- Synthesis and anti-methicillin-resistant Staphylococcus aureus activity of 5,7-dibromo-2-benzoylbenzofurans alone and in combination with antibiotics
-
A series of 5,7-dibromo-2-benzoylbenzofurans were synthesized by the Rap–Stoermer condensation of 5,7-dibromosalicylaldehyde with diverse phenacyl bromides and evaluated for in-vitro antibacterial activities against methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 29213, methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300, and MRSA ATCC 33591 by agar dilution method. The synergistic effects were determined by using the agar dilution checkerboard assay. The derivatives bearing carboxylic acid functional groups exhibited reasonable activity against MRSA strains with the best MIC = 32 μg/mL (9b, 9d). Moreover, the additive or synergistic interactions against MRSA strains was observed in six combinations (1b + cefuroxime/gentamicin, 1c + ciprofloxacin/gentamicin, 9b + gentamicin, and 9c + ciprofloxacin) with the fractional inhibitory concentration index (FICI) values in the range of 0.375–1.0. Significantly, the MICs of these antibiotics were reduced 2–4-fold. The results of the MTT assay illustrated the low mammalian cell cytotoxicity of these potent compounds.
- Phan, Phuong-Thuy T.,Nguyen, Hong-Nhung T.,Kim, Son N.,Pham, Tuan-Anh N.
-
supporting information
p. 786 - 796
(2020/12/09)
-
- Ru-Tethered (R,R)-TsDPEN with DMAB as an efficient catalytic system for high enantioselective one-pot synthesis of chiral β-aminolviaasymmetric transfer hydrogenation
-
This work reflects Ru-tethered-TsDPEN as an active chiral catalyst for one pot selective synthesis of optically active α-substituted alcohols and its derivatives from α-bromo ketones in the presence of dimethylamine borane (DMAB) as the hydrogen source. Various Ru-chiral catalysts have been screened and the methodology proceededviaa (R,R) Ru-tethered TsDPEN catalyst through asymmetric transfer hydrogenation (ATH) of the in-situ formed ketones to the corresponding chiral β-aminol product. Thus, the Ru-tethered TsDPEN-DMAB catalytic system works efficiently with higher yield and high enantiomeric excess over others for the ATH process. Based on a study ofortho,metaandparasubstituted α-bromo acetophenone derivatives, effective enantioselectivity has been observed fororthosubstituted β-aminol. The mechanism has been optimized depending on product analysis with the help of its kinetic AT-IR study. This work also focusses on the synthesis of various β-amino alcohol derivatives where the effect of an EWG and EDG on enantio-selectivity has been studied.
- Mishra, Ashish A.,Bhanage, Bhalchandra M.
-
supporting information
p. 5357 - 5362
(2021/04/06)
-
- SUBSTITUTED IMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS
-
The invention provides substituted imidazole carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.
- -
-
Paragraph 00336
(2021/04/01)
-
- Selective Debromination of α,α,α-Tribromomethylketones with HBr–H2O Reductive Catalytic System
-
A debromination of α,α,α-tribromomethylketones is developed for chemoselective synthesis of α-mono- and α,α-dibromomethylketones with high selectivity under H2O–HBr reductive conditions. This method offers an efficient and direct way to synthesize α-mono or α,α-dibromomethylketone compounds in high to excellent yields through the process of HBr self-circulation in water.
- Cheng, Zhao,Guo, Hongmei,Huang, Guozheng,Rexit, Abulikemu Abudu,Wang, Hui,Zheng, Meng-Xia
-
p. 6455 - 6458
(2020/10/21)
-
- SUBSTITUTED AMINOTHIAZOLES AS INHIBITORS OF NUCLEASES
-
The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3, R4, R5, R6 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.
- -
-
Page/Page column 14-15; 18; 45
(2019/11/12)
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- Synthesis of 5-Aryl-5H-pyrido[2',1':2,3]imidazo[4,5-b]indoles by Domino Pd- and Cu-Catalyzed C-N Coupling Reactions
-
A series of 5-aryl-5H-pyrido[2',1':2,3]imidazo[4,5- b ]indoles was successfully prepared in good yields by a practical four-step strategy. In this procedure, the key step was demonstrated to be the domino Pd-and Cu-catalyzed C-N coupling reactions of 3-br
- Hung, Tran Quang,Quan, Nguyen Minh,Van Dong, Hoang,Nguyen, Trinh Duy,Anh, Hoang Le Tuan,Hung, Trieu Quy,Van Tuyen, Nguyen,Thuan, Ngo Thi,Dang, Tuan Thanh,Langer, Peter
-
p. 303 - 306
(2019/02/12)
-
- Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)
-
An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to the synthesis of anti-inflammatory drug fanetizole using styrene as starting material.
