cas 66739-89-7, 2-(4-CYANOPHENYL)-1 3-DIOXOLANE

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A nitroolefin functionalized DPP fluorescent probe for the selective detection of hydrogen sulfide
In this paper, a nitroolefin functionalized probe DPP-NO2 was designed and synthesized as a selective fluorescent probe for detection of hydrogen sulfide (H2S). The specific reduction reaction between the nitro group and H2/sub
Wang, Lingyun,Chen, Xianggen,Cao, Derong
p. 3367 - 3373
(2017)
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A Colorimetric and Fluorescent Probe Based on Michael Acceptor Type Diketopyrrolopyrrole for Cyanide Detection
A new probe 1 was synthesized by incorporating an α,β-unsaturated ketone to a diketopyrrolopyrrole fluorophore. The probe exhibited a selective and sensitive response to cyanide against other anions. Addition of CN? aqueous solution to 1 result
Wang, Lingyun,Zhuo, Shaochun,Cao, Derong
p. 1 - 8
(2017)
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Porosity-induced emission: exploring color-controllable fluorescence of porous organic polymers and their chemical sensing applications
Most organic dyes dissipate their excitation energy in the aggregated state because of the "aggregation-caused quenching" effect, deteriorating their application in optoelectronic devices. To prevent the "aggregation-caused quenching" effect, we incorpora
Li, Yankai,Bi, Shiming,Liu, Fei,Wu, Shengying,Hu, Jun,Wang, Limin,Liu, Honglai,Hu, Ying
p. 6876 - 6881
(2015)
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Synthesis and remarkable mechano- and thermo-hypsochromic luminescence of a new type of DPP-based derivative
Owing to academic significance and potential applications, mechanofluorochromism has attracted much research interest. However, among the hundreds of mechanofluorochromic organic and metallorganic compounds reported to date, those with high contrast, mult
Liu, Zhongwei,Zhang, Kai,Sun, Qikun,Zhang, Zhenzhen,Tang, Liangliang,Xue, Shanfeng,Chen, Dongmei,Zhang, Haichang,Yang, Wenjun
p. 1377 - 1383
(2018)
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A colorimetric probe based on diketopyrrolopyrrole and tert-butyl cyanoacetate for cyanide detection
A new colorimetric probe 1 comprising a diketopyrrolopyrrole-based Michael receptor, which recognized cyanide anions with high selectivity, was designed and synthesized. Addition of CN- aqueous solution to 1 in THF resulted in a rapid color cha
Wang, Lingyun,Zhu, Linhui,Cao, Derong
p. 7211 - 7218
(2015)
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A cyanide-selective colorimetric "naked-eye" and fluorescent chemosensor based on a diketopyrrolopyrrole-hydrazone conjugate and its use for the design of a molecular-scale logic device
A novel diketopyrrolopyrrole (DPP)-hydrazone based receptor 1 was designed and synthesized as a selective fluorescent and colorimetric chemosensor for cyanide without interference from other common anions including fluoride and acetate. The spectral respo
Wang, Lingyun,Chen, Xianggen,Cao, Derong
p. 96676 - 96685
(2016)
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Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization
Alkenes, ethers, and alcohols account for a significant percentage of bulk reagents available to the chemistry community. The petrochemical, pharmaceutical, and agrochemical industries each consume gigagrams of these materials as fuels and solvents each year. However, the utilization of such materials as building blocks for the construction of complex small molecules is limited by the necessity of prefunctionalization to achieve chemoselective reactivity. Herein, we report the implementation of efficient, sustainable, diaryl ketone hydrogen-atom transfer (HAT) catalysis to activate native C-H bonds for multicomponent dicarbofunctionalization of alkenes. The ability to forge new carbon-carbon bonds between reagents typically viewed as commodity solvents provides a new, more atom-economic outlook for organic synthesis. Through detailed experimental and computational investigation, the critical effect of hydrogen bonding on the reactivity of this transformation was uncovered.
Campbell, Mark W.,Yuan, Mingbin,Polites, Viktor C.,Gutierrez, Osvaldo,Molander, Gary A.
supporting information
p. 3901 - 3910
(2021/04/06)

Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation
Monosubstituted ureas are important scaffolds in organic chemistry. They appear in various biologically active compounds and serve as versatile precursors in synthesis. Monosubstituted ureas were originally prepared using toxic and hazardous phosgene equivalents. Modern methods include transamidation of urea and nucleophilic addition to cyanate salts, both of which suffer from a narrow substrate scope due to the need for a strong acid and prolonged reaction times. We hereby report that ammonium chloride can promote the reaction between amines and potassium cyanate to generate monosubstituted ureas in water. This method proceeds rapidly under microwave irradiation and tolerates a broad range of functional groups. Unlike previous strategies, it is compatible with other nucleophiles, acid-labile moieties, and most of the common protecting groups. The products precipitate out of solution, allowing facile isolation without column chromatography.
Lan, Chunling Blue,Auclair, Karine
supporting information
p. 5135 - 5146
(2021/10/19)

Ester compound based on pyrrolopyrrolediketone and having solid-liquid double fluorescence and application
The invention discloses an ester compound based on pyrrolopyrrolediketone and having solid-liquid double fluorescence, which has the following structural general formula; wherein the R1, R2, R3, R4 and R5 are respectively and independently selected from h
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Paragraph 0037-0039

(2021/03/13)

Beauty in chemistry: A self-organized and dual-phase emissive diketopyrrolopyrrole derivative as high-yield fluorescent material
In the long-span human history, “beauty” has always been the ultimate pursuit of mankind's civilization. In this work, we report the synthesis of a beautiful fluorescent material based on an old-brand pigment named diketopyrrolopyrrole (DPP) with a high y
Han, Jianwei,Sun, Xinyu,Wang, Limin,Yang, Qingying
(2021/08/03)

Pyrrole-pyrroledione-based derivative fluorescent probe and application thereof
The invention discloses a pyrrole-pyrrole-dione-based derivative as shown in the formula I. R Is selected from - CH. 3 . - (CH)2 )n CH3 , (CH)2 )m CH2 X, CH (CH)3 )su
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Paragraph 0029-0031

(2021/11/19)

Discovery of Selective Small-Molecule Inhibitors for the ENL YEATS Domain
Eleven-nineteen leukemia (ENL) protein is a histone acetylation reader essential for disease maintenance in acute leukemias, in particular, the mixed-lineage leukemia (MLL)-rearranged leukemia. In this study, we carried out high-throughput screening of a small-molecule library to identify inhibitors for the ENL YEATS domain. Structure-activity relationship studies of the hits and structure-based inhibitor design led to two compounds, 11 and 24, with IC50 values below 100 nM in inhibiting the ENL-acetyl-H3 interaction. Both compounds, and their precursor compound 7, displayed strong selectivity toward the ENL YEATS domain over all other human YEATS domains. Moreover, 7 exhibited on-target inhibition of ENL in cultured cells and a synergistic effect with the bromodomain and extraterminal domain inhibitor JQ1 in killing leukemia cells. Together, we have developed selective chemical probes for the ENL YEATS domain, providing the basis for further medicinal chemistry-based optimization to advance both basic and translational research of ENL.
Ma, Xinyu R.,Xu, Longxia,Xu, Shiqing,Klein, Brianna J.,Wang, Hongkuan,Das, Sukant,Li, Kuai,Yang, Kai S.,Sohail, Sana,Chapman, Andrew,Kutateladze, Tatiana G.,Shi, Xiaobing,Liu, Wenshe Ray,Wen, Hong
p. 10997 - 11013
(2021/08/03)

BENZIMIDAZOLE COMPOUNDS AND USE THEREOF FOR TREATING ALZHEIMER'S DISEASE OR HUNTINGTON'S DISEASE
Benzimidazole compounds of formula (I), shown below, are disclosed. The compounds are potent human glutaminyl cyclase inhibitors. Also disclosed is a pharmaceutical composition containing one of these compounds and a pharmaceutical acceptable carrier, as well as a method of treating Alzheimer's disease or Huntington's disease by administering to a subject in need thereof an effective amount of such a compound.
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Paragraph 0038; 0047; 0209-0210

(2020/03/23)

Donor-acceptor covalent organic frameworks of nickel(ii) porphyrin for selective and efficient CO2reduction into CO
Donor-acceptor two-dimensional covalent organic frameworks, PD-COF-23 and PD-COF-23-Ni, are constructed and applied for selective CO2 reduction with CO conversion rates of 20.9 μmol g-1 h-1 and 40.0 μmol g-1 h-1, respectively, in the absence of any additional photosensitizers and noble metal co-catalysts within an operation time of 25 h. The multilayer nanosheet structure, efficient charge separation and transport, and internal reductive quenching cycle of the NiTAPP fragments of PD-COF-23-Ni result in its higher photocatalytic efficiency than that of PD-COF-23. This journal is
Diao, Yingxue,Ke, Hanzhong,Qin, Xihao,Xu, Nanfeng,Xu, Zhengtao,Zhu, Xunjin
supporting information
p. 15587 - 15591
(2020/11/24)

