cas 1829-34-1, 3-Bromo-2-hydroxybenzaldehyde

Articles about 1829-34-1Total 58 be found

Article title
Article abstract
Author
Journal number and time
Download

Isomers of Coumarin-Based Cyclometalated Ir(III) Complexes with Easily Tuned Phosphorescent Color and Features for Highly Efficient Organic Light-Emitting Diodes
Three Ir(CλN)2(acac)-type and one Ir(C1λN)(C2λN)(acac)-type coumarin-based cyclometalated Ir(III) complex isomers (IrC5, IrC7, IrC7-A, and IrC8) have been obtained using three coumarin-based isomers of 2-phenylpyridine (ppy)-type cyclometalating ligands (L-C5, L-C7, and L-C8). Two coordination isomers emerging as principal products (IrC7 and IrC7-A) are obtained in the synthesis of corresponding coumarin-based cyclometalated Ir(III) complexes because of two different coordination sites in ligand L-C7 to form a C-Ir bond. To the best of our knowledge, there are no such isomers reported to date. Interestingly, a broad range of phosphorescent color tuning from green (IrC8, λ = 516 nm) to red (IrC5, λ = 608 nm) has been realized through variation of the pyridyl substitution positions on the fused phenyl ring of the coumarin skeleton. In addition, based on natural transition orbital (NTO) analyses, features of the lowest triplet excited states (T1) from these coumarin-based cyclometalated Ir(III) complex isomers can be tuned easily by these ligand isomers as well. IrC5, IrC7, and IrC7-A show prevailing 3MLCT character associated with their T1 states which emit the phosphorescent signals, while the T1 state of IrC8 exhibits the dominant ligand-centered π-π? transition feature. Importantly, owing to the strong rigidity of the coumarin skeleton, all the coumarin-based cyclometalated Ir(III) complex isomers can show high phosphorescent quantum yields φp (ca. 0.4-1). Together with the improved electron-injection/electron-transport (EI/ET) ability, all the phosphorescent emitters display impressive electroluminescence (EL) performance. The device based on IrC8 gives the highest EL efficiencies of external quantum efficiency (ηext) 22.7%, current efficiency (ηL) 79.7 cd A-1, and power efficiency (ηP) 58.2 lm W-1, representing the most state-of-the-art EL ability ever achieved by coumarin-based phosphorescent emitters. All these encouraging data definitely suggest the great potential of the coumarin skeleton in both easy tuning of the photophysical properties of ppy-type Ir(III) phosphorescent complexes and developing high-performance phosphorescent emitters.
Feng, Zhao,Yu, Yue,Yang, Xiaolong,Zhong, Daokun,Song, Dongdong,Yang, Hua,Chen, Xi,Zhou, Guijiang,Wu, Zhaoxin
p. 7393 - 7408
(2019)
Read Online

The 7-phenyl benzoxaborole series is active against Mycobacterium tuberculosis
We identified a series of novel 7-phenyl benzoxaborole compounds with activity against Mycobacterium tuberculosis. Compounds had a range of activity with inhibitory concentrations (IC90) as low as 5.1 μM and no cytotoxicity against eukaryotic cells (IC50 > 50 μM). Compounds were active against intracellular mycobacteria cultured in THP-1 macrophages. We isolated and characterized resistant mutants with mutations in NADH dehydrogenase (Ndh) or the regulatory protein Mce3R. Mutations suggest that Ndh may be the target of this series.
Korkegian, Aaron,O'Malley, Theresa,Xia, Yi,Zhou, Yasheen,Carter, David S.,Sunde, Bjorn,Flint, Lindsay,Thompson, Dean,Ioerger, Thomas R.,Sacchettini, Jim,Alley,Parish, Tanya
p. 96 - 98
(2018)
Read Online

An Oxidative Dearomatization Approach to Tetrodotoxin via a Masked ortho-Benzoquinone
Progress toward a stereoselective synthesis of tetrodotoxin (TTX) is presented. Oxidative dearomatization of a tetrasubstituted guaiacol arene yielded a masked ortho-benzoquinone that intercepted an acyl nitroso species generated in situ by the copper-cat
Robins, Jacob G.,Johnson, Jeffrey S.
supporting information
p. 559 - 563
(2022/01/20)

Compound containing benzo five-membered heterocyclic structure and preparation method and application thereof
The invention relates to the field of medicinal chemistry, and discloses a compound containing a benzo five-membered heterocyclic structure as well as a preparation method and application thereof. The invention also discloses a composition containing the benzo five-membered heterocyclic compound or the pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier, and application of the composition in preparation of PARP-1 and ERK inhibitors. The compound can be used for treating diseases such as tumors.
-
Paragraph 0082-0086

(2021/08/14)

