cas 87-17-2, Salicylanilide | Articles data

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Visible-light-induced direct construction of amide bond from carboxylic acids with amines in aqueous solution
A novel visible-light-promoted N-acylation for the synthesis of amides from easily available carboxylic acids with amines in the presence of I2 within 2.5 h in aqueous solution has been developed. Using sunlight as the visible light source greatly reduces the cost of experiments and produces almost no toxic effects. Hence, this study provides an alternative catalytic system for the construction of a wide range of amides with readily available materials. Moreover, the strategy was successfully applied in the preparation of N-(3-(2,6-dimethoxyphenoxy)-7-nitroquinoxalin-2-yl)benzohydrazide, which displayed a signification anti-proliferation effect on A549, MCF-7 and HCT116 cell lines.
Wang, Jin,Hou, Huiqing,Hu, Yongzhi,Lin, Jin,Wu, Min,Zheng, Zhiqiang,Xu, Xiuzhi
supporting information

(2021/02/09)

Bio-evaluation of fluoro and trifluoromethyl-substituted salicylanilides against multidrug-resistant S. aureus
Methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Staphylococcus aureus (VRSA) are primary causes of skin and soft tissue infections worldwide. To address the emergency caused due to increasing multidrug-resistant (MDR) bacterial infections, a series of novel fluoro and trifluoromethyl-substituted salicylanilide derivatives were synthesized and their antimicrobial activity was investigated. MIC data reveal that the compounds inhibited S. aureus specifically (MIC 0.25–64 μg/mL). The in vitro cytotoxicity of compounds with MIC 1 μg/mL against Vero cells led to identification of four compounds (20, 22, 24 and 25) with selectivity index above 10. These four compounds were tested against MDR S. aureus panel. Remarkably, 5-chloro-N-(4’-bromo-3’-trifluoromethylphenyl)-2-hydroxybenzamide (22) demonstrated excellent activity against nine MRSA and three VRSA strains with MIC 0.031–0.062 μg/mL, which is significantly better than the control drugs methicillin and vancomycin. The comparative time–kill kinetic experiment revealed that the effect of bacterial killing of 22 is comparable with vancomycin. Compound 22 did not synergize with or antagonize any FDA-approved antibiotic and reduced pre-formed S. aureus biofilm better than vancomycin. Overall, study suggested that 22 could be further developed as a potent anti-staphylococcal therapeutic. [Figure not available: see fulltext.]
Akhir, Abdul,Ansari, Shabina B.,Chopra, Sidharth,Kaul, Grace,Lal, Jhajan,Reddy, Damodara N.
p. 2301 - 2315
(2021/10/30)

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
Bai, Jin,Li, Shangzhang,Li, Wanfang,Qu, Erdong,Zheng, Yan
supporting information

(2021/12/27)

Nickel-catalyzed C-O/N-H, C-S/N-H, and C-CN/N-H annulation of aromatic amides with alkynes: C-O, C-S, and C-CN activation
The Ni-catalyzed reaction ofortho-phenoxy-substituted aromatic amides with alkynes in the presence of LiOtBu as a base results in C-O/N-H annulation with the formation of 1(2H)-isoquinolinones. The use of a base is essential for the reaction to proceed. The reaction proceeds, even in the absence of a ligand, and under mild reaction conditions (40 °C). An electron-donating group on the aromatic ring facilitates the reaction. The reaction was also applicable to carbamate (C-O bond activation), methylthio (C-S bond activation), and cyano (C-CN bond activation) groups as leaving groups.
Iyori, Yasuaki,Ueno, Rina,Morishige, Aoi,Chatani, Naoto
p. 1772 - 1777
(2021/02/22)

Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides
A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.
Zhao, Rong,Dong, Wenwen,Teng, Jiangge,Wang, Zhiwei,Wang, Yunzhong,Yang, Jianguo,Jia, Qiang,Chu, Changhu
supporting information

(2020/12/21)

COMPOUNDS AND METHODS OF INHIBITING BACTERIAL CHAPERONIN SYSTEMS
The present disclosure relates to novel compounds and methods of killing or inhibiting the growth of bacteria. In some embodiments, a method of killing or inhibiting the growth of bacteria is provided. The method comprises administering a compound of formula I or a pharmaceutically acceptable salt thereof to bacteria. In some embodiments, a method of killing or inhibiting the growth of bacteria is provided. The method comprises administering an anthelmintic to bacteria.
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Paragraph 0144; 0145

(2020/05/28)

Reversible small molecule inhibitors of MAO A and MAO B with anilide motifs
Background: Ligands consisting of two aryl moieties connected via a short spacer were shown to be potent inhibitors of monoamine oxidases (MAO) A and B, which are known as suitable targets in treatment of neurological diseases. Based on this general blueprint, we synthesized a series of 66 small aromatic amide derivatives as novel MAO A/B inhibitors. Methods: The compounds were synthesized, purified and structurally confirmed by spectroscopic methods. Fluorimetric enzymological assays were performed to determine MAO A/B inhibition properties. Mode and reversibility of inhibition was determined for the most potent MAO B inhibitor. Docking poses and pharmacophore models were generated to confirm the in vitro results. Results: N-(2,4-Dinitrophenyl)benzo[d][1,3]dioxole-5-carboxamide (55, ST-2043) was found to be a reversible competitive moderately selective MAO B inhibitor (IC50 = 56 nM, Ki = 6.3 nM), while N-(2,4-dinitrophenyl)benzamide (7, ST-2023) showed higher preference for MAO A (IC50 = 126 nM). Computational analysis confirmed in vitro binding properties, where the anilides examined possessed high surface complementarity to MAO A/B active sites. Conclusion: The small molecule anilides with different substitution patterns were identified as potent MAO A/B inhibitors, which were active in nanomolar concentrations ranges. These small and easily accessible molecules are promising motifs, especially for newly designed multitargeted ligands taking advantage of these fragments.
Grau, Kathrin,Hagenow, Jens,Hagenow, Stefanie,Hefke, Lena,Khanfar, Mohammad,Proschak, Ewgenij,Stark, Holger
p. 371 - 393
(2020/02/11)