BENZIMIDAZOLE COMPOUNDS AND USE THEREOF FOR TREATING ALZHEIMER'S DISEASE OR HUNTINGTON'S DISEASE
Benzimidazole compounds of formula (I), shown below, are disclosed. The compounds are potent human glutaminyl cyclase inhibitors. Also disclosed is a pharmaceutical composition containing one of these compounds and a pharmaceutical acceptable carrier, as well as a method of treating Alzheimer's disease or Huntington's disease by administering to a subject in need thereof an effective amount of such a compound.
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Page/Page column 13; 20; 21; 59

(2020/03/23)

FUNGICIDAL OXADIAZOLES
Disclosed are compounds of Formula 1, including all geometric and stereoisomers, tautomers, N-oxides, and salts thereof, wherein R1, L and J are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.
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Paragraph 0646-0647

(2020/06/07)

Transformation of aromatic bromides into aromatic nitriles with n-BuLi, pivalonitrile, and iodine under metal cyanide-free conditions
Various aromatic nitriles could be obtained in good yields by the treatment of aryl bromides with n-butyllithium and then pivalonitrile, followed by the treatment with molecular iodine at 70 °C, without metal cyanides under transition-metal-free conditions. The present reaction proceeds through the radical β-elimination of imino-nitrogen-centered radicals formed from the reactions of imines and N-iodoimines under warming conditions.
Uchida, Ko,Togo, Hideo
(2019/09/04)

Identification and Structure–Activity Relationship (SAR) of potent and selective oxadiazole-based agonists of sphingosine-1-phosphate receptor (S1P1)
Agonism of S1P1 receptor has been proven to be responsible for peripheral blood lymphopenia and elicts the identification of various S1P1 modulators. In this paper we described a series of oxadiazole-based S1P1 direct-acting agonists disubstituted on terminal benzene ring, with high potency for S1P1 receptor and favorable selectivity against S1P3 receptor. In addition, two representative agents named 16-3b and 16-3g demonstrated impressive efficacy in lymphocyte reduction along with reduced effect on heart rate when orally administered. Furthermore, these compounds have been shown to possess desired pharmacokinetic (PK) and physicochemical profiles. The binding mode between 16-3b and the activated S1P1 model was also studied.
Liu, Tianqi,Jin, Jing,Chen, Yonghui,Xi, Qiumu,Hu, Jinping,Jia, Wenqiang,Chen, Xiaoguang,Li, Yan,Wang, Xiaojian,Yin, Dali
p. 41 - 57
(2018/10/02)

Liquid-phase hydrogenation of nitriles to amines facilitated by a co(ii)/zn(0) pair: a ligand-free catalytic protocol
The given report introduces a simple and user-friendly in situ method for the production of catalytically active cobalt particles. The approach circumvents the use of air-and moisture-sensitive reductants as well as the application of anhydrous Co-precursor salts. Accordingly, the described catalytic system is readily assembled under open-flask conditions by simply combining the components in the reaction vessel. Therefore, the arduous charging procedure of the reaction autoclave in a glovebox under an inert gas atmosphere is no longer necessary. In fact, the catalytically active material is obtained upon treatment of readily available Co(OAc)2·4 H2O with benign commercial Zn powder. The catalytic performance of the resultant material was tested in the heterogeneous hydrogenation of nitriles to the corresponding primary amines. Both activity and selectivity of the cobalt catalyst are significantly enhanced if a triflate-based Lewis acid and ammonia is added to the reaction mixture.
Timelthaler, Daniel,Topf, Christoph
p. 11604 - 11611
(2019/10/02)

Pyrrolopyrrole diketone-based derivative as well as preparation method and application thereof
The invention discloses a pyrrolopyrrole diketone-based derivative which has a structural general formula shown in the description, in the formula, R is a substituted or unsubstituted alkyl group, a heterocyclic group, an aryl group or a heteroaryl group.
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Paragraph 0050-0052

(2020/01/03)

