cas 59247-47-1, TERT-BUTYL-4-BROMOBENZOATE

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Silver/manganese dioxide nanorod catalyzed hydrogen-borrowing reactions and tert-butyl ester synthesis
Silver/manganese dioxide (Ag@MnO2) nanorods are synthesized and characterized by scanning electron microscopy, transmission electron microscopy, energy dispersive X-ray spectroscopy, X-ray powder diffraction, and X-ray photoelectron spectroscopy. It was discovered that Ag@MnO2 nanorods can realize hydrogen-borrowing reactions in high yields and are also effective for the synthesis of tert-butyl esters from aryl cyanides and tert-butyl hydroperoxide in a short period of time. Mechanistic experiments revealed that this catalytic system acts as a Lewis acid in hydrogen-borrowing reactions, while the synthesis of tert-butyl esters occurs through a radical pathway. This is the first report on the excellent catalytic activity of Ag@MnO2 nanorods as a catalyst.
Luo, Huanhuan,Wang, Dawei,Xu, Zhaojun,Yang, Bobin,Yang, Yike
p. 708 - 715
(2021/03/03)

Non-Catalytic Benefits of Ni(II) Binding to an Si(111)-PNP Construct for Photoelectrochemical Hydrogen Evolution Reaction: Metal Ion Induced Flat Band Potential Modulation
We report here the remarkable and non-catalytic beneficial effects of a Ni(II) ion binding to a Si|PNP type surface as a result of significant thermodynamic band bending induced by ligand attachment and Ni(II) binding. We unambiguously deconvolute the thermodynamic flat band potentials (VFB) from the kinetic onset potentials (Von) by synthesizing a specialized bis-PNP macrochelate that enables one-step Ni(II) binding to a p-Si(111) substrate. XPS analysis and rigorous control experiments confirm covalent attachment of the designed ligand and its resulting Ni(II) complex. Illuminated J-V measurements under catalytic conditions show that the Si|BisPNP-Ni substrate exhibits the most positive onset potential for the hydrogen evolution reaction (HER) (-0.55 V vs Fc/Fc+) compared to other substrates herein. Thermodynamic flat band potential measurements in the dark reveal that Si|BisPNP-Ni also exhibits the most positive VFB value (-0.02 V vs Fc/Fc+) by a wide margin. Electrochemical impedance spectroscopy data generated under illuminated, catalytic conditions demonstrate a surprising lack of correlation evident between Von and equivalent circuit element parameters commonly associated with HER. Overall, the resulting paradigm comprises a system wherein the extent of band bending induced by metal ion binding is the primary driver of photoelectrochemical (PEC)-HER benefits, while the kinetic (catalytic) effects of the PNP-Ni(II) are minimal. This suggests that dipole and band-edge engineering must be a primary design consideration (not secondary to catalyst) in semiconductor|catalyst hybrids for PEC-HER.
Gurrentz, Joseph M.,Rose, Michael J.
(2020/03/27)

A Zirconium Indazole Carboxylate Coordination Polymer as an Efficient Catalyst for Dehydrogenation-Cyclization and Oxidative Coupling Reactions
Rational ligand design is crucial for achieving widespread applications of coordination polymers. The preparation, structural characterisation, and catalytic applications of zirconium (IV) coordination polymer (Zr-IDA), which was derived from 1-(carboxymethyl)-1H-indazole-5-carboxylic acid are reported. The Zr-IDA catalyst contains porous and highly crystalline particles with a quasi-spherical morphology around 100 nm in size, and Zr was coordinated with both O and N as shown by FT-IR and XPS measurements. Importantly, the Zr-IDA catalyst shows great activity, selectivity and stability in the oxidative coupling of benzyl cyanides with tert-butyl hydroperoxide to afford tert-butyl peresters, and the dehydrogenation cyclization of o-phenylenediamines with aromatic alcohols to afford 1,2-disubstituted benzimidazole derivatives. Mechanistic investigations were carried out to study these reactions and the developed catalytic system in more detail.
Sang, Xinxin,Hu, Xinyu,Tao, Rong,Zhang, Yilin,Zhu, Haiyan,Wang, Dawei
p. 123 - 129
(2020/02/21)

