- Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents
-
To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.
- Zhao, Liyu,Sun, Yin,Yin, Wenbo,Tian, Linfeng,Sun, Nannan,Zheng, Yang,Zhang, Chu,Zhao, Shizhen,Su, Xin,Zhao, Dongmei,Cheng, Maosheng
-
-
- Switching from biaryl formation to amidation with convoluted polymeric nickel catalysis
-
A stable, reusable, and insoluble poly(4-vinyl-pyridine) nickel catalyst (P4VP-NiCl2) was prepared through the molecular convolution of poly(4-vinylpyridine) (P4VP) and nickel chloride. We proposed a coordination structure of the Ni center in the precatalyst based on elemental analysis and Ni K-edge XANES, and we confirmed that it is consistent with Ni K-edge EXAFS. The Suzuki?Miyaura-type coupling of aryl halides and arylboronic esters proceeded using P4VP-NiCl2 (0.1 mol % Ni) to give the corresponding biaryl compounds in up to 94% yield. Surprisingly, when the same reaction of aryl halides and arylboronic acid/ester was carried out in the presence of amides, the amidation proceeded predominantly to give the corresponding arylamides in up to 99% yield. In contrast, the reaction of aryl halides and amides in the absence of arylboronic acid/ester did not proceed. P4VP-NiCl2 successfully catalyzed the lactamization for preparing phenanthridinone. P4VP-NiCl2 was reused five times without significant loss of catalytic activity. Pharmaceuticals, natural products, and biologically active compounds were synthesized efficiently using P4VPNiCl2 catalysis. Nickel contamination in the prepared pharmaceutical compounds was not detected by ICP-MS analysis. The reaction was scaled to multigrams without any loss of chemical yield. Mechanistic studies for both Suzuki?Miyaura and amidation were performed.
- Sen, Abhijit,Dhital, Raghu N.,Sato, Takuma,Ohno, Aya,Yamada, Yoichi M.A.
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p. 14410 - 14418
(2020/12/21)
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- Decarboxylative/Oxidative Amidation of Aryl α-Ketocarboxylic Acids with Nitroarenes and Nitroso Compounds in Aqueous Medium
-
The decarboxylative/oxidative amidation of aryl α-ketocarboxylic acids with 5-aryl-3-nitroisoxazole-4-carboxylates and substituted dinitrobenzenes under oxidative aqueous conditions to afford N-aryl amides is described. The reaction is suggested to proceed via a radical pathway in which a benzoyl nitroxyl radical, the key intermediate formed from reaction between nitroarene and benzoyl radical from glyoxalic acid, couples with hydroxyl radical from water to produce amide. Mechanistic insight allowed the scope of the strategy to be expanded to the synthesis of amides via reaction between aryl α-ketocarboxylic acids and nitroso compounds.
- Barak, Dinesh S.,Dahatonde, Dipak J.,Dighe, Shashikant U.,Kant, Ruchir,Batra, Sanjay
-
supporting information
p. 9381 - 9385
(2020/11/30)
-
- Buchwald-Hartwig cross-coupling of amides (transamidation) by selective N-C(O) cleavage mediated by air- And moisture-stable [Pd(NHC)(allyl)Cl] precatalysts: Catalyst evaluation and mechanism
-
The Pd-NHC-catalyzed acyl-type Buchwald-Hartwig cross-coupling of amides by N-C(O) cleavage (transamidation) provides a valuable alternative to the classical methods for amide synthesis. Herein, we report a combined experimental and computational study of the Buchwald-Hartwig cross-coupling of amides using well-defined, air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts. Most crucially, we present a comprehensive evaluation of a series of distinct Pd(ii)-NHC precatalysts featuring different NHC scaffolds and throw-away ligands for the synthesis of functionalized amides that are not compatible with stoichiometric transition-metal-free transamidation methods. Furthermore, we present evaluation of the catalytic cycle by DFT methods for a series of different Pd(ii)-NHC precatalysts. The viability of accessing NHC-supported acyl-palladium(ii) amido complexes will have implications for the design and development of cross-coupling methods involving stable amide electrophiles.
