- Preparation method of N-(aryl/heteroaryl) alkyl-diamide
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The invention relates to a preparation method of N-(aryl/heteroaryl)alkyl- diamide, which comprises the following steps: under the protection of nitrogen, sequentially adding transition metal, phosphine or nitrogen ligand, cocatalyst, alkali, solvent, Nhalogenated cyclodiamide, alkyl aromatic ring or alkyl heteroaromatic ring compound into a reaction container, carrying out oxidative amination reaction at 80-140 DEG C, and till the reaction concludes after 6-48 hours, evaporating and drying a solvent and carrying out column chromatography separation to obtain an N (aryl/heteroaryl) alkyl diamide compound. The invention is simple in synthesis process, mild in reaction condition, high in yield and easy to industrialize.
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Paragraph 0066-0067
(2020/12/29)
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- MANUFACTURING METHOD OF OPTICAL ACTIVE SECONDARY ALCOHOL
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PROBLEM TO BE SOLVED: To provide a method for manufacturing optical active secondary alcohol with high optical purity by hydrogenating a substrate carbonyl compound using a ruthenium complex with a specific optical active diphosphine compound and an amine compound of which synthesis is easy as ligands as a catalyst. SOLUTION: The manufacturing method of optical active secondary alcohol including reacting a substrate carbonyl compound (excluding 3-quinuclidinone, a 3-quinuclidinone derivative having a substituent, and ketone having an aromatic hydrocarbon group and a heterocycle) with hydrogen and/or a hydrogen-donating compound in a presence of a ruthenium complex selected from a compound represented by the following general formula (1) RuXYAB (1) [X and Y are same or different, represent a hydrogen atom or an anionic group, A represents optical active diphosphine represented by the general formula (2), and B represents an amine compound represented by the following general formula (3)]. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPO&INPIT
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Paragraph 0094; 0096; 0098
(2019/03/20)
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- PROCESS FOR PRODUCING OPTICALLY ACTIVE SECONDARY ALCOHOL
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[Object] The object of this invention is to provide a method for producing an optically active secondary alcohol at a high optical purity by hydrogenating a substrate carbonyl compound at a high efficiency using as a catalyst a ruthenium complex bearing as a ligand certain optically active diphosphine compound and a readily synthesized amine compound. [Solution] The method of producing an optically active secondary alcohol according to the present invention is characterized in that a substrate carbonyl compound (provided that 3-quinuclidinone, 3-quinuclidinone derivative having a substituent, and a ketone having an aromatic hydrocarbon group and a heterocycle are excluded) is reacted with hydrogen and/or a hydrogen donating compound in the presence of a ruthenium complex selected from the compounds expressed by following general formula (1) RuXYAB (1) [in the general formula (1), X and Y are the same or different from each other and denote a hydrogen atom or an anionic group, A denotes an optically active diphosphine expressed by the general formula (2), B denotes an amine compound expressed by following general formula (3)].
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Page/Page column 0148; 0149
(2015/02/19)
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- Design, synthesis and preliminary bioactivity evaluations of substituted quinoline hydroxamic acid derivatives as novel histone deacetylase (HDAC) inhibitors
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Inhibition of HDACs activity has become a promising therapeutic strategy in clinical practice to reverse the abnormal epigenetic states of cancer and other diseases. Therefore, HDAC inhibitors become a relatively new class of anti-cancer agent. In the present study, we reported the design and synthesis of a series of novel HDAC inhibitors using various substituted quinoline rings as the cap group. In vitro studies showed that some compounds have good inhibitory activities against HDACs and potent antiproliferative activities in some tumor cell lines. Especially, compound 9w (IC50 = 85 nM), exhibited better inhibitory effect compared with SAHA (IC50 = 161 nM).