A Cyanide-Free Synthesis of Acylcyanides through Ru-Catalyzed C(sp3)-H-Oxidation of Benzylic Nitriles
A practical method for generation of acylcyanides devoid of any external cyanide sources is presented that relies on a mild Ru-catalyzed selective C?H-oxidation of benzylic nitriles. The starting materials are smoothly generated through condensation of the corresponding carboxylic acid amides using silanes. The obtained acylcyanides can be employed in a plethora of transformation as exemplified to some larger extend in the sequence of C?H-oxidation-Tischenko-rearrangement for the generation of structurally diverse benzoyloxycyanohydrines.
Eisele, Pascal,Bauder, Michael,Hsu, Shih-Fan,Plietker, Bernd
p. 689 - 691
(2019/05/07)

HORMONE RECEPTOR MODULATORS FOR TREATING METABOLIC CONDITIONS AND DISORDERS
The invention relates to activators of FXR useful in the treatment of autoimmune disorders, liver disease, intestinal disease, kidney disease, cancer, and other diseases in which FXR plays a role, having the Formula (I): (I), wherein L1, A, X1, X2, R1, R2, and R3 are described herein.
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Page/Page column 216; 217

(2018/03/25)

Chemoselective and Metal-Free Synthesis of Aryl Esters from the Corresponding Benzylic Alcohols in Aqueous Medium Using TBHP/TBAI as an Efficient Catalytic System
A novel and transition-metal-free strategy has been developed for the synthesis of aryl esters starting from corresponding benzylic primary alcohols as the exclusive substrates using tert -butyl hydroperoxide (TBHP) as a terminal oxidant in the presence of catalytic amount of tetrabutylammonium iodide (TBAI) and imidazole, where the aliphatic alcohols remained unaffected. These reactions are highly chemoselective and associated with high yield and wide applicability accommodating a wide range of substituents. Excellent chemoselectivity has also been demonstrated through intramolecular competition experiments. This protocol can be considered as an important analogue of Tishchenko reaction using benzylic alcohols as the substrates instead of benzaldehydes.
Nandy, Sneha,Ghatak, Avishek,Das, Asit Kumar,Bhar, Sanjay
p. 2208 - 2212
(2018/10/02)

Metal-free radical aromatic carbonylations mediated by weak bases
We report a new method of metal-free alkoxycarbonylation. This reaction involves the generation of aryl radicals from arenediazonium salts by a very weak base (HCO2Na) under mild conditions. Subsequent radical trapping with carbon monoxide and alcohols gives alkyl benzoates. The conditions (metal-free, 1 equiv. base, MeCN, r.t., 3 h) tolerate various functional groups (I, Br, Cl, CF3, SF5, NO2, ester). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism.
Koziakov, Denis,Jacobi Von Wangelin, Axel
supporting information
p. 6715 - 6719
(2017/08/22)

SULFONAMIDE COMPOUNDS AS VOLTAGE-GATED SODIUM CHANNEL MODULATORS
The present invention relates to sulfonamide compounds Formula (I) wherein the substituents are as described herein, and their use in a medicine for the treatment of diseases, disorders associated with the inhibition of Voltage-gated sodium channels (VGSC) particularly NaV1.7. It further relates to the compounds herein and their pharmaceutically acceptable salts thereof, pharmaceutical compositions thereof useful in treating diseases, disorders, syndromes and/or conditions associated with the inhibition of Voltage-gated sodium channels (VGSC) particularly NaV1.7. The invention also relates to process for the preparation of the compounds of the invention. (I)
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Page/Page column 91

(2017/03/28)