Heterogeneous Catalytic Oxidative Bromination and Oxidation of Thioethers By Vanadium(IV) Oxido Complex of Benzoylacetone and Effect of Solid Supports
Vanadium(IV) oxido complex of 1-Phenyl-1,3-butanedione [VIVO(bzac)2] (1) was prepared, characterized, and heterogenized onto APTMS modified graphene oxide, as well as imidazole modified polystyrene beads. Graphene oxide supported complex GO-APTMS-[VIVO(bzac)2] (2) and polymer anchored complex PS-im-[VIVO(bzac)2] (3) were used for the oxidative bromination of a number of small organic molecules and oxidation of a series of thioethers. Both 2 and 3 evolve as excellent heterogeneous catalysts. The nature of solid support does not impact substrate conversion (%) during the oxidative bromination of salicylaldehyde, phenol, or styrene, whereas it influences the substrate conversion (%) as well as the product selectivity (%) during the oxidation of thioethers. Graphic Abstract: [Figure not available: see fulltext.]
Kesharwani, Neha,Chaudhary, Nikita,Haldar, Chanchal
p. 3562 - 3581
(2021/03/24)

Synthesis and characterization of dimeric μ-oxidovanadium complexes as the functional model of vanadium bromoperoxidase
Two vanadium (IV) complexes [VIVO(Haeae-sal)(MeOH)]+ (1) and [VIVO(Haeae-hyap)(MeOH)]+ (2) were prepared by reacting [VO(acac)2] with ligands [H2aeae-sal] (I) and [H2aeae-hyap] (II) respectively. Condensation of 2-(2-aminoethylamino)ethanol with salicylaldehyde and 2-hydroxyacetophenone produces the ligands (I) and (II) respectively. Both vanadium complexes 1 and 2 are sensitive towards aerial oxygen in solution and rapidly convert into vanadium(V) dioxido species. Vanadium(V) dioxido species crystalizes as the dimeric form in the solid-state. Single-crystal XRD analysis suggests octahedral geometry around each vanadium center in the solid-state. To access the benefits of heterogeneous catalysis, vanadium(V) dioxido complexes were anchored into the polymeric chain of chloromethylated polystyrene. All the synthesized neat and supported vanadium complexes have been studied by a number of techniques to confirm their structural and functional properties. Bromoperoxidase activity of the synthesized vanadium(V) dioxido complexes 3 and 4 was examined by carrying out oxidative bromination of salicylaldehyde and oxidation of thioanisole. In the presence of hydrogen peroxide, 3 shows 94.4% conversion (TOF value of 2.739 × 102 h?1) and 4 exhibits 79.0% conversion (TOF value of 2.403 × 102 h?1) for the oxidative bromination of salicylaldehyde where 5-bromosalicylaldehyde appears as the major product. Catalysts 3 and 4 also efficiently catalyze the oxidation of thioanisole in the presence of hydrogen peroxide where sulfoxide is observed as the major product. Covalent attachment of neat catalysts 3 and 4 into the polymer chain enhances substrate conversion (%) and their catalytic efficiency increases many folds, both in the oxidative bromination and oxidation of thioether. Polymer supported catalysts 5 displayed 98.8% conversion with a TOF value of 1.127 × 104 h?1 whereas catalyst 6 showed 95.7% conversion with a TOF value of 4.675 × 103 h?1 for the oxidative bromination of salicylaldehyde. These TOF values are the highest among the supported vanadium catalysts available in the literature for the oxidative bromination of salicylaldehyde.
Chaudhary, Nikita,Haldar, Chanchal,Kachhap, Payal,Kesharwani, Neha,Mahato, Arun Kumar,Maurya, Abhishek,Mishra, Vivek Kumar
(2020/02/05)

Organometallic iridium complex phosphorescent material containing coumarin skeleton and preparation method of phosphorescent material
An organometallic iridium complex phosphorescent material containing a coumarin skeleton and a preparation method of the phosphorescent material are disclosed. The coumarin skeleton is introduced intoa traditional 2-phenylpyridine ligand, and through controlling the change of substitution positions and adopting an asymmetric structure type, double regulation and control of the luminescent wavelength and luminous efficiency of an obtained iridium complex is realized, so that the organic electrophosphorescent material having simple structure and excellent performance is obtained. By using the characteristics that the coumarin skeleton structure is highly rigid, simple, easy to synthesize, strong in luminescent property and the like, double regulation and control of the luminescent wavelength and luminous efficiency of the obtained iridium complex is realized.
-
Paragraph 0110; 0114-0116

(2019/04/26)

Macrocyclic Modulators of the Ghrelin Receptor
The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.
-
Paragraph 0481; 0482; 0483

(2018/05/03)

Metal iridium complex and organic electroluminescent device containing metal iridium complex
The invention discloses a metal iridium complex and an organic electroluminescent device containing the metal iridium complex. The general structural formula of the metal iridium complex is as shown in the formula I. The electroluminescence of the metal i
-
Paragraph 0072; 0076; 0077; 0078