Carboxylic acid compound containing diphenyl oxadiazole, and preparation method and medical application of compound
The invention relates to the field of medicinal chemistry, and particularly relates to a carboxylic acid compound (I) containing a diphenyl oxadiazole skeleton, a preparation method and pharmaceuticalpreparation of the compound, and a use of the compound
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Paragraph 0499-0505

(2019/07/16)

Structural and chemical insights into the covalent-allosteric inhibition of the protein kinase Akt
The Ser/Thr kinase Akt (Protein Kinase B/PKB) is a master switch in cellular signal transduction pathways. Its downstream signaling influences cell proliferation, cell growth, and apoptosis, rendering Akt a prominent drug target. The unique activation mechanism of Akt involves a change of the relative orientation of its N-terminal pleckstrin homology (PH) and the kinase domain and makes this kinase suitable for highly specific allosteric modulation. Here we present a unique set of crystal structures of covalent-allosteric interdomain inhibitors in complex with full-length Akt and report the structure-based design, synthesis, biological and pharmacological evaluation of a focused library of these innovative inhibitors.
Uhlenbrock, Niklas,Smith, Steven,Weisner, J?rn,Landel, Ina,Lindemann, Marius,Le, Thien Anh,Hardick, Julia,Gontla, Rajesh,Scheinpflug, Rebekka,Czodrowski, Paul,Janning, Petra,Depta, Laura,Quambusch, Lena,Müller, Matthias P.,Engels, Bernd,Rauh, Daniel
p. 3573 - 3585
(2019/03/28)

Thienopyrimidinone Derivatives That Inhibit Bacterial tRNA (Guanine37- N1)-Methyltransferase (TrmD) by Restructuring the Active Site with a Tyrosine-Flipping Mechanism
Among the >120 modified ribonucleosides in the prokaryotic epitranscriptome, many tRNA modifications are critical to bacterial survival, which makes their synthetic enzymes ideal targets for antibiotic development. Here we performed a structure-based design of inhibitors of tRNA-(N1G37) methyltransferase, TrmD, which is an essential enzyme in many bacterial pathogens. On the basis of crystal structures of TrmDs from Pseudomonas aeruginosa and Mycobacterium tuberculosis, we synthesized a series of thienopyrimidinone derivatives with nanomolar potency against TrmD in vitro and discovered a novel active site conformational change triggered by inhibitor binding. This tyrosine-flipping mechanism is uniquely found in P. aeruginosa TrmD and renders the enzyme inaccessible to the cofactor S-adenosyl-l-methionine (SAM) and probably to the substrate tRNA. Biophysical and biochemical structure-activity relationship studies provided insights into the mechanisms underlying the potency of thienopyrimidinones as TrmD inhibitors, with several derivatives found to be active against Gram-positive and mycobacterial pathogens. These results lay a foundation for further development of TrmD inhibitors as antimicrobial agents.
Zhong, Wenhe,Pasunooti, Kalyan Kumar,Balamkundu, Seetharamsing,Wong, Yee Hwa,Nah, Qianhui,Gadi, Vinod,Gnanakalai, Shanmugavel,Chionh, Yok Hian,McBee, Megan E.,Gopal, Pooja,Lim, Siau Hoi,Olivier, Nelson,Buurman, Ed T.,Dick, Thomas,Liu, Chuan Fa,Lescar, Julien,Dedon, Peter C.
p. 7788 - 7805
(2019/10/11)

Sphingol-1-phosphoric acid receptor modulator compound as well as preparation method and application thereof
The invention relates to a sphingol-1-phosphoric acid receptor modulator compound as well as a preparation method and application thereof, and specifically provides the compound shown in the formula (I), a racemate thereof, a stereisomer, a tautomer, a solvate, an aquo-complex or pharmacologically acceptable salt thereof. The formula is shown in the description.
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Paragraph 0074-0077

(2018/07/30)

FUNGICIDAL OXADIAZOLES
Disclosed are compounds of Formula 1, including all geometric and stereoisomers, tautomers, N-oxides, and salts thereof, wherein R1, A, and J are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.
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Page/Page column 56

(2018/07/29)

Mild, Redox-Neutral Formylation of Aryl Chlorides through the Photocatalytic Generation of Chlorine Radicals
We report a redox-neutral formylation of aryl chlorides that proceeds through selective 2-functionalization of 1,3-dioxolane through nickel and photoredox catalysis. This scalable benchtop approach provides a distinct advantage over traditional reductive carbonylation in that no carbon monoxide, pressurized gas, or stoichiometric reductant is employed. The mild conditions give unprecedented scope from abundant and complex aryl chloride starting materials.
Nielsen, Matthew K.,Shields, Benjamin J.,Liu, Junyi,Williams, Michael J.,Zacuto, Michael J.,Doyle, Abigail G.
p. 7191 - 7194
(2017/06/13)