- Li, Guangchen,Zhou, Tongliang,Poater, Albert,Cavallo, Luigi,Nolan, Steven P.,Szostak, Michal
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p. 710 - 716
(2020/02/25)
-
- 3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalysed metal-free amide bond formation from thioacids and amines at room temperature
-
A 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalysed efficient, mild and metal-free method has been developed for direct amide bond synthesis from simple thioacids and amines as starting materials. This methodology is useful for aromatic, aliphatic, and heteroaromatic thioacids as well as primary, secondary, heterocyclic, and even functionalized amines. A wide substrates scope, operationally mild conditions, and acylation of amines without affecting other functional groups such as alcohols, esters, carbodithioates, among others make this strategy very attractive and practical.
- Samanta, Suvendu,Ray, Shounak,Bhaduri, Samanka Narayan,Samanta, Partha Kumar,Biswas, Papu
-
supporting information
(2020/08/10)
-
- Highly Chemoselective, Transition-Metal-Free Transamidation of Unactivated Amides and Direct Amidation of Alkyl Esters by N-C/O-C Cleavage
-
The amide bond is one of the most fundamental functional groups in chemistry and biology and plays a central role in numerous processes harnessed to streamline the synthesis of key pharmaceutical and industrial molecules. Although the synthesis of amides is one of the most frequently performed reactions by academic and industrial scientists, the direct transamidation of tertiary amides is challenging due to unfavorable kinetic and thermodynamic contributions of the process. Herein, we report the first general, mild, and highly chemoselective method for transamidation of unactivated tertiary amides by a direct acyl N-C bond cleavage with non-nucleophilic amines. This operationally simple method is performed in the absence of transition metals and operates under unusually mild reaction conditions. In this context, we further describe the direct amidation of abundant alkyl esters to afford amide bonds with exquisite selectivity by acyl C-O bond cleavage. The utility of this process is showcased by a broad scope of the method, including various sensitive functional groups, late-stage modification, and the synthesis of drug molecules (>80 examples). Remarkable selectivity toward different functional groups and within different amide and ester electrophiles that is not feasible using existing methods was observed. Extensive experimental and computational studies were conducted to provide insight into the mechanism and the origins of high selectivity. We further present a series of guidelines to predict the reactivity of amides and esters in the synthesis of valuable amide bonds by this user-friendly process. In light of the importance of the amide bond in organic synthesis and major practical advantages of this method, the study opens up new opportunities in the synthesis of pivotal amide bonds in a broad range of chemical contexts.
- Li, Guangchen,Ji, Chong-Lei,Hong, Xin,Szostak, Michal
-
supporting information
p. 11161 - 11172
(2019/08/07)
-
- Well-Defined, Air-Stable, and Readily Available Precatalysts for Suzuki and Buchwald-Hartwig Cross-coupling (Transamidation) of Amides and Esters by N-C/O-C Activation
-
A general class of well-defined, air-stable, and readily available Pd(II)-NHC precatalysts (NHC = N-heterocyclic carbene) for Suzuki and Buchwald-Hartwig cross-coupling of amides (transamidation) and esters by selective N-C/O-C cleavage is reported. Since these precatalysts are highly active and the easiest to synthesize, the study clearly suggests that [Pd(NHC)(acac)Cl] should be routinely included during the development of new cross-coupling methods. An assay for in situ screening of NHC salts in this cross-coupling manifold is presented.
