cas 22446-37-3, (2-HYDROXY-PHENYL)-ACETIC ACID METHYL ESTER

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Levine,Eble,Fischbach
p. 1930
(1948)
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Regioselective Synthesis of Benzofuranones and Benzofurans
Reaction of 3-hydroxy-2-pyrones with nitroalkenes bearing ester groups gives benzofuranones. The reaction allows regioselective preparation of the benzofuranones with programmable substitution at any position. Complex substitution patterns are readily cre
Zhang, Xiaojie,Beaudry, Christopher M.
p. 6931 - 6936
(2021)
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Design and Synthesis of a Series of l-trans-4-Substituted Prolines as Selective Antagonists for the Ionotropic Glutamate Receptors Including Functional and X-ray Crystallographic Studies of New Subtype Selective Kainic Acid Receptor Subtype 1 (GluK1) Antagonist (2S,4R)-4-(2-Carboxyphenoxy)pyrrolidine-2-carboxylic Acid
Ionotropic glutamate receptor antagonists are valuable tool compounds for studies of neurological pathways in the central nervous system. On the basis of rational ligand design, a new class of selective antagonists, represented by (2S,4R)-4-(2-carboxyphenoxy)pyrrolidine-2-carboxylic acid (1b), for cloned homomeric kainic acid receptors subtype 1 (GluK1) was attained (Ki = 4 μM). In a functional assay, 1b displayed full antagonist activity with IC50 = 6 ± 2 μM. A crystal structure was obtained of 1b when bound in the ligand binding domain of GluK1. A domain opening of 13-14° was seen compared to the structure with glutamate, consistent with 1b being an antagonist. A structure-activity relationship study showed that the chemical nature of the tethering atom (C, O, or S) linking the pyrrolidine ring and the phenyl ring plays a key role in the receptor selectivity profile and that substituents on the phenyl ring are well accommodated by the GluK1 receptor.
Krogsgaard-Larsen, Niels,Delgar, Claudia G.,Koch, Karina,Brown, Patricia M. G. E.,M?ller, Charlotte,Han, Liwei,Huynh, Tri H. V.,Hansen, Stinne W.,Nielsen, Birgitte,Bowie, Derek,Pickering, Darryl S.,Kastrup, Jette Sandholm,Frydenvang, Karla,Bunch, Lennart
p. 441 - 457
(2017)
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Copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazoacetates and pyridines: Access to polycyclic indolizines
A copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazo compounds with pyridines, which affords polycyclic fused indolizines in synthetically useful to good yields under mild reaction conditions, has been reported. This method features the use of an inexpensive copper catalyst and readily available starting materials, broad substrate generality, and operational simplicity. Notably, a variety of natural product derivatives are compatible under the current conditions, which shows significant potential of this method for the selective decoration and modification of analogous biomolecules or pharmaceuticals.
Dong, Shanliang,Hu, Wenhao,Huang, Jingjing,Qiu, Lihua,Sha, Hongkai,Xu, Xinfang
p. 1926 - 1932
(2020)
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Structure-Based Design and Preclinical Characterization of Selective and Orally Bioavailable Factor XIa Inhibitors: Demonstrating the Power of an Integrated S1 Protease Family Approach
The serine protease factor XI (FXI) is a prominent drug target as it holds promise to deliver efficacious anticoagulation without an enhanced risk of major bleeds. Several efforts have been described targeting the active form of the enzyme, FXIa. Herein, we disclose our efforts to identify potent, selective, and orally bioavailable inhibitors of FXIa. Compound 1, identified from a diverse library of internal serine protease inhibitors, was originally designed as a complement factor D inhibitor and exhibited submicromolar FXIa activity and an encouraging absorption, distribution, metabolism, and excretion (ADME) profile while being devoid of a peptidomimetic architecture. Optimization of interactions in the S1, S1β, and S1′ pockets of FXIa through a combination of structure-based drug design and traditional medicinal chemistry led to the discovery of compound 23 with subnanomolar potency on FXIa, enhanced selectivity over other coagulation proteases, and a preclinical pharmacokinetics (PK) profile consistent with bid dosing in patients.
Lorthiois, Edwige,Roache, James,Barnes-Seeman, David,Altmann, Eva,Hassiepen, Ulrich,Turner, Gordon,Duvadie, Rohit,Hornak, Viktor,Karki, Rajeshri G.,Schiering, Nikolaus,Weihofen, Wilhelm A.,Perruccio, Francesca,Calhoun, Amy,Fazal, Tanzina,Dedic, Darija,Durand, Corinne,Dussauge, Solene,Fettis, Kamal,Tritsch, Fabien,Dentel, Celine,Druet, Adelaide,Liu, Donglei,Kirman, Louise,Lachal, Julie,Namoto, Kenji,Bevan, Douglas,Mo, Rose,Monnet, Gabriela,Muller, Lionel,Zessis, Richard,Huang, Xueming,Lindsley, Loren,Currie, Treeve,Chiu, Yu-Hsin,Fridrich, Cary,Delgado, Peter,Wang, Shuangxi,Hollis-Symynkywicz, Micah,Berghausen, Joerg,Williams, Eric,Liu, Hong,Liang, Guiqing,Kim, Hyungchul,Hoffmann, Peter,Hein, Andreas,Ramage, Paul,D'arcy, Allan,Harlfinger, Stefanie,Renatus, Martin,Ruedisser, Simon,Feldman, David,Elliott, Jason,Sedrani, Richard,Maibaum, Juergen,Adams, Christopher M.
p. 8088 - 8113
(2020)
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Preparation method of carboxylic ester compound
The invention relates to a preparation method of a carboxylic ester compound, which comprises the following steps: reacting carboxylic acid with methanol in air under the catalysis of nitrite to obtain an ester compound, the preparation method disclosed by the invention has the advantages of rich raw material sources, cheap and easily available catalyst, mild reaction conditions, simplicity and convenience in operation and the like, a series of fatty carboxylic acids can be modified with high yield, and particularly, the traditional esterification method is generally not suitable for esterification of drug molecules. By utilizing the method, a series of known drug molecules can be modified, so that a shortcut is provided for discovering new drug molecules.
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Paragraph 0051-0052

