cas 6232-88-8, 4-Bromomethylbenzoic acid | Articles data

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Extended peptoids: a new class of oligomers based on aromatic building blocks
Peptoids (N-substituted polyglycines) represent a class of bioinspired oligomers that have unique physical and structural properties. Here, we report the construction of 'extended peptoids' based on aromatic building blocks, in which the N-alkylaminoacetyl group of the peptoid backbone has been replaced by an N-alkylaminomethylbenzoyl spacer. Both meta- and para-bromomethylbenzoic acids were synthesized, providing access to a new class of peptoids. Further, inclusion of hydrophilic side chains confers water solubility to these compounds, showing that, like simple peptoids, extended peptoids add an extra dimension to synthetic poly-amide oligomers with potential application in a variety of biological contexts.
Combs, David J.,Lokey, R. Scott
p. 2679 - 2682
(2007)
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P-aminomethyl benzoic acid and preparation method thereof
The invention discloses p-aminomethyl benzoic acid and a preparation method thereof. The method comprises the following steps: hydrolyzing phthalic anhydride as a raw material under an alkaline condition to enable the anhydride structure of phthalic anhydride to be subjected to ring opening to obtain an intermediate 1; performing decarboxylation reaction on the intermediate 1 under the condition that high-temperature liquid water is used as a reaction medium to obtain an intermediate 2; converting original binary acid of the intermediate 1 into monobasic acid, and enabling the intermediate 2 to react with a saturated monochloromethane diethyl ether solution by taking diethyl ether as a solvent under the catalytic action of aluminum chloride to obtain an intermediates 3; and carrying out bromine substitution reaction on the intermediate 3 and N-bromosuccinimide, and carrying out ammoniation reaction under the action of triethylamine and potassium carbonate. The yield of p-aminomethyl benzoic acid prepared by the preparation method of p-aminomethyl benzoic acid is high, and compared with an existing preparation method, most of the used raw materials are low-price raw materials, cyanogroups with high toxicity are not introduced, and the production cost of tranexamic acid is greatly reduced.
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(2020/09/09)

Photoinduced Carbon Tetrabromide Initiated Aerobic Oxidation of Substituted Toluenes to Carboxylic Acids
A mild and metal-free procedure is reported for the aerobic oxidation of substituted toluenes to carboxylic acids by using CBr 4 as initiator under irradiation from a 400 nm blue light-emitting diode.
Li, Xiaoqing,Xu, Xiangsheng,Yan, Xiaoyu,Yan, Xinhuan,Zhang, Guofu,Zheng, Kun
p. 272 - 274
(2020/02/18)

INHIBITORS OF PSEUDOMONAS AERUGINOSA VIRULENCE
Disclosed are piperazine derivative compounds, particularly piperazine derivative compounds having a structure of Formula (I) and methods for preparing these compounds. Also disclosed are use of a therapeutically effective amount of the compound of Formula (I) or a pharmaceutically acceptable salt thereof, or a pharmaceutical composition therefore for inhibiting quorum sensing of a bacteria.
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Paragraph 0125

(2019/04/16)

Synthesis method of benzoic acid compounds
The invention discloses a photocatalytic oxidation synthesis method of benzoic acid compounds, and the photocatalytic oxidation synthesis method comprises the following specific steps: mixing and dissolving toluene compounds and a catalyst in a solvent, reacting for 24-60h in the presence of an oxidant under the conditions of 350-460 nm LED illumination and a temperature of 20-80 DEG C, and performing post-treatment on the reaction liquid to obtain the benzoic acid compounds. The photocatalytic oxidation synthesis method has the advantages of no need of metal catalysts, simple operation and mild reaction conditions; oxygen is used as an oxidant, and the photocatalytic oxidation synthesis method has high atom economy, cheap reagent and environmental protection. The photocatalytic oxidationsynthesis method has good substrate applicability, and various substituents can realize the synthesis of corresponding benzoic acid compounds.
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Paragraph 0170; 0171; 0172; 0173

(2019/12/25)