- Zhou, Tongliang,Li, Guangchen,Nolan, Steven P.,Szostak, Michal
-
supporting information
p. 3304 - 3309
(2019/05/10)
-
- Synthesis, chemical characterization and antimicrobial activity of new acylhydrazones derived from carbohydrates
-
A new series of glycosylated acylhydrazones was synthesized and all the chemical structures were confirmed by High Resolution Mass Spectrometry (HRMS), 1H and 13C Nuclear Magnetic Resonance (1H-NMR; 13C-NMR) and Fourier Transform Infrared (FTIR) spectroscopy methods. The mass accuracy between the calculated and found values observed in HRMS analyses were near or lower than 5 ppm, which are acceptable for proposing a molecular formula using this technique. All of the synthesized compounds were screened for their antibacterial, antifungal and antiviral activities. Five compounds (12, 13, 14, 16 and 19) exerted a modest antifungal activity against the strains evaluated. Derivative 14 showed fungicidal activity against Candida glabrata at 173.8 μM and saccharide unit contributed to the increase of the antifungal potential against this strain. New chemical manipulation of derivative 14 can make it possible to obtain new potentially antimicrobial agents.
- Guilherme, Fernanda Dias,Simonetti, Julia évelin,Folquitto, Lais Regina Santos,Reis, Adriana Cotta Cardoso,Oliver, Josidel Concei??o,Dias, Amanda Latércia Tranches,Dias, Danielle Ferreira,Carvalho, Diogo Teixeira,Brand?o, Geraldo Célio,Souza, Thiago Belarmino de
-
p. 349 - 356
(2019/03/04)
-
- Selective conversion of primary amides to esters promoted by KHSO4
-
Primary amides, either aliphatic or aromatic, are easily converted to the corresponding esters via reflux in lower primary alcohols in the presence of KHSO4. Secondary amides lead to complicated mixtures under analogous conditions, whereastertiary amides were inert. Use of isopropyl alcohol resulted inthe formation of product atslower rate and lower yieldalong withside products, whereas, use of tertiary alcoholsdid not give successful conversion andallyl and benzyl alcohol provided complex mixtures.
- Sattenapally, Narsimha,Sharma, Jhanvi,Hou, Yuqing
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p. 174 - 183
(2018/09/10)
-
- Visible light driven amide synthesis in water at room temperature from Thioacid and amine using CdS nanoparticles as heterogeneous Photocatalyst
-
Highly efficient photocatalytic thioacid mediated amide synthesis at room temperature using CdS nanoparticles as photocatalyst was observed under a household 30?W CFL in water. The operationally mild reaction was tolerant to a number of functional group substitutions on amine and could be scaled up to gram. This heterogeneous photocatalyst was extremely stable and could easily be recovered by simple centrifugation for at least six recycling reactions without any significant loss of catalytic performance. The possible reaction mechanism for the photocatalytic thioacid mediated amide synthesis over the CdS semiconductor has also been proposed on the basis of experimental observations.
- Das, Sudipto,Ray, Shounak,Ghosh, Abhisek Brata,Samanta, Partha Kumar,Samanta, Suvendu,Adhikary, Bibhutosh,Biswas, Papu
-
-
- Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
-
The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.
- Yuan, Yu-Chao,Kamaraj, Raghu,Bruneau, Christian,Labasque, Thierry,Roisnel, Thierry,Gramage-Doria, Rafael
-
supporting information
p. 6404 - 6407
(2017/12/08)
-
- A Cross-Coupling Approach to Amide Bond Formation from Esters
-
A palladium-catalyzed cross-coupling between aryl esters and anilines is reported, enabling access to diverse amides. The reaction takes place via activation of the C-O bond by oxidative addition with a Pd-NHC complex, which enables the use of relatively non-nucleophilic anilines that otherwise require stoichiometric activation with strong bases in order to react. High yields of aromatic, aliphatic, and heterocyclic products are obtained. A range of activated esters are evaluated in the presence and absence of catalyst, demonstrating that the catalytic methodology substantially increases the types of electrophiles that can be utilized for amide bond formation in the absence of harsh bases.
- Ben Halima, Taoufik,Vandavasi, Jaya Kishore,Shkoor, Mohanad,Newman, Stephen G.