Method for synthesizing amide compound through photocatalysis in water phase
The invention discloses a method for synthesizing an amide compound through photocatalysis in a water phase. The method comprises the following steps: putting catalysis amounts of a free radical initiator, an amine derivative, a carboxylic acid derivative, a phase transfer catalyst, an inorganic base and water into a reaction container, carrying out a reaction in a photocatalysis reaction instrument at certain power under a room temperature condition, after a certain time, carrying out extraction by using a small amount of ethyl acetate, and carrying out recrystallization, so as to obtain theamide compound, wherein the free radical initiator is eosin, methyl orange, sodium persulfate, ammonium persulfate or potassium peroxodisulfate, the phase transfer catalyst is tetrabutylammonium bromide, and the power of the photocatalytic reaction instrument is 5W. By adopting the method disclosed by the invention, toxic thionyl chloride or phosphorus oxychloride is not needed for a chlorinationreaction, water is adopted as a solvent, a novel photocatalysis method is used, and the amide compound with a high yield can be prepared through a room-temperature reaction for 2-5 hours with an incandescent light bulb of 5W, and in addition, the method is simple in aftertreatment, and low in cost and is an ideal green synthesis method of amide compounds.
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Paragraph 0018-0030

(2019/10/01)

Electrochemical: N-acylation synthesis of amides under aqueous conditions
An electrochemical N-acylation of carboxylic acids with amines was reported. The sustainable TBAB electrocatalysis proceeded with excellent chemoselectivity and positional selectivity, and with ample scope, allowing electrochemical N-acylation under mild reaction conditions at room temperature in water. Moreover, the synthetic utility of the current method is demonstrated by the synthesis of melatonin.
Ke, Fang,Xu, Yiwen,Zhu, Suning,Lin, Xiaoyan,Lin, Chen,Zhou, Sunying,Su, Huimin
supporting information
p. 4329 - 4333
(2019/08/21)

Phenolic N-monosubstituted carbamates: Antitubercular and toxicity evaluation of multi-targeting compounds
The research of novel antimycobacterial drugs represents a cutting-edge topic. Thirty phenolic N-monosubstituted carbamates, derivatives of salicylanilides and 4-chlorophenol, were investigated against Mycobacterium tuberculosis H37Ra, H37Rv including multidrug- and extensively drug-resistant strains, Mycobacterium avium, Mycobacterium kansasii, Mycobacterium aurum and Mycobacterium smegmatis as representatives of nontuberculous mycobacteria (NTM) and for their cytotoxic and cytostatic properties in HepG2 cells. Since salicylanilides are multi-targeting compounds, we determined also inhibition of mycobacterial isocitrate lyase, an enzyme involved in the maintenance of persistent tuberculous infection. The minimum inhibitory concentrations were from ≤0.5 μM for both drug-susceptible and resistant M. tuberculosis and from ≤0.79 μM for NTM with no cross-resistance to established drugs. The presence of halogenated salicylanilide scaffold results into an improved activity. We have verified that isocitrate lyase is not a key target, presented carbamates showed only moderate inhibitory activity (up to 18% at a concentration of 10 μM). Most of the compounds showed no cytotoxicity for HepG2 cells and some of them were without cytostatic activity. Cytotoxicity-based selectivity indexes of several carbamates for M. tuberculosis, including resistant strains, were higher than 125, thus favouring some derivatives as promising features for future development.
Krátky, Martin,Jan?ourek, Ond?ej,Baranyai, Zsuzsa,Novotná, Eva,Stola?íková, Ji?ina,B?sze, Szilvia,Vin?ová, Jarmila
(2019/08/12)

