- Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand
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Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.
- Liu, Feng,Wu, Na,Cheng, Xu
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supporting information
p. 3015 - 3020
(2021/05/05)
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- Direct Superacid-Promoted Difluoroethylation of Aromatics
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Under superacid conditions, aromatic amines are directly and regioselectively 1,1-difluoroethylated. Low temperature in situ NMR studies confirmed the presence of benzylic α-fluoronium and α-chloronium ions as key intermediates in the reaction. This method has a wide substrate scope and can be applied to the late-stage functionalization of natural alkaloids and active pharmaceutical ingredients.
- Artault, Maxime,Martin-Mingot, Agnès,Thibaudeau, Sébastien,Vitse, Kassandra
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supporting information
(2021/12/22)
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- Preparation method of acetamide compound
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The invention discloses a preparation method of an acetamide compound, the preparation method comprises the following steps: reacting tetracarbonyl dichloride rhodium, 1, 3-bis (diphenylphosphine) propane, tungsten carbonyl, sodium phosphate, sodium iodide, water, a nitro compound and dimethyl carbonate at 120 DEG C for 24 hours, and after the reaction is completed, performing post-treatment to obtain the acetamide compound. According to the preparation method, dimethyl carbonate serves as a C1 source and also serves as a green solvent, operation is easy, reaction starting raw materials are low in price and easy to obtain, the tolerance range of substrate functional groups is wide, and reaction efficiency is high. Various acetamide compounds can be synthesized according to actual needs, so that the practicability of the method is widened while the operation is convenient.
- -
-
Paragraph 0035-0047
(2021/05/19)
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- Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation
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The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.
- Bényei, Attila,Domján, Attila,Egyed, Orsolya,Gonda, Zsombor,Novák, Zoltán,Sályi, Gerg?,Tóth, Balázs L.
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supporting information
(2021/11/09)
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- Catalyst-free generation of acyl radicals induced by visible light in water to construct C-N bonds
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We describe herein a catalyst-free and redox-neutral photochemical strategy for the direct generation of acyl radicals from α-diketones, and its selective conversion of nitrosoarenes to hydroxyamides or amides with AcOH or NaCl as an additive. The reaction was carried out under mild conditions in water with purple LEDs as the light source. A broad scope of substrates was demonstrated. Mechanistic experiments indicate that α-diketones cleave to give acyl radicals, with hydroxyamides being further reduced to amides.
- Ran, Maogang,He, Jiaxin,Yan, Boyu,Liu, Wenbo,Li, Yi,Fu, Yunfen,Li, Chao-Jun,Yao, Qiuli
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supporting information
p. 1970 - 1975
(2021/03/16)
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- A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds
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Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.
- Bao, Zhi-Peng,Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
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supporting information
p. 1955 - 1958
(2021/03/02)
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- Exploring Homogeneous Conditions for Mild Buchwald-Hartwig Amination in Batch and Flow
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Cross-couplings are among the most frequently used reactions in complex molecule synthesis. However, the requirement of stoichiometric base can cause challenges. Harsh, insoluble inorganic bases can lead to poor tolerance of sensitive functional groups, scale-up issues, and difficult adaptation to continuous flow platforms. Herein, we describe the use of high throughput experimentation to identify a number of conditions that enable Buchwald-Hartwig reactions to be carried out using readily available ligands (e.g., XantPhos) with DBU as a soluble, functional-group-tolerant, homogeneous base. Application of this system to diverse aminations in batch and flow are demonstrated, as is the translation of this technique to performing continuous Mizoroki-Heck and Sonogashira coupling reactions.
- Kashani, Saeed K.,Jessiman, Jacob E.,Newman, Stephen G.
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supporting information
p. 1948 - 1954
(2020/03/13)
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- Synthesis of task-specific imidazolium ionic liquid as an efficient catalyst in acetylation of alcohols, phenols, and amines
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Herein, we report the synthesis of task-specific amino-functionalized imidazolium ionic liquid, acetate1-(2-tert-butoxycarbonylamino-ethyl)-3-methyl-3H-imidazol-1-ium; (Boc-NH-EMIM.OAc), as an efficient catalyst for the acetylation of alcohols, phenols, and amines in the presence of acetic anhydride (acetylating reagent). Remarkably, acetic anhydride in the presence of 10?molpercent of catalyst (Boc-NH-EMIM.OAc) under solvent-free conditions showed excellent acetylation activity in shorter duration of time. On the basis of this, a general procedure for acetylation of alcohols, phenols, and amines has been developed. The ionic liquid (Boc-NH-EMIM.OAc) can be readily recovered and reused successfully up to four consecutive cycles without any significant loss of its catalytic activity. We have been able to show that this acetylating method has many advantages. It gives high yields, takes shorter time, and develops the possibility of benign environmental-friendly process.
- Chaubey, Snehkrishn A.,Mishra, Roli
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p. 3259 - 3268
(2020/04/17)
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- A one pot protocol to convert nitro-arenes into: N-aryl amides
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A two-step one pot, experimentally simple protocol, based on readily available and inexpensive reagents allowed the conversion of nitro-arenes directly to N-aryl amides. A metal-free reduction of the nitro group, mediated by trichlorosilane, followed by the addition of an anhydride afforded the corresponding N-aryl carboxyamide, that was isolated after a simple aqueous work up in good-excellent yields. When the methodology was applied to the reaction with γ-butyrolactone, the desired N-aryl butanamide derivative was obtained, featuring a chlorine atom at the γ-position, a functionalized handle that can be used for further synthetic manipulation of the reaction product. Such an intermediate has already been employed as a key advanced precursor of pharmaceutically active compounds.