POLYMERIZABLE COMPOUND, COMPOSITION, POLYMER, OPTICALLY ANISOTROPIC BODY, LIQUID CRYSTAL DISPLAY ELEMENT, AND ORGANIC EL DEVICE
It is an object of the present invention to provide a polymerizable compound having a good liquid crystal property, a good alignment property, sufficient solubility in solvents, high preservation stability in a solution state, and high optical stability; a composition including the polymerizable compound; a polymer produced by polymerizing the polymerizable compound, such as a resin produced using the polymerizable compound; an optically anisotropic body including the polymer; and a liquid crystal display element and an organic EL device that include the optically anisotropic body. As a result of conducting intensive studies in order to achieve the above object, the compound represented by General Formula (I) is developed.
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Paragraph 0169; 0170

(2017/09/25)

A study of oligothiophene-acceptor dyes in p-type dye-sensitized solar cells
Two new dyes, E1 and E2, equipped with triphenylamine as the electron donor, oligothiophene as the linker and different electron acceptor groups, have been designed and synthesized as photosensitizers for p-type dye-sensitized solar cells (p-DSCs). A systematic study of the effect of molecular structures on the observed photophysical properties, the electron/hole recombination process, the overall performance and the interfacial charge separation was carried out. Transient absorption spectroscopy (TAS) shows that the E1 dye with a napthoilene-1,2-benzimidazole (NBI) unit as the acceptor has a longer lifetime in the reduced state than the E2 dye with a malononitrile subunit on the NiO surface.
Sheibani, Esmaeil,Zhang, Lei,Liu, Peng,Xu, Bo,Mijangos, Edgar,Boschloo, Gerrit,Hagfeldt, Anders,Hammarstr?m, Leif,Kloo, Lars,Tian, Haining
p. 18165 - 18177
(2016/02/27)

A New Approach to Non-Coordinating Anions: Lewis Acid Enhancement of Porphyrin Metal Centers in a Zwitterionic Metal-Organic Framework
We describe a new strategy to generate non-coordinating anions using zwitterionic metal-organic frameworks (MOFs). By assembly of anionic inorganic secondary building blocks (SBUs) ([In(CO2)4]-) with cationic metalloporphyrin-based organic linkers, we prepared zwitterionic MOFs in which the complete internal charge separation effectively prevents the potential binding of the counteranion to the cationic metal center. We demonstrate the enhanced Lewis acidity of MnIII- and FeIII-porphyrins in the zwitterionic MOFs in three representative electrocyclization reactions: [2 + 1] cycloisomerization of enynes, [3 + 2] cycloaddition of aziridines and alkenes, and [4 + 2] hetero-Diels-Alder cycloaddition of aldehydes with dienes. This work paves a new way to design functional MOFs for tunable chemical catalysis.
Johnson, Jacob A.,Petersen, Brenna M.,Kormos, Attila,Echeverría, Elena,Chen, Yu-Sheng,Zhang, Jian
supporting information
p. 10293 - 10298
(2016/09/03)

An efficient method for the preparation of: Tert -butyl esters from benzyl cyanide and tert -butyl hydroperoxide under the metal free condition
A novel protocol to synthesize tert-butyl esters from benzyl cyanides and tert-butyl hydroperoxide has been successfully achieved. In the presence of tert-butyl hydroperoxide, Csp3-H bond oxidation, C-CN bond cleavage and C-O bond formation proceeded smoothly in one pot under the metal-free condition.
Chen, Xiuling,Li, Yan,Wu, Minghu,Guo, Haibing,Jiang, Longqiang,Wang, Jian,Sun, Shaofa
p. 102023 - 102027
(2016/11/09)