(2018/07/07)

Synthesis of chiral salalen ligands and their in-situ generated Cu-complexes for asymmetric Henry reaction
Chiral salalen ligands derived from (S)-proline and derivatives of salicyaldehydes were synthesized, and their in-situ generated Cu (II) complexes were evaluated in the asymmetric Henry reaction. Salalen ligand of different substituents on the phenyl moiety showed remarkable effect on the enantioselectivity of nitro-aldol product of 4-nitrobenzaldehyde and nitromethane. Cu (II) complex generated in situ with (S)-2-(tert-butyl)-6-((2-(((2-hydroxy-3-methylbenzylidene)amino)methyl)pyrrolidin-1-yl)methyl) phenol (10?mol%) and Cu (OAc)2.H2O (10?mol%), found to be better catalyst for nitro-aldol reaction between 4-nitrobenzaldehyde and nitromethane, gave corresponding product in 85% yield and 88% enantiomeric excess (ee) in isopropanol at 35°C after 40?hours. The catalyst also used for the Henry reaction with different substituted benzaldehydes and corresponding products were obtained in 22% to 99% yields with 66% to 92% ee. Henry reaction of 4-nitrobenzaldehyde and prochiral nitroethane gave anti-selective product (dr?=?79/21; anti/syn) in a 91% yield with 80% ee.
Dixit, Ashish,Kumar, Pramod,Singh, Surendra
p. 1257 - 1268
(2018/09/25)

Diversely halogenated spiropyrans - Useful synthetic building blocks for a versatile class of molecular switches
Spiropyrans are dyes that can be reversibly switched to a highly colored merocyanine form by a number of stimuli such as light, mechanical force or temperature. To make use of these molecules, there is a requirement to functionalize them appropriately. Herein we report a library of spiropyrans bearing two (pseudo) halide functional groups on either half of the molecule. Such halide substituents are valuable, because they themselves may be used as reactive sites in cross-coupling reactions, for example. Different combinations of halides, for which different reactivities in cross-coupling reactions may be expected, will facilitate selective consecutive cross-coupling reactions and condensations. Data concerning the UV/vis characteristics, the photostationary equilibria of the materials as well as the half-life of the merocyanine forms in solution are presented.
Schulz-Senft, Mathias,Gates, Paul J.,S?nnichsen, Frank D.,Staubitz, Anne
p. 292 - 301
(2016/09/09)

Syntheses and characterization of monobasic tridentate Cu(II) Schiff-base complexes for efficient oxidation of 3,5-di-: tert -butylcatechol and oxidative bromination of organic substrates
Two monomeric copper complexes [CuII(sal-ppzH)Cl2] (1) and [CuII(hyap-ppzH)Cl2] (2) were synthesized by reacting CuCl2·2H2O with the monobasic tridentate Schiff-base ligands [Hsal-ppz] (I) and [Hyap-ppz] (II) (derived by reacting 1-(2-aminoethyl) piperazine with salicylaldehyde and 2-hydroxyacetophenone) respectively. Elemental analysis, IR, UV-Vis, 1H NMR and 13C NMR data confirm the structures of the ligands and those of the complexes. Both complexes are monomeric in nature in the solid state and in solution as well. Single crystal XRD data suggest a distorted square pyramidal geometry for 1 crystallized in the P1 space group. DFT studies established a similar molecular structure for 2. The synthesized metal complexes [CuII(sal-ppzH)Cl2] (1) and [CuII(hyap-ppzH)Cl2] (2) successfully catalyzed the oxidation of 3,5-di-tert-butylcatechol (3,5-DTBC) in methanol in the presence of H2O2 with high Kcat values of 1.182 × 104 mmol h-1 and 2.880 × 104 mmol h-1, respectively. [CuII(sal-ppzH)Cl2] (1) and [CuII(hyap-ppzH)Cl2] (2) were also anchored into the polymeric matrix of chloromethylated polystyrene and were analyzed by TGA, atomic absorption spectroscopy (AAS), EPR, scanning electron microscopy (SEM) as well as energy dispersive X-ray (EDX) analysis. The polymer grafted metal complexes were used as catalyst precursors in the oxidative bromination of salicylaldehyde in the presence of H2O2, KBr and HClO4. Under optimized reaction conditions, both catalysts show nearly quantitative oxidative bromination of salicylaldehyde, with the order of % products formed being 5-bromosalicylaldehyde > 3,5-dibromosalicylaldehyde > 3-bromosalicylaldehyde. Plausible reactive species involved in the catalytic cycle are identified by UV-Vis spectroscopy, pH metric titration, ESI-MS, EPR and DFT studies.
Kumari, Sweta,Mahato, Arun Kumar,Maurya, Abhishek,Singh, Vijay Kumar,Kesharwani, Neha,Kachhap, Payal,Koshevoy, Igor O.,Haldar, Chanchal
p. 13625 - 13646
(2017/11/27)

