Sanjeev Pratap,Singh
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experimental part
p. 1354 - 1356
(2012/09/21)
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- Efficient conversion of aldehydes and ketones into oximes using a nanostructured pyrophosphate catalyst in a solvent-free process
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A nanostructured pyrophosphate (Na2CaP2O7) was synthesized by controlling the speed of its calcination, and then characterized by several methods including TGA, X-ray diffraction, FTIR, SEM, TEM and the determination of the surface area by the BET method. However, several aldehydes and ketones were efficiently and rapidly converted into the corresponding oximes by treatment with hydroxylamine hydrochloride in a solvent-free process under microwave irradiation using this nanostructured pyrophosphate as catalyst. The yields of the products were very high and the time required for their preparation was very short compared to conventional heating experiments and the catalyst was efficiently re-used.
- Elmakssoudi, Abdelhakim,Abdelouahdi, Karima,Zahouily, Mohamed,Clark, James,Solhy, Abderrahim
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- Acetohydroxamic acid: A new reagent for efficient synthesis of nitriles directly from aldehydes using Bi(OTf)3 as the catalyst
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An efficient method for the preparation of nitriles directly from aldehydes by reaction with AHA using Bi(OTf)3 as the catalyst is described. Bi(OTf)3 is shown to be an efficient catalyst also for the conversion of aldoximes into nitriles.
- Sridhar, Madabhushi,Reddy, Mallu Kishore Kumar,Sairam, Vangipuram Venkata,Raveendra, Jillella,Godala, Kondal Reddy,Narsaiah, Chinthala,Ramanaiah, Beeram China,Reddy, Cirandur Suresh
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scheme or table
p. 3421 - 3424
(2012/08/08)
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- Efficient synthesis of oxazoles by dirhodium(ii)-catalyzed reactions of styryl diazoacetate with oximes
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An efficient one-step synthesis of multi-functionalized oxazole derivatives is achieved in high yield by dirhodium(ii)-catalyzed reactions of styryl diazoacetate with aryl oximes. This journal is
- Xu, Xinfang,Zavalij, Peter Y.,Doyle, Michael P.,Hu, Wenhao
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supporting information
p. 11522 - 11524,3
(2012/12/12)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES, N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Page/Page column 46
(2012/11/06)
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- Discovery, synthesis, and biological evaluation of a novel group of selective inhibitors of filoviral entry
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Herein, we report the development of an antifiloviral screening system, based on a pseudotyping strategy, and its application in the discovery of a novel group of small molecules that selectively inhibit the Ebola and Marburg glycoprotein (GP)-mediated infection of human cells. Using Ebola Zaire GP-pseudotyped HIV particles bearing a luciferase reporter gene and 293T cells, a library of 237 small molecules was screened for inhibition of GP-mediated viral entry. From this assay, lead compound 8a was identified as a selective inhibitor of filoviral entry with an IC50 of 30 μM. To analyze functional group requirements for efficacy, a structure-activity relationship analysis of this 3,5-disubstituted isoxazole was then conducted with 56 isoxazole and triazole derivatives prepared using "click" chemistry. This study revealed that while the isoxazole ring can be replaced by a triazole system, the 5-(diethylamino)acetamido substituent found in 8a is required for inhibition of viral-cell entry. Variation of the 3-aryl substituent provided a number of more potent antiviral agents with IC50 values ranging to 2.5 μM. Lead compound 8a and three of its derivatives were also found to block the Marburg glycoprotein (GP)-mediated infection of human cells.
- Yermolina, Maria V.,Wang, Jizhen,Caffrey, Michael,Rong, Lijun L.,Wardrop, Duncan J.
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experimental part
p. 765 - 781
(2011/04/15)
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- A general and convenient route to oxazolyl ligands
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A diverse range of chiral and achiral oxazolyl ligands, which have many applications including catalysis and luminescent devices, are synthesized simply in three steps from readily available and inexpensive phenol and amino alcohol starting materials. The method can be applied to ligands with electron-donating/-withdrawing and sterically demanding/undemanding substituents, and can conveniently be scaled up to >25 g of product.
- Aspinall, Helen C.,Beckingham, Oliver,Farrar, Michael D.,Greeves, Nicholas,Thomas, Christopher D.
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supporting information; experimental part
p. 5120 - 5123
(2011/10/19)
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- Synthesis and antibacterial evaluation of isoxazolinyl oxazolidinones: Search for potent antibacterial
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A series of (5S) N-(3-{3-fluoro-4-[4-(3-aryl-4,5-dihydro-isoxazole-5-carbonyl)-piperazin-1-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide(6a-o) were synthesized and their in vitro antibacterial activity against various resistant Gram-positive and Gram-negative bacteria were evaluated. Most of the synthesized compounds showed 2 to 10 fold lower MIC values compared to linezolid against Staphylococcus aureus ATCC 25923, ATCC 70069, ATCC 29213, Bacillus cereus MTCC 430, Enterococcus faecalis MTCC439, Klebsiella pneumoniae ATCC 27736, and Streptococcus pyogens.