Split-and-Combine Approach Towards Branched Precision Glycomacromolecules and Their Lectin Binding Behavior
Previously, monodisperse and sequence-controlled oligo(amidoamine) scaffolds were synthesized based on the step-wise assembly of tailor-made building blocks on a solid support that allow for the multivalent presentation of sugar ligands. Here, we extend on this concept using a split-and-combine approach to gain access to a small library of linear and branched glycomacromolecules. Azide side chains were introduced in the scaffold by the use of a novel building block allowing for copper-mediated azide-alkyne cycloaddition (CuAAC) of readily available propargyl-functionalized glycans. In the first stage, after assembly of the linear scaffold on solid support, the batch was divided into two. One part of the resin-bound oligomers was end-capped and further used as backbone and the other part was functionalized with propargylated α-d-mannopyranoside in the sidechain, end capped with an alkyne functionality and finally cleaved from solid support to give the branching arm. In the second stage, the linear, glycosylated and alkynylated arms were then coupled to the end capped backbone via CuAAC. In this way, branched glycomacromolecules with two and three branches, respectively, have been synthesized carrying from two to six sugar residues per molecule. Both, linear arms and branched glycomacromolecules were then subjected to a lectin binding assay using surface plasmon resonance (SPR) and model lectin Concanavalin A (Con A) showing the effect of branching as well as valency on the binding kinetics.
Baier, Mischa,Giesler, Markus,Hartmann, Laura
p. 1619 - 1630
(2018/01/11)

1. 3 - Benzoxazine - 2, 4 (3 H) - dione derivatives and their synthesis and use (by machine translation)
The invention relates to a acetylcholine esterase with phosphodiesterase V enzyme inhibition benzoxazine dione derivative and its synthetic method and use, and in particular relates to the structure of the general formula (I) of 1, 3 benzoxazine - 2, 4 (3 H) - dione derivatives, R1 , R2 , R3 , R4 , R5 , R6 , R7 , R8 And R9 The specification of the existing limited to. This invention refers to these compound structure and synthetic method and in vitro acetylcholine esterase with phosphodiesterase V inhibiting activity, can be further developed into new drugs for treating Alzheimer's disease. (by machine translation)
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Paragraph 0020; 0024; 0025

(2018/10/19)

[...] aromatic amines acetylcholine esterase inhibitor synthesis and use (by machine translation)
The present invention provides a formula for the (I) or (II) [...] aromatic amines of the acetylcholine esterase inhibitor and its pharmaceutically acceptable salt or a stereoisomer thereof, a process for their preparation and its in the preparation of acetylcholine esterase inhibitors and treatment of Alzheimer's disease and/or myasthenic application of the medicament, type definition of each group in the specification. The invention of aromatic amine derivatives as [...] of acetylcholine esterase inhibitors with micromolar level to nanomolar inhibiting activity, has further developed into an anti-Alzheimer's disease possibility of drug. (by machine translation)
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Paragraph 0046; 0047; 0048

(2018/10/19)

Tribromoisocyanuric acid as a green reagent for benzylic bromination of alkylarenes
The reaction of diverse alkylarenes with tribromoisocyanuric acid (0.34 mol equiv) in reflux EtOAc in the absence of any catalysts or light irradiation produced the corresponding benzyl bromides in 53-88% yield.
De Almeida, Leonardo S.,Esteves, Pierre M.,De Mattos, Marcio C.S.
p. 6843 - 6845
(2015/11/27)

Controlling the Spatial Organization of Liquid Crystalline Nanoparticles by Composition of the Organic Grafting Layer
Understanding how the spatial ordering of liquid crystalline nanoparticles can be controlled by different factors is of great importance in the further development of their photonic applications. In this paper, we report a new key parameter to control the mesogenic behavior of gold nanoparticles modified by rodlike thiols. An efficient method to control the spatial arrangement of hybrid nanoparticles in a condensed state is developed by changing the composition of the mesogenic grafting layer on the surface of the nanoparticles. The composition can be tuned by different conditions of the ligand exchange reaction. The thermal and optical behavior of the mesogenic and promesogenic ligands were investigated by using differential scanning calorimetry (DSC) and hot-stage polarized optical microscopy. The chemical structure of the synthesized hybrid nanoparticles was characterized by 1HNMR spectroscopy, thermogravimetric analysis (TGA), XPS, and elemental analysis, whereas the superstructures were examined by small-angle X-ray diffraction (SAXSRD) analysis. Structural studies showed that the organic sublayer made of mesogenic ligands is denser with an increasing the average ligand number, thereby separating the nanoparticles in the liquid crystalline phases, which changes the parameters of these phases. Softening nanocrystalline gold: An efficient method to control the spatial arrangement of liquid crystalline gold nanoparticles was developed by changing the composition of the mesogenic grafting layer. Structural studies showed that the organic sublayer is more dense with increasing average ligand number, thereby separating the nanoparticles in the liquid crystalline phases, which changes the parameters of these phases (see figure).
W?jcik, Micha? M.,Olesińska, Magdalena,Sawczyk, Micha?,Mieczkowski, J?zef,G?recka, Ewa
p. 10082 - 10088
(2015/07/07)