- Ma, Chunhua,Miao, Yuqi,Zhao, Minghao,Wu, Ping,Zhou, Jianglu,Li, Zhi,Xie, Xilei,Zhang, Wei
-
p. 3602 - 3607
(2018/05/26)
-
- Facile and efficient preparation of α-halomethyl ketones from α-diazo ketones catalyzed by iron(III) halides and silica gel
-
An efficient and mild method for the synthesis of α-halomethyl ketones from α-diazo ketones was developed using ferric chloride or bromide as the halogen source and silica gel as the hydrogen source, with good to excellent yields.
- Shi, Xinxia,Zhang, Lingqiong,Yang, Pengfei,Sun, Han,Zhang, Yilan,Xie, Chunsong,Ou-yang, Zhen,Wang, Min
-
supporting information
p. 1200 - 1203
(2018/03/08)
-
- Antibacterial synergist, preparation method and uses thereof
-
The present invention relates to an antibacterial synergist, a preparation method and uses thereof, and specifically discloses a compound represented by a formula (I) and having antibacterial synergyactivity, or an optical isomer, a cis-trans isomer or a pharmaceutically acceptable salt thereof, and a preparation method thereof. The present invention further discloses a medical composition containing the compound, and uses thereof. According to the present invention, the compound can effectively enhance the antibacterial activity of polymyxin B against Acinetobacter baumannii and Klebsiella pneumoniae, and can be used for the antibacterial treatment of pathogenic bacteria insensitive to polymyxin or having low bacterial inhibition activity. The formula (I) is defined in the specification.
- -
-
Paragraph 0433; 0434; 0435; 0436
(2018/03/28)
-
- CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
-
A condensed cyclic compound and an organic light-emitting device including the same are provided. The organic light-emitting device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second el
- -
-
Paragraph 0442-0444
(2018/04/18)
-
- N-Thiazolylamide-based free fatty-acid 2 receptor agonists: Discovery, lead optimization and demonstration of off-target effect in a diabetes model
-
Free fatty acid-2 (FFA2) receptor is a G-protein coupled receptor of interest in the development of therapeutics in metabolic and inflammatory disease areas. The discovery and optimization of an N-thiazolylamide carboxylic acid FFA2 agonist scaffold is described. Dual key objectives were to i) evaluate the potential of this scaffold for lead optimization in particular with respect to safety de-risking physicochemical properties, i.e. lipophilicity and aromatic content, and ii) to demonstrate the utility of selected lead analogues from this scaffold in a pertinent in vivo model such as oral glucose tolerance test (OGTT). As such, a concomitant improvement in bioactivity together with lipophilic ligand efficiency (LLE) and fraction sp3 content (Fsp3) parameters guided these efforts. Compound 10 was advanced into studies in mice on the basis of its optimized profile vs initial lead 1 (ΔLLE = 0.3, ΔFsp3 = 0.24). Although active in OGTT, 10 also displayed similar activity in the FFA2-knockout mice. Given this off-target OGTT effect, we discontinued development of this FFA2 agonist scaffold.
- Hoveyda, Hamid R.,Fraser, Graeme L.,Zoute, Ludivine,Dutheuil, Guillaume,Schils, Didier,Brantis, Cyrille,Lapin, Alexey,Parcq, Julien,Guitard, Sandra,Lenoir, Fran?ois,Bousmaqui, Mohamed El,Rorive, Sarah,Hospied, Sandrine,Blanc, Sébastien,Bernard, Jér?me,Ooms, Frédéric,McNelis, Joanne C.,Olefsky, Jerrold M.
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p. 5169 - 5180
(2018/10/02)
-
- Efficient sulfonylation of ketones with sodium sulfinates for the synthesis of β-keto sulfones
-
The oxidative sulfonylation of ketones with sodium sulfinates as the sulfone source and DMSO as the oxidant is reported. A series of β-keto sulfones were obtained in good to excellent yields. The advantages of this efficient protocol include the low cost of DMSO and HBr, and a broad scope.
- Deng, Siqi,Liang, En,Wu, Yinrong,Tang, Xiaodong
-
supporting information
p. 3955 - 3957
(2018/09/27)
-
- One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction
-
Simple one-pot protocols for the syntheses of α-bromoketones and α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), produced in catalytic amounts from 3,4,5,6-tetramethyl-2-iodobenzoic and Oxone. α-Bromoketones are further converted in the same pot to the corresponding α-azidoketones using NaN3/NaHCO3. The one-pot conversions are versatile for a variety of olefins that include cyclic as well as acyclic aliphatic olefins and electron-rich and electron-deficient styrenes. Chemoselective bromohydroxylation of electron-rich double bond and subsequent oxidation to the α-bromoketone is demonstrated for a substrate that contains both electron-rich and deficient double bonds.