2-Hydroxy-N-Phenylbenzamides and their esters inhibit acetylcholinesterase and Butyrylcholinesterase
The development of novel inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) represents a viable approach to alleviate Alzheimer’s disease. Thirty-six halogenated 2-hydroxy-N-phenylbenzamides (salicylanilides) with various substitution patterns and their esters with phosphorus-based acids were synthesized in yields of 72% to 92% and characterized. They were evaluated for in vitro inhibition of AChE from electric eel and BuChE from equine serum using modified Ellman’s spectrophotometric method. The benzamides exhibited a moderate inhibition of AChE with IC50 values in a narrow concentration range from 33.1 to 85.8 μM. IC50 values for BuChE were higher (53.5–228.4 μM). The majority of derivatives inhibit AChE more efficiently than BuChE and are comparable or superior to rivastigmine—an established cholinesterases inhibitor used in the treatment of Alzheimer’s disease. Phosphorus-based esters especially improved the activity against BuChE with 5-chloro-2-{[4-(trifluoromethyl)phenyl]carbamoyl}phenyl diethyl phosphite 5c superiority (IC50 = 2.4 μM). This derivative was also the most selective inhibitor of BuChE. It caused a mixed inhibition of both cholinesterases and acted as a pseudo-irreversible inhibitor. Several structure-activity relationships were identified, e.g., favouring esters and benzamides obtained from 5-halogenosalicylic acids and polyhalogenated anilines. Both 2-hydroxy-N-phenylbenzamides and esters share convenient physicochemical properties for blood-brain-barrier penetration and thus central nervous system delivery.
Krátky, Martin,?těpánková, ?árka,Houngbedji, Neto-Honorius,Vosátka, Rudolf,Vor?áková, Katarína,Vin?ová, Jarmila
(2019/11/20)

Formal Aniline Synthesis from Phenols through Deoxygenative N-Centered Radical Substitution
Phenolic, lignin-derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical-mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N-centered radical source. The applicability of this triethyl phosphite mediated O-atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.
Lardy, Samuel W.,Luong, Kristine C.,Schmidt, Valerie A.
supporting information
p. 15267 - 15271
(2019/12/11)

Hydroxybiphenylamide GroEL/ES Inhibitors Are Potent Antibacterials against Planktonic and Biofilm Forms of Staphylococcus aureus
We recently reported the identification of a GroEL/ES inhibitor (1, N-(4-(benzo[d]thiazol-2-ylthio)-3-chlorophenyl)-3,5-dibromo-2-hydroxybenzamide) that exhibited in vitro antibacterial effects against Staphylococcus aureus comparable to vancomycin, an antibiotic of last resort. To follow up, we have synthesized 43 compound 1 analogs to determine the most effective functional groups of the scaffold for inhibiting GroEL/ES and killing bacteria. Our results identified that the benzothiazole and hydroxyl groups are important for inhibiting GroEL/ES-mediated folding functions, with the hydroxyl essential for antibacterial effects. Several analogs exhibited >50-fold selectivity indices between antibacterial efficacy and cytotoxicity to human liver and kidney cells in cell culture. We found that MRSA was not able to easily generate acute resistance to lead inhibitors in a gain-of-resistance assay and that lead inhibitors were able to permeate through established S. aureus biofilms and maintain their bactericidal effects.
Kunkle, Trent,Abdeen, Sanofar,Salim, Nilshad,Ray, Anne-Marie,Stevens, McKayla,Ambrose, Andrew J.,Victorino, José,Park, Yangshin,Hoang, Quyen Q.,Chapman, Eli,Johnson, Steven M.
supporting information
p. 10651 - 10664
(2019/01/04)

Hydroxy Group Directed Catalytic Hydrosilylation of Amides
Chemo- and site-selective hydrosilylation of α- or β-hydroxy amides using organocatalyst B(C6F5)3 and commercially available hydrosilanes is described. This transformation is operative under mild conditions and tolerates a wide range of functional groups. The reaction was applied for selective reduction of a specific amide group of the therapeutically important cyclic peptide cyclosporin A, demonstrating the potential usefulness of this catalytic method in late-stage structural transformations of drug lead molecules.
Ni, Jizhi,Oguro, Tsubasa,Sawazaki, Taka,Sohma, Youhei,Kanai, Motomu
supporting information
p. 7371 - 7374
(2018/11/25)

Copper-catalyzed synthesis of benzanilides from lignin model substrates 2-phenoxyacetophenones under an air atmosphere
The synthesis of chemicals from biomass-derived compounds is an interesting and challenging topic. In this work, using the lignin-derived 2-phenoxyacetophenones as the feedstock we present a novel approach for the synthesis of benzanilides via the reaction of 2-phenoxyacetophenones with anilines catalyzed by CuCl2 in DMSO at 120 °C under an air atmosphere. This approach has wide scope for 2-phenoxyacetophenones and anilines, and various benzanilides accompanied by the corresponding phenols could be obtained in high yields via changing the 2-phenoxyacetophenones and anilines. The reaction mechanism study indicated that the oxidative cleavage of the C-C bond in 2-phenoxyacetophenones and the formation of a C-N bond occurred simultaneously in the reaction process, resulting in the formation of benzanilides together with phenols.
Liu, Xinwei,Zhang, Hongye,Wu, Cailing,Chen, Yu,Yu, Bo,Liu, Zhimin,Liu, Zhenghui
p. 1223 - 1227
(2018/02/06)

Method used for preparing amides via catalysis of halogenated aromatic hydrocarbons, amines, and carbon monoxide carbonylation with precious metal
The invention discloses a method used for preparing amides via catalysis of halogenated aromatic hydrocarbons, amines, and carbon monoxide carbonylation with precious metal. According to the method, palladium acetate and triphenyl phosphine are taken as catalysts; a super strong alkali system is composed of potassium hydroxide and dimethyl sulphoxide, p-benzoquinone is taken as an oxidizing agent, carbon monoxide gas is taken as a carbonyl source, aniline is taken as a solvent, iodobenzene is taken as a substrate, carbonylation of iodobenzene into azophenyl benzamide at room temperature under normal pressure is realized. The method is high in conversion rate; reaction conditions are mild; less environment pollution is caused; the method is beneficial for large scale industrialized production, and promising application prospect and economic benefits are achieved.
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Paragraph 0019; 0056; 0060