- Massolo, Elisabetta,Pirola, Margherita,Puglisi, Alessandra,Rossi, Sergio,Benaglia, Maurizio
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p. 4040 - 4044
(2020/02/04)
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- KOtBu-Promoted Transition-Metal-Free Transamidation of Primary and Tertiary Amides with Amines
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This work discloses transamidation of primary and tertiary amides with a range of aryl, heteroaryl, and aliphatic amines using potassium tert-butoxide. The reaction proceeds at room temperature under transition-metal-free conditions providing secondary amides in high yields. Moreover, reaction of cyclopropyl amine with tertiary amides proceeds with ring-opening to provide a rapid access to enamides.
- Ghosh, Tridev,Jana, Snehasish,Dash, Jyotirmayee
-
supporting information
p. 6690 - 6694
(2019/09/12)
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- 1-Aryl-3-(4-methoxybenzyl)ureas as potentially irreversible glycogen synthase kinase 3 inhibitors: Synthesis and biological evaluation
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Glycogen synthase kinase 3 (GSK-3)has become known for its multifactorial involvement in the pathogenesis of Alzheimer's disease. In this study, a benzothiazole- and benzimidazole set of 1-aryl-3-(4-methoxybenzyl)ureas were synthesised as proposed Cys199-targeted covalent inhibitors of GSK-3β, through the incorporation of an electrophilic warhead onto their ring scaffolds. The nitrile-substituted benzimidazolylurea 2b (IC50 = 0.086 ± 0.023 μM)and halomethylketone-substituted benzimidazolylurea 9b (IC50 = 0.13 ± 0.060 μM)displayed high GSK-3β inhibitory activity, in comparison to reference inhibitor AR-A014418 (1, IC50 = 0.072 ± 0.043)in our assay. The results suggest further investigation of 2b and 9b as potential covalent inhibitors of GSK-3β, since a targeted interaction might provide improved kinase-selectivity.
- Venter, Jana,Perez, Concepción,van Otterlo, Willem A.L.,Martínez, Ana,Blackie, Margaret A.L.
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p. 1597 - 1600
(2019/05/02)
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- Rhodium(III)-Catalyzed Directed C-H Dienylation of Anilides with Allenes Leads to Highly Conjugated Systems
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Allenes are unique coupling partners in transition-metal-catalyzed C-H functionalization leading to a variety of products via alkenylation, allenylation, allylation, and annulation reactions. The outcome is governed by both the reactivity of the allene and the formation and stability of the organometallic intermediate. An efficient Rh(III)-catalyzed, weakly coordinating group-directed dienylation of electronically unbiased allenes is developed using an N-acyl amino acid as a ligand. Further elaboration of the dienylated products to construct polycyclic compounds is also described.
- Ghosh, Chiranjit,Nagtilak, Prajyot Jayadev,Kapur, Manmohan
-
supporting information
(2019/05/08)
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- Metal-Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones
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The acylation of aryl halides to prepare aryl ketones without metal catalyst represents an important yet challenging topic towards more sustainable ketone synthesis. Herein, we describe a simple and efficient metal-free protocol for the acylation of aryl halides with diketone under the irradiation of light utilizing N-methylpiperidine as base under an air atmosphere. This reaction can tolerate a wide range of functional groups and the corresponding ketones can be obtained in modest to good yields.
- Yao, Qiuli,Liu, Wenbo,Liu, Peng,Ren, Linjing,Fang, Xuehong,Li, Chao-Jun
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supporting information
p. 2721 - 2724
(2019/01/14)
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- An alternative way to analogues of avenanthramides and their antiradical activity
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Abstract: The paper is devoted to the synthesis of arylidene malonic acid monoanilides and cinnamoyl anilines by condensation of malonic acid monoanilides with aromatic aldehydes. The presented synthetic route applies simple, cheap, and commercially available aromatic aldehydes and amines, thus overcoming traditional schemes, which involve derivatives of hydroxycinnamic acids. Besides, a mild and effective pyridine-mediated decarboxylation of carboxylic group at Csp2 in arylidene malonic acid monoanilides leading to cinnamoyl anilines is presented. The structures of obtained selected arylidene derivatives were approved additionally by X-ray analysis. The antiradical properties (2,2-diphenyl-1-picrylhydrazyl and galvinoxyl tests) and structure–activity relationships of the synthesized compounds were studied. Graphical abstract: [Figure not available: see fulltext.].
- Mierina, Inese,Stikute, Agnese,Mishnev, Anatoly,Jure, Mara
-
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- Electrochemical benzylic oxidation of C-H bonds
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Oxidized products have become increasingly valuable as building blocks for a wide variety of different processes and fine chemistry, especially in the benzylic position. We report herein a sustainable protocol for this transformation through C-H functionalization and is performed using electrochemistry as the main power source and tert-butyl hydroperoxide as the radical source for the C-H abstraction. The temperature conditions reported here do not increase above 50 °C and use an aqueous-based medium. A broad substrate scope is explored, along with bioactive molecules, to give comparable and increased product yields when compared to prior reported literature without the use of electrochemistry.
