cas 6303-58-8, 4-Phenoxybutanoic acid | Articles data

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Benzoxepine-5-ketone compound as well as preparation method and application thereof
The invention relates to a benzoxazepine-5-ketone compound as well as a preparation method and application thereof. The benzoxazepine-5-ketone compound has a structure as shown in a formula (I) defined in the description. The benzoxazepine-5-ketone compound can block the excessive generation of pro-inflammatory factors in the brain, and provides a feasible alternative treatment strategy for treating AIS.
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(2021/03/30)

Synthesis and Target Identification of Benzoxepane Derivatives as Potential Anti-Neuroinflammatory Agents for Ischemic Stroke
Benzoxepane derivatives were designed and synthesized, and one hit compound emerged as being effective in vitro with low toxicity. In vivo, this hit compound ameliorated both sickness behavior through anti-inflammation in LPS-induced neuroinflammatory mice model and cerebral ischemic injury through anti-neuroinflammation in rats subjected to transient middle cerebral artery occlusion. Target fishing for the hit compound using photoaffinity probes led to identification of PKM2 as the target protein responsible for anti-inflammatory effect of the hit compound. Furthermore, the hit exhibited an anti-neuroinflammatory effect in vitro and in vivo by inhibiting PKM2-mediated glycolysis and NLRP3 activation, indicating PKM2 as a novel target for neuroinflammation and its related brain disorders. This hit compound has a better safety profile compared to shikonin, a reported PKM2 inhibitor, identifying it as a lead compound in targeting PKM2 for the treatment of inflammation-related diseases.
Gao, Cheng-Long,Hou, Gui-Ge,Liu, Jin,Ru, Tong,Xu, Ya-Zhou,Zhao, Shun-Yi,Ye, Hui,Zhang, Lu-Yong,Chen, Kai-Xian,Guo, Yue-Wei,Pang, Tao,Li, Xu-Wen
supporting information
p. 2429 - 2439
(2020/01/03)

Exploration of New Biomass-Derived Solvents: Application to Carboxylation Reactions
A range of hitherto unexplored biomass-derived chemicals have been evaluated as new sustainable solvents for a large variety of CO2-based carboxylation reactions. Known biomass-derived solvents (biosolvents) are also included in the study and the results are compared with commonly used solvents for the reactions. Biosolvents can be efficiently applied in a variety of carboxylation reactions, such as Cu-catalyzed carboxylation of organoboranes and organoboronates, metal-catalyzed hydrocarboxylation, borocarboxylation, and other related reactions. For many of these reactions, the use of biosolvents provides comparable or better yields than the commonly used solvents. The best biosolvents identified are the so far unexplored candidates isosorbide dimethyl ether, acetaldehyde diethyl acetal, rose oxide, and eucalyptol, alongside the known biosolvent 2-methyltetrahydrofuran. This strategy was used for the synthesis of the commercial drugs Fenoprofen and Flurbiprofen.
Gevorgyan, Ashot,Hopmann, Kathrin H.,Bayer, Annette
p. 2080 - 2088
(2020/02/20)

Chemoselective and Site-Selective Lysine-Directed Lysine Modification Enables Single-Site Labeling of Native Proteins
The necessity for precision labeling of proteins emerged during the efforts to understand and regulate their structure and function. It demands selective attachment of tags such as affinity probes, fluorophores, and potent cytotoxins. Here, we report a method that enables single-site labeling of a high-frequency Lys residue in the native proteins. At first, the enabling reagent forms stabilized imines with multiple solvent-accessible Lys residues chemoselectively. These linchpins create the opportunity to regulate the position of a second Lys-selective electrophile connected by a spacer. Consequently, it enables the irreversible single-site labeling of a Lys residue independent of its place in the reactivity order. The user-friendly protocol involves a series of steps to deconvolute and address chemoselectivity, site-selectivity, and modularity. Also, it delivers ordered immobilization and analytically pure probe-tagged proteins. Besides, the methodology provides access to antibody-drug conjugate (ADC), which exhibits highly selective anti-proliferative activity towards HER-2 expressing SKBR-3 breast cancer cells.
Adusumalli, Srinivasa Rao,Kalra, Neetu,Purushottam, Landa,Rai, Vishal,Rawale, Dattatraya Gautam,Reddy, Neelesh C.,Shukla, Sanjeev,Thakur, Kalyani
p. 10332 - 10336
(2020/04/27)

Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect
An intermolecular, two-component vicinal carboimination of alkenes has been accomplished by energy transfer catalysis. Oxime esters of alkyl carboxylic acids were used as bifunctional reagents to generate both alkyl and iminyl radicals. Subsequently, addition of the alkyl radical to an alkene generates a transient radical for selective radical–radical cross-coupling with the persistent iminyl radical. Furthermore, this process provides direct access to aliphatic primary amines and α-amino acids by simple hydrolysis.
Bellotti, Peter,Glorius, Frank,Patra, Tuhin,Strieth-Kalthoff, Felix
supporting information
p. 3172 - 3177
(2020/02/05)

PROCESS FOR THE DIRECT CONVERSION OF ALKENES TO CARBOXYLIC ACIDS
Process for the direct conversion of alkenes to carboxylic acids.
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Paragraph 0029-0032

(2019/07/10)

Probing the Effects of Heterocyclic Functionality in [(Benzene)Ru(TsDPENR)Cl] Catalysts for Asymmetric Transfer Hydrogenation
A range of TsDPEN catalysts containing heterocyclic groups on the amine nitrogen atom were prepared and evaluated in the asymmetric transfer hydrogenation of ketones. Bidentate and tridentate ligands demonstrated a mutual exclusivity directly related to their function as catalysts. A broad series of ketones were reduced with these new catalysts, permitting the ready identification of an optimal catalyst for each substrate and revealing the subtle effects that changes to nearby donor groups can exhibit.
Barrios-Rivera, Jonathan,Xu, Yingjian,Wills, Martin
supporting information
p. 7223 - 7227
(2019/10/08)

Silver(I)-Catalyzed Widely Applicable Aerobic 1,2-Diol Oxidative Cleavage
The oxidative cleavage of 1,2-diols is a fundamental organic transformation. The stoichiometric oxidants that are still predominantly used for such oxidative cleavage, such as H5IO6, Pb(OAc)4, and KMnO4, generate stoichiometric hazardous waste. Herein, we describe a widely applicable and highly selective silver(I)-catalyzed oxidative cleavage of 1,2-diols that consumes atmospheric oxygen as the sole oxidant, thus serving as a potentially greener alternative to the classical transformations.
Zhou, Zhong-Zhen,Liu, Mingxin,Lv, Leiyang,Li, Chao-Jun
p. 2616 - 2620
(2018/02/13)

Single-Site Labeling of Native Proteins Enabled by a Chemoselective and Site-Selective Chemical Technology
Chemical biology research often requires precise covalent attachment of labels to the native proteins. Such methods are sought after to probe, design, and regulate the properties of proteins. At present, this demand is largely unmet due to the lack of empowering chemical technology. Here, we report a chemical platform that enables site-selective labeling of native proteins. Initially, a reversible intermolecular reaction places the "chemical linchpins" globally on all the accessible Lys residues. These linchpins have the capability to drive site-selective covalent labeling of proteins. The linchpin detaches within physiological conditions and capacitates the late-stage installation of various tags. The chemical platform is modular, and the reagent design regulates the site of modification. The linchpin is a multitasking group and facilitates purification of the labeled protein eliminating the requirement of additional chromatography tag. The methodology allows the labeling of a single protein in a mixture of proteins. The precise modification of an accessible residue in protein ensures that their structure remains unaltered. The enzymatic activity of myoglobin, cytochrome C, aldolase, and lysozyme C remains conserved after labeling. Also, the cellular uptake of modified insulin and its downstream signaling process remain unperturbed. The linchpin directed modification (LDM) provides a convenient route for the conjugation of a fluorophore and drug to a Fab and monoclonal antibody. It delivers trastuzumab-doxorubicin and trastuzumab-emtansine conjugates with selective antiproliferative activity toward Her-2 positive SKBR-3 breast cancer cells.
Adusumalli, Srinivasa Rao,Rawale, Dattatraya Gautam,Singh, Usha,Tripathi, Prabhanshu,Paul, Rajesh,Kalra, Neetu,Mishra, Ram Kumar,Shukla, Sanjeev,Rai, Vishal
p. 15114 - 15123
(2018/11/10)