(2017/10/07)

Synthesis and biological evaluation of JL-A7 derivatives as potent ABCB1 inhibitors
Cancer chemotherapy failure is often due to the overexpression of ATP-binding cassette (ABC) transporters (particularly ABCB1), resulting in a variety of structurally and pharmacologically unrelated drugs efflux. The multidrug resistance (MDR) phenomenon could be reversed by ABCB1 inhibitors. Now, JL-A7 as the lead compound based on a triazol-N-ethyl-tetrahydroisoquinoline scaffold, 18 compounds were designed and synthesized. Substitution in para positions yielded high activities toward ABCB1. Moreover, compound 5 could effectively block the drug efflux function of ABCB1 and increase the accumulation of anti-cancer drugs to achieve effective treatment concentration in MDR cells.
Pan, Miaobo,Cui, Jian,Jiao, Lei,Ghaleb, Hesham,Liao, Chen,Zhou, Jiaqi,Kairuki, Mutta,Lin, Haiyan,Huang, Wenlong,Qian, Hai
p. 4194 - 4202
(2017/07/05)

Ligand-free Pd(0)/SiO2-catalyzed aminocarbonylation of aryl iodides to amides under atmospheric CO pressure
An efficient and facile route for CO-based carbonylation of aryl iodides with amines to synthesize amides has been established by using SiO2 supported Pd(0) as the catalyst in a mild basic environment (K2CO3). This ligand-free heterogeneous reaction model can afford amide products in good to excellent yields (up to 99%) under atmospheric CO pressure and moderate temperature. The supported catalyst also displayed a broad substrate scope, good functional group tolerance and good recyclability. These features render the as-provided carbonylation approach sustainable and applicable in organic synthesis.
Hu, Qinhua,Wang, Lele,Wang, Chen,Wu, Yubin,Ding, Zhengxin,Yuan, Rusheng
p. 37200 - 37207
(2017/08/09)

Salicylanilide N-monosubstituted carbamates: Synthesis and in vitro antimicrobial activity
The research of innovative antimicrobial agents represents a cutting edge topic. Hence, we synthesized and characterised novel salicylanilide N-monosubstituted carbamates. Twenty compounds were evaluated in vitro against eight bacterial strains and eight fungal species. The lowest minimum inhibitory concentrations (MICs) were found to be ≤0.49 μM. Genus Staphylococcus, including methicillin-resistant Staphylococcus aureus, and fungus Trichophyton mentagrophytes showed uniformly the highest rate of susceptibility, whilst Gram-negative bacteria and most of the fungi were less susceptible. A wide range of carbamates provided comparable or superior in vitro antimicrobial activity in comparison to established drugs. Interestingly, extended-spectrum β-lactamase producing strain of Klebsiella pneumoniae was inhibited with MICs starting from 31.25 μM. With respect to Staphylococci, 2-[(4-bromophenyl)carbamoyl]-4-chlorophenyl phenylcarbamate exhibited the lowest MIC values (≤0.98 μM). 2-[(4-Bromophenyl)carbamoyl]-4-chlorophenyl benzylcarbamate showed the widest spectrum of antifungal action. The results indicate that some salicylanilide carbamates can be considered to be promising candidates for future investigation.
Krátky, Martin,Vin?ová, Jarmila
p. 1322 - 1330
(2016/03/01)

Niclosamide is a Negative Allosteric Modulator of Group I Metabotropic Glutamate Receptors: Implications for Neuropathic Pain
Purpose: Novel therapeutics are greatly needed that target specific pathological receptors and pathways involved in Neuropathic Pain (NP). Extending our previous work published in this Journal on Group I metabotropic glutamate receptor (mGluR) modulators, we now investigate the therapeutic potential of niclosamide in modulating aberrant glutamate transmission in NP. Method: Calcium mobilization assays and cross-receptor selectivity experiments are conducted to characterize the pharmacological activity of niclosamide. A focused series of niclosamide analogues is then prepared to elucidate key structural determinants that emerged from computational molecular modeling analysis on drug-receptor interactions. Finally, niclosamide and a carbamate derivative are studied to assess their efficacy in an NP-evoked mechanical hyperalgesia model in rats. Results: Niclosamide is a low-nanomolar allosteric antagonist of Group I mGluRs with high selectivity for Group I over homologous Group III mGluRs. The phenolic hydroxyl group of niclosamide forms a crucial hydrogen bond with mGluR1/5. Its bioactive coplanar conformation is further stabilized by the nitro substituent on the B ring and an intramolecular bond. Mechanical hyperalgesia in NP rats is reversed by niclosamide through three different dosing routes. Conclusion: To our knowledge, this is the first report of the salicylanilide class of compounds as potential treatments for NP.
Ai, Ni,Wood, Richard D.,Yang, Eric,Welsh, William J.
p. 3044 - 3056
(2016/11/13)