Tetraphenylethene-functionalized diketopyrrolopyrrole solid state emissive molecules: Enhanced emission in the solid state and as a fluorescent probe for cyanide detection
Two conjugates of tetraphenylethene (TPE) and diketopyrrolopyrrole (DPP) were synthesized and their fluorescence properties were investigated. Both DPP1 and DPP2 show intense fluorescence and large Stokes shifts in both solution and solid state. In dilute
Wang, Lingyun,Zhu, Linhui,Li, Lin,Cao, Derong
p. 55182 - 55193
(2016/07/06)

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY
The present invention relates to compounds acting both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists, to processes for their preparation, to compositions comprising them, to therapeutic uses and combinations with other pharmaceutical active ingredients.
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Page/Page column 57

(2016/12/22)

Dynamic Covalent Assembly of Peptoid-Based Ladder Oligomers by Vernier Templating
Dynamic covalent chemistry, in conjunction with template-directed assembly, enables the fabrication of extended nanostructures that are both precise and tough. Here we demonstrate the dynamic covalent assembly of peptoid-based molecular ladders with up to 12 rungs via scandium(III)-catalyzed imine metathesis by employing the principle of Vernier templating, where small precursor units with mismatched numbers of complementary functional groups are coreacted to yield larger structures with sizes determined by the respective precursor functionalities. Owing to their monomer diversity and synthetic accessibility, sequence-specific oligopeptoids bearing dynamic covalent pendant groups were employed as precursors for molecular ladder fabrication. The generated structures were characterized using matrix-assisted laser desorption/ionization mass spectrometry and gel permeation chromatography, confirming successful molecular ladder fabrication.
Wei, Tao,Jung, Jae Hwan,Scott, Timothy F.
supporting information
p. 16196 - 16202
(2016/01/15)

Discovery of A-971432, an orally bioavailable selective sphingosine-1-phosphate receptor 5 (S1P5) agonist for the potential treatment of neurodegenerative disorders
S1P5 is one of 5 receptors for sphingosine-1-phosphate and is highly expressed on endothelial cells within the blood-brain barrier, where it maintains barrier integrity in in vitro models (J. Neuroinflamm. 2012, 9, 133). Little more is known about the effects of S1P5 modulation due to the absence of tool molecules with suitable selectivity and drug-like properties. We recently reported that molecule A-971432 (Harris et al., 2010) (29 in this paper) is highly efficacious in reversing lipid accumulation and age-related cognitive decline in rats (Van der Kam, et al., AAIC 2014). Herein we describe the development of a series of selective S1P5 agonists that led to the identification of compound 29, which is highly selective for S1P5 and has excellent plasma and CNS exposure after oral dosing in preclinical species. To further support its suitability for in vivo studies of S1P5 biology, we extensively characterized 29, including confirmation of its selectivity in pharmacodynamic assays of S1P1 and S1P3 function in rats. In addition, we found that 29 improves blood-brain barrier integrity in an in vitro model and reverses age-related cognitive decline in mice. These results suggest that S1P5 agonism is an innovative approach with potential benefit in neurodegenerative disorders involving lipid imbalance and/or compromised blood-brain barrier such as Alzheimer's disease or multiple sclerosis.
Hobson, Adrian D.,Harris, Christopher M.,Van Der Kam, Elizabeth L.,Turner, Sean C.,Abibi, Ayome,Aguirre, Ana L.,Bousquet, Peter,Kebede, Tegest,Konopacki, Donald B.,Gintant, Gary,Kim, Youngjae,Larson, Kelly,Maull, John W.,Moore, Nigel S.,Shi, Dan,Shrestha, Anurupa,Tang, Xiubo,Zhang, Peng,Sarris, Kathy K.
p. 9154 - 9170
(2015/12/23)

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY
The present invention relates to compounds acting both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists, to processes for their preparation, to compositions comprising them, to therapeutic uses and combinations with other pharmaceutical active ingredients.
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Page/Page column 93; 94

(2014/06/24)

