- A strong hydride donating, acid stable and reusable 1,4-dihydropyridine for selective aldimine and aldehyde reductions
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A 1,4-dihydropyridine derivative, lacking carbonyl groups and containing bulky aryl substituents, was synthesized and found to have a high hydride donating ability, acid resistance and reusability. Thermodynamic parameters for electron and hydride transfer in the redox system comprising the 1,4-dihydropyridine and its corresponding pyridinium ion were determined. In addition, studies showed that the 1,4-dihydropyridine with steric hindrance can be used to promote efficient, boron trifluoride catalyzed selective reduction reactions of aldimines and aldehydes under mild conditions.
- Hirao, Yasukazu,Eto, Hajime,Teraoka, Mitsuru,Kubo, Takashi
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supporting information
p. 1671 - 1679
(2022/03/02)
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- Construction and application of 2, 6-dibromopyridine oxidation system
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The invention discloses a construction method of a 2, 6-dibromopyridine oxidation system. The construction method comprises the following steps: using 2, 6-dibromopyridine as a reaction substrate, andorming an acidic ionic liquid and 2, 6-dibromopyridine
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Paragraph 0038-0063
(2020/05/14)
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- Interaction of the dihydropyridine/pyridinium redox pair fixed into a V-shaped conformation
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A new V-shaped molecule incorporating a dihydropyridine and a pyridinium moiety was synthesized and evaluated for its effect on the interaction between the hydride donor-acceptor pair. Spectroscopic, electrochemical, and computational studies have revealed the presence of the charge transfer interaction as a consequence of the electron donor-acceptor association.
- Hirao, Yasukazu,Teraoka, Mitsuru,Kubo, Takashi
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p. 1345 - 1353
(2019/12/23)
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- Synthesis, Structure, and Ligand-Centered Catalytic Properties of MII Coordination Polymers (M=ZnII, CdII, HgII) with Open Pyridyl N-Oxide Sites
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Four MII (M=ZnII, CdII, HgII) coordination polymers were designed and synthesized based on two pyridine N-oxide bridging ligands: 3,5-bis(4-pyridyl)pyridine N-oxide and 2,6-bis(3-pyridyl)pyridine N-oxide. The re
- Cheng, Jun-Yan,Ding, Feng-Wen,Wang, Peng,Zhao, Chao-Wei,Dong, Yu-Bin
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p. 743 - 751
(2016/08/11)
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- Inhibition of cancer-associated mutant isocitrate dehydrogenases: Synthesis, structure-activity relationship, and selective antitumor activity
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Mutations of isocitrate dehydrogenase 1 (IDH1) are frequently found in certain cancers such as glioma. Different from the wild-type (WT) IDH1, the mutant enzymes catalyze the reduction of α-ketoglutaric acid to d-2-hydroxyglutaric acid (D2HG), leading to cancer initiation. Several 1-hydroxypyridin-2-one compounds were identified to be inhibitors of IDH1(R132H). A total of 61 derivatives were synthesized, and their structure-activity relationships were investigated. Potent IDH1(R132H) inhibitors were identified with Ki values as low as 140 nM, while they possess weak or no activity against WT IDH1. Activities of selected compounds against IDH1(R132C) were found to be correlated with their inhibitory activities against IDH1(R132H), as well as cellular production of D2HG, with R2 of 0.83 and 0.73, respectively. Several inhibitors were found to be permeable through the blood-brain barrier in a cell-based model assay and exhibit potent and selective activity (EC50 = 0.26-1.8 μM) against glioma cells with the IDH1 R132H mutation.
- Liu, Zhen,Yao, Yuan,Kogiso, Mari,Zheng, Baisong,Deng, Lisheng,Qiu, Jihui J.,Dong, Shuo,Lv, Hua,Gallo, James M.,Li, Xiao-Nan,Song, Yongcheng
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supporting information
p. 8307 - 8318
(2014/12/11)
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- Biarylphosphonite gold(I) complexes as superior catalysts for oxidative cyclization of propynyl arenes into indan-2-ones
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Striking gold: A series of variously functionalized propynyl arenes was smoothly converted into indan-2-ones by a new gold(I)-catalyzed oxidative cyclization process. [LAu]NTf2 (Tf=trifluoromethanesulfonyl) is a superior catalyst both in terms of yield and kinetics for the present transformation. Copyright
- Henrion, Guilhem,Chavas, Thomas E. J.,Le Goff, Xavier,Gagosz, Fabien
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supporting information
p. 6277 - 6282
(2013/07/11)
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- Synthesis and characterization of highly stable and efficient star-molecules
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A series of well-defined star-shaped molecules have been synthesized by Pd-catalyzed Suzuki cross-coupling starting from very simple reactants with 1,3,5-trisubstituted benzene, 2,4,6-trisubstituted pyridine and trisubstituted phenylcarbazole as the backbones. These star-molecules are all soluble in common organic solvents and electrochemically stable with reversible cyclic voltammographs and high lying HOMOs. They exhibit excellent blue-fluorescence with quantum yield up to 0.87 and high glass transition temperatures. These molecules offer potential as pure blue-light emitting, hole-transport or host materials for optoelectronic applications.