A novel series of indazole-/indole-based glucagon receptor antagonists
A novel, potent series of glucagon receptor antagonists (GRAs) was discovered. These indazole- and indole-based compounds were designed on an earlier pyrazole-based GRA lead MK-0893. Structure-activity relationship (SAR) studies were focused on the C3 and C6 positions of the indazole core, as well as the benzylic position on the N-1 of indazole. Multiple potent GRAs were identified with excellent in vitro profiles and good pharmacokinetics in rat. Among them, GRA 16d was found to be orally active in blunting glucagon induced glucose excursion in an acute glucagon challenge model in glucagon receptor humanized (hGCGR) mice at 1, 3 and 10 mg/kg (mpk), and significantly lowered acute glucose levels in hGCGR ob/ob mice at 3 mpk dose.
Lin, Songnian,Zhang, Fengqi,Jiang, Guoqiang,Qureshi, Sajjad A.,Yang, Xiaodong,Chicchi, Gary G.,Tota, Laurie,Bansal, Alka,Brady, Edward,Trujillo, Maria,Salituro, Gino,Miller, Corey,Tata, James R.,Zhang, Bei B.,Parmee, Emma R.
p. 4143 - 4147
(2015/11/03)

A responsive hyperbranched polymer not only can self-immolate but also can self-cross-link
Though many responsive polymers have been prepared, none of them can both self-immolate and self-cross-link via responding to the changes of the environment. Here, we introduce a new responsive hyperbranched polymer, which not only can self-immolate but also can self-cross-link via responding to the external stimuli. Moreover, the obtained polymer can form a bioreducible nanogel in its aqueous solution simply via heating, and the formed nanogel can self-immolate via UV irradiation.
Yu, Zhi-Qiang,Xu, Xiao-Man,Hong, Chun-Yan,Wu, De-Cheng,You, Ye-Zi
p. 4136 - 4143
(2014/07/22)

Nuclear versus side-chain bromination of 4-methoxy toluene by an electrochemical method
GRAPHICAL ABSTRACT The electrochemical bromination of 4-methoxy toluene by two-phase electrolysis yields 3-bromo 4-methoxy toluene at first, which subsequently undergoes side-chain bromination to give 3-bromo 4-methoxy benzyl bromide as a final product in 86% yield. The two-phase electrolysis consists of 25-50% NaBr as aqueous electrolyte and CHCl3 containing aromatic compound as organic phase. The reaction temperature is maintained at 10-25 °C. The probable orientation of bromine atom in an alkyl aromatic compound (nuclear versus side chain) is explained from the experimental result.
Kulangiappar,Anbukulandainathan,Raju
p. 2494 - 2502
(2014/08/05)

A 4 + 4 strategy for synthesis of zeolitic metal-organic frameworks: An indium-MOF with SOD topology as a light-harvesting antenna
A zeolitic metal-organic framework with a SOD topology, (Et 2NH2)[In(BCBAIP)]·4DEF·4EtOH (H 4BCBAIP: 5-(bis(4-carboxybenzyl)amino)isophthalic acid) (1), has been constructed by a 4 + 4 synthetic strategy from tetrahedral organic building units and In3+ ions. Compound 1 could adsorb organic dyes and be used as a light-harvesting antenna.
Sun, Libo,Xing, Hongzhu,Liang, Zhiqiang,Yu, Jihong,Xu, Ruren
supporting information
p. 11155 - 11157
(2013/11/19)

A PROCESS FOR THE PREPARATION OF HIGHLY PURE 4-(4-METHYL PIPERAZINOMETHYL) BENZOIC ACID DIHYDROCHLORIDE
This invention relates to the preparation of highly pure (>99%) 4-(4-methyl piperazinomethyl) benzoic acid dihydrochloride (I) from commercially available and inexpensive starting materials with enhanced yields. Thus title compound (I) is prepared by the reaction of 4-bromomethyl benzoic acid (II) with 1-methyl piperazine in potassium carbonate presence and in n-butanol medium at room temperature. This invention also provides process for the preparation of 4-bromomethyl benzoic acid (II)
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Page/Page column 6

(2013/03/26)