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p. 2176 - 2180
(2017/08/09)
-
- Pd-PEPPSI: A general Pd-NHC precatalyst for Buchwald-Hartwig cross-coupling of esters and amides (transamidation) under the same reaction conditions
-
Amides are of fundamental interest in many fields of chemistry involving organic synthesis, chemical biology and biochemistry. Here, we report the first catalytic Buchwald-Hartwig coupling of both common esters and amides by highly selective C(acyl)-X (X = O, N) cleavage to rapidly access aryl amide functionality via a cross-coupling strategy. Reactions are promoted by versatile, easily prepared, well-defined Pd-PEPPSI type precatalysts, and proceed in good to excellent yields and with excellent chemoselectivity for the acyl bond cleavage. The method is user friendly because it employs commercially-available, moisture- and air-stable precatalysts. Notably, for the first time we demonstrate selective C(acyl)-N and C(acyl)-O cleavage/Buchwald-Hartwig amination under the same reaction conditions, which allows for streamlining amide synthesis by avoiding restriction to a particular acyl metal precursor. Of broad interest, this study opens the door to using a family of well-defined Pd(ii)-NHC precatalysts bearing pyridine "throw-away" ligands for the selective C(acyl)-amination of bench-stable carboxylic acid derivatives.
- Shi, Shicheng,Szostak, Michal
-
supporting information
p. 10584 - 10587
(2017/09/29)
-
- Substituted pyridoimidazole derivative and preparation thereof, and applications of substituted pyridoimidazole derivative in medicines
-
The present invention discloses a substituted pyridoimidazole derivative and preparation thereof, and applications of the substituted pyridoimidazole derivative in medicines, and particularly relates to a new derivative represented by a general formula (I) and a pharmaceutically acceptable salt thereof or a pharmaceutical composition containing the new derivative, and a preparation method of the new derivative. The present invention further discloses applications of the derivative and the pharmaceutically acceptable salt thereof or the pharmaceutical composition containing the new derivative in Bruton tyrosine kinase inhibitors and in preparation of drugs for treatment and/or prevention of tumors, inflammations, and other diseases, wherein each substituent in the general formula (I) is defined in the specification. The formula (I) is defined in the specification.
- -
-
Paragraph 0172; 0174; 0175
(2017/05/27)
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- Derivative with imidazopyridine, preparation method and application in medicine thereof
-
The invention discloses a derivative with imidazopyridine, a preparation method and application in medicine thereof. Concretely speaking, the invention relates to a novel derivative, medicinal salt of the derivative or pharmaceutical compositions containing the derivative, and the preparation method of the derivative showed in general formula (I). The invention also discloses application of the derivative, medicinal salt of the derivative or pharmaceutical compositions containing the derivative in Bruton tyrosine kinase inhibitor, preparing the medicine for treating or preventing tumor and inflammation diseases. Substituent groups in general formula (I) are identical to definitions in the specification (the structure is shown in the description).
- -
-
Paragraph 0192; 0193; 0194
(2017/08/24)
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- Derivative having imidazopyrazines, preparation method and application thereof of derivative on medicine
-
The invention discloses a derivative having imidazopyrazines, a preparation method and an application thereof of the derivative on medicine. Concretely speaking, the invention relates to a novel derivative shown in a general formula (I) and its medicinal salt or a pharmaceutical composition containing the derivative, and its preparation method. The invention also discloses the derivative or its medicinal salt or an application of the pharmaceutical composition containing the derivative in a Bruton tyrosine kinase inhibitor, and in preparation of medicines for treating and/or preventing diseases such as tumour and inflammation. The substituent in the formula (I) has same definition in the specification.
- -
-
Paragraph 0209; 0210; 0211
(2017/08/27)
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- With substituted pyrazine and imidazole derivatives, their preparation and their use in medicine (by machine translation)
-
The invention discloses a substituted pyrazine and imidazole derivatives, their preparation and their use in medicine. Specifically, the invention relates to a compound of general formula (I) indicated by the new derivative and its pharmaceutically acceptable salt or pharmaceutical composition containing the same, and its preparation method. The invention also discloses the derivative and its pharmaceutically acceptable salt or pharmaceutical composition containing the same in the Bruton tyrosine kinase inhibitors, and in preparing and treating and/or preventing tumor diseases such as inflammation of the application of the medicament. Wherein the general formula (I) of each substituent as defined in the specification. (by machine translation)
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-
Paragraph 0183; 0184; 0185
(2017/10/12)
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- Platinum nanowires catalyzed direct amidation with aldehydes and amines
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Different from the conventional synthesis methods and substrates, we designed a brand new method for synthesizing amides with platinum nanowires as catalysts and tert-butylhydroperoxide (TBHP) as the oxidant. Influence of factors, such as the catalyst, solvents, and the reaction temperature, were studied to determine the optimal reaction conditions. In addition, we explored the substrate generality and observed excellent yields.