- Wang, Lei,Hou, Xuben,Fu, Huansheng,Pan, Xiaole,Xu, Wenfang,Tang, Weiping,Fang, Hao
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p. 4364 - 4374
(2015/08/03)
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- Effective conversion of heteroaromatic ketones into primary amines via hydrogenation of intermediate ketoximes
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A process to access heteroaromatic primary amines from the corresponding heteroaromatic ketones has been developed. A broad range of previously reported methods to convert ketones to primary amines was examined on heterocyclic ketones without success, including Leuckart-Wallach conditions, borane reductions, and transition-metal-catalyzed hydrogenations. Unique among the catalysts examined, Raney cobalt produced the desired primary heterocyclic amine. Raney cobalt hydrogenation of structurally varied heterocyclic ketoximes was demonstrated to form primary amines in good selectivity under mild conditions, and the products are easily isolated in high yield. Additionally, this is the first report of a systematic evaluation of the capabilities of Raney cobalt as an oxime hydrogenation catalyst.
- Baucom, Kyle D.,Guram, Anil S.,Borths, Christopher J.
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p. 201 - 204
(2015/03/03)
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- Peptide deformylase inhibitors
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The present invention relates to a compound of Formula (I): or a pharmaceutically acceptable salt thereof, corresponding pharmaceutical compositions, compound preparation and treatment methods directed to bacterial infections and inhibition of bacterial peptide deformylase (PDF) activity.
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Page/Page column
(2014/12/09)
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- PEPTIDE DEFORMYLASE INHIBITORS
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The present invention relates to a compound of Formula (I): or a pharmaceutically acceptable salt thereof, corresponding pharmaceutical compositions, compound preparation and treatment methods directed to bacterial infections and inhi-bition of bacterial peptide deformylase (PDF) activity
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Page/Page column
(2014/02/15)
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- Synthesis of new chiral 2-functionalized-1,2,3,4-tetrahydroquinoline derivatives via asymmetric hydrogenation of substituted quinolines
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The asymmetric hydrogenation of a series of quinolines substituted by a variety of functionalized groups linked to the C2 carbon atom is providing access to optically enriched 2-functionalized 1,2,3,4-tetrahydroquinolines in the presence of in situ generated catalysts from [Ir(cod)Cl]2, a bisphosphine, and iodine. The enantioselectivity levels were as high as 96% ee.
- Maj, Anna M.,Suisse, Isabelle,Hardouin, Christophe,Agbossou-Niedercorn, Francine
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p. 9322 - 9328
(2013/10/01)
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- Triflic anhydride mediated synthesis of imidazo[1,5-a]azines
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Imidazo[1,5-a]azines are synthesized in moderate to excellent yields using a mild cyclodehydration/aromatization reaction triggered by the use of triflic anhydride (Tf2O) and 2-methoxypyridine (2-MeOPyr). Various substitution patterns and functional groups were found to be compatible under the optimized conditions. In addition, a 5-bromo-3-aryl derivative was also shown to be active in a Sonogashira cross-coupling and direct arylation reactions. A tertiary amide was compatible as a substrate leading to the synthesis of an imidazo[1,5-a]pyridinium triflate.
- Pelletier, Guillaume,Charette, Andre B.
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supporting information
p. 2290 - 2293
(2013/06/26)
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- Conversion of 2-(aminomethyl) substituted pyridine and quinoline to their dicarbonyldiimides using copper(II) acetate
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In air, hydrated ethanolic (95%) solution of 2-(aminomethyl) substituted pyridine and quinoline, on stirring with half equivalent of Cu(OAc)2·H2O, respectively afforded [Cu(bpca)(OAc)(H2O)]·H2O (1) and [Cu(bqca)(OAc)(H2O)] (2) {bpca = bis(2-pyridylcarbonyl)diimide ion and bqca = bis(2-quinolylcarbonyl)diimide ion} in good yields. These reactions involve oxidation of the methylene group and formation of the bond between nitrogen and carbon in N-C({double bond, long}O) through coupling. The complex [Cu(pqca)(OAc)(H2O)]3[Cu2(OAc)4(EtOH)2]1.5 (3) {pqca = (2-pyridylcarbonyl)(2-quinolylcarbonyl)diimide ion} was synthesized by stirring an ethanolic solution of the Schiff base [(2-pyridyl)-N-((2-quinolyl)methylene)methanamine] (L1) and with one equivalent of Cu(OAc)2·H2O. A plausible mechanism for the conversion has been proposed. The free ligands were isolated as crystalline solids from compounds 1-3, by extrusion of Cu2+ ion using EDTA2-. The molecular structures of 1-3 and bqcaH were established by X-ray crystallography and compounds having quinolyl group have π-stacking interactions.
