cas 87-25-2, ETHYL ANTHRANILATE | Articles data

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Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions
Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.
Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter
p. 133 - 146
(2021/11/04)

Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C-C Bond Cleavage of Isatins
A facile and direct electrocatalytic C-C bond cleavage/functionalization reaction of isatins was developed. With isatins as the amino-attached C1 sources, a variety of aminobenzoates, and aminobenzamides were synthesized in moderate to good yields under mild conditions.
Qian, Peng,Liu, Jiaojiao,Zhang, Yan,Wang, Zhiyong
p. 16008 - 16015
(2021/07/31)

Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker
A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.
Liu, Jie,Zhang, Guang-Yu,Zhang, Zhe,Li, Bo,Chai, Fei,Wang, Qi,Zhou, Zi-Dan,Xu, Ling-Ling,Wang, Shou-Kai,Jin, Zhen,Tang, You-Zhi
(2021/05/17)

Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids
We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.
Begam, Hasina Mamataj,Jana, Ranjan,Manna, Kartic,Samanta, Krishanu
supporting information
p. 7443 - 7449
(2020/10/09)

PROCESS FOR THE PREPARATION OF QUINOLONE BASED COMPOUNDS
The present invention relates to an improved process for the preparation of quinolone based compounds of general formula (I) using intermediate compound of general formula (XII). Invention also provides an improved process for the preparation of compound of formula (I-a) using intermediate compound of formula (XII-a) and some novel impurities generated during process. Compounds prepared using this process can be used to treat anemia.
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Paragraph 0288; 0290-0291

(2019/12/06)

Oxidative ring-opening of isatins for the synthesis of 2-aminobenzamides and 2-aminobenzoates
An efficient and practical isatin-based oxidative domino protocol has been developed for the facile synthesis of 2-aminobenzamides and 2-aminobenzoates. The robust nature of this reaction system is reflected by accessible starting materials, room temperature and high-yield gram-scale synthesis.
Wang, Yu-Wei,Zheng, Lei,Jia, Feng-Cheng,Chen, Yun-Feng,Wu, An-Xin
p. 1497 - 1503
(2019/02/13)

Preparation method of ethyl o-aminobenzoate
The invention discloses a preparation method of ethyl o-aminobenzoate. The preparation method comprises the steps that 1, after phthalic anhydride and ammonium hydroxide are mixed, a mixture and a sodium hydroxide solution are mixed for first reaction to obtain first reaction liquid; 2, after the first reaction liquid and ethyl alcohol are mixed, second reaction is carried out to obtain second reaction liquid; 3, after the second reaction liquid and a sodium hypochlorite solution are mixed, third reaction is carried out to obtain third reaction liquid containing the ethyl o-aminobenzoate. Theraw materials used in the preparation method are low in price and easy to get, the preparation method is simple, easy and mild, the high-purity ethyl o-aminobenzoate can be prepared only through two steps, and a product is high in yield, high in purity and easy to separate.
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Paragraph 0024-0055

(2019/01/16)

Halogen-substituted anthranilic acid derivatives provide a novel chemical platform for androgen receptor antagonists
Androgen receptor (AR) antagonists are used for hormone therapy of prostate cancer (PCa). However resistance to the treatment occurs eventually. One possible reason is the occurrence of AR mutations that prevent inhibition of AR-mediated transactivation by antagonists. To offer in future more options to inhibit AR signaling, novel chemical lead structures for new AR antagonists would be beneficial. Here we analyzed structure-activity relationships of a battery of 36 non-steroidal structural variants of methyl anthranilate including 23 synthesized compounds. We identified structural requirements that lead to more potent AR antagonists. Specific compounds inhibit the transactivation of wild-type AR as well as AR mutants that render treatment resistance to hydroxyflutamide, bicalutamide and the second-generation AR antagonist enzalutamide. This suggests a distinct mode of inhibiting the AR compared to the clinically used compounds. Competition assays suggest binding of these compounds to the AR ligand binding domain and inhibit PCa cell proliferation. Moreover, active compounds induce cellular senescence despite inhibition of AR-mediated transactivation indicating a transactivation-independent AR-pathway. In line with this, fluorescence resonance after photobleaching (FRAP) - assays reveal higher mobility of the AR in the cell nuclei. Mechanistically, fluorescence resonance energy transfer (FRET) - assays indicate that the amino-carboxy (N/C)-interaction of the AR is not affected, which is in contrast to known AR-antagonists. This suggests a mechanistically novel mode of AR-antagonism. Together, these findings indicate the identification of a novel chemical platform as a new lead structure that extends the diversity of known AR antagonists and possesses a distinct mode of antagonizing AR-function.
Roell, Daniela,R?sler, Thomas W.,Hessenkemper, Wiebke,Kraft, Florian,Hauschild, Monique,Bartsch, Sophie,Abraham, Tsion E.,Houtsmuller, Adriaan B.,Matusch, Rudolf,van Royen, Martin E.,Baniahmad, Aria
p. 59 - 70
(2019/02/01)