(2021/03/30)

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite
In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.
Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao
supporting information
p. 2713 - 2718
(2021/06/25)

New compound used as rearranged during transfection kinase inhibitor
The present invention relates to a compound, a pharmaceutical composition containing the compound, a preparation method of the compounds, and application of the same as a rearranged during transfection (RET) kinase inhibitor. The compound is a compound shown as formula (I), or a pharmaceutically acceptable salt, a prodrug, a solvent compound, a polymorph, an isomer and a stable isotope derivativethereof. The present invention also relates to the application of the compounds to treatment or prevention of RET kinase mediated related diseases like tumors and a method of using the compounds for the treatment of the diseases.
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Paragraph 0176; 0177

(2021/03/05)

Electrochemical Cross-Dehydrogenative Coupling between Phenols and β-Dicarbonyl Compounds: Facile Construction of Benzofurans
Preparative electrochemical synthesis is an ideal method for establishing green, sustainable processes. The major benefits of an electro-organic strategy over that of conventional chemical synthesis are the avoidance of reagent waste and mild reaction conditions. Here, an intermolecular cross-dehydrogenative coupling between phenols and β-dicarbonyl compounds has been developed to build various benzofurans under undivided electrolytic conditions. Neither transition metals nor external chemical oxidants are required to facilitate the dehydrogenation and dehydration processes. The key factor in success was the use of nBu4NBF4 as the electrolyte and hexafluoroisopropanol as the solvent, which play key roles in the cyclocondensation step. This electrolysis is scalable and can be used as a key step in drug synthesis. On the basis of several experimental results, the mechanism, particularly of the remarkable anodic oxidation and cyclization process, was illustrated.
Ding, Mengning,Shi, Zhuangzhi,Tian, Bailin,Wang, Yandong
(2020/03/23)

Insights into Ruthenium(II/IV)-Catalyzed Distal C?H Oxygenation by Weak Coordination
C?H hydroxylation of aryl acetamides and alkyl phenylacetyl esters was accomplished via challenging distal weak O-coordination by versatile ruthenium(II/IV) catalysis. The ruthenium(II)-catalyzed C?H oxygenation of aryl acetamides proceeded through C?H ac
Bu, Qingqing,Kuniyil, Rositha,Shen, Zhigao,Gońka, El?bieta,Ackermann, Lutz
supporting information
p. 16450 - 16454
(2020/11/02)

Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones
A novel metal-free synthesis of 3,3-disubstituted benzofuran-2-(3H)-ones through reacting α-aryl-α-diazoacetates with triarylboranes is presented. Initially, triarylboranes were successfully investigated in α-arylations of α-diazoacetates, however in the presence of a heteroatom in the ortho position, the boron enolate intermediate undergoes an intramolecular rearrangement to form a quaternary center. The intermediate cyclizes to afford valuable 3,3-disubstituted benzofuranones in good yields.
Santi, Micol,Ould, Darren M. C.,Wenz, Jan,Soltani, Yashar,Melen, Rebecca L.,Wirth, Thomas
supporting information
p. 7861 - 7865
(2019/04/25)

TRI-SUBSTITUTED ARYL AND HETEROARYL DERIVATIVES AS MODULATORS OF PI3-KINASE AND AUTOPHAGY PATHWAYS
The present disclosure relates to tri-substituted aryl and heteroaryl derivatives, pharmaceutical compositions containing them, and methods of using them, including methods for modulating autophagy or preventing, reversing, slowing or inhibiting the PI3K-AKT-MTOR pathway, and methods of treating diseases that are associated with autophagy or the PI3K-AKT-MTOR pathway.
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Paragraph 0286; 0287

(2019/11/04)