- Chandra, Ajeet,Parida, Keshaba Nanda,Moorthy, Jarugu Narasimha
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p. 5827 - 5832
(2017/09/09)
-
- One-Pot Synthesis of Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridin-5-yl(aryl)methanones through Sequential Sonogashira Coupling/Alkyne–Carbonyl Metathesis
-
An efficient one-pot route for the construction of naphtho[1′,2′:4,5]imidazo[1,2-a]pyridin-5-yl(aryl)methanones and 5-phenylnaphtho[1′,2′:4,5]imidazo[1,2-a]pyridines by sequential Sonogashira coupling reaction followed by trifluoroacetic acid promoted alk
- Baig, Mirza Feroz,Shaik, Siddiq Pasha,Krishna, Namballa Hari,Chouhan, Neeraj Kumar,Alarifi, Abdullah,Kamal, Ahmed
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p. 4026 - 4034
(2017/07/28)
-
- α-Ketothioamide Derivatives: A Promising Tool to Interrogate Phosphoglycerate Dehydrogenase (PHGDH)
-
Given the putative role of PHGDH in cancer, development of inhibitors is required to explore its function. In this context, we established and validated a straightforward enzymatic assay suitable for high-throughput screening and we identified inhibitors with similar chemical scaffolds. Through a convergent pharmacophore approach, we synthesized α-ketothioamides that exhibit interesting in vitro PHGDH inhibition and encouraging cellular results. These novel probes may be used to understand the emerging biology of this metabolic target.
- Ravez, Séverine,Corbet, Cyril,Spillier, Quentin,Dutu, Alice,Robin, Anita D.,Mullarky, Edouard,Cantley, Lewis C.,Feron, Olivier,Frédérick, Rapha?l
-
supporting information
p. 1591 - 1597
(2017/03/08)
-
- Simple synthesis of 3-hydroxyquinolines via Na2S2O4-mediated reductive cyclization of (2-(2-nitrophenyl)oxiran-1-yl)(aryl)methanones (o-nitrobenzalacetophenone oxides)
-
An efficient sodium dithionite (Na2S2O4)-mediated method for construction of 3-hydroxyquinolines via in situ Meinwald rearrangement/intramolecular reductive cyclization of o-nitrobenzalacetophenone oxides has been developed. The practical approach is of excellent functional group compatibility with as high as 98% yield under mild reaction conditions. Moreover, further manipulation successfully furnished 4-bromo substituted derivatives which may provide a promising potential application in exploring biologically active analogs of 3-hydroxyquinolines.
- Mamedov, Vakhid A.,Mamedova, Vera L.,Syakaev, Victor V.,Korshin, Dmitry E.,Khikmatova, Gul'naz Z.,Mironova, Ekaterina V.,Bazanova, Olga B.,Rizvanov, Il'dar Kh.,Latypov, Shamil K.
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p. 5082 - 5090
(2017/07/28)
-
- Discovery of novel 2-(3-phenylpiperazin-1-yl)-pyrimidin-4-ones as glycogen synthase kinase-3β inhibitors
-
We herein describe the results of further evolution of glycogen synthase kinase (GSK)-3β inhibitors from our promising compounds containing a 2-phenylmorpholine moiety. Transformation of the morpholine moiety into a piperazine moiety resulted in potent GSK-3β inhibitors. SAR studies focused on the phenyl moiety revealed that a 4-fluoro-2-methoxy group afforded potent inhibitory activity toward GSK-3β. Based on docking studies, new hydrogen bonding between the nitrogen atom of the piperazine moiety and the oxygen atom of the main chain of Gln185 has been indicated, which may contribute to increased activity compared with that of the corresponding phenylmorpholine analogues. Effect of the stereochemistry of the phenylpiperazine moiety is also discussed.
- Usui, Yoshihiro,Uehara, Fumiaki,Hiki, Shinsuke,Watanabe, Kazutoshi,Tanaka, Hiroshi,Shouda, Aya,Yokoshima, Satoshi,Aritomo, Keiichi,Adachi, Takashi,Fukunaga, Kenji,Sunada, Shinji,Nabeno, Mika,Saito, Ken-Ichi,Eguchi, Jun-ichi,Yamagami, Keiji,Asano, Shouichi,Tanaka, Shinji,Yuki, Satoshi,Yoshii, Narihiko,Fujimura, Masatake,Horikawa, Takashi
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p. 3726 - 3732
(2017/07/27)
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- Citric Acid-catalyzed Synthesis of 2,4-Disubstituted Thiazoles from Ketones via C–Br, C–S, and C–N Bond Formations in One Pot: A Green Approach
-
An improved and greener protocol has been developed for the synthesis of 2,4-disubstituted thiazoles via C–Br, C–S, and, C–N bond formations in a single step from readily available ketones, N-bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α-bromoketones, ease of carrying out, cleaner reaction profile, broad substrate scope, freedom from chromatographic purification, and suitability for large-scale synthesis.