Metal-free carbonylations by photoredox catalysis
The synthesis of benzoates from aryl electrophiles and carbon monoxide is a prime example of a transition-metalcatalyzed carbonylation reaction which is widely applied in research and industrial processes. Such reactions proceed in the presence of Pd or Ni catalysts, suitable ligands, and stoichiometric bases. We have developed an alternative procedure that is free of any metal, ligand, and base. The method involves a redox reaction driven by visible light and catalyzed by eosin Y which affords alkyl benzoates from arene diazonium salts, carbon monoxide, and alcohols under mild conditions. Tertiary esters can also be prepared in high yields. DFT calculations and radical trapping experiments support a catalytic photoredox pathway without the requirement for sacrificial redox partners.
Majek, Michal,Von Wangelin, Axel Jacobi
supporting information
p. 2270 - 2274
(2015/02/19)

Copper-mediated oxidative homocoupling and rearrangement of N-alkoxyamides: An efficient method for the preparation of aromatic esters
N-Alkoxyamides are successfully converted into their corresponding esters in a moderate to satisfactory yields via copper-catalyzed oxidative homocoupling and Heron rearrangement. The process tolerates a wide variety of functional groups and allows the synthesis of sterically hindered ester products not readily accessible by traditional acylation chemistry. A radical-mediated pathway has been tentatively proposed for the oxidative process.
Duan, Xiyan,Yang, Kun,Tian, Shuang,Ma, Junying,Li, Yaning,Zou, Jiao,Zhang, Dongliang,Cui, Huanqing
supporting information
p. 4634 - 4637
(2015/07/08)

Modulators of methyl modifying enzymes, compositions and uses thereof
Agents for modulating methyl modifying enzymes, compositions and uses thereof are provided herein.
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Page/Page column 137; 138; 202; 203

(2015/12/26)

Discovery of 1,1′-Biphenyl-4-sulfonamides as a New Class of Potent and Selective Carbonic Anhydrase XIV Inhibitors
New 1,1′-biphenylsulfonamides were synthesized and evaluated as inhibitors of the ubiquitous human carbonic anhydrase isoforms I, II, IX, XII, and XIV using acetazolamide (AAZ) as reference compound. The sulfonamides 1-21 inhibited all the isoforms, with Ki values in the nanomolar range of concentration, and were superior to AAZ against all of them. X-ray crystallography and molecular modeling studies on the adducts that compound 20, the most potent hCA XIV inhibitor of the series (Ki = 0.26 nM), formed with the five hCAs, provided insight into the molecular determinants responsible for the high affinity of this molecule toward the target enzymes. The results pave the way to the development of 1.1′-biphenylsulfonamides as a new class of highy potent hCA XIV inhibitors.
La Regina, Giuseppe,Coluccia, Antonio,Famiglini, Valeria,Pelliccia, Sveva,Monti, Ludovica,Vullo, Daniela,Nuti, Elisa,Alterio, Vincenzo,De Simone, Giuseppina,Monti, Simona Maria,Pan, Peiwen,Parkkila, Seppo,Supuran, Claudiu T.,Rossello, Armando,Silvestri, Romano
supporting information
p. 8564 - 8572
(2015/11/24)

Discovery, design, and synthesis of indole-based EZH2 inhibitors
The discovery and optimization of a series of small molecule EZH2 inhibitors is described. Starting from dimethylpyridone HTS hit (2), a series of indole-based EZH2 inhibitors were identified. Biochemical potency and microsomal stability were optimized during these studies and afforded compound 22. This compound demonstrates nanomolar levels of biochemical potency (IC50 = 0.002 μM), cellular potency (EC50 = 0.080 μM), and afforded tumor regression when dosed (200 mpk SC BID) in an EZH2 dependent tumor xenograft model.
Gehling, Victor S.,Vaswani, Rishi G.,Nasveschuk, Christopher G.,Duplessis, Martin,Iyer, Priyadarshini,Balasubramanian, Srividya,Zhao, Feng,Good, Andrew C.,Campbell, Robert,Lee, Christina,Dakin, Les A.,Cook, Andrew S.,Gagnon, Alexandre,Harmange, Jean-Christophe,Audia, James E.,Cummings, Richard T.,Normant, Emmanuel,Trojer, Patrick,Albrecht, Brian K.
supporting information
p. 3644 - 3649
(2015/08/11)