Selective hydrogenation of nitroarenes using an electrogenerated polyoxometalate redox mediator
The 2-electron reduced form of the polyoxometalate silicotungstic acid (H4[SiW12O4]) is shown to be an effective and selective hydrogenation agent for a range of nitroarenes without the need for any co-catalyst. The ease of generation of the active species and its recyclability suggest that a new approach to this important class of chemical conversions is possible.
Macdonald, Lewis,Rausch, Benjamin,Symes, Mark D.,Cronin, Leroy
supporting information
p. 1093 - 1096
(2018/02/07)

2-[2-(2-methoxyl phenoxyl) ethylamino]-3-aryl-4-quinazolinones compound and application thereof
The invention belongs to the technical field of medicines, and relates to a 2-[2-(2-methoxyl phenoxyl) ethylamino]-3-aryl-4-quinazolinones derivative and application thereof. The 2-[2-(2-methoxyl phenoxyl) ethylamino]-3-aryl-4-quinazolinones derivative comprises a stereisomer of the compound and pharmacologically applicable salt. The general structural formula is as follows: as shown in the description, wherein R is as described in claims and the description. The 2-[2-(2-methoxyl phenoxyl) ethylamino]-3-aryl-4-quinazolinones derivative and salt formed by addition of a pharmacologically applicable acid of the compound can be combined with an existing medicine or used independently to form an influenza virus inhibitor which is used for treating influenza and particularly has a relatively curative effect on various types of influenza A.
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Paragraph 0047; 0050

(2018/03/25)

2-[3-(4-morpholinyl)propylamine]-3-aryl-4-quinolinone compounds and application thereof
The invention belongs to the technical field of medicines and relates to 2-[3-(4-morpholinyl)propylamine]-3-aryl-4-quinolinone compounds and an application thereof. 2-[3-(4-morpholinyl)propylamine]-3-aryl-4-quinolinone derivatives comprise stereisomers and pharmaceutically applicable salts of the compounds and have the general structural formula shown in the description, wherein R is described inthe claims and description. The 2-[3-(4-morpholinyl)propylamine]-3-aryl-4-quinolinone derivatives and pharmaceutically applicable acid-added salts of the compounds can be combined with existing medicines or used separately to serve as influenza virus inhibitors to treat influenza and have better curative effects on various type-A influenza in particular.
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Paragraph 0040; 0048

(2018/04/21)

Unprecedented alkylation of carboxylic acids by boron trifluoride etherate
The alkylation of carboxylic acids by an ethyl moiety of boron trifluoride etherate in the absence of ethyl alcohol from the reaction system is unexpected and novel. Both aromatic and aliphatic carboxylic acids were clearly alkylated affording good yields in short reaction times with the exception of nicotinic acid that necessitated an overnight reaction. It was noted that while ortho-substituted hydroxyl groups of carboxylic acids investigated were not affected by alkylation, those of meta- and para-substituted carboxylic acids were partially etherified. Furthermore, the alkylation reaction was found to be compatible with a range of functional groups such as halogens, amino and nitro groups except for the alkene function of undecylenic acid that underwent polymerisation with concomitant alkylation of its carboxylic acid function.
Jumbam, Ndze D.,Maganga, Yamkela,Masamba, Wayiza,Mbunye, Nomthandazo I.,Mgoqi, Esethu,Mtwa, Sphumusa
p. 387 - 392
(2018/09/06)

Method for preparing aminobenzoic acid or ester thereof
The invention discloses a method for preparing aminobenzoic acid or ester thereof. The method comprises the following steps: S1, sequentially adding nitrobenzoic acid or ester, a solvent and an active nickel catalyst in a reactor; S2, while stirring, introducing hydrogen gas to replace air in a system for 3-4 times, controlling the pressure of the hydrogen gas, and performing a stirring reaction at preset temperature for a scheduled time so as to realize catalytic hydrogenation; S3, performing filtration under reduced pressure, washing filter cakes with a solvent which is the same as the solvent in S1, and collecting the active nickel catalyst; S4, performing reduced-pressure concentration on filtrate obtained in the S3 to obtain a solid namely the product of the aminobenzoic acid or the ester thereof. The method disclosed by the invention can be performed in neutral condition, normal temperature, low pressure or normal pressure, is high in synthetizing yield and low in cost, and has commercial value and environmental protection efficacy; the yield of the obtained product can be 95% or above, and the purity of the product can be 98.5% or above.
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Paragraph 0020

(2017/07/21)

Aromatic azido-selective reduction via the staudinger reaction using tri-n-butylphosphonium tetrafluoroborate with triethylamine
An efficient method for the reduction of aromatic azides to anilines via the Staudinger reaction using tri-n-butylphosphonium tetrafluoroborate with triethylamine in aqueous tetrahydrofuran solution is reported. The method enables the aromatic azido-selective reduction of 3-azido-5-(azidomethyl)benzene derivatives to efficiently afford anilines bearing an azidomethyl group.
Meguro, Tomohiro,Yoshida, Suguru,Hosoya, Takamitsu
supporting information
p. 473 - 476
(2017/04/03)