CARBON MONOXIDE-RELEASING MOLECULES AND THERAPEUTIC APPLICATIONS THEREOF
Carbon monoxide-releasing organic molecules are described herein. The molecules can be synthesized prior to administration (e.g., ex vivo) or formed in vivo. In those embodiments where the molecules are formed in vivo, reactants are administered under physiological conditions and undergo a cycloaddition reaction to form a product which releases carbon monoxide. In applying such reactions for therapeutic applications in vivo, the cycloaddition and CO release typically occur only under near-physiological or physiological conditions. For example, in some embodiments, the cycloaddition reaction and/or release of carbon monoxide occur at a temperature of about 37° C and pH of about 7.4. Pharmaceutical compositions and methods for release carbon monoxide are also described.
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Paragraph 0313; 0314

(2018/06/06)

For the preparation of 2 - (2 - hydroxy-phenyl) acetic acid alkyl esters
The invention relates to a method for preparing 2-(2-hydroxylphenyl)alkyl acetate represented as the general formula II. The R is a C1-10 alkyl group in a linear chain or with branched chain. The invention relates to the one-pot method for utilizing (2-halogenated phenyl)acetic acid or (2-halogenated phenyl) acetonitrile to prepare 2-(2-hydroxylphenyl)alkyl acetate. Since a middle part (2-hydroxylphenyl) acetic acid is prevented from being separated, the one-pot method is higher in efficiency.
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Paragraph 0046-0053

(2018/12/13)

Preparation method of o-hydroxyphenylacetic acid methyl ester
The invention discloses a preparation method of o-hydroxyphenylacetic acid methyl ester, comprising the following steps: Step S1, adding a solid catalyst into o-hydroxyphenylacetic acid, carrying out heating reflux, letting o-hydroxyphenylacetic acid be dehydrated so as to generate benzofuranone; Step S2, carrying out transesterification by adding methanol into the reaction system in the Step S1 so as to generate o-hydroxyphenylacetic acid methyl ester; and Step S3, filtering to remove the catalyst for repeated use, concentrating a solution, and cooling for crystallization so as to obtain o-hydroxyphenylacetic acid methyl ester. The method provided by the invention is easy to operate and has high conversion rate. After separated, the solid catalyst can be repeatedly used. In addition, catalytic efficiency is not obviously reduced after repeated use of the catalyst.
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Paragraph 0019; 0020; 0023; 0024; 0027; 0028; 0031; 0032

(2017/03/08)

SUBSTITUTED AROMATIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF OSTEOPOROSIS
The present invention concerns the use of compounds for preventing and/or treating osteoporosis, for stimulating bone formation, for stimulating bone remodeling, for stimulating the differentiation and mineralization of osteoblasts, for inhibiting bone resorption and for modulating serum level of adiponectin in a subject. These uses have been found for compounds represented by Formula I and pharmaceutically acceptable salts thereof. wherein A is C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(O)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R1 is H, F or OH; R2 is H, F, OH, C6 alkyl, C5 alkenyl, C6 alkenyl, C(O)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R3 is H, F, OH or CH2Ph; R4 is H, F, or OH; Q is 1) (CH2)mC(O)OH wherein m is 1 or 2, 2) CH(F)-C(O)OH, 3) CF2-C(O)OH or 4) C(O)-C(O)OH.
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Paragraph 00121

(2016/05/02)

SUBSTITUTED AROMATIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR TISSUE SELF-REPAIR AND REGENERATION
Described herein are compounds of Formula I, or pharmaceutically acceptable salts thereof, or combinations thereof, as well as uses thereof. Such uses include promoting tissue self-repair or tissue regeneration of an organ, stimulating the generation of tissue growth, modulating (e.g. increasing) the level of a tissue-repair marker, treating physical injury in an organ, tissue, or cell, promoting wound healing as well as anti-aging applications. Corresponding compositions, methods and uses are also described. Formula I wherein A is C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(0)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R1 is H, F of OH; R2 is H, F, OH, C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(0)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R3 is H, F, OH, or CH2Ph; R4 is H, F or OH; Q is 1) (CH2),C(0)OH wherein m is 1 or 2 2) CH(CH3)C(0)OH, 3) C(CH3)2C(0)OH, 4) CH(F)-C(0)OH, 5) CF2-C(0)OH or 6) C(0)-C(0)OH.
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Paragraph 00115

(2016/06/13)

PYRANOCHROMENYLPHENOL DERIVATIVES AND PHARMACEUTICAL COMPOSITION FOR TREATING METABOLIC SYNDROME OR INFLAMMATORY DISEASE
Provided is a compound of the following Formula (I), a pharmaceutically acceptable salt thereof, or a solvate thereof. Further, provided is a pharmaceutical composition for preventing or treating a metabolic syndrome or an inflammatory disease, including the same. in the formula, R1 is a hydrogen atom, methyl, methoxy, or a halogen atom; R2 is a hydrogen atom; a substituted or unsubstituted straight or branched C1-C6 alkyl group; a halogen atom; a substituted or unsubstituted straight or branched C1-C6 alkoxy group; or a substituted or unsubstituted straight or branched C1-C4 thioalkyl group; R3 and R4 are each independently a hydrogen atom, or a C1-C2 alkyl group; and in the case of the substituted alkyl, the substituted alkoxy, and the substituted thioalkyl, the substituent is a straight or branched C1-C5 alkyl group, a halogen atom, a straight or branched C1-C5 alkoxy group, or a straight or branched C1-C3 thioalkyl group.
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Paragraph 0066