Direct N-acylation of azoles via a metal-free catalyzed oxidative cross-coupling strategy
The KI-catalyzed N-acylation of azoles via direct oxidative coupling of C-H and N-H bonds has been developed. It could be smoothly scaled up to gram synthesis of acyl azoles. The reaction occurred by the coupling of acyl radicals and azoles to form the acyl azole radical anion, followed by its further oxidation. This journal is the Partner Organisations 2014.
Zhao, Jingjing,Li, Pan,Xia, Chungu,Li, Fuwei
supporting information
p. 4751 - 4754
(2014/05/06)

Direct conversion of N -alkoxyamides to carboxylic esters through tandem nbs-mediated oxidative homocoupling and thermal denitrogenation
Treatment of N-alkoxyamides with NBS in toluene was found to conveniently afford the corresponding carboxylic esters, including those bearing a bulky or long-chain substituent, in satisfactory to excellent yields. This approach not only represents a convenient and economic approach to a direct transformation of an alkoxyamide moiety into the carboxylic ester functional group, via oxidative homocoupling and the subsequent thermal denitrogenation, but also facilitates the synthesis of sterically hindered carboxylic esters.
Zhang, Ningning,Yang, Rui,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
p. 8705 - 8711
(2013/09/24)

Red fluorescent probe for monitoring the dynamics of cytoplasmic calcium ions
We see red (and yellow and green): Probe 1 was developed for the visualization of cytoplasmic Ca2+, a pivotal second messenger in many biological responses. The new probe is suitable for multicolor imaging for the simultaneous detection of metal ions or proteins and is superior to the existing red fluorescent probe Rhod-2 for the monitoring of cytoplasmic Ca2+ oscillation in cultured cells (see fluorescence images of cells with 1 (top) and Rhod-2 (bottom)).
Egawa, Takahiro,Hirabayashi, Kazuhisa,Koide, Yuichiro,Kobayashi, Chiaki,Takahashi, Naoya,Mineno, Tomoko,Terai, Takuya,Ueno, Tasuku,Komatsu, Toru,Ikegaya, Yuji,Matsuki, Norio,Nagano, Tetsuo,Hanaoka, Kenjiro
supporting information
p. 3874 - 3877
(2013/05/22)

MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF
Agents for modulating methyl modifying enzymes, compositions and uses thereof are provided herein
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Paragraph 00260; 00261; 00431; 00432

(2013/06/05)

Copper-catalyzed oxidative esterification of aldehydes with dialkyl peroxides: Efficient synthesis of esters of tertiary alcohols
Copper-catalyzed oxidative esterification of aldehydes with dialkyl peroxides has been developed. This protocol affords a novel approach for the synthesis of carboxylic esters of tertiary alcohols under mild conditions. Depending on the catalyst system, a variety of tertiary esters were produced in good to excellent yields.
Zhu, Yefeng,Wei, Yunyang
p. 13668 - 13670
(2013/08/23)

Preparation of t-butyl-3-bromo-5-formylbenzoate through selective metal-halogen exchange reactions
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Arredondo, Juan D.,Li, Hongmei,Balsells, Jaume
p. 460 - 470
(2014/04/17)