A kind of 3,4-dichloro-thiazole derivatives and process for their preparation and use
The invention provides 3,4-dichloro isothiazole derivatives, their preparation method and application. The invention relates to a heterocyclic compound containing 3,4-dichloro isothiazol, and the compound is represented by the following chemical structural general formula. The invention discloses the structural general formula of the compound, a synthetic method of the compound and applications of the compound as pesticide, bactericide, anti-plant virus agent, and plant activator, and a technology of mixing the compound with agriculturally acceptable auxiliary agents or synergists for preparing pesticide, bactericide, anti-plant virus agent, and plant activator. The invention further discloses the combined application of the compound and the commercial pesticide, bactericide, anti-plant virus agent, and plant activator in controlling diseases, insect pests, and virus diseases in agriculture, forestry and gardening, and a preparation method of the compound and the commercial pesticide, bactericide, anti-plant virus agent, and plant activator.
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Paragraph 0053-0056; 0103

(2016/10/08)

Synthetic studies and antibacterial activity of nucleobases and their N- and S-glucosides from 2-amino benzoic acid and its benzamido derivatives
A series of S-glucosides 11a-14a and their benzamido derivatives 11b-14b have been synthesized by reacting D-glucose with thiol groups of 5-(2′-aminophenylene)-1,3,4-oxadiazole-2-thioles 7(a,b), 5-(2′-aminophenylene)-1,3,4-thiadiazole-2-thiols 8(a,b), 5-(2′-aminophenylene)-1,2,4-triazole-3-thiols 9(a,b) and 5-(2′-aminophenylene)-4-N-amino-1,2,4-triazole-3-thiols 10(a,b). The thiols 7(a,b)-10(a,b) have been synthesized from hydrazides 3(a,b) which already been synthesized from 2-aminobenzoic acid and its benzamido derivative. All synthesized compounds were characterized by IR, UV,1H- and13C- NMR. Nucleobases and a representative of S-glycoside were tested in vitro against the following microorganisms: two Gram-positive bacteria Staphylococcus aureus and Bacillus cereusand two Gram-negative bacteria Escherichia coli, Pseudomonas aeruginosa and they exhibited significant effects. Amykacine was used as positive standard.
Benhammadi, Samia,Iraten, Salima,Othman, Adil A.
p. 2567 - 2576
(2016/11/22)

Competitive homolytic and heterolytic decomposition pathways of gas-phase negative ions generated from aminobenzoate esters
An alkyl-radical loss and an alkene loss are two competitive fragmentation pathways that deprotonated aminobenzoate esters undergo upon activation under mass spectrometric conditions. For the meta and para isomers, the alkyl-radical loss by a homolytic cleavage of the alkyl-oxygen bond of the ester moiety is the predominant fragmentation pathway, while the contribution from the alkene elimination by a heterolytic pathway is less significant. In contrast, owing to a pronounced charge-mediated ortho effect, the alkene loss becomes the predominant pathway for the ortho isomers of ethyl and higher esters. Results from isotope-labeled compounds confirmed that the alkene loss proceeds by a specific γ-hydrogen transfer mechanism that resembles the McLafferty rearrangement for radical cations. Even for the para compounds, if the alkoxide moiety bears structural motifs required for the elimination of a more stable alkene molecule, the heterolytic pathway becomes the predominant pathway. For example, in the spectrum of deprotonated 2-phenylethyl 4-aminobenzoate, m/z 136 peak is the base peak because the alkene eliminated is styrene. Owing to the fact that all deprotonated aminobenzoate esters, irrespective of the size of the alkoxy group, upon activation fragment to form an m/z 135 ion, aminobenzoate esters in mixtures can be quantified by precursor ion discovery mass spectrometric experiments.
Xia, Hanxue,Zhang, Yong,Pavlov, Julius,Jariwala, Freneil B.,Attygalle, Athula B.
p. 245 - 253
(2016/03/15)

Oxidative esterification via photocatalytic C-H activation
Direct oxidative esterification of alcohol via photocatalytic C-H activation has been developed using VO@g-C3N4 catalyst; an expeditious esterification of alcohols occurs under neutral conditions using visible light as the source of energy.
Verma, Sanny,Baig, R. B. Nasir,Han, Changseok,Nadagouda, Mallikarjuna N.,Varma, Rajender S.
p. 251 - 254
(2015/12/31)

Synthesis of novel triazoles and a tetrazole of escitalopram as cholinesterase inhibitors
A novel serie of escitalopram triazoles (60-88) and a tetrazole (89) have been synthesized and subjected to a study to establish the inhibitory potential of these compounds toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Some selectivity in inhibition has been observed. The 4-chlorophenyl- (75, IC50, 6.71 ± 0.25 μM) and 2-methylphenyl- (70, IC50, 9.52 ± 0.23 μM) escitalopram triazole derivatives depicted high AChE inhibition, while 2-fluorophenyl- (76, IC50 = 4.52 ± 0.17 μM) and 4-fluorophenyl- (78, IC50 = 5.31 ± 0.43 μM) have found to be excellent BChE inhibitors. It has also been observed that ortho, meta and para substituted electron donating groups increase the inhibition, while electron withdrawing groups reduce the inhibition. Docking analyses of inhibitors with AChE have depicted the binding energies for 70 and 75 as ΔGbind -6.42 and -6.93 kcal/mol, respectively, while ligands 76 and 78 have shown the binding affinity ΔGbind -9.04 and -8.51 kcal/mol, respectively, for BChE.
Mehr-Un-Nisa,Munawar, Munawar A.,Chattha, Fauzia A.,Kousar, Samina,Munir, Jawaria,Ismail, Tayaba,Ashraf, Muhammad,Khan, Misbahul A.
p. 6014 - 6024
(2015/11/11)