Orthogonal Discrimination among Functional Groups in Ullmann-Type C-O and C-N Couplings
The copper-catalyzed arylation of nucleophiles has been established as an efficient methodology for the formation of C-C and C-heteroatom bonds. Considering the advances during the last two decades, the ligand choice plays a key role in such transformations and can strongly influence the catalytic efficiency. The applicability of these Ullmann-type coupling reactions regarding the orthogonal selectivity of different functional groups constitutes a challenging subject for current synthetic strategies. Herein, we report a useful toolkit of Cu-based catalysts for the chemoselective arylation of a wide-range of nucleophiles in competitive reactions using aryl iodides and bromides. We show in this work that the arylation of all kinds of amides can be orthogonal to that of amines (aliphatic or aromatic) and phenol derivatives. This high chemoselectivity can be governed by the use of different ligands, yielding the desired coupling products under mild conditions. The selectivity trends are maintained for electronically biased iodobenzene and bromobenzene electrophiles. Radical clock experiments discard the occurrence of radical-based mechanisms.
Rovira, Mireia,Soler, Marta,Güell, Imma,Wang, Ming-Zheng,Gómez, Laura,Ribas, Xavi
supporting information
p. 7315 - 7325
(2016/09/09)

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles
The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.
Nimnual, Phongprapan,Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
p. 8657 - 8667
(2015/09/15)

6,7-Dimethoxy-2-{2-[4-(1H-1,2,3-triazol-1-yl)phenyl]ethyl}-1,2,3,4-tetrahydroisoquinolines as superior reversal agents for P-glycoprotein-mediated multidrug resistance
P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a major obstacle for successful cancer chemotherapy. Based on our previous study, 17 novel compounds with the 6,7-dimethoxy-2-{2-[4-(1H-1,2,3-triazol-1-yl)phenyl]ethyl}-1,2,3,4-tetrahydroisoquinoline scaffold were designed and synthesized. Among them, 2-[(1-{4-[2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl]phenyl}-1H-1,2,3-triazol-4-yl)methoxy]-N-(p-tolyl)-benzamide (compound 7h) was identified as a potent modulator of P-gp-mediated MDR, with high potency (EC50 = 127.5 ± 9.1 nM), low cytotoxicity (TI > 784.3), and long duration (> 24 h) in reversing doxorubicin (DOX) resistance in K562/A02 cells. Compound 7h also enhanced the effects of other MDR-related cytotoxic agents (paclitaxel, vinblastine, and daunorubicin), increased the accumulation of DOX and blocked P-gp-mediated rhodamine 123 efflux function in K562/A02 MDR cells. Moreover, 7h did not have any effect on cytochrome (CYP3A4) activity. These results indicate that 7h is a relatively safe modulator of P-gp-mediated MDR that has good potential for further development.
Liu, Baomin,Qiu, Qianqian,Zhao, Tianxiao,Jiao, Lei,Li, Yunman,Huang, Wenlong,Qian, Hai
p. 336 - 344
(2015/02/05)

Synthesis and biological activity of new salicylanilide N,N-disubstituted carbamates and thiocarbamates
The development of novel antimicrobial drugs represents a cutting edge research topic. In this study, 20 salicylanilide N,N-disubstituted carbamates and thiocarbamates were designed, synthesised and characterised by IR, 1H NMR and 13C NMR. The compounds were evaluated in vitro as potential antimicrobial agents against Mycobacterium tuberculosis and nontuberculous mycobacteria (Mycobacterium avium and Mycobacterium kansasii) as well as against eight bacterial and fungal strains. Additionally, we investigated the inhibitory effect of these compounds on mycobacterial isocitrate lyase and cellular toxicity. The minimum inhibitory concentrations (MICs) against mycobacteria were from 4 μM for thiocarbamates and from 16 μM for carbamates. Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus, were inhibited with MICs from 0.49 μM by thiocarbamates, whilst Gram-negative bacteria and most of the fungi did not display any significant susceptibility. All (thio)carbamates mildly inhibited isocitrate lyase (up to 22%) at a concentration of 10 μM. The (thio)carbamoylation of the parent salicylanilides led to considerably decreased cytotoxicity and thus improved the selectivity indices (up to 175). These values indicate that some derivatives are attractive candidates for future research.
Kratky, Martin,Volkova, Marie,Novotna, Eva,Trejtnar, Frantisek,Stolarikova, Jirina,Vinsova, Jarmila
p. 4073 - 4082
(2014/08/18)

Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
A new practical ligand-free protocol for copper-catalyzed C-heteroatom cross-coupling reactions (Ullmann-type) is described. The use of dimethyl sulfoxide (DMSO) as the solvent overcomes the need to use organic auxiliary ligands; thus, DMSO is revealed as a nontoxic and superior solvent for Ullmann-type coupling reactions. This method allows the arylation of a wide range of amides, alcohols, and amines under practical conditions with bromobenzene and iodobenzene derivatives and will likely find direct application in current organic synthesis. The competitive reactivity among different functional groups is reported and rationalized, and the possibility to achieve selective arylation reactions is demonstrated. Copyright
Gueell, Imma,Ribas, Xavi
p. 3188 - 3195
(2014/06/09)

CO and O2 binding studies of new model complexes for CcO
A very efficient, simple synthesis of a porphyrin mimic for cytochrome c oxidase is presented. This complex contains a covalently attached copper binding site and a phenyl ring that mimics the Tyr part of the enzyme. Structural studies revealed that the copper binding tridentate ligand is situated on top of the porphyrin plane and the hydroxyl of the phenyl ring is oriented towards the center of the molecule. Moreover, Fe at the reduced form of the model is capable of binding CO, as confirmed by FT-IR and upon photolysis CO is bound to Cu site. Finally, electrochemical studies using rotating ring-disk electrode showed that the complexes reduce oxygen via two mechanisms (2e- and 4e-) and have low stability.
Ladomenou, Kalliopi,Charalambidis, Georgios,Coutsolelos, Athanassios G.
p. 47 - 53
(2013/07/25)