Enantioselective synthesis of 2,3-disubstituted: Trans -2,3-dihydrobenzofurans using a Br?nsted base/thiourea bifunctional catalyst
The diastereo- and enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives (15 examples, up to 96 : 4 dr, 95 : 5 er) via intramolecular Michael addition has been developed using keto-enone substrates and a bifunctional tertiary amine-thiourea catalyst. This methodology was extended to include non-activated ketone pro-nucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.
Barrios Antúnez, Diego-Javier,Greenhalgh, Mark D.,Fallan, Charlene,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information
p. 7268 - 7274
(2016/08/05)

Cis-Dioxomolybdenum(VI) complexes with unsymmetric linear tetradentate ligands: Syntheses, structures and bromoperoxidase activities
Reactions of [MoO2(acetylacetonate)2], 2-((2-(2-hydroxyethylamino)ethylamino)methyl)-4-R-phenols (H2Ln, n = 1-5 for R = H, Me, OMe, Cl and Br, respectively) and KOH in 1:1:2 mole ratio in methanol afford a series of complexes having the general formula cis-[MoO2(Ln)] (1, 2, 3, 4, 5) in 81-86% yields. The complexes have been characterized using elemental analysis, spectroscopy (infrared, UV-visible, and 1H NMR, 13C NMR and 13C-DEPT NMR) and electrochemical measurements. The molecular structures of 1, 2, 3, 4 have been determined using single-crystal X-ray crystallography. In each of 1, 2, 3, 4, the ONNO-donor 6,5,5-membered fused chelate rings forming (Ln)2- and the two mutually cis oxo groups assemble a distorted octahedral N2O4 coordination sphere around the metal centre. In the crystal lattice, each of 1, 2, 3, 4 forms a one-dimensional infinite chain structure via intermolecular N-H...O hydrogen bonding interactions. In cyclic voltammograms, the diamagnetic complexes display an irreversible metal-centred reduction in the potential range -0.73 to -0.88 V (vs Ag/AgCl). The physicochemical data are consistent with a very similar gross molecular structure for all of 1, 2, 3, 4, 5. All the complexes exhibit decent bromoperoxidase activities and are also able to effectively catalyse benzoin and methyl(phenyl)sulfide oxidation reactions.
Kurapati, Sathish Kumar,Pal, Samudranil
p. 116 - 124
(2016/02/18)

Intermediates for macrocyclic compounds
The present invention is directed to novel macrocyclic compounds of formula (I) and their pharmaceutically acceptable salts, hydrates or solvates: wherein R1, R2, R3, R4, R5, R6, n1, m, p Z1, Z2, and Z3 are as describe in the specification. The invention also relates to compounds of formula (I) which are antagonists of the motilin receptor and are useful in the treatment of disorders associated with this receptor and with or with motility dysfunction.
-
Page/Page column 33; Sheet 18

(2015/11/30)

Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization
Hydrazone-carboxylic acids undergo intramolecular cyclization in the presence of pivaloyl chloride, iPr2NEt, and catalytic DABCO to form a range of substituted fused tricyclic 2,3-dihydro-1,3,4-oxadiazoles in high yields.
Fugard, Alison J.,Thompson, Bethany K.,Slawin, Alexandra M. Z.,Taylor, James E.,Smith, Andrew D.
supporting information
p. 5824 - 5827
(2015/12/11)

Zinc polyoxometalate on activated carbon: An efficient catalyst for selective oxidation of alcohols with hydrogen peroxide
[PW11ZnO39]5- was immobilized on activated carbon and characterized using Fourier transform infrared, X-ray diffraction, Brunauer-Emmett-Teller and elemental analysis techniques. Effective oxidation of various alcohols wit
Assady, Elham,Yadollahi, Bahram,Riahi Farsani, Mostafa,Moghadam, Majid
p. 561 - 565
(2015/08/04)

Complexes of cis-dioxomolybdenum(VI) with unsymmetrical tripodal NO3-donor ligands: Synthesis, characterization and catalytic applications
A series of cis-dioxomolybdenum(VI) complexes of general formula cis-[MoO2(HLn)] (1-4) have been synthesized in 80-85% yields by reacting equimolar amounts of [MoO2(acac)2] (acac- = acetylacetonate) with 2,2′-(2-hydroxy-3,5-R1,R2-benzylazanediyl)diethanols (H3Ln, n = 1-4) in methanol. Characterization of the complexes has been performed by elemental analysis, spectroscopic (IR, UV-Vis, 1H and 13C NMR) and electrochemical measurements. The molecular structures of all four complexes have been determined by single-crystal X-ray diffraction studies. In each of these analogous complexes, the metal centre is in a distorted octahedral NO5 coordination sphere assembled by the single edge shared 5,5,6-membered chelate rings forming NO3-donor (HLn)2- and two cis oriented oxo groups. Crystal structures of the complexes reveal formation of discrete centrosymmetric dimeric species via a pair of reciprocal intermolecular O-HO hydrogen bonding interactions. Spectroscopic data of all the complexes are consistent with their molecular structures. In the cyclic voltammograms, the redox-active complexes display a quasi-reversible to irreversible metal centred reduction with the cathodic peak potential in the range -0.92 to -1.12 V (versus Ag/AgCl). All the complexes have been evaluated for their catalytic activities in oxidative bromination reactions of styrene and salicylaldehyde and in benzoin oxidation reaction.
Kurapati, Sathish Kumar,Maloth, Swamy,Pal, Samudranil
p. 66 - 73
(2015/03/30)