- Huang, Hai-Fang,Xu, Shi-Hua,He, Yan-Bo,Zhu, Cai-Cai,Fan, He-Liang,Zhou, Xue-Hua,Gao, Xi-Cun,Dai, Yan-Feng
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p. 705 - 713
(2013/03/13)
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- PYRIDINE AND ISOQUINOLINE DERIVATIVES AS SYK- AND JAK-KINASE INHIBITORS
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The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by inhibition of Syk kinase and/or Janus kinases.
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Page/Page column 58
(2012/04/17)
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- Pyridine- and isoquinoline-derivatives as Syk and JAK kinase inhibitors
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The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by inhibition of Syk kinase and/or Janus kinases.
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Paragraph 0174
(2013/03/26)
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- ANTIBACTERIAL COMPOUNDS
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The present invention provides a compound of the following formula and salts thereof: Also provided is the use of these compounds as antibacterials, compositions comprising them and processes for their manufacture.
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Page/Page column 22
(2012/04/18)
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- A flexible synthesis of C-6 and N-1 analogues of a 4-amino-1,3- dihydroimidazo[4,5-c]pyridin-2-one core
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A flexible route which enables access to derivatives of 4-amino-1,3-dihydroimidazo[4,5-c]pyridin-2-ones is described. Issues of selectivity, reaction safety, and low yields in original routes are overcome with the key improvements to the route, including
- Hay, Duncan A.,Adam, Fiona M.,Bish, Gerwyn,Calo, Frederick,Dixon, Rachel,Fray, M. Jonathan,Hitchin, James,Jones, Peter,Paradowski, Michael,Parsons, Gemma C.,Proctor, Katie J.W.,Pryde, David C.,Smith, Nicholas N.
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supporting information; experimental part
p. 5728 - 5732
(2011/12/03)
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- Magnesiation of pyridine N-oxides via iodine or bromine-magnesium exchange: A useful tool for functionalizing pyridine N-oxides
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Iodo- or 2-bromopyridine N-oxides were readily magnesiated with i-PrMgCl ? LiCl via the iodine or bromine-magnesium exchange. The bromine adjacent to pyridine N-oxide (at the 2- or 6-position) can be regioselectively magnesiated in the presence of other position substituted halogens. This method was tested in various substituted pyridine N-oxide systems, and has been successfully applied to the total synthesis of caerulomycins E and A.
- Duan, Xin-Fang,Zi-Qian, Ma.,Zhang, Fang,Zhang, Zhan-Bin
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supporting information; experimental part
p. 939 - 942
(2009/06/20)
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- NOVEL PHARMACEUTICALS
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The present invention relates to immune response modifiers of formula (I), which act selectively through agonism, of Toll-Like Receptors (TLRs), uses thereof, processes for the preparation thereof, intermediates used in the preparation thereof and compositions containing said inhibitors. These inhibitors have utility in a variety of therapeutic areas including the treatment of infectious disease such as Hepatitis (e.g. HCV, HBV), genetically related viral infection and cancer.
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Page/Page column 50
(2010/11/28)
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- PYRIDINE DERIVATIVES AND THEIR USE AS MEDICAMENTS FOR TREATING DISEASES RELATED TO MCH RECEPTOR
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The present invention encompasses novel substituted pyridine compounds of Formula (I), which act as MCH receptor antagonists. These compositions and pharmaceutical compositions thereof are useful in the prophylaxis or treatment of improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure, obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia, myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit disorder, substance abuse disorders and dyskinesias including Parkinson's disease, epilepsy, and addiction.
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Page/Page column 84
(2010/10/20)
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- PHARMACOLOGICALLY ACTIVE IMIDAZO[4,5-C]PYRIDINES
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The invention relates to 6-substituted imidazo[4,5-c]pyridines of formula 1, in which X is O (oxygen) or NH and Y has either the meaning -CH2-AR or Y denotes the group gp (gp) wherein Z has the meaning -CHR8- or -CHR8-CHR9-. The compounds have gastric secretion inhibiting and excellent gastric and intestinal protective action properties.
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Page/Page column 41
(2010/02/11)
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- The development of a practical and reliable large-scale synthesis of 2,6-diamino-4-bromopyridine
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A novel, safer, and efficient synthetic route to 2,6-diamino-4-bromopyridine has been developed. In discovery research a five-step synthesis afforded 2,6-diamino-4-bromopyridine in 56% yield with a double Curtius rearrangement as a key transformation. Due to potential safety concerns on larger scale an alternative synthetic strategy was necessary. Starting from 2,4-dibromopyridine-N-oxide two complementary procedures have been developed to access 2,6-diamino-4-bromopyridine. The four-step procedure yielded in 28% overall, and the five-step procedure, in 33% overall 2,6-diamino-4-bromopyridine in a safe and straightforward manner using a regioselective 2,6-diamination reaction as key step. Additionally, a general route to unsymmetrical substituted pyridine N-oxide derivatives is disclosed.