Aldehydes can switch the chemoselectivity of electrophiles in protein labeling
We show that the chemoselectivity of an electrophile in protein labeling can be promiscuous. An aldehyde enables switching of chemoselectivity of an epoxide and a sulfonate ester along with an enhanced rate of reaction. The chemical technology renders single-site installation of diverse probes on a protein and delivers analytically pure tagged proteins.
Adusumalli, Srinivasa Rao,Rawale, Dattatraya Gautam,Rai, Vishal
p. 9377 - 9381
(2019/01/03)

NOVEL NITROGEN-CONTAINING COMPOUND OR SALT THEREOF, OR METAL COMPLEX THEREOF
The present invention provides a compound represented by the formula (1) or a salt thereof, or a complex of the compound or the salt with a metal, in the formula (1), A1 represents a chelate group; R1 represents a hydrogen atom or the like; R2 represents a hydrogen atom or the like; and Z1, Z2, Z3, Z4, and Z5 are the same or different and each represent a nitrogen atom or CR3 or the like wherein R3 represents a hydrogen atom or an optionally substituted C1-6 alkyl group or the like; L1 represents a group represented by the formula (3) wherein R13, R14, R15, and R16 are the same or different and each represent a hydrogen atom or the like; L2 represents an optionally substituted C1-6 alkylene group; and L3 represents an optionally substituted C1-6 alkylene group.
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(2016/08/17)

Catalytic Access to Alkyl Bromides, Chlorides and Iodides via Visible Light-Promoted Decarboxylative Halogenation
Herein is reported the catalytic, visible light-promoted, decarboxylative halogenation (bromination, chlorination, and iodination) of aliphatic carboxylic acids. This operationally-simple reaction tolerates a range of functional groups, proceeds at room temperature, and is redox neutral. By employing an iridium photocatalyst in concert with a halogen atom source, the use of stoichiometric metals such as silver, mercury, thallium, and lead can be circumvented. This reaction grants access to valuable synthetic building blocks from the large pool of cheap, readily available carboxylic acids.
Candish, Lisa,Standley, Eric A.,Gómez-Suárez, Adrián,Mukherjee, Satobhisha,Glorius, Frank
p. 9971 - 9974
(2016/07/19)

TREATMENT AGENT FOR DIAGNOSIS OR TREATMENT OF DISEASE ASSOCIATED WITH INTEGRIN
PROBLEM TO BE SOLVED: To provide a treatment agent for diagnosis or treatment of disease associated with integrin. SOLUTION: A treatment agent comprises a complex of a compound represented by formula (1) or salt thereof and metal. In the formula (1), A1 is a chelate group; R1 and R2 independently represent H, alkyl, or an amino protective group; Z1-Z5 independently represent N or CR3; R3 is H or a substituted/unsubstituted C1-6 alkyl group or the like; L1 is a group represented by formula (3); L2 and L3 independently represent a substituted/unsubstituted C1-6 alkylene group. In the formula (3), R13-R16 independently represent H, alkyl or the like. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0455-0457

(2018/10/03)

Discovery of Lu AA33810: A highly selective and potent NPY5 antagonist with in vivo efficacy in a model of mood disorder
The structure-activity relationship of a series of tricyclic-sulfonamide compounds 11-32 culminating in the discovery of N-[trans-4-(4,5-dihydro-3,6- dithia-1-aza-benzo[e]azulen-2-ylamino)-cyclohexylmethyl]-methanesulfonamide (15, Lu AA33810) is reported. Compound 15 was identified as a selective and high affinity NPY5 antagonist with good oral bioavailability in mice (42%) and rats (92%). Dose dependent inhibition of feeding was observed after i.c.v. injection of the selective NPY5 agonist ([cPP1-7,NPY19-23,Ala 31,Aib32,Gln34]-hPP). In addition, ip administration of Lu AA33810 (10 mg/kg) produced antidepressant-like effects in a rat model of chronic mild stress.
Packiarajan, Mathivanan,Marzabadi, Mohammad R.,Desai, Mahesh,Lu, Yalei,Noble, Stewart A.,Wong, Wai C.,Jubian, Vrej,Chandrasena, Gamini,Wolinsky, Toni D.,Zhong, Hualing,Walker, Mary W.,Wiborg, Ove.,Andersen, Kim
scheme or table
p. 5436 - 5441
(2011/10/12)