Optimization of sphingosine-1-phosphate-1 receptor agonists: Effects of acidic, basic, and zwitterionic chemotypes on pharmacokinetic and pharmacodynamic profiles
The efficacy of the recently approved drug fingolimod (FTY720) in multiple sclerosis patients results from the action of its phosphate metabolite on sphingosine-1-phosphate S1P1 receptors, while a variety of side effects have been ascribed to its S1P3 receptor activity. Although S1P and phospho-fingolimod share the same structural elements of a zwitterionic headgroup and lipophilic tail, a variety of chemotypes have been found to show S1P1 receptor agonism. Here we describe a study of the tolerance of the S1P1 and S1P3 receptors toward bicyclic heterocycles of systematically varied shape and connectivity incorporating acidic, basic, or zwitterionic headgroups. We compare their physicochemical properties, their performance in in vitro and in vivo pharmacokinetic models, and their efficacy in peripheral lymphocyte lowering. The campaign resulted in the identification of several potent S1P1 receptor agonists with good selectivity vs S1P3 receptors, efficacy at 1 mg/kg oral doses, and developability properties suitable for progression into preclinical development.
Skidmore, John,Heer, Jag,Johnson, Christopher N.,Norton, David,Redshaw, Sally,Sweeting, Jennifer,Hurst, David,Cridland, Andrew,Vesey, David,Wall, Ian,Ahmed, Mahmood,Rivers, Dean,Myatt, James,Giblin, Gerard,Philpott, Karen,Kumar, Umesh,Stevens, Alexander,Bit, Rino A.,Haynes, Andrea,Taylor, Simon,Watson, Robert,Witherington, Jason,Demont, Emmanuel,Heightman, Tom D.
supporting information
p. 10424 - 10442
(2015/02/19)

Facile one-pot transformation of phenols into o-cyanophenols
The treatment of phenols with paraformaldehyde in the presence of MgCl2 and Et3N in THF at 80 C, followed by reaction with molecular iodine and aq. ammonia at room temperature provided the corresponding o-cyanophenols in moderate to good yields. The present reaction is a one-pot transformation of phenols into o-cyanophenols using much less expensive reagents than are typically used; the reaction is free of both transition-metals and cyanide. The utility of this reaction was highlighted during our preparation of Febuxostat from p-bromophenol.
Nakai, Yuhta,Moriyama, Katsuhiko,Togo, Hideo
p. 6077 - 6083
(2015/03/30)

Asymmetric induction via short-lived chiral enolates with a chiral C-O axis
A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be ～1 s at -78 C.
Yoshimura, Tomoyuki,Tomohara, Keisuke,Kawabata, Takeo
supporting information
p. 7102 - 7105
(2013/06/27)

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)

Cu-Mn spinel oxide catalyzed regioselective halogenation of phenols and N-heteroarenes
A novel simple, mild chemo- and regioselective method has been developed for the halogenation of phenols using Cu-Mn spinel oxide as a catalyst and N-halosuccinimide as halogenating agent. In the presence of Cu-Mn spinel oxide B, both electron-withdrawing and electron-donating groups bearing phenols gave monohalogenated products in good to excellent yields with highest para-selectivity. The para-substituted phenol gave monohalogenated product with good yield and ortho-selectivity. N-Heteroarenes such as indoles and imidazoles also gave monohalogenated products with high selectivity. Unlike the copper-catalyzed halogenation, the present method works well with electron-withdrawing group bearing phenols and gives comparatively better yields and selectivity. The Cu-Mn spinel catalyst is robust and reused three times under optimized conditions without any loss in catalytic activity. Nonphenolics did not undergo this transformation.
Singh, Parvinder Pal,Thatikonda, Thanusha,Kumar, K. A. Aravinda,Sawant, Sanghapal D.,Singh, Baldev,Sharma, Amit Kumar,Sharma,Singh, Deepika,Vishwakarma, Ram A.
scheme or table
p. 5823 - 5828
(2012/09/05)