Recyclable, highly efficient and low cost nano-MgO for amide synthesis under SFRC: A convenient and greener 'NOSE' approach
A clean synthesis of amide derivatives has successfully been accomplished utilizing reusable nano-MgO under 'SFRC' (solvent free reaction condition). The 'green-ness' of this protocol makes it a benign alternative for the large scale synthesis.
Das, Vijay Kumar,Devi, Rashmi Rekha,Thakur, Ashim Jyoti
p. 118 - 125
(2013/06/26)

Palladium-catalyzed amidation of aryl halides using 2-dialkylphosphino- 2′-alkoxyl-1,1′-binaphthyl as ligands
Palladium-catalyzed intermolecular C-N bond-forming reactions between aryl halides and amides are described using 2-dialkylphosphino-2′-alkoxyl-1, 1′-binaphthyl, which is both bulky and electron-rich, as the ligand. A variety of amides, including aliphatic and aromatic primary amides, lactams, and carbamates, were viable substrates for the amidation, which exhibited good functional group compatibility. By tuning the substituents at the 2,2′-position of 1,1′-binaphthyl of the ligand, the palladium-catalyzed amidation of bulky aryl halides was realized and this coupling reaction was used to synthesize 2-amino-2′-methoxy-1,1′- binaphthyl in high yield.
Ma, Fangfang,Xie, Xiaomin,Zhang, Lei,Peng, Zhiyong,Ding, Lina,Fu, Lei,Zhang, Zhaoguo
experimental part
p. 5279 - 5285
(2012/08/07)

Antifungal activity of salicylanilides and their esters with 4-(trifluoromethyl)benzoic acid
Searching for novel antimicrobial agents still represents a current topic in medicinal chemistry. In this study, the synthesis and analytical data of eighteen salicylanilide esters with 4-(trifluoromethyl)benzoic acid are presented. They were assayed in vitro as potential antimycotic agents against eight fungal strains, along with their parent salicylanilides. The antifungal activity of the presented derivatives was not uniform and moulds showed a higher susceptibility with minimum inhibitory concentrations (MIC) ≥ 0.49 μmol/L than yeasts (MIC ≥ 1.95 μmol/L). However, it was not possible to evaluate a range of 4-(trifluoromethyl)benzoates due to their low solubility. In general, the most active salicylanilide was N-(4-bromophenyl)-4-chloro-2- hydroxybenzamide and among esters, the corresponding 2-(4-bromophenylcarbamoyl)- 5-chlorophenyl 4-(trifluoromethyl) benzoate exhibited the lowest MIC of 0.49 μmol/L. However, the esterification of salicylanilides by 4-(trifluoromethyl)benzoic acid did not result unequivocally in a higher antifungal potency.
Kratky, Martin,Vinsova, Jarmila
p. 9426 - 9442
(2012/11/14)

A highly efficient copper-catalyzed method for the synthesis of 2-hydroxybenzamides in water
An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33-96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides. Georg Thieme Verlag Stuttgart · New York.
Balkrishna, Shah Jaimin,Kumar, Sangit
p. 1417 - 1426
(2012/06/30)

One-pot synthesis of salicylanilides by direct amide bond formation from salicyclic acid under microwave irradiation
A highly efficient protocol for the preparation of aromatic amides is described by the direct reactions between salicyclic acid and aromatic amines in the presence of phosphorous trichloride under microwave irradiation. The method has several advantages over the conventional methods, including operational simplicity, good yield, and reduced reaction time.
Lu, Cheng-Rong,Zhao, Bei,Jiang, Ying-Peng,Ding, Hao,Yang, Sheng
experimental part
p. 1257 - 1266
(2011/05/07)

Synthesis and antiproliferative activities against Hep-G2 of salicylanide derivatives: Potent inhibitors of the epidermal growth factor receptor (EGFR) tyrosine kinase
A series of salicylanilide derivatives (compounds 1-32) were synthesised by reacting substituted salicylic acids and anilines. The chemical structures of these compounds were determined by 1H-NMR, electrospray ionisation mass spectrometry (ESI-MS) and elemental analysis. The compounds were assayed for their antiproliferative activities against the Hep-G2 cell line by the 3-(4,5-dimethylthylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the compounds tested, 22 and 28 showed the most favouable antiproliferative activities with 50% inhibitory concentration (IC50) values of 1.7 and 1.3 μM, respectively, which were comparable to the positive control of 5-fluorouracil (IC50 = 1.8 μM). A solid-phase ELISA assay was also performed to evaluate the ability of compounds 1-32 to inhibit the autophosphorylation of the epidermal growth factor receptor tyrosine kinase (EGFR TK). Docking simulations of 22 and 28 were carried out to illustrate the binding mode of the molecule into the EGFR active site, and the result suggested that both compounds 22 and 28 could bind the EGFR kinase well.
Zhu, Zhen-Wei,Shi, Lei,Ruan, Xiao-Ming,Yang, Ying,Li, Huan-Qiu,Xu, Suo-Ping,Zhu, Hai-Liang
experimental part
p. 37 - 45
(2011/10/30)