- Xu, Dawei,Shi, Linyan,Ge, Danhua,Cao, Xueqin,Gu, Hongwei
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p. 478 - 481
(2016/04/19)
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- A nanowire the platinum accepts method for catalytic synthesis of amides (by machine translation)
-
The invention relates to a nanowire the platinum accepts method for catalytic synthesis of amides. Specifically, the method comprises the following steps: adding the reaction vessel in the nanowire the platinum accepts in alcoholic, decompression except mellow, further adding alchlor, reaction solvent, pyridine, amine compounds, aldehyde compound and an oxidizing agent, under the mixing conditions, the heating reaction in in oil bath, after purification by column chromatography, to obtain amides, wherein: the states the aldehyde class compounds, amine compounds, alchlor, pyridine, the platinum accepts molar ratio of the oxidizing agent and 0.5-3 : 0.5-3 : 0.1-0.5: 0.5-2 : 0.1% - 2% : 0.5-5, the heating of the reaction temperature is 80-140°C, the reaction time is 16-24 hours. Because the nanowire the platinum accepts as the catalyst, the invention is not only high catalytic activity, and the performance is stable, at the same time the method of the present invention can obtain a higher yield, mild condition, process is simple, easy to operate. (by machine translation)
- -
-
Paragraph 0111-0113
(2017/02/28)
-
- Peroxide-mediated direct synthesis of amides from aroyl surrogates
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An efficient and metal-free method has been developed for the direct synthesis of amides from readily available azobenzenes reacting with aroyl surrogates such as alcohols, methylarenes. A variety of amides were afforded in moderate to good yields through this reaction. It is another example reported by our group for the use of azobenzene as the new radical acceptor.
- Hong, Gang,Wu, Shengying,Zhu, Xiaoyan,Mao, Dan,Wang, Limin
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p. 436 - 441
(2015/12/31)
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- Dimethyl sulfoxide participant iron-mediated cascade oxidation/α-formylation reaction of substituted 2,3-dihydropyrroles under air and protonic acid free condition
-
An efficient and Bronsted acid free one-pot protocol to directly generate structurally sophisticated α-formylpyrrole derivatives in moderate to good yields has been demonstrated, involving an iron-mediated domino oxidation/formylation reaction of readily available 2,3-dihydro-1H-pyrroles in dimethyl sulfoxide and air atmosphere, in which dimethyl sulfoxide acts as the formyl donor. A possible mechanism is presented.
- Zhang, Zhiguo,Tian, Qing,Qian, Jingjing,Liu, Qingfeng,Liu, Tongxin,Shi, Lei,Zhang, Guisheng
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p. 8182 - 8188
(2015/03/18)
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- Semi-catalytic reduction of secondary amides to imines and aldehydes
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Secondary amides can be reduced by silane HSiMe2Ph into imines and aldehydes by a two-stage process involving prior conversion of amides into iminoyl chlorides followed by catalytic reduction mediated by the ruthenium complex [Cp(i-Pr3P)Ru(NCCH3)2]PF6 (1). Alkyl and aryl amides bearing halogen, ketone, and ester groups were converted with moderate to good yields under mild reaction conditions to the corresponding imines and aldehydes. This procedure does not work for substrates bearing the nitro-group and fails for heteroaromatic amides. In the case of cyano substituted amides, the cyano group is reduced to imine.
- Lee, Sun-Hwa,Nikonov, Georgii I.