Luminescent 'On-Off' CdSe/ZnS quantum dot chemodosimeter for hydroxide based on photoinduced electron transfer from a carboxylate moiety
A CdSe-ZnS quantum dot (QD) has been surface functionalised by a place exchange reaction with p-mercaptomethyl benzoate synthesized by a three-step procedure. The resulting lumophore-spacer-receptor QD-conjugate was characterized by IR, UV-visible and fluorescence spectroscopy. The emission profile of the QD reveals a narrow emission peak centred at 542 nm. Addition of hydroxide to the solution containing the QD-conjugate results in quenching of the original fluorescence, which is attributed to a photoinduced electron transfer reaction from the electron-rich benzoate moiety to the QD valence band. This is the first reported example of fluorescent quenching of a CdSe-ZnS QD luminescence by an aryl carboxylate moiety.
Gauci, Lara A.,Kelland, Lindsay G.,Magri, David C.
p. 793 - 798
(2013/07/26)

Stabilized vesicles consisting of small amphiphiles for stepwise photorelease via UV light
A small amphiphile consisting of hydrophilic tetraethylene glycol monoacrylate and hydrophobic alkyl chain which were connected by an o-nitrobenzyl unit, a photolabile group, was designed and synthesized. The critical aggregate concentration of the synthesized amphiphile was determined to be about 3 × 10-5 M by the fluorescence probe technique. Nanosized vesicles were prepared and stabilized by in-situ radical polymerization without altering the morphology. The polymeric vesicle was highly stable which retained vesicular shape under dilution or UV irradiation. Hydrophobic guests can be encapsulated within the vesicle membrane and released out of the vesicle by UV stimulus through splitting the amphiphilic structure of the amphiphile. Distinguished dose-controlled photorelease of the polymeric vesicle is achieved due to the maintenance of the vesicular shape integrity which makes the guest release depend on the cleavage amount of amphiphilic structure during UV irradiation. This study provides a promising strategy to develop stable drug delivery systems for sustained and phototriggered release.
Dong, Jianming,Zeng, Yi,Xun, Zhiqing,Han, Yongbin,Chen, Jinping,Lee, Ying-Ying,Li, Yi
scheme or table
p. 1733 - 1737
(2012/06/15)

COMPOUNDS USEFUL AS INHIBITORS OF ATR KINASE
The present invention relates to pyrazine and pyridine compounds useful as inhibitors of ATR protein kinase. The invention also relates to pharmaceutically acceptable compositions comprising the compounds of this invention; methods of treating various diseases, disorders, and conditions using the compounds of this invention; processes for preparing the compounds of this invention; intermediates for the preparation of the compounds of this invention; and methods of using the compounds in in vitro applications, such as the study of kinases in biological and pathological phenomena; the study of intracellular signal transduction pathways mediated by such kinases; and the comparative evaluation of new kinase inhibitors. The compounds of this invention have formula I wherein the variables are as defined herein.
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Page/Page column 76

(2011/12/02)

Environmentally benign electrophilic and radical bromination 'on water': H2O2-HBr system versus N-bromosuccinimide
A H2O2-HBr system and N-bromosuccinimide in an aqueous medium were used as a 'green' approach to electrophilic and radical bromination. Several activated and less activated aromatic molecules, phenylsubstituted ketones and styrene were efficiently brominated 'on water' using both systems at ambient temperature and without an added metal or acid catalyst, whereas various non-activated toluenes were functionalized at the benzyl position in the presence of visible light as a radical activator. A comparison of reactivity and selectivity of both brominating systems reveals the H2O2-HBr system to be more reactive than NBS for benzyl bromination and for the bromination of ketones, while for electrophilic aromatic substitution of methoxy-substituted tetralone it was higher for NBS. Also, higher yields of brominated aromatics were observed when using H2O2-HBr 'on water'. Bromination of styrene reveals that not just the structure of the brominating reagent but the reaction conditions: amount of water, organic solvent, stirring rate and interface structure, play a key role in defining the outcome of bromination (dibromination vs bromohydroxylation). In addition, mild reaction conditions, a straightforward isolation procedure, inexpensive reagents and a lower environment impact make aqueous brominating methods a possible alternative to other reported brominating protocols.
Podgor?ek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej
experimental part
p. 4429 - 4439
(2009/10/09)

Benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines as novel Na+/H+ exchanger inhibitors, synthesis and protection against ischemic-reperfusion injury
A novel series of benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines were designed and synthesized as Na+/H+exchanger inhibitors. Most of them were found to inhibit NHE1-mediated platelet swelling in a concentration-dependent manner, and to have significant cardioprotective effect against myocardial ischemic-reperfusion injury, among which compounds 10a and 34 were more potent than cariporide in both in vivo and in vitro tests.
Zhang, Rui,Lei, Lin,Xu, Yun-Gen,Hua, Wei-Yi,Gong, Guo-Qing
p. 2430 - 2433
(2008/04/18)