Beyond conventional routes, an unprecedented metal-free chemoselective synthesis of anthranilate esters via a multicomponent reaction (MCR) strategy
A hitherto unreported route for the synthesis of anthranilate esters is demonstrated using 2-nitrobenzaldehyde, malonitrile and an alcohol or amine via a metal and oxidant free multicomponent reaction (MCR) strategy. This process simultaneously installs an ester and urea or urethane functionality via CO and CN bond formations via concurrent oxidation of the aldehyde group and reduction of the nitro group involving an intramolecular redox process.
Sarkar, Satavisha,Khan, Abu T.
supporting information
p. 12673 - 12676
(2015/08/06)

Palladium-catalyzed oxidative carbonylation of aromatic C-H bonds of N -alkylanilines with CO and alcohols for the synthesis of o -aminobenzoates
A Pd(II)-catalyzed C-H monocarbonylation of N-alkylanilines for the synthesis of o-aminobenzoates has been developed. Various aliphatic alcohols and phenol were tolerated in the reaction to afford the corresponding o-aminobenzoates in good yields under mild balloon pressure of CO.
Chen, Ming,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
p. 1258 - 1263
(2015/01/30)

Design, green synthesis, and anti-inflammatory activity of schiff base of 1,3,4-oxadiazole analogues
Cyclooxygenase enzyme is a validated therapeutic target for designing drug molecules with anti-inflammatory activity. Herein, a series of various schiff base of 1,3,4-oxadiazole analogues were designed. Considering reasonable structural similarity of the target compounds with the commonly used anti-inflammatory drug indomethacin, it was decided to dock the target compounds into the active site of the molecular target of indomethacin. Prior to docking, the active sites of the proteins are identified. The docking study is performed using the UCSF DOCK 6.5 program. And also the utilization of principles involved in green chemistry is significantly reducing chemical waste and reaction times. To illustrate these advantages in the synthesis of bioactive oxadiazole derivatives, various environmentally benign protocols that involve greener alternatives were studied. The efficiency of microwave heating technology has resulted in remarkable reductions of reaction times (reduced from days and hours to minutes and seconds) with better product yield. The structures of newly synthesized compounds have been elucidated on the basis of IR, 1H NMR, 13C NMR, LC-MS and elemental analysis. An evaluation of the anti-inflammatory activity of the prepared compounds has indicated that some of them exhibited moderate to significant activity as compared to indomethacin.
Sahoo, Biswa Mohan,Dinda, Subas Chandra,Kumar, B.V.V. Ravi,Panda, Jnyanaranjan,Brahmkshatriya, Pathik S.
p. 82 - 89
(2014/01/06)

Highly efficient four-component synthesis of 4(3H)-quinazolinones: Palladium-catalyzed carbonylative coupling reactions
Given the importance of quinazolinones and carbonylative transformations, a palladium-catalyzed fourcomponent carbonylative coupling system for the synthesis of diverse 4(3H)-quinazolinone in a concise and convergent fashion has been developed. Starting from 2-bromoanilines (1 mmol), trimethyl orthoformate (2 mmol), and amines (1.1 mmol), under 10 bar of CO, the desired products were isolated in good yields in the presence of Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%) in 1,4-dioxane (2 mL) at 1008C, using N,Ndiisopropylethylamine (2 mmol) as the base. Notably, the process tolerates the presence of various reactive functional groups and is very selective for quinazolinones, and was used in the synthesis of the precursor to the bioactive dihydrorutaempine.
He, Lin,Li, Haoquan,Neumann, Helfried,Beller, Matthias,Wu, Xiao-Feng
p. 1420 - 1424
(2014/03/21)

Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents
A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 ± 0.2, 30.0 ± 1.2, 18.3 ± 1.4 μM, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 μM, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 μg/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study.
Du, Qian-Ru,Li, Dong-Dong,Pi, Ya-Zhou,Li, Jing-Ran,Sun, Jian,Fang, Fei,Zhong, Wei-Qing,Gong, Hai-Bin,Zhu, Hai-Liang
p. 2286 - 2297
(2013/05/09)

Reduction of aromatic nitro compounds to amines using zinc and aqueous chelating ethers: Mild and efficient method for zinc activation
A mild, environmentally friendly method for reduction of aromatic nitro group to amine is reported, using zinc powder in aqueous solutions of chelating ethers. The donor ether acts as a ligand and also serves as a co-solvent. Water is the proton source. This procedure is also a new method for the activation of zinc for electron transfer reduction of aromatic nitro compounds. The reduction is accomplished in a neutral medium and other reducing groups remained unaffected. The ethers used are dioxolane, 1,4-dioxane, ethoxymethoxyethane, dimethoxymethane, 1,2-dimethoxyethane, and diglyme.
Kumar, Pookot Sunil,Lokanatha Rai, Kuriya M.
p. 772 - 778
(2013/07/26)