Detection of HSO4 - Ion based on the hydrolysis of diketopyrrolopyrrole-derived schiff base with chromogenic and fluorogenic dual signals
A new diketopyrrolopyrrole-based Schiff base L was synthesized and its anion sensing behavior was explored. L showed exclusive response toward HSO 4 - ion and also distinguished HSO4 - from other anions by color changes (from dark red to orange) and 21 fold fluorescence enhancement at 370 nm in aqueous solution (THF/H 2O=8/1, v/v). The sensing mechanism was suggested to proceed via a hydrolysis process. The results provided colorimetric and fluorimetric assays to selectively detect the presence of a HSO4 - over a wide range of other interfering anions. The results could potentially be used as a dual colorimetric-fluorescent probe for monitoring HSO4 - levels in physiological and environmental systems.
Wang, Lingyun,Yang, Lingling,Cao, Derong
p. 1347 - 1355
(2014/07/22)

Selective inhibitors of bacterial t-RNA-(N1G37) methyltransferase (TrmD) that demonstrate novel ordering of the lid domain
The tRNA-(N1G37) methyltransferase (TrmD) is essential for growth and highly conserved in both Gram-positive and Gram-negative bacterial pathogens. Additionally, TrmD is very distinct from its human orthologue TRM5 and thus is a suitable target for the design of novel antibacterials. Screening of a collection of compound fragments using Haemophilus influenzae TrmD identified inhibitory, fused thieno-pyrimidones that were competitive with S-adenosylmethionine (SAM), the physiological methyl donor substrate. Guided by X-ray cocrystal structures, fragment 1 was elaborated into a nanomolar inhibitor of a broad range of Gram-negative TrmD isozymes. These compounds demonstrated no activity against representative human SAM utilizing enzymes, PRMT1 and SET7/9. This is the first report of selective, nanomolar inhibitors of TrmD with demonstrated ability to order the TrmD lid in the absence of tRNA.
Hill, Pamela J.,Abibi, Ayome,Albert, Robert,Andrews, Beth,Gagnon, Moriah M.,Gao, Ning,Grebe, Tyler,Hajec, Laurel I.,Huang, Jian,Livchak, Stephania,Lahiri, Sushmita D.,McKinney, David C.,Thresher, Jason,Wang, Hongming,Olivier, Nelson,Buurman, Ed T.
supporting information
p. 7278 - 7288
(2013/10/21)

Synthesis of tris-hydroxymethyl-based nitrone derivatives with highly reactive nitronyl carbon
A novel series of α-phenyl-N-tert-butyl nitrone derivatives, bearing a hydrophobic chain on the aromatic ring and three hydroxyl functions on the tert-butyl group, was synthesized through a short and convenient synthetic route based on a one-pot reduction/condensation of tris(hydroxymethyl)nitromethane with a benzaldehyde derivative. Because of the presence of hydroxyl functions on the tert-butyl group, an intramolecular Forrester-Hepburn reaction leading to the formation of an oxazolidine-N-oxyl compound was observed by electron paramagnetic resonance (EPR). The mechanism of cyclization was further studied by computational methods showing that intramolecular hydrogen bonding and high positive charge on the nitronyl carbon could facilitate the nucleophilic addition of a hydroxyl group onto the nitronyl carbon. At high nitrone concentrations, a second paramagnetic species, very likely formed by intermolecular nucleophilic addition of two nitrone molecules, was also observed but to a lesser extent. In addition, theoretical data confirmed that the intramolecular reaction is much more favored than the intermolecular one. These nitrones were also found to efficiently trap carbon-centered radicals, but complex spectra were observed due to the presence of oxazolidine-N-oxyl derivatives.
Choteau, Fanny,Tuccio, Beatrice,Villamena, Frederick A.,Charles, Laurence,Pucci, Bernard,Durand, Gregory
scheme or table
p. 938 - 948
(2012/03/11)

Synthesis and anticonvulsant activities of (R)-N-(4′-substituted) benzyl 2-acetamido-3-methoxypropionamides
The structure-activity relationship (SAR) for the N-benzyl group in the clinical antiepileptic agent (R)-lacosamide [(R)-N-benzyl 2-acetamido-3- methoxypropionamide, (R)-3] has been explored. Forty-three compounds were prepared and then evaluated at the National Institute of Neurological Disorders and Stroke Anticonvulsant Screening Program for seizure protection in the maximal electroshock (MES) and subcutaneous Metrazol models. Comparing activities for two series of substituted aryl regioisomers (2′, 3′, 4′) showed that 4′-modified derivatives had the highest activity. Significantly, structural latitude existed at the 4′-site. The SAR indicated that nonbulky 4′-substituted (R)-3 derivatives exhibited superb activity, independent of their electronic properties. Activities in the MES test of several compounds were comparable with or exceeded that of (R)-3 and surpassed the activities observed for the traditional antiepileptic agents phenytoin, phenobarbital, and valproate. 2009 American Chemical Society.
Salomé, Christophe,Salomé-Grosjean, Elise,Park, Ki Duk,Morieux, Pierre,Swendiman, Robert,DeMarco, Erica,Stables, James P.,Kohn, Harold
supporting information; experimental part
p. 1288 - 1305
(2010/07/10)