PROCESS FOR THE PREPARATION OF THE ANTI-CANCER DRUG IMATINIB AND ITS ANALOGUES
The present invention discloses a process of the manufacture of imatinib of formula (Ia) and its new analogues I (b-d) through the intermediate of formula (II). The mesylate (methane sulfonate ) salt of imatinib base (Ia[(4-(4-methylpiperazin-1-ylmethyl)-N4 [methyl-3-(4-pyridin-3-yl)pyrimidn-2-yl amino)phenyl]benzamide])is a popular life -saving drug to treat chronic myelogenous leukemia (CML).
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Page 45-46

(2008/06/13)

The complex synergy of water in the metal/bromide autoxidation of hydrocarbons caused by benzylic bromide formation
One of the most active and selective catalysts in homogeneous liquid phase oxidation using molecular oxygen (O2) is a mixture of cobalt, manganese and bromide salts in acetic acid. It has been used to produce hundreds of different carboxylic acids in high yield and purity including the commercial production of terephthalic acid from p-xylene. Water is normally a by-product in these reactions and it is shown here that its concentration is an important reaction variable. In anhydrous acetic acid, with reagents with sufficiently strong electron-withdrawing substitutents (toluene, 4-carboxytoluene, 4-chlorotoluene), all of the active bromide becomes inactive via benzylic bromide formation. The Co/Mn/ Br catalyst is therefore converted to a Co/Mn catalyst which is dubbed 'catalyst failure' because of its undesirable characteristics of lower activity, decreased selectivity especially towards over-oxidation and color formation. For 4-chlorotoluene, increasing the water concentration to 5 weight % initially decreases the rate of reaction but eventually is more active and selective because the oxidation and hydrolysis of the benzylic bromide allows for sufficient active catalytic bromide. It is shown that benzylic bromides do not 'promote' the reaction and that both oxidation and solvolysis of the benzylic bromide occurs during autoxidation. During polymethylbenzene oxidation, benzylic bromide formation occurs only with the most reactive methyl group. The complex factors during metal/bromide autoxidation -some favored by increased water concentration and others detrimental - are outlined.
Partenheimer, Walt
p. 297 - 306
(2007/10/03)

HETEROAROMATIC GLUCOKINASE ACTIVATORS
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(2008/06/13)

Parallel synthesis of glycomimetic libraries: targeting a C-type lectin.
We have developed methods for the parallel synthesis of two libraries of non-carbohydrate-based analogues of mannose on a solid support. The natural product shikimic acid was used as a key building block. The ability of the compounds to block the binding of the C-type lectin MBP-A to a mannosylated surface was assessed in a high-throughput assay. Ten library members with inhibitory activities equivalent to that of alpha-methyl mannopyranoside were identified. [reaction: see text]
Schuster, Michael C,Mann, David A,Buchholz, Tonia J,Johnson, Kathryn M,Thomas, William D,Kiessling, Laura L
p. 1407 - 1410
(2007/10/03)

Heteroaromatic glucokinase activators
2,3-Di-substituted N-heteroaromatic propionamides with said substitution at the 2-position being a substituted phenyl group and at the 3-position being a cycloalkyl ring, said propionamides being glucokinase activators which increase insulin secretion in the treatment of type II diabetes.
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(2008/06/13)

Synthesis of peptide-N-alkylamides on a new PS-TTEGDA polymer support using photolabile anchoring group
Peptide-N-alkylamides were synthesised on a new highly solvating copolymer of 4% tetraethyleneglycol diacrylate-cross-linked polystyrene (PS- TTEGDA) support. The polymer was synthesised by suspension polymerisation using a free radical initiator. The synthesis of C-terminal peptide-N- alkylamide involve prior incorporation of a photolabile linker, 3-nitro-4- bromo-methylbenzoic acid to the aminomethylated support. The N-alkylamino group act as an anchoring group for the peptide as well as a latent function for the C-terminal modification of the attached peptide. Irradiation of the peptide-resin with 350 nm light in TFE/DCM resulted in the release of peptide-N-alkylamides. Synthetic utility of the new support was demonstrated by the synthesis of Boc-amino acid-N-alkylamides and C-terminal peptide-N- alkyl amides in 75-80% yields and with high purity.
Kumar,Pillai, V. N. Rajasekharan
p. 10437 - 10446
(2007/10/03)