Synthesis, antimicrobial evaluation, ot-QSAR and mt-QSAR studies of 2-amino benzoic acid derivatives
A series of 2-amino benzoic acid derivatives (1-28) were synthesized and evaluated for their in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. The results of antimicrobial studies indicated that, in general, the synthesized compounds were found to be bacteriostatic and fungistatic in action. QSAR studies performed by the development of one target and multi target models indicated that multi-target model was effective in describing the antimicrobial activity as well demonstrated the effect of structural parameters viz. LUMO, 3χv and W on antimicrobial activity of 2-amino benzoic acid derivatives. Springer Science+Business Media, LLC 2010.
Mahiwal, Kuldeep,Kumar, Pradeep,Narasimhan, Balasubramanian
experimental part
p. 293 - 307
(2012/09/07)

QSAR modeling of synthesized 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potent antibacterial agents
Present communication elicits the designing and synthesis of 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potential antibacterial agents. A number of substituted 2-amino benzothiazoles, 2-amino-5-[(E)-phenyl diazenyl] benzoic acid, and 2-phenyl-4H benzo[d] [1,3] oxazin-4-one were synthesized as the precursor substrates. The compounds were synthesized in excellent yields and the structures were corroborated on the basis of IR, 1H NMR, Mass, and elemental analysis data. These compounds were screened in vitro for their antibacterial activity against a representative panel of Gram positive and Gram negative bacteria and models were generated through quantitative structure-activity relationship (QSAR).The activity contributions due to structural and substituent effects were determined using sequential regression procedure. The antimicrobial assay data show that the synthesized compounds are found to manifest profound antimicrobial activity. Springer Science+Business Media, LLC 2011.
Sharma, Pratibha,Kumar, Ashok,Kumari, Prerna,Singh, Jitendra,Kaushik
experimental part
p. 1136 - 1148
(2012/08/28)

Hofmann-type rearrangement of imides by in situ generation of imide-hypervalent iodines(III) from iodoarenes
The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted by the formation of an imide-λ3-iodane intermediate.
Moriyama, Katsuhiko,Ishida, Kazuma,Togo, Hideo
p. 946 - 949
(2012/05/05)

One-pot aromatic amination based on carbon-nitrogen coupling reaction between aryl halides and azido compounds
An efficient copper-mediated C-N coupling reaction between various aryl halides and azido compounds to produce the corresponding aromatic primary amines was established. The present amination is apparently involved in both the reduction of an azido functionality to the corresponding primary amino group and its cross-coupling reaction with aryl halides in a one-pot manner. The present amination could be applied to the synthesis of procaine, a local anesthetic drug. A mechanistic study indicated that 2-aminoethanol could work as a major hydrogen donor and the reaction would proceed without the formation of the intermediary aryl azide.
Maejima, Toshihide,Shimoda, Yutaka,Nozaki, Kei,Mori, Shigeki,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao
experimental part
p. 1712 - 1722
(2012/03/08)

Synthesis and cytotoxicity of some d-mannose click conjugates with aminobenzoic acid derivatives
Two sets of new conjugates obtained from d-mannose derivatives and o-, m-, and p-substituted benzoic acid esters interconnected through a triazole ring were synthesized by Cu(I) catalyzed azide-alkyne cycloaddition. All synthesized compounds were tested for their in vitro cytotoxic activity against seven cancer cell lines with/without multidrug resistance phenotype as well as non-tumor MRC-5 and BJ fibroblasts. Butyl ester of 4-aminobenzoic acid 6c showed the highest activity among all tested compounds, however, it was active only against K562 myeloid leukemia cells. N-Glycosyltriazole conjugates, both acetylated and nonacetylated at mannose moiety, were almost completely inactive. In contrast, some of the acetylated O-glycosyl conjugates showed cytotoxic activity which was cell line dependent and strongly affected by position of benzoic acid substitution as well as a length of its ester alkyl chain; the most potent compound was acetylated mannoside conjugated with octyl ester of m-substituted benzoic acid. However, deacetylation resulting in hydrophilicity increase of the glycosides almost completely abolished their cytotoxic potency.
Hradilová, Ludmila,Poláková, Monika,Dvo?áková, Barbora,Hajdúch, Marián,Petru?, Ladislav
p. 1 - 6
(2013/01/15)