- Marko, Jason A.,Durgham, Anthony,Bretz, Stacey Lowery,Liu, Wei
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supporting information
p. 937 - 940
(2019/01/23)
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- Imidazolium chloride: An efficient catalyst for transamidation of primary amines
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A highly efficient and convenient protocol of imidazolium chloride (30 mol %) catalyzed amidation of amines with moderate to excellent yields was reported. The protocol shows broad substrate scope for aromatic, aliphatic, and heterocyclic primary amines.
- Tian, Qingqiang,Gan, Zongjie,Wang, Xuetong,Li, Dan,Luo, Wen,Wang, Huajun,Dai, Zeshu,Yuan, Jianyong
-
supporting information
(2018/09/10)
-
- Identification, structure modification, and characterization of potential small-molecule SGK3 inhibitors with novel scaffolds
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The serum and glucocorticoid-regulated kinase (SGK) family has been implicated in the regulation of many cellular processes downstream of the PI3K pathway. It plays a crucial role in PI3K-mediated tumorigenesis, making it a potential therapeutic target for cancer. SGK family consists of three isoforms (SGK1, SGK2, and SGK3), which have high sequence homology in the kinase domain and similar substrate specificity with the AKT family. In order to identify novel compounds capable of inhibiting SGK3 activity, a high-throughput screening campaign against 50,400 small molecules was conducted using a fluorescence-based kinase assay that has a Z' factor above 0.5. It identified 15 hits (including nitrogen-containing aromatic, flavone, hydrazone, and naphthalene derivatives) with IC50 values in the low micromolar to sub-micromolar range. Four compounds with a similar scaffold (i.e., a hydrazone core) were selected for structural modification and 18 derivatives were synthesized. Molecular modeling was then used to investigate the structure-activity relationship (SAR) and potential protein–ligand interactions. As a result, a series of SGK inhibitors that are active against both SGK1 and SGK3 were developed and important functional groups that control their inhibitory activity identified.
- Gong, Grace Qun,Wang, Ke,Dai, Xin-Chuan,Zhou, Yan,Basnet, Rajesh,Chen, Yi,Yang, De-Hua,Lee, Woo-Jeong,Buchanan, Christina Maree,Flanagan, Jack Urquhart,Shepherd, Peter Robin,Chen, Ying,Wang, Ming-Wei
-
p. 1902 - 1912
(2018/07/31)
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- Synthesis of oxindole from acetanilide via Ir(iii)-catalyzed C-H carbenoid functionalization
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Herein we disclose the first report on the synthesis of oxindole derivatives from acetanilide via Ir(iii)-catalyzed intermolecular C-H functionalization with diazotized Meldrum's acid. A broad range of substituted anilides were found to react smoothly under the Ir(iii)-catalytic system to afford the corresponding N-protected oxindoles. The N-protecting groups, such as Ac, Bz or Piv, can be easily removed to furnish the oxindole. Various synthetic applications of the synthesized oxindole were also demonstrated.
- Patel, Pitambar,Borah, Gongutri
-
supporting information
p. 443 - 446
(2017/01/03)
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- Co/NHPI-mediated aerobic oxygenation of benzylic C-H bonds in pharmaceutically relevant molecules
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A simple cobalt(ii)/N-hydroxyphthalimide catalyst system has been identified for selective conversion of benzylic methylene groups in pharmaceutically relevant (hetero)arenes to the corresponding (hetero)aryl ketones. The radical reaction pathway tolerates electronically diverse benzylic C-H bonds, contrasting recent oxygenation reactions that are initiated by deprotonation of a benzylic C-H bond. The reactions proceed under practical reaction conditions (1 M substrate in BuOAc or EtOAc solvent, 12 h, 90-100 °C), and they tolerate common heterocycles, such as pyridines and imidazoles. A cobalt-free, electrochemical, NHPI-catalyzed oxygenation method overcomes challenges encountered with chelating substrates that inhibit the chemical reaction. The utility of the aerobic oxidation method is showcased in the multigram synthesis of a key intermediate towards a drug candidate (AMG 579) under process-relevant reaction conditions.
- Hruszkewycz, Damian P.,Miles, Kelsey C.,Thiel,Stahl, Shannon S.
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p. 1282 - 1287
(2017/02/10)
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- Photo-Fries rearrangement of aryl acetamides: Regioselectivity induced by the aqueous micellar green environment
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Photochemical reactions tend to give more than one photoproduct. However, such a reaction can be a powerful synthetic tool when it is possible to conduct it in regioselective conditions yielding a single photoproduct. Water-surfactant solutions as reaction media can be considered as an approach in this context because they show products with different features than those from isotropic solutions. Here we describe results obtained from studying the effect on the prototypical photoreaction, known as the photo-Fries reaction of several substituted acetanilides and α-naphthyl acetamide within surfactant micelles (ionic and non-ionic micelles). This reaction involves homolytic cleavage of a C-N bond to yield a singlet radical pair. The surfactant micelles control the rotational and translational mobility of the radical pair, resulting in noticeable photoproduct selectivity.
- Iguchi, Daniela,Erra-Balsells, Rosa,Bonesi, Sergio M.