Generation of an Ugi library of phosphate mimic-containing compounds and identification of novel dual specific phosphatase inhibitors
The four-component Ugi reaction was utilized to prepare a library of dipeptidic compounds in order to explore the binding requirements of the key cell cycle phosphatase, Cdc25. Several phosphate surrogates were incorporated into the Ugi product to mimic either the mono- or bis-phosphorylated substrate.
Bergnes, Gustave,Gilliam, Carla L.,Boisclair, Michael D.,Blanchard, Jill L.,Blake, Katharine V.,Epstein, David M.,Pal, Kollol
p. 2849 - 2854
(2007/10/03)

Catalytic processes of oxidation by hydrogen peroxide in the presence of Br2 or HBr. Mechanism and synthetic applications
The mechanism and the synthetic applications for the oxidation of alcohols, ethers, and aldehydes by H2O2 catalyzed by Bf2 or Br- in a liquid two-phase system (aqueous and organic) are reported. Aliphatic and benzylic primary alcohols and ethers show an opposite behavior, which has been rationalized on the ground of the different electronic configurations of the intermediate alkyl (π-type) and acyl (σ-type) radicals and their influence on enthalpic and polar effects. A two-phase system is particularly useful also for an efficient benzylic bromination by Br2 or Br-; the substitution of the benzyl bromide by OH, OR, and OCOR regenerates Br-, which can be recycled. The evaluation of the relative reactivities of the involved substrates and intermediates has allowed to develop a variety of simple, facile, convenient, and selective syntheses of alcohols, aldehydes, ketones, esters, and benzyl bromides, which fulfill the conditions for practical applications.
Amati, Alessandro,Dosualdo, Gabriele,Zhao, Lihua,Bravo, Anna,Fontana, Francesca,Minisci, Francesco,Bjorsvik, Hans-Rene
p. 261 - 269
(2013/09/08)

An Alternative Method for the Selective Bromination of Alkylbenzenes Using NaBrO3/NaHSO3 Reagent
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Kikuchi, Daisuke,Sakaguchi, Satoshi,Ishii, Yasutaka
p. 6023 - 6026
(2007/10/03)

Carboxylate compounds, liquid crystal materials liquid crystal compositions and liquid crystal elements
There is provided a carboxylic acid compound represented by the following formulae (I) to (IV): STR1 a liquid crystal material consisting of the carboxylic acid ester compound, a liquid crystal composition comprising the carboxylic acid ester compound, and a liquid crystal element using the carboxylic acid ester compound. There can be obtained advantages such as low operating temperature, high speed switching, very small electric power consumption, and high-stable contrast.
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(2008/06/13)

Synthesis and peptide binding properties of a C2 symmetric macrobicycle
A novel macrobicycle featuring an amidopyridine unit as a carboxylic acid binding site, and amide functionality to provide further hydrogen bonding interactions with suitable guests has been prepared. The ability of this novel macrobicycle to bind peptide derivatives has been investigated.
Waymark, Christopher P.
p. 3051 - 3054
(2007/10/02)

Synthesis and biological evaluation of some new phosphonates
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Garuti,Ferranti,Ronerti,Katz,Budriesi,Chiarini
p. 295 - 297
(2007/10/02)

Selective hydrogenolysis of bis(hydroxymethyl)aromatic compounds
Selective hydrogenolysis of symmetric bis(hydroxymethyl)aromatic compounds has been performed over Raney nickel in alkaline solution for 24-36 h at 20°C. The yield of the corresponding monohydrogenolysis product was in the range of 75-96%. The usefulness of the reaction was demonstrated by the synthesis of 4-(bromomethyl)benzoic acid.
Behrens,Egholm,Buchardt
p. 1235 - 1236
(2007/10/02)

Carboxylic acid ester compounds, and their related matters and method of producing the same
This invention relates to carboxylic acid ester compounds or liquid crystal compounds represented by the following formula [A], liquid crystal compositions and liquid crystal elements using these compounds, the method of producing said liquid crystal elements, and other uses. STR1 wherein R represents one radical selected from the group consisting of an alkyl group having 6-18 carbon atoms, an alkoxy group having 6-18 carbon atoms, and a halogenated alkyl group having 6-18 carbon atoms, X represents --CF3 or --CH2 --CH3, m is an integral number of 1-10 when X is --CF3, and an integral number of 2-10 when X is --CH2 --CH3, and C* represents an asymmetric carbon atom.
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(2008/06/13)