(2016/11/28)

PYRANOCHROMENYL PHENOL DERIVATIVE, AND PHARMACEUTICAL COMPOSITION FOR TREATING METABOLIC SYNDROME OR INFLAMMATORY DISEASE
Provided are a pyranochromenyl phenol derivative, a pharmaceutically acceptable salt thereof, or a solvate thereof. Also provided is a pharmaceutical composition for preventing or treating metabolic syndrome or inflammatory disease comprising same. The present invention is efficacious in preventing or treating metabolic syndrome or inflammatory disease and is chemically stable.
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Paragraph 0096-0097

(2016/10/11)

NOVEL COMPOUNDS FOR THE TREATMENT OF CANCER AND INFLAMMATORY DISEASES
The present invention relates to novel compounds and pharmaceutical compositions thereof which may be useful in the treatment and/or prevention of various conditions. The present invention also provides methods of preparing such compounds and compositions, and methods of using the same.
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Paragraph 0193-0195

(2015/07/16)

CARBON MONOXIDE-RELEASING MOLECULES FOR THERAPEUTIC APPLICATIONS AND METHODS OF MAKING AND USING THEREOF
Carbon monoxide-releasing organic molecules are described herein. The molecules can be synthesized prior to administration (e.g., ex vivo) or formed in vivo. In those embodiments where the molecules are formed in vivo, reactants are administered under physiological conditions and undergo a cycloaddition reaction to form a product which releases carbon monoxide. In applying such reactions for therapeutic applications in vivo, the cycloaddition and CO release typically occur only under near-physiological or physiological conditions. For example, in some embodiments, the cycloaddition reaction and/or release of carbon monoxide occur at a temperature of about 37C and pH of about 7.4. Pharmaceutical compositions and methods for release carbon monoxide are also described.
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Paragraph 0290

(2016/01/01)

Measuring method for measuring and using a kit or flagment autoantibody autoantibody or fragments thereof, and their azoxystrobin deriv., azoxystrobin
PROBLEM TO BE SOLVED: To provide a method for measuring the levels of an azoxystrobin as a fungicide left in samples such as of farm products or processed products. SOLUTION: An antibody specific to azoxystrobin is obtained by using a composite, as an immunogen, of an azoxystrobin derivative and a polymeric compound. The method for assaying azoxystrobin using such an antibody is provided. An assay kit therefor is prepared. COPYRIGHT: (C)2011,JPOandINPIT
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Paragraph 0068

(2016/10/20)

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF
The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.
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Page/Page column 10

(2014/10/15)

Enantioselective access to benzannulated spiroketals using a chiral sulfoxide auxiliary
This article describes our efforts to develop an asymmetric synthesis of bisbenzannulated spiroketals using a chiral sulfoxide auxiliary. Our primary focus was on the synthesis of the 3H-spiro[benzofuran-2,2′-chroman] ring system, the spirocyclic core of the rubromycin family. Our strategy employed the use of lithium-halogen exchange on a racemic bromospiroketal in order to attach a chiral sulfoxide, thus producing two diastereomers. The diastereomers were separable, enabling isolation of each spiroketal enantiomer. Subsequent cleavage of the sulfoxide group from each diastereomer yielded the respective parent spiroketal in high enantiopurity.
Aitken, Harry R. M.,Furkert, Daniel P.,Hubert, Jonathan G.,Wood, James M.,Brimble, Margaret A.
p. 5147 - 5155
(2013/08/15)

Insights into soluble guanylyl cyclase activation derived from improved heme-mimetics
Recently, the structure of BAY 58-2667 bound to the Nostoc sp. H-NOX domain was published. On the basis of this structural information, we designed BAY 58-2667 derivatives and tested their effects on soluble guanylyl cyclase (sGC) activity. Derivative 20 activated sGC 4.8-fold more than BAY 58-2667. Co-crystallization of 20 with the Ns H-NOX domain revealed that the increased conformational distortion at the C-terminal region of αF helix containing 110-114 residues contributes to the higher activation triggered by 20.
Von Wantoch Rekowski, Margarete,Kumar, Vijay,Zhou, Zongmin,Moschner, Johann,Marazioti, Antonia,Bantzi, Marina,Spyroulias, Georgios A.,Van Den Akker, Focco,Giannis, Athanassios,Papapetropoulos, Andreas
supporting information
p. 8948 - 8952
(2013/12/04)