- Gundala, Trivikram Reddy,Godugu, Kumar,Nallagondu, Chinna Gangi Reddy
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p. 1408 - 1416
(2017/10/23)
-
- First Catalyzed Hydration of Haloalkynes by a Recyclable Catalytic System
-
The hydration of haloalkynes to give α-halomethyl ketones was achieved based on a combination of a Cu(OAc)2 catalyst and a TFA (trifluoroacetic acid) promoter. This is the first synthesis of chloro/bromo/iodo methyl ketones through a hydration reaction catalyzed by a recyclable catalytic system. The catalytic system has a wide substrate scope and excellent chemoselectivity, and the procedure can also be scaled up.
- Zou, Huaxu,He, Weibao,Dong, Qizhi,Wang, Ruijia,Yi, Niannian,Jiang, Jun,Pen, Dongming,He, Weimin
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p. 116 - 121
(2016/01/26)
-
- Highly Efficient Synthesis of α-Halomethylketones via Ce(SO4)2/Acid Co-Catalyzed Hydration of Alkynes
-
A general atom-economical approach for the synthesis of α-halomethyl ketones is demonstrated through Ce(SO4)2/acid co-catalyzed hydration of a wide range of haloalkynes. The reactions are conducted under convenient conditions and provide products with excellent regioselectivity in good to excellent yields, with broad substrate scope. This protocol is an alternative to conventional α-halogenation of ketones.
- Zou, Huaxu,Jiang, Jun,Yi, Niannian,Fu, Wenqiang,Deng, Wei,Xiang, Jiannan
-
supporting information
p. 1251 - 1254
(2016/12/27)
-
- In(OTf)3/acid co-catalyzed hydration of 1-haloalkynes to α-halomethyl ketones
-
A novel and efficient In(OTf)3and HOAc cooperatively catalyzed hydration of 1-haloalkynes is described. This method provides ready access to α-chloromethyl ketones, α-bromomethyl ketones and α-iodomethyl ketones in moderate to high yields from simple, inexpensive starting materials. A broad substrate scope is achieved, and the reaction is compatible with various functional groups, including alkoxy, trifluoromethyl, halide, hydroxyl, cyclohexyl, and heterocyclic groups.
- Zeng, Ming,Huang, Rui-Xue,Li, Wen-Yi,Liu, Xiao-Wen,He, Fu-Ling,Zhang, Yi-Yuan,Xiao, Fang
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p. 3818 - 3822
(2016/07/06)
-
- 1,3-Dibromo-5,5-dimethylhydantoin (DBH) mediated one-pot syntheses of α-bromo/amino ketones from alkenes in water
-
α-Bromo ketones are versatile intermediates of high practical utility. Traditional approaches to these compounds are restricted to a relatively hazardous/complex reagent combination, a long reaction time, the use of non-environmentally friendly solvents, or a limited substrate scope. Herein, we describe the development of a new methodology for the preparation of α-bromo ketones from alkenes using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a bromine source and an oxidant simultaneously. This easy to carry out two-step one-pot protocol proceeds in water and provides high yield of a great variety of α-bromo ketones. Addition of an amine to the intermediate α-bromo ketone further enables the preparation of α-amino ketones in a one-pot sequence.
- Xu, Senhan,Wu, Ping,Zhang, Wei
-
p. 11389 - 11395
(2016/12/18)
-
- Discovery of a new class of 16-membered (2: Z,11 Z)-3,11-di(aryl/naphthyl)-1,13-dioxa-5,9-dithia-2,12-diazacyclohexadeca-2,11-dienes as anti-tumor agents
-
A series of new 16-membered small macrocyclic compounds, (2Z,11Z)-3,11-di(aryl/naphthyl)-1,13-dioxa-5,9-dithia-2,12-diazacyclohexadeca-2,11-dienes (1a-k) were designed and developed by a simple and practical synthetic route from readily available substrates using simple organic transformations. Evaluation of in vitro anti-tumor activities on human triple negative breast cancer cells MDAMB-231 cell lines reveal that the macrocycles, 1a, 1f, 1g, 1i and 1k are promising anti-tumor compounds as evidenced from inhibition of cell migration and proliferation, upregulation of anti-tumor genes p53, MDA7 and TRAIL. The anti-proliferative effect of macrocycles is specific to cancer cells but no cytotoxic effect on normal breast epithelial cells has been observed (MCF10A). The developed synthetic route is free from metals, protecting groups and air-free techniques. The structure of macrocycle (1e) is confirmed by single crystal XRD studies.