Electron-transfer-induced reductive cleavage of chlorinated aryloxyalkanoic acids
We investigated the degradation of chlorinated herbicides, with an aryloxyalkanoic acid skeleton, under reductive electron transfer reaction conditions. Although Li and Na metals proved useless, activated forms of these metals, either their soluble naphthalene radical anions or 1,2-diarylethane dianions, promoted the degradation of the starting materials to various extents. Indeed, lithium naphthalenide promoted both extensive dehalogenation and dealkylation of chlorinated aryloxyalkanoic acids, with formation of the corresponding phenols as the main reaction products. In contrast, the employment of 1,2-diphenyl-1,2-disodioethane as a reducing agent led, in most examples, to the chemoselective recovery of the corresponding dechlorinated acids.
Azzena, Ugo,Pittalis, Mario
experimental part
p. 3360 - 3362
(2011/06/11)

BENZOPYRAN AND BENZOXEPIN PI3K INHIBITOR COMPOUNDS AND METHODS OF USE
Benzopyran and benzoxepin compounds of Formulas I and II, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including p110 alpha and other isoforms of PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formulas I and II for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.
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Page/Page column 177

(2009/10/06)

FATTY ACID AMIDE HYDROLASE INHIBITORS
Disclosed are compounds of formula R-X-Y that may be used to inhibit the action of fatty acid amide hydrolase (FAAH). Inhibition of fatty acid amide hydrolase (FAAH) will slow the normal degradation and inactivation of endogenous cannabinoid ligands by FAAH hydrolysis and allow higher levels of those endogenous cannabinergic ligands to remain present. These higher levels of endocannabinoid ligands provide increased stimulation of the cannabinoid CBl and CB2 receptors and produce physiological effects related to the activation of the cannabinoid receptors. They will also enhance the effects of other exogenous cannabinergic ligands and allow them to produce their effects at lower concentrations as compared to systems in which fatty acid amide hydrolase (FAAH) action is hot inhibited. Thus, a compound that inhibits the inactivation of endogenous cannabinoid ligands by fatty acid amide hydrolase (FAAH) may increase the levels of endocannabinoids and, thus, enhance the activation of cannabinoid receptors. Thus, the compound may not directly modulate the cannabinoid receptors but has the effect of indirectly stimulating the cannabinoid receptors by increasing the levels of endocannabinoid ligands. It may also enhance the effects and duration of action of other exogenous cannabinergic ligands that are administered in order to elicit a cannabinergic response.
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Page/Page column 44-45

(2008/06/13)

Synthesis, biological evaluation, structural-activity relationship, and docking study for a series of benzoxepin-derived estrogen receptor modulators
The estrogen receptors ERα and ERβ are recognized as important pharmaceutical targets for a variety of diseases including osteoporosis and breast cancer. A series of novel benzoxepin-derived compounds are described as potent selective modulators of the human estrogen receptor modulators (SERMs). We report the antiproliferative effects of these compounds on human MCF-7 breast tumor cells. These heterocyclic compounds contain the triarylethylene arrangement as exemplified by tamoxifen, conformationally restrained through the incorporation of the benzoxepin ring system. The compounds demonstrate potency at nanomolar concentrations in antiproliferative assays against an MCF-7 human breast cancer cell line with low cytotoxicity together with low nanomolar binding affinity for the estrogen receptor. The compounds also demonstrate potent antiestrogenic properties in the human uterine Ishikawa cell line. The effect of a number of functional group substitutions on the ER binding properties of the benzoxepin molecular scaffold is examined through a detailed docking and 2D-QSAR computational investigation. The best QSAR model developed for ERαβ selectivity yielded R2 of 0.84 with an RMSE for the training set of 0.30. The predictive quality of the model was Q2 of 0.72 and RMSE of 0.18 for the test set. One particular compound (26b) bearing a 4-fluoro substituent, exhibits 15-fold selectivity for ERβ and both our docking and QSAR studies converge on the correlation between enhanced lipophilicity and enhanced ERβ binding for this benzoxepin ring scaffold.
Barrett, Irene,Meegan, Mary J.,Hughes, Rosario B.,Carr, Miriam,Knox, Andrew J.S.,Artemenko, Natalia,Golfis, Georgia,Zisterer, Daniela M.,Lloyd, David G.
scheme or table
p. 9554 - 9573
(2009/04/06)