New chalcone dimers from Caesalpinia ferrea Mart act as potent inhibitors of DNA topoisomerase II
New chalcone dimers, pauferrol B (2), and pauferrol C (3), were isolated from the stems of Caesalpinia ferrea Mart, and their structures were determined on the basis of 2D NMR spectroscopy. These new chalcone dimers showed potent inhibitory activities against human topoisomerase II and cell proliferation via the induction of apoptosis in human leukemia HL 60 cells. Absolute configurations of 2 and 3 were estimated by the comparison of CD spectra with a dihydrobenzofuran derivative 4, which was enantioselectively synthesized from 2-hydroxyphenyl acetic acid.
Ohira, Susumu,Takaya, Kyouhei,Mitsui, Taichi,Kido, Masahiro,Kakumoto, Kazuyuki,Hayashi, Ken-Ichiro,Kuboki, Atsuhito,Tani, Hiroyuki,Ikeda, Shogo,Iinuma, Munekazu,Akao, Yukihiro,Nozaki, Hiroshi
p. 5052 - 5055
(2013/09/02)

Aerobic oxidative heck/dehydrogenation reactions of cyclohexenones: Efficient access to meta-substituted phenols
Jockeying for the (meta)position: A new dicationic palladium(II) catalyst, employing a 6,6′-dimethyl-2,2′-bipyridine ligand, promotes both the aerobic oxidative Heck coupling and dehydrogenation reactions of cyclohexenones. These reactions may be combined in a one-pot sequence to enable the straightforward synthesis of meta-substituted phenols (see scheme). Copyright
Izawa, Yusuke,Zheng, Changwu,Stahl, Shannon S.
supporting information
p. 3672 - 3675
(2013/04/23)

Controlled anion migrations with a mixed metal Li/K-TMP amide: General application to benzylic metalations
A general method is described for benzylic metalation of o-, m-, and p-substituted toluenes using a mixed metal amide base generated from BuLi/KOtBu/TMP at -78 °C in THF. The excellent selectivity achieved can be rationalized by the ability of the mixed metal amide base to facilitate an anion migration from the kinetic (o-aryl) to the benzylic metalation site. Remarkably, this controlled anion migration is achievable with catalytic amounts of TMP at -78 °C.
Fleming, Patricia,Oshea, Donal F.
supporting information; experimental part
p. 1698 - 1701
(2011/04/17)

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL
This invention relates to compounds having structural Formula I: and pharmaceutically acceptable salts thereof which are inhibitors of the Renal Outer Medullary Potassium (ROMK) channel (Kir1.1). The compounds of Formula I are useful as diuretics and natriuretics and therefore are useful for the therapy and prophylaxis of disorders resulting from excessive salt and water retention, including cardiovascular diseases such as hypertension and chronic and acute heart failure
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Page/Page column 134

(2010/11/18)

Synthesis, characterization and structure-activity relationship analysis of novel depsides as potential antibacterials
Twenty-six depsides were synthesized to screen for their antibacterial activity. All of them were reported for the first time. Their chemical structures were clearly determined by 1H NMR, 13C NMR, ESI mass spectra and elemental analyses, coupled with one selected single-crystal structure. All the compounds were assayed for antibacterial activities against three Gram-positive bacterial strains (Bacillus subtilis ATCC 6633, Staphylococcus aureus ATCC 6538 and Streptococcus faecalis ATCC 9790) and three Gram-negative bacterial strains (Escherichia coli ATCC 35218, Pseudomonas aeruginosa ATCC 13525 and Enterobacter cloacae ATCC 13047) by MTT method. Compound 2-(2-methoxy-2-oxoethyl)phenyl 3-nitrobenzoate (C10) and 2-(2-ethoxy-2-oxoethyl)phenyl 3-nitrobenzoate (C23) showed powerful antibacterial activities against B. subtilis with MIC of 0.78 μg/mL while compound 2-(2-methoxy-2-oxoethyl)phenyl 2-(3,4-diethoxyphenyl)acetate (C8) and 2-(2-ethoxy-2-oxoethyl)phenyl 2-(3,4-diethoxyphenyl)acetate (C21) exhibited significant antibacterial activities against E. coli with MIC of 1.562 μg/mL, which were superior to the positive controls penicillin G and kanamycin B, respectively. On the basis of the biological results, structure-activity relationships were discussed.
Lv, Peng-Cheng,Xiao, Zhu-Ping,Fang, Rui-Qin,Li, Huan-Qiu,Zhu, Hai-Liang,Liu, Chang-Hong
experimental part
p. 1779 - 1787
(2009/05/26)