- Varshney, Vandana,Mishra, Nripendra N.,Shukla, Praveen K.,Sahu, Devi P.
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scheme or table
p. 3573 - 3576
(2010/03/31)
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- From chemistry to biology: Furanic complexes as samples
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In order to demonstrate the links between chemistry and biology, some biological properties of a few furanic compounds have been described, starting from the synthesis and the structural characteristics. Also some features of the furan compounds with oximes; semicarbazones and thiosemicarbazones have been pointed out.
- Bouet, Gilles
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scheme or table
p. 111 - 118
(2010/10/01)
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- A tungsten-tin mixed hydroxide as an efficient heterogeneous catalyst for dehydration of aldoximes to nitriles
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(Chemical Equation Presented) Mix and match: A tungsten-tin mixed hydroxide (W-Sn hydroxide), prepared by the simple coprecipitation method, acts as a reusable heterogeneous catalyst for the dehydration of various aldoximes to the corresponding nitriles (see scheme, top). Furthermore, the W-Sn hydroxide catalyst could be applied to the direct one-pot synthesis of nitriles from hydroxylamine and the corresponding aldehydes (see scheme, bottom).
- Yamaguchi, Kazuya,Fujiwara, Hiroshi,Ogasawara, Yoshiyuki,Kotani, Miyuki,Mizuno, Noritaka
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p. 3922 - 3925
(2008/03/11)
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- A one-pot synthesis of primary amides from aldoximes or aldehydes in water in the presence of a supported rhodium catalyst
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(Equation Presented) Dehydration/Rehydration in Water: Supported rhodium hydroxide (Rh(OH)x/ Al2O3) is an effective heterogeneous catalyst for the synthesis of primary amides from aldoximes and aldehydes in water in a reaction that is entirely free of hazardous and carcinogenic organic solvents (see scheme).
- Fujiwara, Hiroshi,Ogasawara, Yoshiyuki,Yamaguchi, Kazuya,Mizuno, Noritaka
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p. 5202 - 5205
(2008/03/13)
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- Synthesis, characterisation and antimicrobial studies of CuII, NiII and CoII complexes of furan- and thiophene-2- aldoximes
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Complexes of CuII, NiII and CoII with furan- and thiophene-2-aldoximes have been synthesized. The structures of the synthesised compounds have been established by spectral and magnetic studies. All the synthesised complexes have been screened for their antimicrobial activities.
- Abdul Jameel,Syed Ali Padusha
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p. 608 - 610
(2007/10/03)
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- Catalytic effect of wet molecular sieve 3A in dry media on syntheses of oximes and 1,3-dioximes
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A simple, efficient and eco-friendly method has been developed for the condensation of hydroxylamine hydrochloride with aldehydes, ketones and 1,3-diketones in the presence of powdered molecular sieves (3A) as catalyst. Aldoximes, ketoximes and 1,3-dioximes were obtained in excellent yields.
- Bigdeli, Mohammadali,Rahmati, Abbas
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p. 605 - 607
(2007/10/03)
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- Metalloporphyrin and heteropoly acid catalyzed oxidation of C=NOH bonds in an ionic liquid: Biomimetic models of nitric oxide synthase
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Water soluble iron(III) porphyrins and phosphotungstic acid in an ionic liquid are effective catalysts for the H2O2 mediated oxidation of the CNOH bond in N-hydroxyarginine and other oximes. The carbonyl compounds generated as the oxidation products can be easily isolated from the reaction media. These systems serve as biomimetic models of nitric oxide synthase (NOS) and the catalyst immobilized in an ionic liquid can be easily recycled and reused.
- Jain, Nidhi,Kumar, Anil,Chauhan, Shive M.S.
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p. 2599 - 2602
(2007/10/03)
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- One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles
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3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional
- Hansen, Trond V.,Wu, Peng,Fokin, Valery V.
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p. 7761 - 7764
(2007/10/03)
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- Rh-catalyzed one-pot and practical transformation of aldoximes to amides
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Wilkinson's complex has been found to catalyze the one-pot transformation of aldoximes to the corresponding amides with high selectivity and efficiency under essentially neutral conditions.
- Park, Soyoung,Choi, Yoon-aa,Han, Hoon,Yang, Soon Ha,Chang, Sukbok
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p. 1936 - 1937
(2007/10/03)
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