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p. 105 - 116
(2016/01/20)
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- AIBN-promoted amidation of anilines with 1, 3-diketones via oxidative cleavage of C–C bond under aerobic conditions
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N-Acylation of anilines with 1, 3-diketones promoted by AIBN (2-2′-azoisobutyronitrile) under metal-free and peroxide-free conditions in the presence of molecular oxygen as oxidant has been described. This protocol proceeds by the oxidative cleavage of C–C bond with simultaneous intermolecular C–N bond formation under mild conditions.
- Rao, Sadu Nageswara,Mohan, Darapaneni Chandra,Adimurthy, Subbarayappa
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p. 4889 - 4894
(2016/07/18)
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- Microwave Heated Continuous Flow Palladium(II)-Catalyzed Desulfitative Synthesis of Aryl Ketones
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A protocol for Pd(II)-catalyzed desulfitative synthesis of aryl ketones from sodium aryl sulfinates and nitriles in continuous flow has been developed. The reactions proceed with microwave heating using microwave transparent tube reactors, affording the desired aryl ketones in fair to good yields. Microwave transparent aluminum oxide reactors were identified as a safe and thermostable alternative to borosilicate glass reactors.
- Skillinghaug, Bobo,Rydfjord, Jonas,S?vmarker, Jonas,Larhed, Mats
-
supporting information
p. 2005 - 2011
(2017/02/10)
-
- Amino-ethanone thiosemicarbazone derivatives and its application
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The invention discloses an aminoacetophenone thiosemicarbazone derivative shown as a formula I and application thereof. In the formula I, an amino group connected with R is at 3 position or 4 position of the phenyl ring, and R is selected from C1-C6 alky or halogenated alkyl or alkoxy, aryl or substituted aryl. The related compounds are novel in structure and simple to prepare, are strong in inhibition activity on tyrosinase and have extremely obvious application prospect.
- -
-
Paragraph 0024; 0025
(2016/12/01)
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- Mild and efficient palladium-catalyzed direct trifluoroethylation of aromatic systems by C-H activation
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The introduction of trifluoroalkyl groups into aromatic molecules is an important transformation in the field of organic and medicinal chemistry. However, the direct installation of fluoroalkyl groups onto aromatic molecules still represents a challenging and highly demanding synthetic task. Herein, a simple trifluoroethylation process that relies on the palladium-catalyzed C-H activation of aromatic compounds is described. With the utilization of a highly active trifluoroethyl(mesityl)iodonium salt, the developed catalytic method enables the first highly efficient and selective trifluoroethylation of aromatic compounds. The robust catalytic procedure provides the desired products in up to 95 % yield at 25 °C in 1.5 to 3 hours and tolerates a broad range of functional groups. The utilization of hypervalent reagents opens new synthetic possibilities for direct alkylations and fluoroalkylations in the field of transition-metal-catalyzed C-H activation.
- T?th, Balázs L.,Kovács, Szabolcs,Sályi, Gerg?,Novák, Zoltán
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supporting information
p. 1988 - 1992
(2016/02/18)
-
- Fused tricyclic hepatitis virus inhibitor and application thereof
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The invention belongs to the field of medical chemistry, relates to a fused tricyclic hepatitis virus inhibitor and application thereof, and particularly, provides a compound of the general formula I or pharmaceutically acceptable salt, isomer, solvate, crystal or prodrug thereof, and a medicine composition containing the compounds and application of the compounds or the composition in medicine preparation. The compound has the good inhibiting activity on hepatitis C virus, meanwhile has the low toxicity on host cells, and is high in effectiveness, good in safety and likely to become the medicine for treating and/or preventing diseases relevant to HCV infection.
- -
-
Paragraph 0525; 0526; 0527; 0528
(2016/12/26)
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- Zn(II) porphyrin based nano-/microscale metal-organic frameworks: Morphology dependent sensitization and photocatalytic oxathiolane deprotection
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With Zn(ii) porphyrin as a building block, nano-/microscale MOFs with different morphologies were synthesized as sensitizers for O2 (forming 1O2). The sensitization efficiency was observed to enhance remarkably with the decrease of morphological dimension of the sample. With high sensitization ability, the one-dimensional MOF could selectively photocatalyze the deprotection of oxathiolanes to ketones.
- Zhao, Fang-Yao,Li, Wen-Juan,Guo, An,Chang, Lan,Li, Yue,Ruan, Wen-Juan
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p. 26199 - 26202
(2016/03/25)
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- Structure-based modification of 3-/4-aminoacetophenones giving a profound change of activity on tyrosinase: From potent activators to highly efficient inhibitors
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In this study, we developed 3-/4-aminoacetophenones and their structure-based 3-/4-aminophenylethylidenethiosemicarbazide derivatives, respectively, as novel tyrosinase activators and inhibitors. Notably, all the obtained thiosemicarbazones displayed more potent tyrosinase inhibitory activities than kojic acid. Especially, compound 7k was found to be the most active tyrosinase inhibitor with IC50 value of 0.291 1/4M. The structure-activity relationships (SARs) analysis showed that: (1) the amine group was absolutely necessarily for determining the tyrosinase activation activity; (2) the introduction of thiosemicarbazide group played a very vital role in transforming tyrosinase activators into tyrosinase inhibitors; (3) the phenylethylenethiosemicarbazide moiety was crucial for determining the tyrosinase inhibitory activity; (4) the type of acyl group had no obvious effect on the inhibitory activity; (5) the position of amide substituent on the phenyl ring influenced the tyrosinase inhibitory potency. Moreover, the inhibition mechanism and inhibition kinetics study revealed that compound 7k was reversible and non-competitive inhibitor, and compound 8h was reversible and competitive-uncompetitive mixed-II type inhibitor.