Discovery of a brain-penetrant S1P3-sparing direct agonist of the S1P1 and S1P5 receptors efficacious at low oral dose
2-Amino-2-(4-octylphenethyl)propane-1,3-diol 1 (fingolimod, FTY720) has been recently marketed in the United States for the treatment of patients with remitting relapsing multiple sclerosis (RRMS). Its efficacy has been primarily linked to the agonism on
Demont, Emmanuel H.,Arpino, Sandra,Bit, Rino A.,Campbell, Colin A.,Deeks, Nigel,Desai, Sapna,Dowell, Simon J.,Gaskin, Pam,Gray, James R. J.,Harrison, Lee A.,Haynes, Andrea,Heightman, Tom D.,Holmes, Duncan S.,Humphreys, Philip G.,Kumar, Umesh,Morse, Mary A.,Osborne, Greg J.,Panchal, Terry,Philpott, Karen L.,Taylor, Simon,Watson, Robert,Willis, Robert,Witherington, Jason
supporting information; experimental part
p. 6724 - 6733
(2011/12/04)

Optimization of the potency and pharmacokinetic properties of a macrocyclic ghrelin receptor agonist (Part I): Development of ulimorelin (TZP-101) from Hit to Clinic
High-throughput screening of Tranzyme Phar-ma's proprietary macrocycle library using the aequorin Ca2+-bioluminescence assay against the human ghrelin receptor (GRLN) led to the discovery of novel agonists against this G-protein coupled receptor. Early hits such as 1 (Ki = 86 nM, EC50 = 134 nM) though potent in vitro displayed poor pharmacokinetic properties that required optimization. While such macrocycles are not fully rule-of-five compliant, principally due to their molecular weight and clogP, optimization of their pharmacokinetic properties proved feasible largely through conformational rigidification. Extensive SAR led to the identification of 2 (Ki = 16 nM, EC50 = 29 nM), also known as ulimorelin or TZP-101, which has progressed to phase III human clinical trials for the treatment of postoperative ileus. X-ray structure and detailed NMR studies indicated a rigid peptidomimetic portion in 2 that is best defined as a nonideal type-I′ β-turn. Compound 2 is 24% orally bioavailable in both rats and monkeys. Despite its potency, in vitro and in gastric emptying studies, 2 did not induce growth hormone (GH) release in rats, thus demarcating the GH versus GI pharmacology of GRLN. (Figure presented)
Hoveyda, Hamid R.,Marsault, Eric,Gagnon, René,Mathieu, Axel P.,Vézina, Martin,Landry, Annick,Wang, Zhigang,Benakli, Kamel,Beaubien, Sylvie,Saint-Louis, Carl,Brassard, Martin,Pinault, Jean-Fran?ois,Ouellet, Luc,Bhat, Shridhar,Ramaseshan, Mahesh,Peng, Xiaowen,Foucher, Laurence,Beauchemin, Sophie,Bhérer, Patrick,Veber, Daniel F.,Peterson, Mark L.,Fraser, Graeme L.
supporting information; experimental part
p. 8305 - 8320
(2012/01/15)

COMPOUNDS
The present invention relates to novel compounds having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders.
-
Page/Page column 40-41

(2011/11/12)

COMPOUNDS AS AGONISTS OF S1P1 RECEPTORS
Compounds of formula (I), processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases mediated by S1P1 receptors.
-
Page/Page column 82; 83

(2011/11/12)

Synthesis of ACAT inhibitors through substitution using allylic picolinate and copper reagent
Amide of an octanoic acid possessing an aryl group at C3 position is a highly potent ACAT inhibitor. In this paper, we describe a synthetic access to this class of compounds as optically active forms. The key reaction is substitution of the allylic picoli
Kobayashi, Yuichi,Lalitnorasate, Paveena,Kaneko, Yuki,Kiyotsuka, Yohei,Endo, Yoshiki
scheme or table
p. 6018 - 6021
(2010/11/21)

SPIROAMINOOXAZOLINE ANALOGUES AS ALPHA2C ADRENERGIC RECEPTOR MODULATORS
In its many embodiments, the present invention provides a novel class of spiroaminooxazoline analogues as modulators of α2C adrenergic receptor, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more conditions associated with the α2C adrenergic receptors using such compounds or pharmaceutical compositions.
-
Page/Page column 88

(2010/04/28)

COMPOUNDS
The present invention relates to novel oxadiazole derivatives having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders.
-
Page/Page column 38

(2010/07/10)

Oxidative bromination reaction using vanadium catalyst and aluminum halide under molecular oxygen
The vanadium-catalyzed oxidative bromination reaction of arenes, alkenes, and alkynes was performed in the presence of AlBr3 to provide an alternative method for conventional bromination using hazardous bromine. The catalytic cycle is formed under molecular oxygen, which is more advantageous to vanadium bromoperoxidase (VBrPO) requiring hydrogen peroxide as a terminal oxidant.
Kikushima, Kotaro,Moriuchi, Toshiyuki,Hirao, Toshikazu
supporting information; experimental part
p. 340 - 342
(2010/03/04)