Cyclopentadienyl-free rare-earth metal amides [{(CH2SiMe 2){(2,6iPr2C6H3)N} 2}Ln{N(SiMe3)2}(THF)] as highly efficient versatile catalysts for C-C and C-N bond formation
Efficient methods have been developed for the direct synthesis of amides from aldehydes and a straightforward route to propiolamidines using cyclopentadienyl-free rare-earth metal amides [{(CH2SiMe 2){(2,6-iPr2C6H3)N} 2}Ln{N(SiMe3)2}(THF)] [Ln = Yb (1), Y (2), Dy (3), Sm (4), Nd (5)] as versatile catalysts, The results indicate that in the direct synthesis of amides from aldehydes the catalysts have the activity order 2>1～3～4～5. These methods have the advantage of easy preparation of the catalysts, low catalyst loading, high conversion of substrates to products, mild reaction conditions, and compatibility with a wide range of substrates.
Wu, Yunjun,Wang, Shaowu,Zhang, Lijun,Yang, Gaosheng,Zhu, Xiancui,Zhou, Zhihong,Zhu, Hong,Wu, Shihong
supporting information; experimental part
p. 326 - 332
(2010/04/06)

Anion-triggered substituent-dependent conformational switching of salicylanilides. New hints for understanding the inhibitory mechanism of salicylanilides
(Chemical Equation Presented) A series of salicylanilides (1a-h) bearing varied substituents at the 3′- or 4′-position of the anilino moiety (substituent = p-OCH3, p-CH3, m-CH3, H, p-Cl, m-Cl, p-CO2CH3, and p-CN) were synthesized. In acetonitrile all of the substituted salicylanilides 1a-h predominantly adopt the "closed-ring" conformation facilitated by a strong intramolecular OH...O=C hydrogen bond. In the presence of H2PO4 -, the conformation of 1a-h was found to be modulated by the substituent. With our proposed proton-transfer fluorescence probing method, we were able to show that the conformation of 1a-f bearing a not highly electron-withdrawing substituent was switched to the "open-ring" form by H2PO4-, whereas 1h bearing a highly electron-withdrawing substituent, p-CN, remained in the "closed-ring" conformation. The significance of these findings for understanding, from a molecular structural point of view, the mechanism of salicylanilide-based inhibitors for inhibiting the protein tyrosine kinase epidermal growth factor receptor was discussed.
Guo, Lin,Wang, Qiang-Li,Jiang, Qian-Qian,Jiang, Qiu-Ju,Jiang, Yun-Bao
p. 9947 - 9953
(2008/09/17)

Thermosensitive recording material and color developer compound therefor
A thermosensitive recording material has a support and a thermosensitive coloring layer formed thereon containing a leuco dye and a color developer capable of inducing color formation in the leuco dye upon application of heat thereto, with the color developer including at least one compound (A) having in a molecule thereof at least two aromatic ring moieties with specific structures, selected from the group consisting of an aromatic ring moiety having at least one carboxyl group and electron-attracting functional group, an aromatic ring moiety having at least one carboxyl group and electron-donating functional group, and an aromatic ring moiety having at least one carboxyl group, free of the electron-attracting and electron-donating functional groups. An aromatic carboxylic acid compound serving as the above-mentioned compound (A) and the producing method thereof are also disclosed.
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(2008/06/13)

Triphenylphosphine-2,4,4,6-tetrabromo-2,5-cyclohexadienone complex as a reagent for preparation of carboxylic acid bromides
Triphenylphosphine-2,4,4,6-tetrabromo-2,5-cyclohexadienone complex was successfully used as a new reagent for the synthesis of carboxylic acid bromides which were isolated as individual substances or were identified by conversion into the corresponding anilides. The reaction is chemoselective, and it can be applied to polyfunctional compounds, e.g., hydroxy acids.
Matveeva,Podrugina,Sandakova,Zefirov
p. 1469 - 1472
(2007/10/03)

Synthesis of Substituted Salicylanilides under Microwave Irradiation
Salicylanilides were prepared in 70-95% yields in 4-8 min from phenyl salicylate or phenyl 4-methoxysalicylate and substituted anilines under microwave irradiation under solvent free conditions.
Veverkova, Eva,Meciarova, Maria,Toma, Stefan,Balko, Jozef
p. 1215 - 1219
(2007/10/03)

4-Acylhydrazinomethylene-2-phenyloxazol-5(4H)-ones as acylating agents: Synthesis of salicylanilides and 1,2,4-triazolo[4,3-b] pyridazines
A simple and general method for the acylation of an amino or hydrazino group by the application of hydrazides has been developed. It starts from hydrazides (2), which are converted with 4-ethoxymethylene-2-phenyl-oxazol-5(4H)-one (1) to the corresponding 4-acylhydrazinomethylene-2-phenyloxazol-5(4H)-ones (3). The latter react with nitrogen-containing nucleophiles in 1,4-dioxane in the presence of triethylamine or zirconium(IV) chloride to give the corresponding amides (7) or mixtures of hydrazides (12) and 1,2,4-triazolo[4,3-b]pyridazines (11). Upon prolonged heating, compounds (11) are the main products.
Po?gan, Franc,Polanc, Slovenko,Ko?evar, Marijan
p. 1011 - 1019
(2007/10/03)