Synthesis and characterization of perylene-bithiophene-triphenylamine triads: Studies on the effect of alkyl-substitution in p-type NiO based photocathodes
We report the synthesis of new donor-π-acceptor (D-π-A) dyes and their application in dye-sensitized solar cells (DSCs) with nickel(ii) oxide (NiO)-based photocathodes. These D-π-A sensitizers incorporate a triphenylamine donor, a bithiophene π-bridge, and a perylenemonoimide (PMI) acceptor group. Two carboxylate groups attached to the triphenylamine afford strong anchoring to the NiO surface. The dyes in this series were varied firstly by the inclusion of an ethynyl linker between bithiophene and the triphenylamine moieties (1vs. 2), thereby increasing the length of the conjugated bridge. Despite very similar optoelectronic properties, the ethynyl-containing dye 2 showed a ～25% improvement in power conversion efficiency in p-DSCs compared to 1, mostly attributed to the increased current density. Contrary to initial expectations, there was no major influence of the distance between the PMI unit of the dye and the NiO surface on the photoinduced dye anion lifetime, as measured by nanosecond transient absorption spectroscopy (TAS). Furthermore, altering the position of the alkyl chains on the bridging bithiophene in 3 and 4 resulted in a modest red shift in the dye absorption on account of increased charge delocalisation between the PMI and the π-bridge, owing to a reduced torsion angle between the PMI and the adjacent thiophene unit. Quantum-chemical DFT calculations were performed in order to evaluate these torsion angles and to study their influence on the electron density distribution in the relevant molecular orbitals. These changes of the molecular structure of the isomeric dyes 3 and 4 did not translate into improved photovoltaic performance, which is primarily attributed to lower charge photogeneration rates probed by transient absorption spectroscopy. While for p-type DSCs impressive overall solar-to-electric conversion efficiency of 0.04-0.10% under full sun illumination (simulated AM1.5G sunlight, 100 mW cm-2) and a broad incident photon to current efficiency (IPCE) response (350-700 nm) is demonstrated for these new dyes, the study clearly shows the need for judicious design rules for p-type sensitizers for application in photocathodic DSCs.
Weidelener, Martin,Mishra, Amaresh,Nattestad, Andrew,Powar, Satvasheel,Mozer, Attila J.,Mena-Osteritz, Elena,Cheng, Yi-Bing,Bach, Udo,Baeuerle, Peter
p. 7366 - 7379
(2012/06/01)

Asymmetric synthesis of a glucagon receptor antagonist via friedel-crafts alkylation of indole with chiral α-phenyl benzyl cation
Development of a practical asymmetric synthesis of a glucagon receptor antagonist drug candidate for the treatment of type 2 diabetes is described. The antagonist consists of a 1,1,2,2-tetrasubstituted ethane core substituted with a propyl and three aryl groups including a fluoro-indole. The key steps to construct the ethane core and the two stereogenic centers involved a ketone arylation, an asymmetric hydrogenation via dynamic kinetic resolution, and an anti-selective Friedel-Crafts alkylation of a fluoro-indole with a chiral α-phenyl benzyl cation. We also developed two new efficient syntheses of the fluoro-indole, including an unusual Larock-type indole synthesis and a Sugasawa-heteroannulation route. The described convergent synthesis was used to prepare drug substance in 52% overall yield and 99% ee on multikilogram scales.
Chung, John Y. L.,Steinhuebel, Dietrich,Krska, Shane W.,Hartner, Fred W.,Cai, Chaoxian,Rosen, Jonathan,Mancheno, Danny E.,Pei, Tao,Dimichele, Lisa,Ball, Richard G.,Chen, Cheng-Yi,Tan, Lushi,Alorati, Antony D.,Brewer, Sarah E.,Scott, Jeremy P.
p. 1832 - 1845
(2013/01/15)

Squaraine-arylamine sensitizers for highly efficient p-type dye-sensitized solar cells
New near-IR (NIR) squaraine dyes (p-SQ1 and p-SQ2) containing one and two anchoring groups were synthesized and used as the sensitizers of p-type DSSCs. The dye (0.113%) with two anchoring groups (p-SQ2) shows better performance than the dye (0.053%) with only one anchoring group (p-SQ1). Cosensitized p-type DSSCs using two dyes with complementary absorption were tested. They have broadened IPCE spectra and good cell performance.
Chang, Chia-Hao,Chen, Yung-Chung,Hsu, Chih-Yu,Chou, Hsien-Hsin,Lin, Jiann T.
supporting information
p. 4726 - 4729,4
(2020/09/16)