- You, Ao,Zhou, Jie,Song, Senchuan,Zhu, Guoxun,Song, Huacan,Yi, Wei
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p. 255 - 262
(2015/03/04)
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- Synthesis of Some New Thiazole Derivatives and Their Biological Activity Evaluation
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New 2-(4-arylpiperazine-1-yl)-N-[4-(2-(4-substituted phenyl)thiazol-4-yl)phenyl]acetamide derivatives were synthesized and evaluated for their antimicrobial and anticholinesterase activities. Acetylcholinesterase inhibitory activities of the compounds were found weak contrary to expectations. It is unlikely that antifungal activity of the compounds was found significant, especially against Candida parapsilosis.
- Yurtta?, Leyla,?zkay, Yusuf,Karaca Gen?er, Hülya,Acar, Ulviye
-
-
- Cleavage of C-N bonds in guanidine derivatives and its relevance to efficient C-N bonds formation
-
Efficient nonenzymatic decomposition of guanidine derivatives with high structural and functional diversity into anilide products is achieved in the presence of PdII/Cu(II) carboxylates/CO, relying on a dual C-N bonds cleavage strategy. In this decomposition process, the cooperative action of PdII species, Cu(II) carboxylates, and CO provides not only the N-acylating agents but also an initiator to trigger this C-N bonds cleavage sequence. The current results indicate that PdII/Cu(II) carboxylates/CO system provides a convenient and practical method for highly selective cleavage of unreactive C-N single bonds.
- Chang, Denghu,Zhu, Dan,Zou, Peng,Shi, Lei
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p. 1684 - 1693
(2015/03/30)
-
- Synthesis and anticancer activity evaluation of N-[4-(2-methylthiazol-4-yl) phenyl]acetamide derivatives containing (benz)azole moiety
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A new class of novel thiazole-(benz)azole derivatives was synthesized to investigate their anticancer activity. The structure of the compounds was confirmed by IR, 1H-NMR, and MS spectral data and elemental analyses. Anticancer effect of the compounds was evaluated against A549 and C6 tumor cell lines. MTT, analysis of DNA synthesis, acridine orange/ethidium bromide staining method and analysis of caspase-3 activation assays were performed for anticancer activity investigations. Compounds 6f and 6g, which carry 5-chloro and 5-methylbenzimidazole groups showed significant anticancer activity. Potential of these compounds to direct tumor cells to apoptotic pathway, which is a precondition of anticancer action, was also observed.
- Yurtta?, Leyla,?zkay, Yusuf,Akalin-?ift?i, Gül?en,Ulusoylar-Yildirim, ?afak
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p. 175 - 184
(2014/04/03)
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- Synthesis, anticandidal activity, and cytotoxicity of some thiazole derivatives with dithiocarbamate side chains
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Some thiazole derivatives bearing dithiocarbamic acid esters were synthesized in order to investigate their anticandidal activity and cytotoxicity. The structures of the obtained final compounds (6a-j) were confirmed by spectral data (IR, 1H NMR, 13C NMR, and MS) and elemental analysis. The anticandidal activity of the compounds was determined (6a-j) using the microbroth dilution method and their cytotoxicity was evaluated according to the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against normal cells. Contrary to expectations, weak antifungal activity was observed with IC50values ranging between 30 and 403 μg/mL.
- Yurtta, Leyla,?zkay, Yusuf,?ztürk, ?mer,Kaplancikli, Zafer Asim,Demirci, Fatih,G?ger, Gamze,Ulusoylar Yildirim, afak,Abu Mohsen, Usama
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p. 815 - 824
(2014/12/10)
-
- Fluorescent polarity probes for identifying bovine serum albumin: Amplification effect of para-substituted benzene
-
Fluorescent probes 1-3 with coumarin as the fluorophore were designed and synthesized for the determination of bovine serum albumin (BSA). All three probes exhibited evidently solvatochromic UV-vis and fluorescence spectra. Compound 3 was the most effective towards the solvent's polarity: 155 nm (vs. 60 nm for 1 and 100 nm for 2) red shift in the emission maximum was found as the solvent changing from cyclohexane to phosphate buffer solution. These compounds were applied to detect BSA based on the hypothesis that the polarity of the microenvironment surrounding the probe will undergo significant change when the probe moves from the bulk solution to the hydrophobic domains of BSA. 3 was the most sensitive towards BSA and the detection limit of BSA was 0.6 μg/mL with 3 as the probe, which ensured the detection of BSA content in fetal bovine serum with good recovery.
- Bai, Hongyan,Qian, Junhong,Tian, Haiyu,Pan, Wenwen,Zhang, Lingyi,Zhang, Weibing
-
-
- Palladium(II)-catalyzed desulfitative synthesis of aryl ketones from sodium arylsulfinates and nitriles: Scope, limitations, and mechanistic studies
-
A fast and efficient protocol for the palladium(II)-catalyzed production of aryl ketones from sodium arylsulfinates and various organic nitriles under controlled microwave irradiation has been developed. The wide scope of the reaction has been demonstrated by combining 14 sodium arylsulfinates and 21 nitriles to give 55 examples of aryl ketones. One additional example illustrated that, through the choice of the nitrile reactant, benzofurans are also accessible. The reaction mechanism was investigated by electrospray ionization mass spectrometry and DFT calculations. The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The palladium(II) intermediates detected by ESI-MS and the DFT calculations provide a detailed understanding of the catalytic cycle. (Figure Presented).