Vanadium-catalyzed oxidative bromination promoted by Br?nsted acid or Lewis acid
The oxidative bromination of arenes was induced by a vanadium catalyst in the presence of a bromide salt and a Br?nsted acid or a Lewis acid under molecular oxygen, which provides an eco-friendly bromination method as compared with a conventional bromination one with bromine. This catalytic reaction could be applied to the bromination of alkenes and alkynes to give the corresponding vic-bromides. Use of aluminum halide as a Lewis acid in place of a Br?nsted acid was demonstrated to provide a more practical protocol for the oxidative bromination. From ketones, α-bromination products were obtained. AlBr3 was found to serve as both a bromide source and a Lewis acid to induce the bromination smoothly. 51V NMR experiment showed that this catalytic bromination is likely to depend on the redox cycle of a vanadium catalyst under molecular oxygen.
Kikushima, Kotaro,Moriuchi, Toshiyuki,Hirao, Toshikazu
experimental part
p. 6906 - 6911
(2010/09/18)

Synthesis and solid-state, solution, and luminescence properties of near-infrared-emitting neodymium(3+) complexes formed with ligands derived from salophen
A series of free ligands, H2L1, H2L 2, H2L3, and H2L4, designed for the coordination and sensitization of near-infrared(NIR)-emitting Nd3+ were synthesized
Uh, Hyounsoo,Badger, Paul D.,Geib, Steven J.,Petoud, Stephane
experimental part
p. 2313 - 2329
(2010/03/30)

OXADIAZOLE DERIVATIVES ACTIVE ON SPHINGOSINE-1-PHOSPHATE (SIP)
The present application discloses oxadiazole based compounds of Formula (I) active on sphingosine-1-phosphate (S1P) in particular useful to treat lupus erythematosus. A is phenyl or a 5 or 6-membered heteroaryl ring; R1 is up to two substituent
-
Page/Page column 81-82

(2009/07/25)

DI-SUBSTITUTED PHENYL COMPOUNDS
Di-substituted phenyl compounds which are inhibitors of phosphodiesterase 10 are described as are processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of mammals, including human(s) f
-
Page/Page column 85

(2010/01/30)

MACROCYCLIC GHRELIN RECEPTOR MODULATORS AND METHODS OF USING THE SAME
The present invention provides novel conformationally-defined macrocyclic compounds that can function as selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, bone disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.
-
Page/Page column 37-39

(2008/12/07)

ANTIBACTERIAL AGENTS
2H-chromen-2-one derivatives useful in the treatment of bacterial infections in mammals, particularly humans, are disclosed herein.
-
Page/Page column 28

(2008/06/13)

Synthesis of substituted salicylamines and dihydro-2H-1,3-benzoxazines
Phenols were converted to their magnesium salts with the MgCl2-Et3N base system and subsequently reacted with Eschenmoser's salt, affording N,N-dimethyl substituted benzylamines in high to excellent yields. A series of mono N-substituted benzylamines were prepared in one-pot syntheses by ortho-formylation of phenols to corresponding salicylaldehydes, which in turn reacted with amines to imines. The imines were subsequently reduced to mono N-substituted benzylamines. Some of these benzylamines were further converted, without work-up, to mono N-substituted dihydro-2H-1,3-benzoxazines.
Anwar, Hany F.,Skatteb?l, Lars,Hansen, Trond Vidar
p. 9997 - 10002
(2008/02/13)

COMPOUNDS AND METHODS FOR INHIBITING THE INTERACTION OF BCL PROTEINS WITH BINDING PARTNERS
-
-
Page/Page column 134

(2008/06/13)

INHIBITORS OF TRYPTASE
The present invention related to certain inhibitors of tryptase that are inhibitors of tryptase, pharmaceutical composition comprising these compounds and method of treating asthma, allergic rhinitis, and/or Chronic Obstructive Pulmonary Disease utilizing these compounds.
-
Page/Page column 151-152

(2008/06/13)

Novel 5-azaindole factor VIIa inhibitors
The discovery and development of 5-azaindole factor VIIa inhibitors will be described.
Riggs, Jennifer R.,Hu, Huiyong,Kolesnikov, Aleksandr,Leahy, Ellen M.,Wesson, Kieron E.,Shrader, William D.,Vijaykumar, Dange,Wahl, Troy A.,Tong, Zhiwei,Sprengeler, Paul A.,Green, Michael J.,Yu, Christine,Katz, Brad A.,Sanford, Ellen,Nguyen, Margaret,Cabuslay, Ronnel,Young, Wendy B.
p. 3197 - 3200
(2007/10/03)