Anthranilic acid-based inhibitors of phosphodiesterase: Design, synthesis, and bioactive evaluation
Our previous studies identified two 2-benzoylaminobenzoate derivatives 1, which potently inhibited superoxide (O2-) generation induced by formyl-l-methionyl-l-leucyl-l-phenylalanine (FMLP) in human neutrophils. In an attempt to improve their activities, a series of anthranilic acid derivatives were synthesized and their anti-inflammatory effects and underlying mechanisms were investigated in human neutrophils. Of these, compounds 17, 18, 46, 49, and 50 showed the most potent inhibitory effect on FMLP-induced release of O2- in human neutrophils with IC50 values of 0.20, 0.16, 0.15, 0.06, and 0.29 μM, respectively. SAR analysis showed that the activities of most compounds were dependent on the ester chain length in the A ring. Conversely, a change in the linker between the A and B ring from amide to sulfonamide or N-methyl amide, as well as exchanges in the benzene rings (A or B rings) by isosteric replacements were unfavorable. Further studies indicated that inhibition of O2- production in human neutrophils by these anthranilic acids was associated with an elevation in cellular cAMP levels through the selective inhibition of phosphodiesterase 4. Compound 49 could be approved as a lead for the development of new drugs in the treatment of neutrophilic inflammatory diseases.
Cheng, Yih-Dih,Hwang, Tsong-Long,Wang, Han-Hsiang,Pan, Tai-Long,Wu, Chin-Chung,Chang, Wen-Yi,Liu, Yi-Ting,Chu, Tzu-Chi,Hsieh, Pei-Wen
experimental part
p. 7113 - 7125
(2011/11/04)

Copper-mediated reductive amination of aryl halides with trimethylsilyl azide
(Chemical equation presented) Look, no azide! Trimethylsilyl azide was reductively cross-coupled with a variety of aryl halides in the presence of a copper species and amines, such as triethylamine or aminoethanol, to give the corresponding primary aryl amine in good yields without the formation of the expected aryl azide (see scheme).
Monguchi, Yasunari,Maejima, Toshihide,Mori, Shigeki,Maegawa, Tomohiro,Sajiki, Hironao
supporting information; experimental part
p. 7372 - 7375
(2010/08/20)

Sodium borohydride-mediated transesterification
In the presence of sodium borohydride, esters react with alcohols with formation of the corresponding esters. The reaction is sensitive to the solvent, structure of the ester, and is often concurrent with reduction. Thioesters containing an ester group can be selectively cleaved by the reagent. Both esters and thioesters attached to solid support are resistant toward sodium borohydride. The in situ prepared sodium tetraalkoxyborate is introduced as an efficient reagent and catalyst for transesterification.
Sereda, Grigoriy,Pothula, Swetha,Dreessen, James
scheme or table
p. 1312 - 1321
(2010/07/05)

AZABIPHENYLAMINOBENZOIC ACID DERIVATIVES AS DHODH INHIBITORS
New azabiphenylaminobenzoic acid derivatives having the chemcial structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of the dehydroorotate dihydrogenase (DHODH)
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Page/Page column 66

(2009/04/25)

Alkylidenephosphoranes in heterocyclic synthesis: Reactivity of benzoxazinones with resonance-stabilized phosphorus ylides
2H-3,1-Benzoxazine-2,4(1H)-dione and its N-methyl analogue react with alkylidenephosphoranes to give substituted quinolines and benzazepines as well as indanone and furan derivatives. Reaction mechanisms to explain the formation of products obtained are outlined. Georg Thieme Verlag Stuttgart.
Kamel, Azza A.,Abdou, Wafaa M.
p. 1269 - 1273
(2007/12/27)

HETEROCYCLIC AND BICYCLIC COMPOUNDS, COMPOSITIONS AND METHODS
The present invention provides, among other things, new bicyclo heterocyclic compounds, compositions comprising these heterocyclic compounds, methods of making the heterocyclic compounds, and methods of using these heterocyclic compounds for treating a variety of conditions and disease states associated with, for example, cellular proliferation, inflammation, glycosidase expression, or the low expression of Perlecan.
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Page/Page column 116

(2010/11/08)

PLATINUM COMPLEX COMPOUNDS PRODUCTION THEREOF AND TREATMENT OF CANCER DISEASES
The invention relates to novel platinum complex compounds, a method for production and use thereof in the treatment of cancer diseases.
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Page/Page column 23-24

(2010/02/12)

2-Arylaminopyrimidine derivatives as PLK inhibitors
Anilino-pyrimidine and 1,2,4-triazine compounds (1) are new. Anilino-pyrimidine and 1,2,4-triazine compounds of formula (1), their tautomers, racemates, enantiomers and/or diastereomers and acid-addition salts are new. X : NR 1a>, O or S; Y : CH or N; Z : hydrogen, halo, (halo)1-3C alkyl, 2-3C alkenyl, 2-3C alkynyl, formyl, 1-3C (halo)alkylcarbonyl, 2-3C alkenyl-, 2-3C alkynyl-carbonyl or pseudohalo; A : (hetero)aryl group (i) or (ii); R a> - R f>e.g. hydrogen, halo or nitro; R 1> and R 1a>hydrogen or methyl; R 2>e.g. Cl, Br, I, OR 6>; R 3>e.g. -CONR 1>-L-Q 3-Q 4-R 9>, -NR 1>-CO-L-Q 3-Q 4-R 9>; R 4>e.g. OR 6>, COR 6>, CONR 6>R 7>, NR 6>R 7>, NR 6>COR 7>, NR 6>SO 2R 7>, N=CR 6>R 7>, SR 6>, SOR 6>, SO 2R 6>, SO 2NR 6>R 7> or pseudohalogen, or any of 1-8C alkyl, 2-10C alkenyl or alkynyl, 3-8C cycloalkyl, (hetero)aryl or heterocyclyl; R 5>hydrogen, halo, trifluoromethyl, 1-3C alkyl or OR 6>; R 6>, R 7>e.g. hydrogen or any of 1-5C alkyl, 2-5C alkenyl or alkynyl, 3-10C cycloalkyl, (hetero)aryl or heterocyclyl; L : e.g. bond or residue of 1-16C alkyl, 2-16C alkenyl or alkynyl, 3-10C cycloalkyl, (hetero)aryl or heterocyclyl; Q 3 and Q 4bond or a mono- or bi-cyclic heterocyclyl, optionally substituted by one or more of Me, Et, halo, amino, hydroxy or pseudohalo; R 9>as L but not a bond; and T : N, O or S. Full definitions are given in the DEFINITIONS (Full Definitions) field. [Image] [Image] ACTIVITY : Cytostatic; Antiinflammatory; Immunosuppressive; Virucide; Anti-HIV; Dermatological; Nootropic; Neuroprotective; Nephrotropic; Vulnerary; Antibacterial; Fungicide; Antiparasitic; Antipsoriatic; Osteopathic; Cardiovascular-Gen; Vasotropic; Gastrointestinal-Gen. MECHANISM OF ACTION : Kinase inhibitor; Polo-like kinase (PLK) inhibitor. In a trial, (1) was found to have EC 50 against recombinant human PLK1 of below 5, generally 1 mu M. No results for specific compounds were given.
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Page/Page column 50