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supporting information
p. 8888 - 8893
(2014/06/09)
-
- METHOD FOR THE CATALYTIC REDUCTION OF ACID CHLORIDES AND IMIDOYL CHLORIDES
-
The present application relates to methods for the catalytic reduction of acid chlorides and/or imidoyl chlorides. The methods comprise reacting the acid chloride or imidoyl chloride with a silane reducing agent in the presence of a catalyst such as [Cp(Pri3P)Ru(NCMe)2]+[PF6]?.
- -
-
Paragraph 0161
(2014/08/19)
-
- Synthesis of 1-aroyl-3,5-dimethyl-1H-pyrazoles as anti-HCV and anticancer agents
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1-Aroyl-3,5-dimethyl-1H-pyrazole derivatives (7-12) were synthesized from some hydrazides (1-6) with acetylacetone (2,4-pentanedione) by microwave irradiation. Their structures were elucidated by FT-IR and 1H-NMR spectral data and elemental analysis. Compound activities were evaluated against HCV NS5B and in cell based HCV reporters. Compound 8 was the most promising of this series in inhibiting intracellular NS5B activity and HCV RNA replication in reporter cells. The selected compounds 9, 10 and 12 by National Institue of Health were screened for their anticancer activity against 60 human tumor cell lines. Compound 9 (3-[(3,5-dimethyl-1H-pyrazol-1-yl)carbonyl]-2′,4′- difluorobiphenyl-4-ol) possessed significant activity against human immortalized myelogenous leukemia (K-562) exhibiting cell growth promotion 30.05%, with inhibition of 69.95% at 10-5M concentration. Compounds 3 and 9 were evaluated for cell viability and growth inhibition by K-562 cells of MTT assay, at different doses (10-6- 10-2M). Further, compound 9 exhibited anticancer activity against K-562 cells with IC50 value of 4 μM . Apoptosis levels of compound 9 were determined for three different concentrations (10-6, 10-5 and 10-3M) at two time points (24 and 48 h). Compound 9 induced apoptosis of K-562 cells, thus suggesting that compound 9 might be a potential chemopreventive agent for chronic myelogenous leukemia.
- Aydin, Sevil,Kaushik-Basu, Neerja,Oezbas-Turan, Suna,Akbuga, Juelide,Tiber, Pinar Mega,Orun, Oya,Gurukumar,Basu, Amartya,Kuecuekguezel, S. Gueniz
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p. 121 - 131
(2014/03/21)
-
- Design, synthesis, and activity evaluation of broad-spectrum small-molecule inhibitors of anti-apoptotic Bcl-2 family proteins: Characteristics of broad-spectrum protein binding and its effects on anti-tumor activity
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On the basis of the comparison of the structure of the Bim BH3: Bcl-x L complex and that of the ABT-737: Bcl-xL complex, a series of class A compounds were designed. These compounds had the basic skeleton of ABT-737 and the h2 residues of Bim BH3. These residues had shown themselves to be relevant to Bim BH3's broad-spectrum binding properties in saturation mutagenesis assays. Unlike ABT-737, which is a selective inhibitor of anti-apoptotic members of the Bcl-2 protein family, the class A compounds showed broad-spectrum binding activity to target proteins similar to those of Bim BH3 peptide. Then class B compounds were synthesized by modifying the structure of the most effective class A compound, A-4. Most of these class B compounds showed better binding affinity to the target proteins than the class A compounds had. They also showed themselves more effective than ABT-737 at inhibiting growth in multiple tumor cell lines known to express Bcl-x L, Bcl-2, and Mcl-1 proteins at high levels. Compounds B-11 and B-12 had the strongest anti-tumor activity of any compounds we produced. This study suggests that it is feasible to design small-molecule inhibitors based on the structure of Bim BH3, which shows broad-spectrum binding to Bcl-xL, Bcl-2, and Mcl-1 proteins. Our results also suggest that the broad-spectrum properties of small-molecule inhibitors binding to target proteins play a critical role in inhibiting the growth of many tumor cells. Finally, our study provides a series of lead compounds that merit further research into anti-cancer therapeutics.