- Skillinghaug, Bobo,Sk?ld, Christian,Rydfjord, Jonas,Svensson, Fredrik,Behrends, Malte,S?vmarker, Jonas,Sj?berg, Per J. R.,Larhed, Mats
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p. 12018 - 12032
(2015/01/16)
-
- Design, synthesis and evaluation of new thiazole-piperazines as acetylcholinesterase inhibitors
-
In this study, some new 2-(4-substituted piperazine-1-yl)-N-[4-(2- methylthiazol-4-yl)phenyl]acetamide derivatives were synthesized. The synthesized compounds were screened for their anticholinesterase activity on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes by in vitro Ellman's method. The structural elucidation of the compounds was performed by using IR, 1H-NMR, 13C-NMR and FAB+-MS spectral data and elemental analyses results. Biological assays revealed that at 0.1 μM concentration, the most active compounds against AChE were 5n, 5o and 5p that indicated 96.44, 99.83 and 89.70% inhibition rates, respectively. Besides, IC50 value of the compound 5o was determined as 0.011 μM, whereas IC50 value of standard drug donepezil was 0.054 μM. The synthesized compounds did not show any notable inhibitory activity against BChE.
- Yurttas, Leyla,Kaplancikli, Zafer Asim,Oezkay, Yusuf
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p. 1040 - 1047
(2013/10/01)
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- Nanoceria-catalyzed highly efficient procedure for N-formylation of amines at room temperature under solvent-free conditions
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Nanoceria-catalyzed simple and efficient protocol for the N-formylation of amines using formic acid at room temperature under solvent-free conditions shows high yield of desired product chemoselectivity and improvement in reaction time.
- Patil, Umakant B.,Singh, Abhilash S.,Nagarkar, Jayashree M.
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supporting information
p. 524 - 526
(2013/06/05)
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- NOVEL AZO COMPOUND, AQUEOUS SOLUTION, INK COMPOSITION, INK FOR INKJET RECORDING, INKJET RECORDING METHOD, INK CARTRIDGE FOR INKJET RECORDING AND INKJET RECORDING
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The present invention relates to an aqueous solution and an ink composition, which can provide a stable ink which has a good hue as black ink, imparts colored images or colored materials having an excellent fastness, and furthermore, has a small change in physical properties, particularly suppressed bronzing even when preserved over a long period of time. In addition, there is provided a method of forming an image, which provides ink for printing or recording, such as inkjet, and prevents a reduction in image quality of the formed image (a method of preventing a reduction in image quality). An aqueous solution containing (a) a preservative and (b) at least one azo compound represented by the following Formula (1) or a salt thereof, in which the content of (b) is 1% by mass to 25% by mass. (In Formula (1), G represents a nitrogen atom or -C(R2)=. R2 represents a hydrogen atom, a sulfo group, a carboxyl group, a substituted or unsubstituted carbamoyl group or a cyano group. X1, X2, X3, X4, X5, X6 and X7 each independently represents a hydrogen atom or a monovalent substituent. Y2, Y3 and Y4 each independently represents a hydrogen atom or a monovalent substituent. Y2, Y3 and Y4 may be bonded with each other to form a ring. All of Y2, Y3 and Y4 do not represent hydrogen atoms at the same time. M each independently represents a hydrogen atom or a monovalent countercation.)
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Paragraph 0291; 0292
(2013/06/27)
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- NOVEL AZO COMPOUND, AQUEOUS SOLUTION, INK COMPOSITION, INK FOR INKJET RECORDING, INKJET RECORDING METHOD, INK CARTRIDGE FOR INKJET RECORDING AND INKJET RECORDING
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Provided is an aqueous solution and an ink composition having a favorable color as black ink, providing a colored image or a colored material having excellent fastness by removing a change in image quality of a record by a difference in recording paper, and providing stable ink having a small change in physical properties, particularly, suppressed bronze gloss, even though preservation is performed over a long period of time. In addition, there is provided a method of forming an image, which provides ink for printing or recording, such as inkjet, and prevents a reduction in image quality of the formed image (a method of preventing a reduction in image quality). An aqueous solution including: (a) a preservative, and (b) at least one kind of an azo compound represented by the following Formula (1) or a salt thereof, wherein a content of (b) is 1% by mass to 25% by mass: wherein, in Formula (1), A represents a substituted phenyl group or a substituted or unsubstituted nitrogen-containing 5-membered heterocyclic group, G represents a nitrogen atom or -C(R2)=, R2 represents a hydrogen atom, a sulfo group, a carboxy group, a substituted or unsubstituted carbamoyl group or cyano group, Y2, Y3 and Y4 each independently represents a hydrogen atom or a monovalent substituent, Y2, Y3 and Y4 may be bonded to each other to form a ring, all of Y2, Y3 and Y4 do not represent a hydrogen atom at the same time, and M each independently represents a hydrogen atom or a monovalent countercation.
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Paragraph 0323; 0324
(2013/06/28)
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- Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates
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The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Trypanosoma cruzi in in vitro assays (IC50 57 μM), and no mutagenic profile was observed in micronucleous tests. Although the in vitro inhibition test showed that 10-μM doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity.