Amphiphilic amide nitrones: A new class of protective agents acting as modifiers of mitochondrial metabolism
Our group has demonstrated that the amphiphilic character of α-phenyl-N-tert-butyl nitrone based agents is a key feature in determining their bioactivity and protection against oxidative toxicity. In this work, we report the synthesis of a new class of am
Durand, Grégory,Poeggeler, Burkhard,Ortial, Stéphanie,Polidori, Ange,Villamena, Frederick A.,B?ker, Jutta,Hardeland, Rüdiger,Pappolla, Miguel A.,Pucci, Bernard
scheme or table
p. 4849 - 4861
(2010/10/19)

AGONISTS AND ANTAGONISTS OF THE S1P5 RECEPTOR, AND METHODS OF USES THEREOF
Disclosed are compounds that are agonists or antagonists of the S1P5 receptor, compositions comprising said compounds, and methods of using said compounds and compositions. In certain embodiments, said compounds are 1-benzylazetidine-3-carboxylic acid derivatives. In certain embodiments, said methods relate to the treatment of neuropatic pain and/or a neurodegenerative disorder. In certain embodiments, said compounds may be used in combination with a second therapeutic agent.
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Page/Page column 106

(2010/09/03)

PYRAZOLE-I, 2, 4 -OXAD IAZOLE DERIVATIVES AS S.PHING0SINE-1-PH0SPHATE AGONISTS
Disclosed are compounds of Formula (I) or a pharmaceutically acceptable salt thereof, wherein: n is zero or an integer selected from 1 through 4; R1 is cycloalkyl, aryl, heteroaryl, or heterocyclyl, each optionally substituted with one to five substituents independently selected from C1 to C6 alkyl, C1 to C4 haloalkyl, benzyl, OR4, and/or halogen; and R2, R3, R4, and n are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.
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Page/Page column 48

(2010/08/08)

NOVEL AMPHIPHILIC DERIVATIVES OF ALPHA-C-PHENYL-N-TERT-BUTYLNITRONE
Compounds derived from α-C-phenyl-N-tert-butylnitrone, a process for the preparation thereof and use thereof for the preparation of medicaments for use in preventing or treating oxidative stress-related diseases.
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Page/Page column 7; sheet 2

(2009/12/24)

Synthesis of α,α-difluoro-β-amino esters or gem-difluoro-β-lactams as potential metallocarboxypeptidase inhibitors
The synthesis of gem-difluorinated β-lactams and gem-difluorinated β-amino acids, each possessing a potential basic functional group, from ethyl bromodifluoroacetate and either imines (for β-lactams) or N-(α-aminoalkyl)benzotriazoles (for β-amino esters) was investigated. A series of these compounds were used for the design of novel metallocarboxypeptidase inhibitors. N-Alkylation and N-acylation of these two versatile scaffolds were carried out, leading to the expected targets in moderate to good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Boyer, Nicolas,Gloanec, Philippe,De Nanteuil, Guillaume,Jubault, Philippe,Quirion, Jean-Charles
experimental part
p. 4277 - 4295
(2009/04/10)

Amine Compounds
There is provided a compound exhibiting an activity of suppressing immune response with reduced adverse drug reactions, which compound is useful in the chemotherapy for preventing or treating, for example, a wide range of various autoimmune diseases including systemic erythematodes, chronic rheumatoid arthritis, Type I diabetes, inflammatory bowel disease, biliary cirrhosis, uveitis, multiple sclerosis or other disorders, or chronic inflammatory diseases, or cancers, lymphoma or leukemia, or resistance to organ or tissue transplantation or rejection against transplantation. Novel amine compounds having an S1P1/Edg1 receptor agonist effect, possible stereoisomers or racemic bodies of the compounds, or pharmacologically acceptable salts, hydrates or solvates of the compound, the stereoisomers or the racemic bodies, or prodrugs of the compounds, the stereoisomers, the racemic bodies, the salts, the hydrates or the solvates, are provided.
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Page/Page column 171