- Zheng, Can-Hui,Yang, Hui,Zhang, Meng,Lu, Shi-Hai,Shi, Duo,Wang, Juan,Chen, Xiu-Hua,Ren, Xiao-Hui,Liu, Jia,Lv, Jia-Guo,Zhu, Ju,Zhou, You-Jun
-
supporting information; experimental part
p. 39 - 44
(2012/02/16)
-
- Synthesis of 5-(4-aminophenyl)-2-(arylamino)-1,3,4-thiadiazoles and their schiff base derivatives as antimycobacterial agents
-
The condensation reaction of 5-(4-aminophenyl)-N-aryl-1,3,4-thiadiazol-2- ylamines with salicylaldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 5-bromosalicylaldehyde, 5-chlorosalicylaldehyde, 4-methoxybenzaldehyde, 3-nitrobenzaldehyde, and 4-nitro
- Dilmaghani,Jazani,Nasuhi Pur,Shokoufeh,Ghadiri,Fakhraee
-
scheme or table
p. 362 - 367
(2012/08/27)
-
- Use of molecular oxygen as a reoxidant in the synthesis of 2-substituted benzothiazoles via palladium-catalyzed C-H functionalization/intramolecular C-S bond formation
-
Molecular oxygen (O2) was successfully employed as a reoxidant in cyclizations of thiobenzanilides 1a-s through a palladium-catalyzed C-H functionalization/intramolecular C-S bond formation process, leading to an efficient, green method for the synthesis of 2-arylbenzothiazoles 2a-s. Addition of cesium fluoride (CsF) greatly enhanced the reactions, which produced variously substituted 2-arylbenzothiazoles with good functional group tolerance. Thioureas 4a-j were also found to be suitable substrates for the cyclization process using a palladium/O2 catalyst system, thus generating 2-aminobenzothiazoles 5a-j. One-pot syntheses of 2-aminobenzothiazoles 5a-j from aryl isothiocyanates 6 and amines 7 were also successful.
- Inamoto, Kiyofumi,Hasegawa, Chisa,Kawasaki, Junpei,Hiroya, Kou,Doi, Takayuki
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experimental part
p. 2643 - 2655
(2010/12/25)
-
- Facile conversion of thioamides into the corresponding amides in the presence of tetrabutylammonium bromide
-
Desulfurization of thioamides was accomplished using a semicatalytic amount of Bu4NBr. The corresponding amides were obtained in high yields, with good functional group compatibility. Georg Thieme Verlag Stuttgart - New York.
- Inamoto, Kiyofumi,Shiraishi, Mitsugu,Hiroya, Kou,Doi, Takayuki
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experimental part
p. 3087 - 3090
(2010/10/21)
-
- Synthesis and anticonvulsant activity of new N-(alkyl/Sub-stituted aryl)-N'-[4-(5-cyclohexylamino)-1,3,4-thiadiazole-2-ylphenyl]thioureas
-
A series of novel thiourea derivatives carrying the 5-cylohexylamino-1,3,4- thiadiazole moiety was synthesized and their anticonvulsant activity was evaluated. Structures of the synthesized compounds have been confirmed by IR, 1H-NMR, and eleme
- Karakus, Sevgi,Kocyigit-Kaymakcioglu, Bedia,Toklu, Hale Z.,Aricioglu, Feyza,Rollas, Sevim
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scheme or table
p. 48 - 53
(2009/06/17)
-
- Iron-catalyzed N-arylations of amides
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A method was proposed for iron-catalyzed N-arylation of primary amides and its applicability to the synthesis of N-heterocycles by intramolecular ring closures. The method used a catalyst system of 10 mol % of FeCl3 and 20 mol % of N,N'-dimethylethylenediamine (DMEDA). The study found that secondary amides of N-methylbenzamide and N-benzylbenzamide produce N-arylated products in trace amounts. The method developed an iron-based catalyst system for efficient N-arylations of primary amides with aryl iodides. The study used a sealable tube equipped with a magnetic stir bar charged with amide, or K 3PO4, or K2CO3, or FeCl3. The study used NMR spectroscopic analysis to determine the identity and purity of the products. The method observed that different substituted aryl iodides made a positive impact on the reaction.