Synthesis and crystal structure of a depside derivative 2-(2-Methoxy-2-oxoethyl)phenyl 2-(3,4-Dimethoxyphenyl)acetate
A depside derivative, 2-(2-methoxy-2-oxoethyl)phenyl 2-(3,4- dimethoxyphenyl)acetate (3), was synthesized through a facile approach in high yields. Its structure was confirmed by 1H NMR, 13C NMR, ESI mass spectra, elemental analyses and X-ray single crystal diffraction study. Crystal structure analysis revealed that compound 3 crystallized in the monoclinic, space group P21/c with the following unit cell parameters: a = 10.173(2) A, b = 10.459(2) A, c = 16.516(3) A, α = 90°, β = 102.30(3)°, γ = 90°, V = 1717.0(6) A3, Z = 4.
Lv, Peng-Cheng,Wang, Kai-Rui,Mao, Wen-Jun,Fang, Rui-Qin,Chen, Jin,Xiong, Jing,Zhu, Hai-Liang
experimental part
p. 927 - 930
(2010/06/19)

1-HETEROCYCLYL-1,5-DIHYDRO-PYRAZOLO[3,4-D] PYRIMIDIN-4-ONE DERIVATIVES AND THEIR USE AS PDE9A MODULATORS
The invention relates to novel 1,6-disubstituted pyrazolopyrimidinones, Formula (I) with Hc is a mono-, bi- or tricyclic heterocyclyl group, the ring members of which are carbon atoms and at least 1, preferably 1, 2 or 3, heteroatom(s), which are selected from the group of nitrogen, oxygen and sulphur, which is in the form of -S(O)r - with r being 0, 1 or 2, and - said heterocyclyl group is or comprises 1 non-aromatic, saturated, or partly unsaturated monocyclic ring which comprises at least 1 heteroatom as ring member and - said heterocyclyl group is bound to the scaffold by said 1 non- aromatic, saturated, or partly unsaturated monocyclic ring which comprises at least 1 heteroatom as ring member. According to one aspect of the invention the new compounds are for the manufacture of medicaments, in particular medicaments for the treatment of conditions concerning deficits in perception, concentration, learning or memory. The new compounds are also for the manufacture of medicaments for the treatment of Alzheimer's disease.
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Page/Page column 167-168

(2009/10/30)

Diazonamide support studies: Stereoselective formation of the C10 chiral center in both the CDEFG and AEFG fragments
(Chemical Equation Presented) The synthesis of both the AEFG macrolactam and the CDEFG bis-indole/tyrosine units found in the marine natural product diazonamide A is presented. Key to the success of the synthesis is the highly stereoselective direct C-arylation of an oxindole by an aryllead(IV) reagent derived from tyrosine.
Lin, Jinzhen,Gerstenberger, Brian S.,Stessman, Nhu Y. T.,Konopelski, Joseph P.
supporting information; experimental part
p. 3969 - 3972
(2009/05/30)

NOVEL COMPOUNDS AS AGONIST FOR PPAR GAMMA AND PPAR ALPHA, METHOD FOR PREPARATION OF THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
The present invention relates to novel compounds accelerating the activity of Peroxisome proliferator-activated receptor gamma (PPARγ) and alpha (PPARα), processes of preparing the same, and pharmaceutical compositions containing the same as an active agent.
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Page/Page column 171

(2010/11/27)

Esterification-nitration of ortho-hydroxyphenyl carboxylic acids and benzole acids with cerium(IV) ammonium nitrate (CAN)
A convenient and useful esterification was realized, and this reaction proceeded without a dehydrating reagent or water removal equipment. A series of ortho -hydroxyphenyl carboxylic acids and benzoic acids were transformed to their corresponding methyl esters under CAN/CH3OH reaction conditions. Whereas in an aprotic solvent, acetonitrile, sp3-C tethered ortho-hydroxyphenyl carboxylic acids undergo simultaneous o,p-dinitration and intramolecular esterification reactions in good yields. Also, 2-((1E)-2-nitrovinyl)-4-nitro-phenol (3e) showed selective cytotoxicities to ward MCF-7, HEP G2, and HEP 3B cell lines with IQovalues of 23.50, 7.33, and7.59ug/mL,respectively.
Pan, Wen-Bin,Wei, Li-Mei,Wei, Li-Lan,Wu, Chin-Chung,Wu, Yang-Chang
p. 173 - 180
(2007/10/03)

tert-buyldiphenylsilylethyl ("TBDPSE"): A practical protecting group for phenols
(Chemical Equation Presented) A new protection group for phenols, the 2-(tert-butyldiphenylsilyl)ethyl (TBDPSE) group, has been prepared and investigated. Protection of a variety of substituted phenols proceeds in good to excellent yield. The group is stable to mild acid, base, hydrogenolysis conditions, and lithium/ halogen exchange on the protected phenol. Removal is achieved with strong acid or standard fluoride treatment.
Gerstenberger, Brian S.,Konopelski, Joseph P.
p. 1467 - 1470
(2007/10/03)