(2008/12/08)

A simple and efficient synthesis of new mono- and bis([1,2,4]-oxadiazol)- benzaldehyde building blocks
An efficient approach to bis([1,2,4]-oxadiazol)benzaldehydes as well as the corresponding mono-benzaldehyde derivatives has been developed starting from benzamidoxime, which is readily obtained from 4-cyanobenzaldehyde. All these new compounds were synthe
Crestey, Francois,Lebargy, Cyril,Lasne, Marie-Claire,Perrio, Cecile
p. 3406 - 3410
(2008/09/20)

The fluorescence labelling of primary amines with perylenetetracarboxdiimides
The synthesis of perylenetetracarboxdiimide-labelled aldehydes is described as well as their condensation with primary amines. Thus, a highly fluorescent and light-fast fluorescence labelling process has been demonstrated. Application of this method to bi
Langhals, Heinz,Becherer, Thomas,Lindner, Joerg,Obermeier, Andreas
p. 4328 - 4336
(2008/04/13)

INHIBITORS OF AKT ACTIVITY
The present invention is directed to compounds which contain substituted naphthyridines which inhibit the activity of Akt, a serine/threonine protein kinase. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for treating cancer comprising administration of the compounds of the invention. These substituted naphthyridines have unexpected advantageous properties when compared to other naphthyridines reported in PCT publication WO2003/086394, such unexpected advantageous properties may include increased cellular potency/solubility, greater selectivity, enhanced pharmacokinetic properties, lack of off target activity and so on.
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Page/Page column 42-43; 55

(2010/11/08)

INHIBITORS OF AKT ACTIVITY
The instant invention provides for compounds that inhibit Akt activity. In particular, the compounds disclosed selectively inhibit one or two of the Akt isoforms. The invention also provides for compositions comprising such inhibitory compounds and method
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Page/Page column 38

(2008/06/13)

INHIBITORS OF AKT ACTIVITY
The instant invention provides for substituted naphthyridine compounds that inhibit Akt activity. In particular, the compounds disclosed selectively inhibit one or two of the Akt isoforms. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting Akt activity by administering the compound to a patient in need of treatment of cancer.
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Page/Page column 80

(2010/11/25)

AMIDE COMPOUND AND METHOD OF CONTROLLING PLANT DISEASE WITH THE SAME
A amid compound of the formula (1): wherein, in the formula, R51 represents a halogen atom, a C1-C6 alkyl group and the like; R52 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group and the like; R53 represents a halogen atom and the like; R56 represents a halogen atom and the like; R57 represents a hydrogen atom and the like; R58 and R59 independently represent a hydrogen atom, a C1-C3 alkyl group and the like; R60 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group, or a C3-C6 alkynyl group; R61 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group or a C3-C6 alkynyl group or a C2-C4 cyanoalkyl group; R62, R63 and R64 represent a hydrogen atom, a halogen atom and the like; X represents a oxygen atom or a sulfur atom; has an excellent activity against plant diseases.
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Page/Page column 110

(2010/02/14)

Synthesis of photoswitchable hemithioindigo-based ω-amino acids and application in Boc-based peptide assembly
Efficient procedures for the preparation of the N-Boc-protected aldehydes 5a and 5b are described which are valuable precursors for the synthesis of hemithioindigo-based ω-amino acids and peptides. Georg Thieme Verlag Stuttgart.
Herre, Stephan,Steinle, Wencke,Rueck-Braun, Karola
p. 3297 - 3300
(2007/10/03)

INHIBITORS OF AKT ACTIVITY
The present invention is directed to compounds which contain substituted pyridazines and pyrimidines moieties which inhibit the activity of Akt, a serine/threonine protein kinase. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for treating cancer comprising administration of the compounds of the invention.
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Page/Page column 49

(2010/02/14)

NOVEL METHODS FOR THE TREATMENT OF INFLAMMATORY DISEASES
Methods of inhibiting the cytokine or biological activity of Macrophage Migration Inhibitory Factor (MIF) comprising contacting MIF with a compound of formula (I) are provided. The invention also relates to methods of treating diseases or conditions where MIF cytokine or biological activity is implicated comprising administration of compounds of formula (I), either alone or as a part of combination therapy. Novel compounds of formula (I) are also provided for.
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Page 90

(2010/02/09)