- Sahu, Rojalin,Padhi, Sumanta Kumar,Jena, Himanshu Sekhar,Manivannan, Vadivelu
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experimental part
p. 1448 - 1454
(2010/07/05)
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- Design, synthesis, and biological activities of novel 2-cyanoacrylates containing oxazole, oxadiazole, or quinoline moieties
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A series of novel 2-cyanoacrylates containing an oxazole, oxadiazole, or quinoline moiety were designed and synthesized, and their structures were characterized by 1H NMR and elemental analysis (or high-resolution mass spectrometry). Their herbicidal activities against four weeds were evaluated, and the result indicated that some of the title compounds showed excellent herbicidal activities against rape and amaranth pigweed in postemergence treatment at a dose of 375 g/ha. Furthermore, most of these cyanoacrylates exhibited interesting plant growth regulatory activities.
- Zhao, Qiqi,Liu, Shaohua,Li, Yonghong,Wang, Qingmin
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experimental part
p. 2849 - 2855
(2010/04/30)
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- The mechanism of the (bispidine)copper(ii)-catalyzed aziridination of styrene: A combined experimental and theoretical study
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Experimental and DFT-based computational results on the aziridination mechanism and the catalytic activity of (bispidine)copper(I) and -copper(II) complexes are reported and discussed (bispidine = tetra- or pentadentate 3,7-diazabicyclo[3.1.1]-nonane derivative with two or three aromatic N donors in addition to the two tertiary amines). There is a correlation between the redox potential of the copper(II/I) couple and the activity of the catalyst. The most active catalyst studied, which has the most positive redox potential among all (bispidine)-copper(II) complexes, performs 180 turnovers in 30 min. A detailed hybrid density functional theory (DFT) study provides insight into the structure, spin state, and stability of reactive intermediates and transition states, the oxidation state of the copper center, and the denticity of the nitrene source. Among the possible pathways for the formation of the aziridine product, the stepwise formation of the two N-C bonds is shown to be preferred, which also follows from experimental results. Although the triplet state of the catalytically active copper nitrene is lowest in energy, the two possible spin states of the radical intermediate are practically degenerate, and there is a spin crossover at this stage because the triplet energy barrier to the singlet product is exceedingly high.
- Comba, Peter,Lang, Carolin,De Laorden, Carlos Lopez,Muruganantham, Amsaveni,Rajaraman, Gopalan,Wadepohl, Hubert,Zajaczkowski, Marta
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experimental part
p. 5313 - 5328
(2009/05/27)
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- Structure-function studies on a synthetic guanosine receptor that simultaneously binds Watson-Crick and Hoogsteen sites
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A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via 1H NMR complexation studies in 5% DMSO-d6-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure-function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.
- Quinn, Jordan R.,Zimmerman, Steven C.
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p. 7459 - 7467
(2007/10/03)
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- Quaternary salts as hypoglycemic agents
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The synthesis of imidazo?1,2-a!pyridinium, imidazo?1,5-a!pyridinium, pyrrolo?1,2-a!pyrazinium, pyrazolo?1,5-a!pyridinium, imidazo?2,1-a!isoquinolinium and imidazo?5,1-a!isoquinolinium quaternary salts and their use as hypoglycemic agents.
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- Imidazopyridinium compounds as hypoglycemic agents
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The synthesis of imidazo[1,2-a]pyridinium, imidazo[1,5-a]pyridinium, pyrrolo[1,2-a]pyrazinium, pyrazolo[1,5-a]pyridinium, imidazo[2,1-a]isoquinolinium and imidazo[5,1-a]isoquinolinium quaternary salts and their use as hypoglycemic agents.
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