Novel substitued naphthalene compounds and liquid crystal compositions containing same
In accordance with the present invention, there is provided substituted naphthalene compounds represented by the following formula [I]. STR1 wherein R1 represents alkyl of 1-18 carbon atoms, R2 represents alkyl of 1-18 carbon atoms, X is a group represented by --OCH2 -- or --CH2 CH2 --, and n is 0 or 1. In accordance with the invention, moreover, there is provided liquid crystal compositions containing the substituted naphthalene compounds represented by the above-mentioned formula [I].
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(2008/06/13)

OXIDATION BY THE SALTS OF METALS. IV. OXIDATIVE HALOGENATION OF TOLUENE AND PARA-SUBSTITUTED TOLUENES WITH ELECTRON-WITHDRAWING GROUPS PROMOTED BY CERIUM(IV) SALTS IN AQEOUS SOLUTIONS OF TRIFLUOROACETIC ACID
The oxidation of toluene and para-substituted toluenes with electron-withdrawing groups (para-toluic acid, methyl para-toluate, and para-nitrotoluene) by ammonium cerium(IV) nitrate and ammonium cerium(IV) sulfate was investigated in aqueous solutions of trifluoroacetic acid in the presence of alkali-metal chlorides and bromides.The rate and selectivity of oxidative halogenation in the side chain and/or aromatic ring under the investigated conditions depends strongly both on the nature of the substrate and the halide ion and on the reaction conditions and the ligand environment of the cerium(IV) atom.The oxidation of nitrotoluene takes place only in the presence of the bromide-containing systems and leads to the production of 4-nitrobenzyl bromide.For the other substrates halogenation in the aromatic ring can be realized with yields close to quantitative with ammonium cerium(IV) nitrate as oxidizing agent in concentrated aqueous solutions of trifluoroacetic acid (10 vol.percent of water).It was shown that the halogenating agents in this case are mainly the products from oxidation of the halide ions by the nitronium ions formed in the strongly acidic medium from the nitrate ions contained in the ammonium cerium(IV) nitrate.Bromination of the substituted toluenes in the presence of ammonium cerium(IV) sulfate and in the ammonium cerium(IV) nitrate-alkali-metal bromide systems with more than 10 vol.percent of water takes mainly in the side chain and can be used as a method for the production of 4-substituted benzyl halides with preparative yields.The effect of the composition of the solvent and the ratio of the oxidizing agent and alkali-metal halide on the rate and selectivity of oxidative bromination was studied.Possible reaction mechanisms are discussed.
Makhon'kov, D.I.,Cheprakov, A.V.,Rodkin, M.A.,Mil'chenko, A.Yu.,Beletskaya, I.P.
p. 24 - 32
(2007/10/02)

A Three-Dimensional Orthogonal Protection Scheme for Solid-Phase Peptide Synthesis under Mild Conditions
Several Nα-dithiasuccinoyl (Dts) amino acids (1) were esterified, by use of N,N'-dicyclohexylcarbodiimide (DCC) and without racemization, to tert-butyl 4-(hydroxymethyl)-3-nitrobenzoate (8).The resultant handle derivatives 4 were treated with trifluoroacetic acid to yield crystalline 4-(Nα-Dts-aminoacyloxymethyl)-3-nitrobenzoic acids (3), which were quantitatively incorporated onto aminomethylcopoly(styrene-1percent divinylbenzene)-resins by DCC-mediated couplings to give the starting point for stepwise solid-phase synthesis of peptides anchored as o-nitrobenzyl (ONb) esters.Assembly of the protected leucine-enkephalin-resin derivative Dts-Tyr(t-Bu)-Gly-Gly-Phe-Leu-ONb-resin (2) was achieved from the appropiate Dts-amino acids by a highly efficient protocol.By carrying out, in each conceivable order, either in solution or on the solid phase, one two, or all three of the following orthogonal treatments , the common resin-bound intermediate 2 became the source of four partially or fully deblocked leucine-enkephalin derivatives.These four, namely Dts-Tyr(t-Bu)-Gly-Gly-Phe-Leu-OH, Dts-Tyr-Gly-Gly-Phe-Leu-OH, H-Tyr(t-Bu)-Gly-Gly-Phe-Leu-OH, and H-Tyr-Gly-Gly-Phe-Leu-OH, were each obtained pure in good yields and were characterized by amino acid composition, HPLC, 300-MHz 1H NMR, and fast atom bombardment mass spectrometry.The protected dipeptidyl sequence Prot-D-Val-L-Pro-ONb-resin was assembled with three different Nα-amino protecting groups and exposed to the recommended deblocking reagents.Loss of chains from the resin by diketopiperazine formation was very rapid with Prot=9-fluorenylmethoxycarbonyl (Fmoc) and also substantial with Prot=tert-butoxycarbonyl (Boc), but rather negligible wit h Prot=Dts.Thus, these experiments demonstrate the feasibility and benefits of a mild three-dimensional orthogonal protection scheme based on Dts for Nα-amino protection, tert-butyl derivatives for side chains, and o-nitrobenzyl esters for anchoring.
Barany, George,Albericio, Fernando
p. 4936 - 4942
(2007/10/02)