Design, synthesis, and biological evaluation of diminutive forms of (+)-spongistatin 1: Lessons learned
The design, synthesis, and biological evaluation of two diminutive forms of (+)-spongistatin 1, in conjunction with the development of a potentially general design strategy to simplify highly flexible macrocyclic molecules while maintaining biological activity, have been achieved. Examination of the solution conformations of (+)-spongistatin 1 revealed a common conformational preference along the western perimeter comprising the ABEF rings. Exploiting the hypothesis that the small-molecule recognition/binding domains are likely to comprise the conformationally less mobile portions of a ligand led to the design of analogues, incorporating tethers (blue) in place of the CD and the ABCD components of the (+)-spongistatin 1 macrolide, such that the conformation of the retained (+)-spongistatin 1 skeleton would mimic the assigned solution conformations of the natural product. The observed nanomolar cytotoxicity and microtubule destabilizing activity of the ABEF analogue provide support for both the assigned solution conformation of (+)-spongistatin 1 and the validity of the design strategy.
Smith, Amos B.,Risatti, Christina A.,Atasoylu, Onur,Bennett, Clay S.,Liu, Junke,Cheng, Hongsheng,Tendyke, Karen,Xu, Qunli
supporting information; experimental part
p. 14042 - 14053
(2011/11/05)

CRYSTALLINE POLYMORPHIC FORMS OF AN ANTIDIABETIC COMPOUND
The present invention relates to polymorphic forms of a compound of formula A: This compound is useful as a glucagon receptor antagonist and serves as a pharmaceutically active ingredient for the treatment of type 2 diabetes and related conditions, such as hyperglycemia, obesity, dyslipidemia, and the metabolic syndrome. Hydrates, hemihydrates, anhydrates and similar polymorphic forms are included.
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Page/Page column 14

(2010/08/04)

Highly selective and efficient conversion of aryl bromides to t-butyl benzoates with di-t-butyl dicarbonate
t-Butyl benzoates can be accessed from aromatic compounds bearing multiple halogen substituents via selective metal-halogen exchange with lithium tri-n-butylmagnesium ate complex followed by trapping with di-t-butyl dicarbonate.
Li, Hongmei,Balsells, Jaume
p. 2034 - 2037
(2008/09/19)

MODIFIED MALONATE DERIVATIVES
The present invention relates to a novel class of modified malonate derivatives. The modified malonate compounds can be used to treat cancer. The modified malonate compounds can also inhibit histone deacetylase and are suitable for use in selectively inducing terminal differentiation, and arresting cell growth and/or apoptosis of neoplastic cells, thereby inhibiting proliferation of such cells. Thus, the compounds of the present invention are useful in treating a patient having a tumor characterized by proliferation of neoplastic cells. The compounds of the invention may also be useful in the prevention and treatment of TRX-mediated diseases, such as autoimmune, allergic and inflammatory diseases, and in the prevention and/or treatment of diseases of the central nervous system (CNS), such as neurodegenerative diseases. The present invention further provides pharmaceutical compositions comprising the modified malonate derivatives and safe dosing regimens of these pharmaceutical compositions, which are easy to follow, and which result in a therapeutically effective amount of the modified malonate derivatives in vivo.
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Page/Page column 72-73

(2010/11/25)

Design of novel histone deacetylase inhibitors
Histone deacetylase (HDAC) inhibitors that target Class I and Class II HDACs are of synthetic and therapeutic interest and ongoing clinical studies indicate that they show great promise for the treatment of cancer. Moreover, ZolinzaR (vorinostat) was recently approved by the FDA for the treatment of the cutaneous manifestations of cutaneous T-cell lymphoma [Nat. Rev. Drug Disc. 2007, 6, 21]. As part of a broader effort to more fully explore the structure-activity relationships (SAR) of HDAC inhibitors, we sought to identify novel HDAC inhibitor structures through iterative design by utilizing low affinity ligands as synthetic starting points for SAR development. Novel and potent HDAC inhibitors have been identified using this approach and herein we report the optimization of the recognition elements of a novel series of malonyl-derived HDAC inhibitors.
Siliphaivanh, Phieng,Harrington, Paul,Witter, David J.,Otte, Karin,Tempest, Paul,Kattar, Sam,Kral, Astrid M.,Fleming, Judith C.,Deshmukh, Sujal V.,Harsch, Andreas,Secrist, Paul J.,Miller, Thomas A.
p. 4619 - 4624
(2008/02/11)