Efforts toward oral bioavailability in factor VIIa inhibitors
Efforts toward developing orally bioavailable factor VIIa inhibitors starting from parenteral lead compound 1 are described. SAR resulted in improved physicochemical properties, leading to enhanced oral absorption in rat.
Vijaykumar, Dange,Rai, Roopa,Shaghafi, Michael,Ton, Tony,Torkelson, Steve,Leahy, Ellen M.,Riggs, Jennifer R.,Hu, Huiyong,Sprengeler, Paul A.,Shrader, William D.,O'Bryan, Colin,Cabuslay, Ronnell,Sanford, Ellen,Gjerstadt, Erik,Liu, Liang,Sukbuntherng, Juthamas,Young, Wendy B.
p. 3829 - 3832
(2007/10/03)

Substituted biaryl compounds as factor XIa inhibitors
The present invention provides compounds of Formula (I): or a stereoisomer, tautomer, pharmaceutically acceptable salt or solvate form thereof, wherein the variables A, L, Z, R3, and ring B are as defined herein. The compounds of Formula (I) ar
-
Page/Page column 31

(2008/06/13)

Synthesis of halogenated phenols by directed ortho-lithiation and ipso-iododesilylation reactions of O-aryl N-isopropylcarbamates
The regioselective synthesis of halogenated phenols via directed ortho-lithiation reactions of in situ N-silylated O-aryl N-isopropylcarbamates is reported. This protocol is complemented by ipso-iododesilylation reactions of C-silylated carbamates and iodine-magnesium exchange reactions, which are facilitated by the adjacent carbamoyl group. These methods provide an entry into a series of o-fluoro-, o-iodo-, and o,o′-diiodophenols in high yields which are otherwise difficult to obtain. Georg Thieme Verlag Stuttgart.
Kauch, Matthias,Hoppe, Dieter
p. 1578 - 1589
(2007/10/03)

Ortho-formylation of phenols; preparation of 3-bromosalicylaldehyde: (3-bromo-2-hydroxybenzaldehyde)
-
Hansen, Trond Vidar,Skatteb?l, Lars,Guthrie, David,Curran, Dennis P.
p. 64 - 68
(2017/09/08)

One-pot synthesis of substituted catechols from the corresponding phenols
Phenols are converted to salicylaldehydes with paraformaldehyde, MgCl 2-Et3N in THF, and when subsequently treated with aqueous NaOH and H2O2 afford the corresponding catechols. The sequence is conveniently carried out as a one-pot procedure.
Hansen, Trond Vidar,Skatteb?l, Lars
p. 3357 - 3358
(2007/10/03)

One-pot synthesis of ortho-hydroxycinnamate esters
Phenols are converted to salicylaldehydes with paraformaldehyde, MgCl 2-Et3N in THF, and subsequent treatment with methyl (triphenylphosphoranylidene)acetate gave the corresponding methyl ortho-hydroxycinnamate derivatives. The sequence is conveniently carried out as a one-pot procedure.
Anwar, Hany F.,Skatteb?l, Lars,Skramstad, Jan,Hansen, Trond Vidar
p. 5285 - 5287
(2007/10/03)

Ligand tuning in the chromium-salen-mediated asymmetric epoxidation of alkenes
A series of Cr(salen) complexes have been synthesised from 5-substituted-3-bromosalicylaldehydes and trans-1,2-cyclohexanediamine. These have been used to probe the Cr(salen)-mediated asymmetric epoxidation of alkenes. No simple correlation was found between the electronic character of the salen-substituents and the enantioselectivity - multiple oxidation pathways are proposed as a possible explanation. Enantioselectivities of up to 90% have been achieved using a novel, synthetically accessible Cr(salen) complex.
McGarrigle,Murphy,Gilheany
p. 1343 - 1354
(2007/10/03)

2-(2-HYDROXYBIPHENYL-3-YL)-1H-BENZOIMIDAZOLE-5-CARBOXAMIDINE DERIVATIVES AS FACTOR VIIA INHIBITORS
The present invention relates to novel inhibitors of Factors VIIa, IXa, Xa, XIa, in particular Factor VIIa, pharmaceutical compositions comprising these inhibitors, and methods for using these inhibitors for treating or preventing thromboembolic disorders, cancer or rheumatoid arthritis. Processes for preparing these inhibitors are also disclosed.
-
Page 69-70

(2008/06/13)

Method for producing optically active salicylaldimine copper complex
There is provided a method for producing an optically active salicylaldimine copper complex, which method is characterized in that an optically active amino alcohol compound represented by the following formula (1) is reacted with copper hydroxide (II) in an organic solvent. wherein R1 and R2 which are the same or different, each represent lower alkyl groups and the like which may be substituted, X1 and X2 which are the same or different, each represent a hydrogen atom, lower alkyl groups and the like, and the symbol * designates an asymmetric carbon atom.
-
(2008/06/13)