The easy preparation of many benzylic bromides using molecular bromine as a halogenating in the presence of catalytic amounts of lanthanum tri-acetate
Many benzylic brominations were easily achieved by molecular bromine in CCl4 in presence of 1 percent of La (OAc)3 and a standard room lighting lamp.The selectivity is excellent except for certain electron-rich systems (p-methylaniline, p-cresol).
Ouertani, Mohsen,Girard, Pierre,Kagan, Henry B.
p. 327 - 328
(2007/10/02)

Antibacterial agents, and 4-thio azetidinone intermediates
This invention relates to 2-substituted and 2,6-disubstituted penem compounds of the formula STR1 wherein Y is hydrogen, halo or certain organic substituents and X represents certain organic substituents. Also included in the invention are pharmaceutically acceptable salts of the above compounds and derivatives of the above compounds in which the carboxyl group at the 3-position is protected as by an easily removable ester protecting group. The compounds of the present invention are potent antibacterial agents or are of use as intermediates in the preparation of such agents.
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(2008/06/13)

Oxidation by the salts of metals. I. Anaerobic oxidation of p-toluic acid by the salts of transition metals in trifluoroacetic acid in the presence of alkali-metal halides
The oxidation of p-toluic acid by the salts of metals with variable valence was investigated in trifluoroacetic acid and its aqueous solutions in the presence of alkali-metal halides (chlorides or bromides).The reaction leads to the formation of the products from oxidative halogenation in the aromatic ring and/or the side chain.The rate and direction of the reaction depend both on the nature of the oxidizing agent and the halide ion and on the ratio of the components in the p-toluic acid-Hlg--CF3CO2H-H2O system.Preferential halogenation in the ring is observed for Ce(IV) and Pb(IV) in the presence of sodium bromide and for all the oxidizing agents in the presence of potassium chloride.In the case of Co(III) and Mn(III) bromination in the presence of Br- takes place mainly in the side chain and is greatly accelerated by additions of water.Conditions were found for the production of 3-chloro- and 3-bromo-p-toluic acid and 4-carboxybenzyl bromide with preparative yields.
Beletskaya, I. P.,Dem'yanov, P. I.,Makhon'kov, D. I.,Zel'dis, I. M.,Burenko, S. N.
p. 583 - 591
(2007/10/02)

Oxidation by the salts of metals. II. Anaerobic oxidation of 4-methylbenzoic acid by Co(III) acetate in the presence of sodium bromide in aqueous trifluoroacetic acid. Production of 4-hydroxymethylbenzoic acid
The oxidation of 4-methylbenzoic acid by Co(III) acetate was investigated in aqueous solutions of trifluoroacetic acid in the presence of sodium bromide.The conditions were found for the production of 4-bromomethylbenzoic acid for the purpose of further h
Beletskaya, I. P.,Dem'yanov, P. I.,Makhon'kov, D. I.,Zel'dis, I. M.
p. 591 - 594
(2007/10/02)

Peptide Synthesis. Part 2. Procedures for Solid-phase Synthesis using Nα-fluorenylmethoxycarbonylamino-acids on Polyamide Supports. Synthesis of Substance P and of Acyl Carrier Protein 65-74 Decapeptide
Use of base-labile Nα-9-fluorenylmethoxycarbonylamino-acids in combination with acid-labile t-butyl or p-alkoxybenzyl side-chain or carboxy-terminal (resin-linkage) protecting groups enables solid-phase peptide synthesis to be carried out under exceptionally mild reaction conditions.The repetitive and vigorous acidic treatments required in conventional synthesis are avoided.High-yield syntheses of a decapeptide and of an undecapeptide amide (Substance P) are described using this new combination of protecting groups on polyamide supports.
Atherton, Eric,Logan, Christopher J.,Sheppard, Robert C.
p. 538 - 546
(2007/10/02)

Preparation of a new o-nitrobenzyl resin for solid-phase synthesis of tert-butyloxycarbonyl-protected peptide acids.
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Rich,Gurwara
p. 1575 - 1579,1577, 1578
(2007/10/06)