AMINO ALCOHOL DERIVATIVE OR PHOSPHONIC ACID DERIVATIVE AND MEDICINAL COMPOSITION CONTAINING THESE
The present invention relates to amino alcohol derivatives or phosphonic acid derivatives having excellent immunosuppressive activity, pharmacologically acceptable salts thereof or pharmacologically acceptable esters thereof, and to pharmaceutical compositions comprising said compounds as an active ingredient: [wherein, ???R1 and R2 each represent a hydrogen atom, or a protecting group of the amino group; ???R3 represents a hydrogen atom, or a protecting group of the hydroxyl group; ???R4 represents a lower alkyl group; ???n represents an integer of from 1 to 6; ???X represents an oxygen atom or a nitrogen atom unsubstituted or substituted with a lower alkyl group or the like; ???Y represents an ethylene group; ???Z represents a C1-C10 alkylene group; ???R5 represents an aryl group, or an aryl group substituted with substituents; ???R6 and R7 each represents a hydrogen atom; provided that when R5 represents a hydrogen atom, then Z represents a group other than a single bond or a straight chain C1-C10 alkylene group] .
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Page 310-311

(2008/06/13)

Conformational analysis of 3-substituted-2,3,4,5-tetrahydro-1-benzoxepin by 1H and 13C nuclear magnetic resonance
2,3,4,5-Tetrahydro-1-benzoxepin (8) and its 3-substituted derivatives (9-13) have been studied by 1H and 13C dynamic nuclear magnetic resonance in a few solvent systems.The results show that, while 8 and its methyl derivative 9 exist solely in chair forms (C for 8 and Ce:Ca (96:4) for 9), the twist-boat (TB) conformation contributes significantly to the conformational equilibra of the derivatives 3-methoxy 10 (Ca:Ce:TB, 70:20:10), 3,3-dimethyl 11 (C:TB, 90:10), 3,3-methylmethoxy 12 (Ca:Ce:TB, 89:4:7), and 3,3-dimethoxy 13 (C:TB, 92:8).The analysis of several factors (steric, electrostatic, and electronic) on the conformational behaviour of these molecules shows why the TB form is a viable conformational alternative to destabilized chair forms in this benzoxepin system.
Lachapelle, A.,St-Jacques, M.
p. 2575 - 2594
(2007/10/02)

Novel compositions
Substituted alkenoates and alkanoates, intermediates therefor, synthesis thereof, and their use for the control of pests.
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(2008/06/13)

Liquid Crystalline Properties of Cholesteryl ω-Arylalkanoates
The thermal properties of the homologous series of cholesteryl ω-(4-benzoylphenyl)- (I), ω-(4-benzylphenyl)- (II), ω-benzoyl- (III), and ω-phenoxyalkanoate (IV) have been investigated.For series I and II the cholesteric-isotropic (Ch-I) transition temperatures, enthalpies, and entropies show a remarkable alternation.For series III and IV, the transition temperatures, enthalpies, and entropies exhibit weak alternation and their trends are opposite to those for series I and II, and the cholesteryl ω-phenylalkanoates.The cholesteric-isotropic transition temperatures are discussed in terms of the geometrical and electrical alternations stemming from the terminal aryl groups, and also the relative importance between these two terms.
Koden, Mitsuhiro,Miyake, Shiro,Takenaka, Shunsuke,Kusabayashi, Shigekazu
p. 2387 - 2390
(2007/10/02)