- Bodireddy, Mohan Reddy,Mahla, Ranjeet Singh,Khaja Mohinuddin, P. Md.,Reddy, G. Trivikram,Raghava Prasad, D. Vijaya,Kumar, Himanshu,Reddy, N. C. Gangi
-
p. 75651 - 75663
(2016/08/24)
-
- Copper-catalyzed synthesis of benzo[b]thiophene-fused imidazopyridines via the cleavage of C-H bond and C-X bond
-
A new and straightforward approach to synthesize benzo[b]thiophene-fused imidazopyridines has been developed by tandem cross-coupling reaction of K2S with 2-(2-bromophenyl)imidazo[1,2-a]pyridines, and K2S as sulfur source constructed
- Huang, Hui,Dang, Pan,Wu, Lijun,Liang, Yun,Liu, Jianbing
-
supporting information
p. 574 - 577
(2016/01/20)
-
- Synthesis and antimicrobial evaluation of aminoguanidine and 3-amino-1,2,4-triazole derivatives as potential antibacterial agents
-
A series of aminoguanidine derivatives bearing a 1,3,4-oxadiazole or piperazine moiety has been synthesized and fully characterized together with a series of 3-amino-1,2,4-triazole derivatives, and the resulting compounds were evaluated for their antibacterial activity. Most of these compounds showed broad-spectrum antibacterial activities against both Gram-positive and Gramnegative bacteria with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values in the range of 1-64 μg/mL, including multidrug-resistant clinical isolates and a fungus. Notably, compounds 19e and 19f exhibited higher levels of activity than gatifloxacin and moxifloxacin against several methicillin-resistant Staphylococcus aureus (3167 and 3506) and quinolone-resistant S. aureus (3505 and 3519) strains with MIC and MBC values in the range of 1-2 μg/mL. These two compounds also displayed significant antifungal activity against Candida albicans 7535 with MIC value of 1 μg/mL, which were equivalent to MIC value of standard drug fluconazole. These results therefore indicate that aminoguanidine derivatives that do not contain a piperazine moiety are interesting scaffolds for the development of novel antibacterial agents.
- Zhang, Tian-Yi,Li, Chao,Li, Ya-Ru,Li, Xiao-Zhen,Sun, Liang-Peng,Zheng, Chang-Ji,Piao, Hu-Ri
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p. 1063 - 1075
(2016/11/25)
-
- Direct Transformation of Ethylarenes into Primary Aromatic Amides with N -Bromosuccinimide and I2-Aqueous NH3
-
A variety of ethylarenes were converted into the corresponding primary aromatic amides in good yields via treatment with N-bromosuccinimide in the presence of a catalytic amount of 2,2′-azobis(isobutyronitrile) in a mixture of ethyl acetate and water, acetonitrile and water, or chloroform and water, followed by reaction with molecular iodine and aq NH3 in one pot. It was found that aryl α-bromomethyl ketones and/or aryl methyl ketones were formed at the first reaction step and their iodoform-type reaction occurred at the second reaction step to provide primary aromatic amides. The present reaction is a useful and practical transition-metal-free method for the preparation of primary aromatic amides from ethylarenes. (Chemical Equation Presented).
- Shimokawa, Shohei,Kawagoe, Yuhsuke,Moriyama, Katsuhiko,Togo, Hideo
-
supporting information
p. 784 - 787
(2016/03/01)
-
- PYRROLE AMIDE INHIBITORS
-
The present invention provides for compounds of formula (I) wherein R1, R2, R3, and R10 have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including inflammatory diseases, cancer, and AIDS. Also provided are pharmaceutical compositions comprising one or more compounds of formula (I).
- -
-
Paragraph 0562
(2014/09/30)
-
- Efficient synthetic approach to substituted benzo[b]furans and benzo[b]thiophenes by iodine-promoted cyclization of enaminones
-
An efficient synthetic approach to the substituted benzo[b]furan and benzo[b]thiophene scaffolds by iodine-mediated cyclization of the corresponding enaminones is described. This protocol was applied to a large series of these latter precursors to afford the respective benzoheterocycles substituted at the C-2 position by a carbonyl group functionality. A study of the factors that control this process reveals that the reactivity depends on the presence of electron-donor groups in the aryl ring of the aryloxycarbonylic and arylthiocarbonylic moieties.