- Nettekoven, Matthias,Jenny, Christian
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- Influence of the 5-HT6 receptor on acetylcholine release in the cortex: Pharmacological characterization of 4-(2-bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine, a potent and selective 5-ht6 receptor antagonist
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A small series of aryl pyridyl sulfones has been prepared and investigated for its 5-HT6 receptor binding properties. Thereof, pyrrolidinyl derivative 11 proved to be a very potent (pKi 9) and selective 5-HT6 receptor antagonist. By means of in vivo microdialysis in the frontal cortex and a passive avoidance paradigm, where 11 reversed a scopolamine induced retention deficit, a functional correlation between 5-HT6 receptors and cholinergic neurotransmission could be shown, supporting the therapeutic potential of 5-HT6 receptors in the treatment of cognitive deficits.
- Riemer, Claus,Borroni, Edilio,Levet-Trafit, Bernard,Martin, James R.,Poli, Sonia,Porter, Richard H. P.,B?s, Michael
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p. 1273 - 1276
(2007/10/03)
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- Synthesis of novel poly(dithienylpyridines)
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This paper describes the chemical and electrochemical synthesis of novel copolymers of thiophene and pyridine. Di-iodination of 3-hydroxypyridine 12 followed by O-substitution gave a series of ethers 14b-d and esters/carbamates 15a-d which were reacted with the stannylated bithiophene derivative 17 in a Stille cross-coupling reaction yielding poly (1b-d) and poly (2a-d) respectively. These chemical polymerisation reactions generally resulted in highly insoluble materials which were difficult to characterise. Ethers 14b-d and esters/carbamates 15a-d gave O-substituted 3-hydroxy-2,6-di(2-thienyl)pyridines 1b-d and 2a-d respectively in Stille cross-coupling reactions with the stannylated thiophene 16. Ethers 1b-d underwent electrochemical polymerisation allowing the synthesis of O-alkylated polymers, poly (1b-d), with electrochemical band-gaps of 1.4 to 1.6 eV. In contrast, the esters/carbamates 2a-d could not be electropolymerised.
- Chapman, Glen M.,Stanforth, Stephen P.,Berridge, Rory,Pozo-Gonzalo, Cristina,Skabara, Peter J.
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p. 2292 - 2298
(2007/10/03)
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- Short and efficient syntheses of analogues of way-100635: New and potent 5-HT1A receptor antagonists
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Simple syntheses of four new and potent analogues of the 5-HT1A receptor ligand, WAY-100635 are described, namely the 6- pyridinyl)-fluoro-, the pyrimidine- and the 5-pyridinyl)-bromo-analogues. The first three analogues were obtained by aromat
- Marchais, Sandrine,Nowicki, Bartek,Wikstr?m, H?kan,Brennum, Lise T.,Halldin, Christer,Pike, Victor W.
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p. 695 - 702
(2007/10/03)
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- 7. Lanthanide Complexes of Polyacid Ligands Derived from 2,6-Bis(pyrazol-1-yl)pyridine, Pyrazine, and 6,6′-Bis(pyrazol-1-yl)-2,2′-bipyridine: Synthesis and Luminescence Properties
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The synthesis of three novel pyrazole-containing complexing acids, N,N,N′,N′-{2,6-bis[3-(aminomethyl)pyrazol-1-yl]-4-methoxypyridine} tetrakis(acetic acid) (1), N,N,N′, N′-{2,6-bis[3-(aminomethyl)pyrazol-1-yl]pyrazine}tetrakis(acetic acid) (2), and N,N,N′,N′-{6,6′-bist[3-(aminomethyl)pyrazol-1-yl]-2,2′- bipyridine}tetrakis(acetic acid) (3) is described. Ligands 1-3 formed stable complexes with EuIII, TbIII, SmIII and DyIII in H2O whose relative luminescence yields, triplet-state energies, and emission decay lifetimes were measured. The number of H2O molecules in the first coordination sphere of the lanthanide ion were also determined. Comparison of data from the EuIII and TbIII complexes of 1-3 and those of the parent trisheterocycle N,N,N′,N′-{2,6-bis[3-(aminomethyl)pyrazol-1-yl]pyridine} tetrakis(acetic acid) showed that the modification of the pyridine ring for pyrazine or 2,2′-bipyridine strongly modify the luminescence properties of the complexes. MeO Substitution at C(4) of 1 maintain the excellent properties described for the parent compound and give an additional functional group that will serve for attaching the label to biomolecules in bioaffinity applications.
- Rodriguez-Ubis, Juan Carlos,Sedano, Rosa,Barroso, Gemma,Juanes, Olga,Brunet, Ernesto
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- 4,4'-Donor-Substituted and 6,6'-Difunctionalized 2,2'-Bipyridines
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The previously unknown 4,4'-dimethoxy-substituted 6,6'-diacyl-2,2'-bipyridines 7, 8 (acyl = acetyl, formyl) are prepared.Some old procedures in the synthetic sequence were optimized. - Keyword: 2,2'-Bipyridines, building blocks for complex ligands
- Neumann, Uwe,Voegtle, Fritz
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p. 589 - 592
(2007/10/02)
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