(2010/02/14)

Ru(iv)-catalyzed isomerization of allylamines in water: A highly efficient procedure for the deprotection of N-allylic amines
A general and efficient method for the deprotection of N-allylic substrates in aqueous media, using catalytic amounts of the bis(allyl)-ruthenium(iv) complexes [Ru(η3 : η2 : η3-C 12H18)Cl2] (1) and [{Ru(η3 : η-C10H16)(μ-Cl)Cl}2] (2), has been developed. The Royal Society of Chemistry 2005.
Cadierno, Victorio,Garcia-Garrido, Sergio E.,Gimeno, Jose,Nebra, Noel
p. 4086 - 4088
(2007/10/03)

A novel intramolecular photocyclization of N-(2-bromoalkanoyl) derivatives of 2-acylanilines via 1,8-hydrogen abstraction
The photochemical reactions of different N-(2-acylphenyl)-2-bromo-2- methylpropanamides have been investigated. Irradiation of the N-unsubstituted anilides 1a-1c gave the corresponding dehydrobromination, cyclization, and bromo-migration products 2, 3, and 4, respectively (Table 1). Irradiation of the N-alkyl anilides 1e-1g afforded the corresponding deacylation and cyclization products 5 and 6, respectively, whereas irradiation of the N-alkyl anilides 1i-1k, carrying 2-benzoyl groups on the aromatic rings, afforded the unexpected tricyclic lactams 7 (besides 2, 5, and 6). The formation of the cyclization products 6 could be rationalized in terms of an electrocyclic ring closure of the 6π-electron-conjugated enamides 2 produced by dehydrobromination of 1, followed by thermal 1,5-acyl migration (Path B in the Scheme). The formation of the bridged lactams 7 probably follows a mechanism involving the 1,7-diradical 8 generated by ζ-H-abstraction (1.8-H transfer) by an excited acyl O-atom (Path A).
Nishio, Takehiko,Koyama, Hiroyuki,Sasaki, Daigo,Sakamoto, Masami
p. 996 - 1003
(2007/10/03)

Synthesis of 2-quinolones via palladium-catalyzed carbonylative annulation of internal alkynes by N-substituted o-iodoanilines
The palladium-catalyzed annulation of internal alkynes by N-substituted o-iodoanilines under 1 atm of carbon monoxide results in the formation of 3,4-disubstituted 2-quinolones. The nature of the substituent on the nitrogen is crucial to obtaining high yields of 2-quinolones. The best results are obtained using alkoxycarbonyl, p-tolylsulfonyl, and trifluoroacetyl substituents. The nitrogen substituent is lost during the course of the reaction resulting in the formation of N-unsubstituted 2-quinolones. A variety of internal alkynes, bearing alkyl, aryl, heteroaryl, hydroxyl, and alkoxyl substituents, are effective in this process. Electron-rich and electron-poor N-substituted o-iodoanilines, as well as heterocyclic analogues, can be employed as annulating agents.
Kadnikov, Dmitry V.,Larock, Richard C.
p. 6772 - 6780
(2007/10/03)

Synthesis and structure-activity relationship of diarylamide derivatives as selective inhibitors of the proliferation of human coronary artery smooth muscle cells
A series of diarylamide derivatives were synthesized and evaluated for their inhibitory activities against human coronary artery smooth muscle cells (SMCs) and human coronary artery endothelial cells (ECs). Compound 2w was superior to the lead compound, Tranilast, in terms of the potency of the activity and cell selectivity.
Gita, Haruhisa,Sobe, Yoshiaki,Akaku, Haruo,Ekine, Rena,Oto, Yuso,Isawa, Satoru,Hayashi, Hideya
p. 549 - 551
(2007/10/03)