- Labarrios, Ehecatl,Jerezano, Alberto,Jimenez, Fabiola,Del Carmen Cruz, Maria,Delgado, Francisco,Zepeda, L. Gerardo,Tamariz, Joaquin
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p. 954 - 971
(2014/08/05)
-
- Synthesis of phenacyl bromides via K2S2O 8-mediated tandem hydroxybromination and oxidation of styrenes in water
-
Non-transition metal-catalyzed synthesis of phenacyl bromides was achieved through K2S2O8-mediated tandem hydroxybromination and oxidation of styrenes. The advantages of this reaction are its excellent functional group compatibility, mild reaction conditions (60 °C) and use of pure water as reaction medium. Based upon experimental observations, a plausible reaction mechanism is proposed.
- Jiang, Qing,Sheng, Wenbing,Guo, Cancheng
-
p. 2175 - 2179
(2013/09/24)
-
- Base-catalyzed synthesis of substituted indazoles under mild, transition-metal-free conditions
-
Back to basics: A transition-metal-free method developed for the synthesis of indazoles involves an inexpensive catalytic system composed of a diamine and K2CO3. Various (Z)-2-bromoacetophenone tosylhydrazones were converted into indazoles at room temperature in excellent yields (see example; Ts=p-toluenesulfonyl). The yield was improved by photoisomerization with UV light when E/Z isomeric mixtures of the starting material were used. Copyright
- Thome, Isabelle,Besson, Claire,Kleine, Tillmann,Bolm, Carsten
-
supporting information
p. 7509 - 7513
(2013/07/26)
-
- One-pot sequential C-N coupling and cross dehydrogenative couplings: Synthesis of novel azole fused imidazo[1,2-a]pyridines
-
An efficient one-pot protocol has been developed using sequential C-N coupling and intramolecular dehydrogenative cross-couplings for the synthesis of azole fused imidazo[1,2-a]pyridine derivatives in good yields (62-78%). The Royal Society of Chemistry 2
- Pericherla, Kasiviswanadharaju,Khedar, Poonam,Khungar, Bharti,Kumar, Anil
-
supporting information
p. 2924 - 2926
(2013/04/24)
-
- Copper-catalyzed tandem azide-alkyne cycloaddition, Ullmann type C-N coupling, and intramolecular direct arylation
-
A ligand-free copper-catalyzed tandem azide-alkyne cycloaddition (CuAAC), Ullmann-type C-N coupling, and intramolecular direct arylation has been described. The designed strategy resulted in the synthesis of a novel trazole-fused azaheterocycle framework.
- Pericherla, Kasiviswanadharaju,Jha, Amitabh,Khungar, Bharti,Kumar, Anil
-
supporting information
p. 4304 - 4307
(2013/09/24)
-
- Silver(I)-Catalyzed conia-ene reaction: Synthesis of 3-pyrrolines via a 5-endo-dig cyclization
-
A novel method has been developed for the synthesis of 3-pyrrolines from β-ketopropargylamines via a 5-endo-dig carbocyclization. This transformation involves a silver-catalyzed Conia-ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2-substituted pyrroles under base-mediated conditions. Copyright
- Boominathan, Siva Senthil Kumar,Hu, Wan-Ping,Senadi, Gopal Chandru,Wang, Jeh-Jeng
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supporting information
p. 3570 - 3574
(2014/01/06)
-
- Oxidative bromination of ketones using ammonium bromide and oxone
-
A highly efficient, environmentally safe and economic method for selective α-monobromination of aralkyl, cyclic, acyclic, 1,3-diketones and β-keto esters and α,α-dibromination of 1,3-diketones and β-keto esters without catalyst is reported using ammonium bromide as a bromine source and oxone as an oxidant. The reaction proceeds at ambient temperature and yields range from moderate to excellent. Bromination of unsymmetrical ketones takes place at the less substituted α-position predominantly. Aromatisation of tetralones is also carried out with this reagent system.
- MacHarla, Arun Kumar,Chozhiyath Nappunni, Rohitha,Marri, Mahender Reddy,Peraka, Swamy,Nama, Narender
-
supporting information; experimental part
p. 191 - 195
(2012/01/17)
-
- NOVEL COMPOUNDS
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Disclosed are retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.
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Page/Page column 66
(2012/03/26)
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- Synthesis and bioactivity evaluation of rhodanine derivatives as potential anti-bacterial agents
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Five series of (Z)-5-(4-(2-oxo-2-phenylethoxy)benzylidene)-2- thioxothiazolidin-4-one derivatives (I-V) were synthesized, characterized, and evaluated for their anti-bacterial activity. Most of the synthesized compounds showed potent inhibition against several Gram-positive bacteria (including multidrug-resistant clinical isolates) with MIC values in the range of 1-32 μg/mL. Compounds IIIi, Vb and Vc presented the most potent activity, showing four-fold more potency than norfloxacin (MIC = 8 μg/mL and 4 μg/mL) and 64-fold more activity than oxacillin (MIC > 64 μg/mL) against MRSA CCARM 3167 and 3506 strains with MIC values of 1 μg/mL, and 64-fold more potency than norfloxacin (MIC > 64 μg/mL) and comparable activity to oxacillin (MIC = 1 μg/mL) against the QRSA CCARM 3505 and 3519 strains. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 μg/mL.