Regioselective dealkylation of 2-alkoxybenzoic acid and its amide derivatives with aliphatic amines
The methoxy group of o-anisic acid was cleaved with aliphatic amines in aprotic dipolar solvents. This cleavage reaction was especially smooth when piperazine in dimethylacetamide was used. This method was applicable to a variety of dealkylations of o-alkoxybenzoic acid and ist amide derivatives with high regio-selectivity.
Nishioka, Hiroyasu,Nagasawa, Masaaki,Yoshida, Kiyoshi
p. 243 - 246
(2007/10/03)

4-derivatives coumarin-3-phosphonic acids and esters
In the Arbuzov reactions of 2′-bromoacetoxyphenone with trimethyl phosphite the derivatives in position 4 of 3-phosphonocoumarinic acids and esters were obtained.
Kostka, Krzysztof,Pastuszko, Slawomir,Kotynski, Andrzej,Budzisz, Elzbieta
p. 199 - 209
(2007/10/03)

Salicylic acid derivatives
The heat-sensitive recording material disclosed comprises a colorless or pale colored dyestuff precursor, one or more salicylic acid derivative of the formula (1) or metal salt of the derivative and an aliphatic amide compound having 18?60 carbon atoms in molecular structure, and is excellent in thermal response and preservation stability of white portions and images. STR1 wherein X1 and X2 are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aralkyl group or an aryl group, Y1 and Y2 are an oxygen atom or a sulfur atom, R1 is a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and R2 is an alkyl group, an alkenyl group, an aralkyl group or an aryl group.
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(2008/06/13)

Pyrolysis of O-Allyl Salicylic Amides and Esters, and Related Compounds: Foemation of Isoindolones and Phthalides
Flash vacuum pyrolysis of O-allyl salicylic alkylamides and alkyl esters gives isoindolones and phthalides, respectively, in low (20-40percent) yield.The mechanism involves generation of the phenoxyl radical, regiospecific hydrogen-atom transfer from the alkylamide (or alkyl ester) group and cyclization.A similar sequence was observed with thiophenoxyl radicals.
Black, Michael,Cadogan, J. I. G.,McNab, Hamish
p. 155 - 160
(2007/10/02)

Desulphurization of thioamides by cobalt chloride-hydrogen peroxide
Thioamides (1-9) are converted to amides (10-18) with extrusion of sulphur, utilizing hydrogen peroxide and cobalt chloride at room temperature in a rapid, economic and effluent free reaction.
Borthakur, N,Goswami, A
p. 800 - 801
(2007/10/02)

Phenolic compounds
A phenolic compound having formula (I): STR1 wherein X represents a chlorine atom or a methyl group, and a recording material comprising a coloress or light-colored leuco dye and the above phenolic compound serving as a color developer for the leuco dye are disclosed.
-
(2008/06/13)

A Simple Conversion of Carboxylic Acids into Carboxamides
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Rastogi, R. C.,Khan, R. H.,Baruah, K. R.
p. 161 - 162
(2007/10/02)

UNE NOUVELLE RECYCLISATION DE CATIONS 1,3-HETEROCYCLIQUES EN CATIONS BENZIMIDAZOLIUM ET PERIMIDINIUM
In this work we have examined the new recyclisation of 1,3-heterocyclic cations activated towards 1,4-binucleophyles : o-phenylenediamines and 1,8-naphthalenediamines.This reaction leads to the formation of benzimidazolium and perimidinium cations.
Vedernikova, I. V.,Konstantinchenko, A. A.,Ryabukhin, Yu. I.
p. 175 - 181
(2007/10/02)

O,O-Diethyldithiophosphoric acid. A new condensing agent for acylation of amines by carboxylic acid
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Hossain,Borthakur
p. 1062 - 1063
(2007/10/02)

Salicylanilide and its heterocyclic analogues. A comparative study of their antimicrobial activity
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Daidone,Maggio,Schillaci
p. 441 - 442
(2007/10/02)

PHOTOCHEMICAL AND THERMAL REACTIONS OF 2-ARYLOXYBENZOHYDROXAMIC ACIDS
2-Aryloxybenzohydroxamic acids 1-7 were subjected to photolysis in benzene or methanol.In each case corresponding N-arylsalicylamides 8-10 were obtained in good yields.Compounds 1-7 on thermolysis in decaline also produced 8-10.
Hosangadi, B. D.,Nimbalkar, M. M.,Patel, N. R.
p. 5857 - 5860
(2007/10/02)

BORON TRICHLORIDE CATALYZED ORTHO CARBONYLATION OF PHENOLS: SYNTHESIS OF 2-HYDROXY-ARYL-CARBOXYAMIDES AND -KETONES.
In the presence of equimolar quantity of BCl3, phenols 1 react with isocyanates and acyl chlorides to give, usually with good-excellent yields, 2-hydroxy-aryl-carboxy-amides 2 and 2-hydroxy-aryl-ketones 3 respectively.A distinctive behaviour of BCl3 in comparison with other Lewis acids is observed.
Piccolo, Oreste,Filippini, Lucio,Tinucci, Laura,Valoti, Ermanno,Citterio, Attilio
p. 885 - 892
(2007/10/02)