- Blau, Lorena,Menegon, Renato Farina,Trossini, Gustavo H. G.,Molino, Jo?o Vitor Dutra,Vital, Drielli Gomes,Cicarelli, Regina Maria Barretto,Passerini, Gabriela Duó,Bosquesi, Priscila Longhin,Chin, Chung Man
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p. 142 - 151
(2013/10/01)
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- H2O2-mediated oxidative formation of amides from aromatic amines and 1,3-diketones as acylation agents via C-C bond cleavage at room temperature in water under metal-free conditions
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1,3-Diketones, as novel acylation agents, reacted with aromatic amines promoted by commercially available H2O2 (30% aq.) as the sole oxidant at room temperature under metal-free conditions in water, leading to a novel and rapid amide bond formation strategy. The reported method is high-yielding, simple and mild, and is the first example of the use of 1,3-diketones as acylation agents via C-C bond cleavage.
- Sun, Xi,Wang, Min,Li, Pinhua,Zhang, Xiuli,Wang, Lei
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supporting information
p. 3289 - 3294
(2013/12/04)
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- Hydration of terminal alkynes catalyzed by water-soluble cobalt porphyrin complexes
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Water-soluble cobalt(III) porphyrin complexes were found to promote the hydration of terminal alkynes to give methyl ketones. The alkyne hydration proceeded in good to excellent yield with 0.1 to 2 mol % cobalt catalyst 1 and was compatible with the presence of acid/base- or redox-sensitive functional groups such as alkyl silyl ethers; allyl ethers; trityl ethers; benzyl ethers; carboxylic esters; boronic esters; carboxamides; nitriles; and nitro, iodo, and acetal groups. Some of the alkyne substrates tested here are otherwise difficult to hydrate. The alkyne hydration can be performed on a gram scale, and the catalyst can be recovered by aqueous workup.
- Tachinami, Tadashi,Nishimura, Takuho,Ushimaru, Richiro,Noyori, Ryoji,Naka, Hiroshi
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supporting information
p. 50 - 53
(2013/02/23)
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- Iron-catalyzed indirect hydration of alkynes in presence of methanesulfonic acid
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We have demonstrated that the FeCl2·4H2O and methanesulfonic acid systems show high reaction efficiency for the indirect hydration of various alkynes in DCE. The reaction proceeds under mild conditions to produce various ketones from alkynes. A mechanistic study of the reaction intermediates showed that the alkyne was readily converted into vinyl sulfonate corresponding to the addition of MsOH to the C-C triple bonds, which in turn was transformed to the ketone in the presence of MsOH.
- Park, Jungmin,Yeon, Jihee,Lee, Phil Ho,Lee, Kooyeon
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p. 4414 - 4417
(2013/07/26)
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- Mild and efficient nickel-catalyzed heck reactions with electron-rich olefins
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A new efficient protocol for the nickel-catalyzed Heck reaction of aryl triflates with vinyl ethers is presented. Mild reaction conditions that equal those of the corresponding palladium-catalyzed Heck reaction are applied, representing a practical and more sustainable alternative to the conventional regioselective arylation of vinyl ethers. A catalytic system comprised of Ni(COD)2 and 1,1″-bis(diphenylphosphino)ferrocene (DPPF) in combination with the tertiary amine Cy2NMe proved effective in the olefination of a wide range of aryl triflates. Both electron-deficient and electron-rich arenes proved compatible, and the corresponding aryl methyl ketone could be secured after hydrolysis in yields approaching quantitative. Good functional group tolerance was observed matching the characteristics of the analogous Pd-catalyzed Heck reaction. The high levels of catalytic activity were explained by the intermediacy of a cationic nickel(II) complex potentially responsible for the successive β-hydride elimination and base promoted catalyst regeneration. Although these elementary reactions are normally considered challenging, DFT calculations suggested this pathway to be favorable under the applied reaction conditions.
- Gogsig, Thomas M.,Kleimark, Jonatan,Nilsson Lill, Sten O.,Korsager, Signe,Lindhardt, Anders T.,Norrby, Per-Ola,Skrydstrup, Troels
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p. 443 - 452
(2012/03/07)
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- Antimicrobial and cytotoxicity potential of acetamido, amino and nitrochalcones
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Background: Chalcones constitute one of the major classes of natural products belonging to the flavonoid family, and they have been reported as having a range of important therapeutic activities, including some chalcones are effective as antimicrobial agents. Currently, the search for new structures with antimicrobial activity has been intensified due to the emergence of many strains resistant to antibiotics currently used to treat infectious diseases. Method: 3 chalcone series (amino, acetamido and nitrochalcones) were prepared (23 compounds) and evaluated for their antimicrobial and cytotoxic potential. The effects of substituents on their respective activities also was evaluated. Results & Conclusion: The results showed that 4 aminochalcones (2, 4, 8, 9), 3 acetoamidochalcones (10, 14, 18) and 3 nitrochalcones (20, 22, 23), exhibited antifungal effects. The aminochalcones were more toxic than the acetamidochalcones, while the nitrochalcones did not present any toxic effect. It was verified that there seems to be structure-activity correlation in some electron-donating and withdrawing substituents groups in rings A and B of the synthetized chalcone analogues and its antifungal and cytotoxic activity. Georg Thieme Verlag KG Stuttgart New York.