- Song, Ming-Xia,Zheng, Chang-Ji,Deng, Xian-Qing,Wang, Qing,Hou, Shao-Pu,Liu, Ting-Ting,Xing, Xiao-Lan,Piao, Hu-Ri
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experimental part
p. 403 - 412
(2012/10/08)
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- Azido carbonyl compounds as DNA cleaving agents
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Irradiation of azido carbonyl compounds using UV light (≥310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (≥350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode.
- Chowdhury, Nilanjana,Dutta, Sansa,Karthick,Anoop, Anakuthil,Dasgupta, Swagata,Pradeep Singh
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- NOVEL COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERS
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The present invention is directed to novel compounds of formula (I) and their use in treating metabolic diseases.
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Page/Page column 50
(2011/12/14)
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- Direct synthesis of α-bromoketones from alkylarenes by aerobic visible light photooxidation
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The direct synthesis of α-bromoketones from alkylarenes by aerobic photooxidation with hydrobromic acid is reported. The key success for this direct oxidative reaction is due to control of bromination with acetic acid and ethanol, which are generated in situ by solvolysis of ethyl acetate in the course of the reaction.
- Tada, Norihiro,Ban, Kazunori,Hirashima, Shin-Ichi,Miura, Tsuyoshi,Itoh, Akichika
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supporting information; experimental part
p. 4701 - 4704
(2010/11/17)
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- Copper-catalyzed cyclization of Z-oximes into 3-methyl-1,2-benzisoxazoles
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A practical and effective room temperature copper-catalyzed cyclization of Z-oximes is developed. 3-Methyl-1,2-benzisoxazoles are obtained in 58-79% yields. Also, the Z-selective synthesis of o-bromo acetophenone oximes is presented for the first time.
- Udd, Sandra,Jokela, Reija,Franzén, Robert,Tois, Jan
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supporting information; experimental part
p. 1030 - 1033
(2010/04/02)
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- Z-Selective synthesis of o-bromoacetophenone N-tosylhydrazones and formation of 3-methylindazoles in aqueous ethanol
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A practical and effective Z-selective synthesis of o-bromoacetophenone N-tosylhydrazones is developed. Subsequent cyclization of Z-tosylhydrazones to furnish 3-methylindazoles is accomplished with the aid of copper and DMEDA in aqueous ethanol. Cyclization reactions are complete at ambient temperature in 10 min to afford the desired compounds in excellent yields.
- Kylm?l?, Tuula,Udd, Sandra,Tois, Jan,Franzén, Robert
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supporting information; experimental part
p. 3613 - 3615
(2010/08/22)
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- Highly efficient route to functionalized tetrahydrocarbazoles using a tandem cross-metathesis/intramolecular-hydroarylation sequence
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The scope of the novel ruthenium-catalyzed tandem cross-metathesis/ intramolecular-hydroarylation sequence is described. This methodology offers a practical and efficient synthesis of structurally diverse and complex tetrahydrocarbazoles in good to excellent yields (up to 98%). Moreover, preliminary efforts towards the development of an enantioselective version of the current process by sequential catalysis with ruthenium complex and chiral amine are presented, with high yields and enantioselectivities (up to 88% yield and 91% ee).
- An, Xiao-Lei,Chen, Jia-Rong,Li, Chang-Feng,Zhang, Fu-Gen,Zou, You-Quan,Guo, Ying-Cen,Xiao, Wen-Jing
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supporting information; experimental part
p. 2258 - 2265
(2011/06/11)
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- BORON-CONTAINING SMALL MOLECULES
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This invention provides, among other things, novel compounds useful for treating bacterial infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.
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Page/Page column 136
(2009/01/23)
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- Synthesis, structure, and biological activity of novel 1H-1,2,4-triazol-1- yl-thiazole derivatives
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2-Amino-4-aryl-5-(1H-1,2,4-triazol-1-yl)thiazole derivatives were synthesized from the reaction of α-bromo substituted acetophenone and thiourea. The structures were confirmed by elemental analysis, 1H NMR and single crystal X-ray diffraction analysis. Biological evaluation showed that some of them possess antifungal and plant growth regulatory activities. Copyright Taylor & Francis Group, LLC.