1,2-AZOLE DERIVATIVES WITH HYPOGLYCEMIC AND HYPOLIPIDEMIC ACTIVITY
A compound represented by the formula (1) wherein ring A is a ring optionally having 1 to 3 substituents; ring B is a 1,2-azole ring which may further have 1 to 3 substituents; Xa, Xb and Xc are the same or different and each is a bond, - O -, - S - and the like; Ya is a divalent aliphatic hydrocarbon residue having 1 to 20 carbon atoms; Yb and Yc are the same or different and each is a bond or a divalent aliphatic hydrocarbon residue having 1 to 20 carbon atoms; ring C is a monocyclic aromatic ring which may further have 1 to 3 substituents; and R represents -OR4 (R4 is hydrogen atom or optionally substituted hydrocarbon group) and the like, or a salt thereof or a prodrug thereof is useful as an agent for the prophylaxis or treatment of diabetes and the like.
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Page 247

(2010/02/05)

Facile Intramolecular O→C Ester Migration in Benzylphosphonium Salts
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Nussbaumer, Peter,Bilban, Melitta
p. 7660 - 7662
(2007/10/03)

COMPOUNDS, COMPOSITIONS AND METHODS FOR INHIBITING THE BINDING OF PROTEINS CONTAINING AN SH2 DOMAIN TO COGNATE PHOSPHORYLATED PROTEINS
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(2008/06/13)

The palladium-catalyzed asymmetric α-allylations of carbonyl compounds with chiral allyl esters via enamines and imines
A novel and excellent method for asymmetric α-allylation of carbonyl compounds via their chiral enamines or imines bearing allyl esters has been developed. Readily available chiral allyl esters having chirality at the α- position of the ester carbonyl group, such as (S)-proline and other (S)-α- amino acid allyl esters, have been found to serve as good asymmetric allylating reagents in palladium-catalyzed reactions of the chiral enamines and imines derived from them. The use of (S)-proline or (S)-valine allyl esters as the amino parts in the enamines or imines provided the highest optical yields of the corresponding α-allyl carbonyl compounds. A mechanism for asymmetric induction is proposed based on the stereochemical results obtained.
Hiroi,Abe,Suya,Sato,Koyama
p. 203 - 213
(2007/10/02)

Fungicides
Compounds of formula: STR1 and stereoisomers thereof, wherein X, Y and Z, which are the same or different, are hydrogen, halogen, hydroxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aralkyl, optionally substituted arylalkoxy, optionally substituted aryloxyalkyl, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, cyano, --CO2 R1, --CONR2 R3, or --COR4 ; or X and Y, when they are in adjacent positions of the phenyl ring, join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; W is a C-linked optionally substituted five membered heterocylic ring, containing one to four hetero-atoms, which are the same or different, and which are nitrogen, sulphur or oxygen and wherein adjacent substituents may together form a fused aromatic or hetero-aromatic ring; A is an oxygen or sulphur atom; and R1, R2, R3 and R4, which are the same or different, are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, optionally substituted aryl or optionally substituted aralkyl; and metal complexes thereof. The compounds are useful as fungicides and also insecticides.
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(2008/06/13)

ARYL THIOPYRANO[2,3,4-C,D]INDOLES AS INHIBITORS OF LEUKOTRIENE BIOSYNTHESIS
Compounds having the formula I: are inhibitors of 5-lipoxygenase and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cyto-protective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, psoriasis, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.
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(2008/06/13)

A convenient and mild procedure for the preparation of hydroxyesters from lactones and hydroxyacids
An alcoholic solution of lactones and hydroxyacids stored on Amberlyst-15 results in the formation of corresponding hydroxyesters in high yields.
Anand,Selvapalam
p. 2743 - 2747
(2007/10/02)

Certain 2-pyridyl oxy-phenyl acrylates having fungicidal, insecticidal, nematocidal and plant growth regulating activity
This invention relates to derivatives of acrylic acid useful in agriculture (especially as fungicides but also as plant growth regulators, insecticides and nematocides), to processes for preparing them, to agricultural (especially fungicidal) compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants, to regulate plant growth and to kill or control insect or nematode pests. The invention provides a compound having the formula (I): STR1 and stereoisomers thereof, wherein W is a substituted pyridinyl or substituted pyrimidinyl group linked to A by any of its ring carbon atoms; A is either an oxygen atom or S(O)n wherein n is 0, 1 or 2; X, Y and Z, which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl (including haloalkyl), optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, (including haloalkoxy), optionally substituted alkylthio, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, nitro, cyano, --CO2 R3, --CONR4 R5, --COR6 or --S(O)m R7 (wherein m is 0, 1 or 2) groups, or any two of the groups X, Y and Z, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; R1 and R2, which are the same or different, are optionally substituted alkyl (including fluoroalkyl) groups provided that when W is 5-trifluoromethylpyridin-2-yl, A is oxygen, X is hydrogen, and R1 and R2 are both methyl, Y and Z are not both hydrogen, Y is not F, Cl, methyl, nitro, 5--CF3, 5--SCH3 or 4--(CH3)2 N if Z is hydrogen and Y and Z together are not 3-nitro-5-chloro, 3,5-dinitro, 4,5-dimethoxy or 4,5-methylenedioxy; and R3, R4, R5, R6 and R7, which are the same or different, are hydrogen atoms or optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted aralkyl groups; and metal complexes thereof.
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(2008/06/13)