A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine
A simple method for the reduction of aromatic nitro compounds to aromatic amines was developed using samarium and catalytic amounts of iodine.
Banik, Bimal K.,Mukhopadhyay, Chhanda,Venkatraman,Becker, Frederick F.
p. 7243 - 7246
(2007/10/03)

Pharmacologically active pyridine derivatives and processes for the preparation thereof
N-phenyl-2-pyrimidineamine derivatives of formula I STR1 wherein the substituents are as defined in claim 1 and the derivatives of formula I can be used, for example, in the treatment of tumour diseases.
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(2008/06/13)

An efficient general method for esterification of aromatic carboxylic acids
Treatment of a variety of aromatic carboxylic acids with alcohols in the presence of thionyl chloride results in excellent yields of corresponding esters. This esterification system is compatible with a wide assortment of functional groups.
Hosangadi, Bhaskar D.,Dave, Rajesh H.
p. 6375 - 6378
(2007/10/03)

Steric effects in acid-catalyzed decomposition and base-catalyzed cyclization of 1-(2-alkoxycarbonyl-phenyl)-3-phenyltriazenes
Eight derivatives of 1-(2-alkoxycarbonylphenyl)-3-phenyltriazene (R = methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl, and allyl) have been synthesized and their UV-VIS, IR, 1H and 13C NMR spectra measured. The NMR spectra have been interpreted in detail. The kinetics of acid-catalyzed decomposition and base-catalyzed cyclization of the title compounds have been measured in 52.1% w/w methanol at 25.0 °C. The unit reaction order has been verified and the cyclization product has been identified. The pH-profiles obtained have been used to calculate the catalytic rate constants kA (acid-catalyzed decomposition) and kB (base-catalyzed cyclization) of all the derivatives; the constants have been interpreted with regard to inductive and steric effects. The catalytic rate constant kA has been found to be independent of the substituents. The catalytic rate constant kB depends statistically significantly upon both inductive and steric effects, the sensitivity to the former being more significant. The experimental results and their interpretation confirm the base-catalyzed cyclization mechanism with formation of tetrahedral intermediate as the rate-limiting step.
Pytela, Oldrich,Halama, Ales
p. 751 - 763
(2007/10/03)

Schiff bases
Schiff bases having the formula STR1 wherein R1 signifies CH3, C2 H5 R2 signifies H, CH3 R3 signifies H, C1-4 -alkyl R4, R5, R6, R7 signify H, CH3, C2 H5, CH2 CH2 CH3, CH(CH3)2, X signifies methylene, ethylidene, propylidene, ethylene, propylene, 2,3-butylidene, total number of carbon atoms of R4, R5, R6, R7, ≤6 are novel odorants.
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(2008/06/13)

Reduction of Aromatic Nitro Compounds with Baker's Yeast
The reduction of the nitro group of aromatic nitro compounds with baker's yeast was strongly influenced by the nature of the substituent on nitrobenzene, and in the reaction of acyl nitrobenzenes, selective reduction occurred to give optically active nitro alcohol and amino alcohol and amino ketone without giving any amino alcohol.Keywords baker's yeast; nitro compound; selective reduction; acyl nitrobenzene; chiral nitro alcohol
Takeshita, Mitsuhiro,Yoshida, Sachiko,Kiya, Rieko,Higuchi, Naoko,Kobayashi, Yumi
p. 615 - 617
(2007/10/02)

CONVENIENT SYNTHESIS OF ESTERS OF 2-PYRROLECARBOXYLIC ACID AND OF PYRIDINECARBOXYLIC ACIDS BY SOLID-LIQUID PHASE TRANSFER CATALYSIS WITHOUT ADDED SOLVENT
By reaction of aromatic K-carboxylates having nucleophilic N-atom in solid-liquid phase transfer catalysis (PTC) conditions without added solvent (catalyst : tetraalkylammonium halide) with alkylating reagents, the corresponding esters are prepared.By a judicious choice of experimental conditions, the amounts of N-alkylated products can be lowered.From 2-pyrrolecarboxylic acid, the three isomers of pyridinecarboxylic acid and o-aminobenzoic acid, corresponding esters of ethyl, benzyl, n-octyl and n-cetyl, generally are obtained with good yields.
Barry, Jean,Bram, Georges,Petit, Alain
p. 875 - 880
(2007/10/02)

Polar Effects in Free Radical Reactions. Homolytic Aromatic Amination by the Amino Radical Cation, +NH3: Reactivity and Selectivity
Small amounts of Fe(II) salt initiate redox chains with hydroxyamino-O-sulfonic acid (HSA) and aromatic compounds leading to the amination of the aromatic ring.The positional and substrate selectivity with a variety of substituted benzenes show the important role of the electrophilic character of the radical +NH3.Hammett relationships with ? and ?+ are roughly observed.The lower sensitivity to polar effects of the radical +NH3 compared with (CH3)2+NH is explained by the different reaction enthalpies.The different positional selectivity obtained with anisole and the redox system +NH3OH/Ti(III) is discussed.
Citterio, Attilio,Gentile, Anna,Minisci, Francesco,Navarrini, Valter,Serravalle, Marco,Ventura, Susanna
p. 4479 - 4482
(2007/10/02)