- Ling, Shao,Xin, Zhou,Qing, Zhang,Jian-Bing, Liu,Zhong, Jin,Jian-Xin, Fang
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p. 199 - 207
(2007/10/03)
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- Synthesis of benzo[b]naphtho[2,3-d]furan-6,11-dione via one-pot remote anionic fries rearrangement and metalation reaction
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The use of a lithiation reaction to transform the bromo-arylcarbamate 8a into the corresponding benzo[b]naphtho[2,3-d]furan-6,11-dione (2) is described.
- Azevedo, Mariangela S.,Alves, Glaucia B. C.,Cardoso, Jari N.,Lopes, Rosangela S. C.,Lopes, Claudio C.
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p. 1262 - 1268
(2007/10/03)
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- Discovery and evaluation of potent P1 aryl heterocycle-based thrombin inhibitors
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In an effort to discover potent, clinically useful thrombin inhibitors, a rapid analogue synthetic approach was used to explore the P1 region. Various benzylamines were coupled to a pyridine/pyrazinone P2-P 3 template. One compound with an o-thiadiazole benzylic substitution was found to have a thrombin Ki of 0.84 nM. A study of ortho-substituted five-membered-ring heterocycles was undertaken and subsequently demonstrated that the o-triazole and tetrazole rings were optimal. Combination of these potent P1 aryl heterocycles with a variety of P2-P3 groups produced a compound with an extraordinary thrombin inhibitory activity of 1.4 pM. It is hoped that this potency enhancement in P1 will allow for more diversification in the P 2-P3 region to ultimately address additional pharmacological concerns.
- Young, Mary Beth,Barrow, James C.,Glass, Kristen L.,Lundell, George F.,Newton, Christina L.,Pellicore, Janetta M.,Rittle, Kenneth E.,Selnick, Harold G.,Stauffer, Kenneth J.,Vacca, Joseph P.,Williams, Peter D.,Bohn, Dennis,Clayton, Franklin C.,Cook, Jacquelynn J.,Krueger, Julie A.,Kuo, Lawrence C.,Lewis, S. Dale,Lucas, Bobby J.,McMasters, Daniel R.,Miller-Stein, Cynthia,Pietrak, Beth L.,Wallace, Audrey A.,White, Rebecca B.,Wong, Bradley,Yan, Youwei,Nantermet, Philippe G.
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p. 2995 - 3008
(2007/10/03)
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- One-step preparation of symmetrical 1,4-diketones from α-halo ketones in the presence of Zn-I2 as a condensation agent
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Eleven 1,4-diphenylbutane-1,4-diones have been prepared in one step from the corresponding α-halo acetophenones under the action of Zn-I 2 as a condensation agent with moderate to high yields. The mechanistic pathway of the reaction can be explained by the Wurtz-like self-condensation of α-halo ketones. Similarly, 3-chloropentane-2,4-dione gave 3,4-diacetylhexane-2,5-dione, a Wurtz-like condensation product.
- Ceylan, Mustafa,Guerdere, M. Burcu,Budak, Yakup,Kazaz, Cavit,Secen, Hasan
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p. 1750 - 1754
(2007/10/03)
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- Prenyl transferase inhibitors
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A family of imidazole compounds useful for inhibiting the activity of prenyl transferases. The compounds are covered by the following formula: wherein X is (CHR11)n3(CH2)n4Z(CH2)n5 where Z is O, N(R12), S, or a bond; Y is CO, CH2, CS, or a bond; R1 is or N(R24R23); and the remaining substituents are as defined in the disclosure.
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- Synthesis of an annulenoannulenone, 3H-benzo[e]cycl[3.3.2]Azin-3-one
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A new nitrogen-bridged annulenoannulenone, 3H-benzo[e]cycl[3.3.2]- azin-3-one (10a) was synthesized from the starting phenylpyridine (6) via the reaction of the indolizine derivative (9a) with polyphosphoric acid (PPA) as the key step.
- Matsuda, Yoshiro,Kohra, Shinya,Katou, Keisuke,Uemura, Takashi,Yamashita, Kouhei
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p. 405 - 411
(2007/10/03)
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- Antifungal amine derivatives and processing for producing the same
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Novel amine derivatives having an excellent antimycotic effect represented by general formula (1) below and salts thereof are provided. [in the formula (1, R1represents a C1-5alkyl group which may be halogenated, R2represents 4-(1,1-dimethylalkyl)benzyl group, 4-(1-methyl-phenylethyl)benzyl group, 1-or 2-naphthylmethyl group, or a hydrocarbon group having 3,3-dimethyl-1-butynyl group or a phenyl group at its terminal and 1 to 3 double bonds; R3represents oxygen atom or a methylene group which may be substituted by a C1-4alkyl group; and R4represents 1-or 2 naphthyl group or a phenyl group which may be substituted.
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