- Correa, Arkaitz,Elmore, Simon,Bolm, Carsten
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experimental part
p. 3527 - 3529
(2009/04/11)
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- Rhodium-catalysed addition reaction of aryl- and alkenylboronic acids to isocyanates
-
The addition reaction of aryl- and alkenylboronic acids to isocyanates is catalysed by a rhodium(i) complex, affording secondary amides under mild conditions. The Royal Society of Chemistry.
- Miura, Tomoya,Takahashi, Yusuke,Murakami, Masahiro
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p. 3577 - 3579
(2008/03/12)
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- PYRIMIDINYL-PYRAZOLE INHIBITORS OF AURORA KINASES
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The present invention provides a compound represented by Formula (I): or a pharmaceutically acceptable salt thereof, or a solvate thereof, or a combination thereof, wherein the substituents are as defined herein. The present invention also relates to a co
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Page/Page column 31
(2010/11/26)
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- Synthesis, characterization and biological activities of substituted oxadiazole, triazole, thiadiazole and 4-thiazolidinone derivatives
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The synthesis and biological activities (anti-inflammatory and antibacterial) of a number of 2,5-substituted 1,2,4-triazole, 1,3,4-thiadiazole/oxadiazole and 2,3-substituted-4-thiazolidinone derivatives are described. The anti-inflammatory activity was ca
- Amir, Mohd,Khan,Zaman
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p. 2189 - 2194
(2007/10/03)
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- Synthesis, characterization of novel coupling products and 4-arylhydrazono-2-pyrazoline-5-ones as potential antimycobacterial agents
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Novel coupling products 7a-d and 4-arylhydrazono-2-pyrazoline-5-ones 8a-e were synthesized and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Rv and Mycobacterium avium. Compound 7b was found to be the most potent derivatives of the 7a-d series by an MIC value of 6.25 μg/ml.
- Kuecuekguezel, S. Gueniz,Rollas, Sevim
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p. 583 - 588
(2007/10/03)
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- Some 3-Thioxo/Alkylthio-1,2,4-triazoles with a Substituted Thiourea Moiety as Possible Antimycobacterials
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A series of novel N-alkyl/aryl-N'-[4-(4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thione-5-yl)phenyl]thioureas 1-19 and three S-alkylated representatives of the former, N-alkyl/aryl-N'-[4-(3-aralkylthio-4-alkyl/aryl-4H-1,2,4-triazole-5-yl)phenyl]thioureas 20-22, were synthesized and tested for antimycobacterial activity against Mycobacterium tuberculosis H37Rv as well as Mycobacterium fortuitum ATCC 6841 which is a rapid growing opportunistic pathogen. Compounds 4 and 9-11 were found to possess the same MIC value with that of Tobramycin against M. fortuitum ATCC 6841 whereas 1-3 and 21 had positive response against M. tuberculosis H37Rv at varying degrees. Compound 21 was identified as the most potent derivative of the 1-22 series by an MIC value of 6.25 μg/ml and selectivity index of 1.6
- Kuecuekguezel, Ilkay,Kuecuekguezel, S. Gueniz,Rollas, Sevim,Kiraz, Muammer
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p. 1703 - 1708
(2007/10/03)
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- Electrophilic animation of organozinc reagents with acetone O-(2,4,6-trimethylphenylsulfonyl)oxime and O-methylhydroxylamine
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Reaction of diorganozincs and triorganozincates with acetone O-(2,4,6-trimethylphenylsulfonyl)oxime or O-methylhydroxylamine in the presence of CuCN provides a new one-flask method for electrophilic amination of organozinc reagents. Considering the lithium- or magnesium-to-zinc transmetallation, this method also extends the scope of electrophilic amination of organolithiums and Grignard reagents. The Royal Society of Chemistry 1999.
- Erdik, Ender,Daskapan, Tahir
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p. 3139 - 3142
(2007/10/03)
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