Fe(III)-Catalyzed Aromatic Hydroxylation with H2O2 in the Presence of a Variety of Electron-Transfer Agents
Electron-transfer agents such as N,N,N',N'-tetramethylphenylenediamine (TMPD), ferrocenes, and phenothiazines have been found to mediate the hydroxylation of benzene with H2O2 in the presence of Fe3+.Of these, TMPD catalyst is the most effective to provide phenol in 80percent or better yield based on added H2O2 under the optimized conditions.A general mechanism, involving the rate-determining reduction of Fe3+ to Fe2+ with such mediators, is suggested.
Tamagaki, Seizo,Sasaki, Masaaki,Tagaki, Waichiro
p. 153 - 158
(2007/10/02)

Fungicides
This invention relates to derivatives of acrylic acid of the formula: STR1 useful as fungicides, to processes for preparing them, to fungicidal compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants. The values of the variables are provided herein.
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(2008/06/13)

Novel arylacetic acid derivatives
A compound having a potentially inhibitory effect on 15-hydroxy-prostaglandin dehydrognase (PGDH) and having the formula STR1 in which R1 and R2 are hydrogen or lower alkyl; R3 is hydrogen, lower alkyl or substituted or unsubstituted phenyl; R4, R5, and R6 are hydrogen, halogen, lower alkyl, lower alkoxy, cyano, carboxy or nitro; at least one of the groups R4 to R6 being hydrogen; R7 to R11 are hydrogen, halogen, cyano, lower alkyl, trifluoromethyl, lower alkoxy, hydroxy, lower acyl, lower alkoxycarbonyl, N,N,-diloweralkyl-aminocarbonyl or N,N-loweralkylene-aminocarbonyl; and R8 and R10 may in addition be carboxy; at least two of R7 to R11 always being hydrogen; and --A-- is --CO--, --CH2 --CO--, --CH=CH--, --CH=CH--CO-- or corresponding groups in which a hydrogen atom is replaced by a lower alkyl group. The invention comprises also lactones of those compounds in which R1 is hydrogen, and salts of those compounds which contain at least one carboxy group.
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(2008/06/13)

Esters of thiadiazole oxypropanolaine derivatives and pharmaceutical uses
Novel compounds of the general formula STR1 wherein R1 is lower alkyl, lower cycloalkyl, lower alkenyl, lower alkynyl, lower alkyl carboxymethyl, aryl carboxymethyl, aryl, or aralkyl; A is a direct bond, lower alkylene, or lower alkenylene; x is 1 or 2, provided that when x is greater than 1, different occurrences of the STR2 group may be the same or different; Ar is heterocyclic, unsubstituted aromatic or aromatic substituted with lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, halogen, acetamido, amino, nitro, lower alkylamino, hydroxy, lower hydroxyalkyl or cyano; W is alkylene containing from 1 to about 10 carbon atoms; and B is --NR2 COR3, --NR2 CONR3 R4, --NR2 SO2 R3, --NR2 SO2 NR3 R4, or --NR2 COOR5, wherein R2, R3, R4 and R5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R3 and R5 are not hydrogen when B is --NR2 SO2 R3 or --NR2 COOR5, or R3 and R4 may together with N form a 5 to 7 membered heterocyclic group; and the pharmaceutically acceptable salts thereof.
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(2008/06/13)

Aromatization of arene 1,2-oxides. 1,2-Oxides of methyl phenylacetate and methyl trans-cinnamate
Substituent migration is observed only to a minor extent during aromatization of the 1,2-oxide of methyl phenylacetate to methyl (o-hydroxyphenyl)acetate; the major aromatization pathway does not involve substituent migration. Substituent migration is not observed during aromatization of the 1,2-oxide of methyl trans-cinnamate to methyl o-coumarate.
Chao, Herbert S.-I.,Berchtold, Glenn A.
p. 1191 - 1194
(2007/10/02)

Photochemistry of Methoxy-substituted Quinoline and Isoquinoline N-Oxides
The photochemistry of quinoline 1-oxides and isoquinoline 2-oxides bearing a methoxy-group in the pyridine ring was investigated in protic and aprotic media.The formation of various photoisomers, viz. 3,1-benzoxazepines, 2(1H)-quinolones, N-(2-isocyanobenzyl)formamides, 4(1H)-quinolones, and 3-hydroxyquinolines from the different methoxyquinoline 1-oxides, and 1,3-benzoxazepines and 1(2H)-isoquinolones from the different methoxyisoquinoline 2-oxides, was observed along with deoxygenation and formation of products derived from hydration and decomposition of the primary products.The position of the methoxy-group has an important directing effect on the photoreactions.
Albini, Angelo,Fasani, Elisa,Dacrema, Lucia Maggi
p. 2738 - 2742
(2007/10/02)