Low-Temperature Formation of Functionalized Grignard Reagents from Direct Oxidative Addition of Active Magnesium to Aryl Bromides
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Lee, Jun-Sik,Velarde-Ortiz, Raffet,Guijarro, Albert,Wurst, Joshua R.,Rieke, Reuben D.
p. 5428 - 5430
(2007/10/03)

Structure-activity relationships of novel 2-substituted quinazoline antibacterial agents
High-throughput screening of in-house compound libraries led to the discovery of a novel antibacterial agent, compound 1 (MIC: 12-25 μM against S. pyogenes). In an effort to improve the activity of this active compound, a series of 2-substituted quinazolines was synthesized and evaluated in several antibacterial assays. One such compound (22) displayed improved broad- spectrum antibacterial activity against a variety of bacterial strains. This molecule also inhibited transcription/translation of bacterial RNA, suggesting a mechanism for its antibiotic effects. Structure-activity relationship studies of 22 led to the synthesis of another 24 compounds. Although some of these molecules were found to be active in bacterial growth assays, none were as potent as 22. Compound 22 was tested for its ability to cure a systemic K. pneumonia infection in the mouse and displayed moderate effects compared with a control antibiotic, gentamycin.
Kung, Pei-Pei,Casper, Martin D.,Cook, Kimberley L.,Wilson-Lingardo, Laura,Risen, Lisa M.,Vickers, Timothy A.,Ranken, Ray,Blyn, Lawrence B.,Wyatt, Jacqueline R.,Cook, P. Dan,Ecker, David J.
p. 4705 - 4713
(2007/10/03)

Highly Selective Adenosine A2 Receptor Agonists in a Series of N-Alkylated 2-Aminoadenosines
A wide variety of 2-substituted aminoadenosines were prepared for comparison with the moderately A2 receptor selective adenosine agonist 2-anilinoadenosine (CV-1808).High selectivity combined with significant affinity at the A2 receptor in rat membranes was observed for those amines bearing a two-carbon chain to which was attached an aryl, heteroaryl, or alicyclic moiety. 2-(2-Phenethylamino)adenosine (3d), a 14-fold A2 selective compound, was modified by introduction of a variety of substituents in the benzene ring and the side chain.Some of these changes led to improved A2 affinity and increased selectivity.Replacement of the phenyl moiety by cyclohexenyl produced a 210-fold selective agonist 3ag (CGS 22989) whereas the cyclohexanyl analogue 3af (CGS 22492) was 530-fold selective at the A2 site.These compounds showed hypotensive activity in rat models over a range of doses without the bradycardia observed with less selective agonists.
Francis, John E.,Webb, Randy L.,Ghai, Geetha R.,Hutchison, Alan J.,Moskal, Michael A.,et al.
p. 2570 - 2579
(2007/10/02)

Convergent and efficient palladium-effected synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF)
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Taylor,Wong
p. 3618 - 3624
(2007/10/02)

Process for the preparation of fused pyridine compounds
2-Amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-en-1-yl]pyrido[2,3,-d]pyrimidines and 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-yn-1-yl]pyrido[2,3-d]pyrimidines are prepared through the reaction of a haloaromatic compound and an unsaturated compound in the presence of a palladium catalyst. The products are chemical intermediates for the preparation of antineoplastic agents. A typical embodiment is the reaction of a protected 2-amino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine and an ester of 4-iodobenzoic acid.
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(2008/06/13)