- Trist?o,Campos-Buzzi,Corrêa,Cruz,Cechinel Filho,Bella Cruz
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p. 590 - 594
(2013/03/13)
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- Iron-doped single-walled carbon nanotubes as new heterogeneous and highly efficient catalyst for acylation of alcohols, phenols, carboxylic acids and amines under solvent-free conditions
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Iron-doped single-walled carbon nanotubes (Fe/SWCNTs) represent an efficient and new heterogeneous reusable catalyst for the acylation of a variety of alcohols, phenols, carboxylic acids and amines with acid chlorides or acid anhydrides under solvent-free conditions. The reactions of various primary, secondary, tertiary, and benzylic alcohols, diols, phenols, as well as aromatic and aliphatic amines give acylated adducts in good to excellent yields.
- Sharghi, Hashem,Jokar, Mahboubeh,Doroodmand, Mohammad Mahdi
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experimental part
p. 426 - 442
(2011/04/15)
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- Pyridone derivatives as NK3 antagonists
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The present invention relates to compounds useful in therapy, in particular in the treatment of psychosis, to compositions comprising said compounds, and to methods of treating diseases comprising the administration of said compounds.
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Page/Page column 17-18
(2011/06/26)
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- COMPOUNDS AND METHODS FOR INHIBITING NHE-MEDIATED ANTIPORT IN THE TREATMENT OF DISORDERS ASSOCIATED WITH FLUID RETENTION OR SALT OVERLOAD AND GASTROINTESTINAL TRACT DISORDERS
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The present disclosure is directed to corn- pounds and methods for the treatment of disorders associated with fluid retention or salt overload, such as heart failure (in particular, congestive heart failure), chronic kidney disease, end-stage renal disease, liver disease, and peroxisome proliferator-activated receptor (PPAR) gamma agonist-induced fluid retention. The present disclosure is also directed to compounds and methods for the treatment of hypertension. The present disclosure is also directed to compounds and methods for the treatment of gastrointestinal tract disorders, including the treatment or reduction of pain associated with gastrointestinal tract disorders. The methods generally comprise administering to a mammal in need thereof a pharmaceutically effective amount of a compound, or a pharmaceutical composition comprising such a compound, that is designed to be substantially active in the gastrointestinal (GI) tract to inhibit NHE-mediated antiport of sodium ions and hydrogen ions therein. More particularly, the method comprises administering to a mammal in need thereof a pharmaceutically effective amount of a compound, or a pharmaceutical composition comprising such a compound, that inhibits NHE-3, -2 and/ or -8 mediated antiport of sodium and/or hydrogen ions in the GI tract and is designed to be substantially impermeable to the layer of epithelial cells, or more specifically the epithelium of the GI tract. As a result of the compound being substantially impermeable, it is not absorbed and is thus essentially systemically non-bioavailable, so as to limit the exposure of other internal organs (e.g., liver, heart, brain, etc.) thereto. The present disclosure is still further directed to a method wherein a mammal is administered such a compound with a fluid-absorbing polymer, such that the combination acts as described above and further provides the ability to sequester fluid and/or salt present in the GI tract
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Page/Page column 185
(2010/08/04)
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- A green approach to chemoselective N-acetylation of amines using catalytic amount of zinc acetate in acetic acid under microwave irradiation
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It has been found for the first time that zinc acetate alone can act as a selective A'-acetylating agent without any solvent under closed vessel microwave irradiation. It is also observed that the use of a catalytic amount of this reagent in acetic acid is sufficient enough for smooth running of A'-acetylation of a number of structurally diverse amines, and the reaction is chemoselective with respect to phenols, thiols, acids and alcohols. Herein is reported a simple, efficient, cost-effective and environmentally benign alternative method for chemoselective A'-acetylation of amines using catalytic amount of zinc acetate in acetic acid under microwave irradiation. The reaction procedure requires no other solvent, and is rapid with good to excellent yields.
- Brahmachari,Laskar,Sarkar
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experimental part
p. 1274 - 1281
(2010/12/24)
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- Hydrogen-bonding-promoted oxidative addition and regioselective arylation of olefins with aryl chlorides
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The first, general, and highly efficient catalytic system that allows a wide range of activated and unactivated aryl chlorides to couple regioselectively with olefins has been developed. The Heck arylation reaction is likely to be controlled by the oxidative addition of ArCl to Pd(0). Hence, an electron-rich diphosphine, 4-MeO-dppp, was introduced to facilitate the catalysis. Solvent choice is critical, however; only sluggish arylation is observed in DMF or DMSO, whereas the reaction proceeds well in ethylene glycol at 0.1-1 mol % catalyst loadings, displaying excellent regioselectivity. Mechanistic evidence supports that the arylation is turnover-limited by the oxidative addition step and, most importantly, that the oxidative addition is accelerated by ethylene glycol, most likely via hydrogen bonding to the chloride at the transition state as shown by DFT calculations. Ethylene glycol thus plays a double role in the arylation, facilitating oxidative addition and promoting the subsequent dissociation of chloride from Pd(II) to give a cationic Pd(II)-olefin species, which is key to the regioselectivity observed.
- Ruan, Jiwu,Iggo, Jonathan A.,Berry, Neil G.,Xiao, Jianliang
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supporting information; experimental part
p. 16689 - 16699
(2011/02/23)
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