- Insertion and fragmentation of 2-ferrocenylmethylidene-1, 3-diketones upon their reactions with N-methylhydrazine
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(Chemical Equation Presented) Reactions of 2-ferrocenylmethylidene-1,3- diketones (1a-c) with methylhydrazine afford mainly insertion products (~40-58%), viz., 1-(N′-acyl-N′-methylhydrazino)-1-ferrocenyl-2- acylethanes (7a-d), together with lesser amounts
- Klimova, Elena I.,Vazquez Lopez, Eduardo A.,Martinez Mendoza, Juan M.,Ramirez, Lena Ruiz,Alamo, Marcos Flores,Backinowsky, Leon V.
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Read Online
- One-Pot Reaction to Obtain N,N′-Disubstituted Guanidines of Pyrazolo[4,3- e ][1,2,4]triazolo[1,5- c ]pyrimidine Scaffold as Human A3 Adenosine Receptor Antagonists
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In this paper we describe an extension SAR study of pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine nucleus as A3AR antagonist. Our initial aim was to replace the phenylcarbamoyl moiety at the 5 position of PTP nucleus with a thiourea functiona
- Baraldi, Pier Giovanni,Baraldi, Stefania,Saponaro, Giulia,Aghazadeh Tabrizi, Mojgan,Romagnoli, Romeo,Ruggiero, Emanuela,Vincenzi, Fabrizio,Borea, Pier Andrea,Varani, Katia
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Read Online
- One-Pot Catalytic Enantioselective Synthesis of 2-Pyrazolines
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A scalable, one-pot, enantioselective catalytic synthesis of 2-pyrazolines from beta-substituted enones and hydrazines is described. Pivoting on a two-stage catalytic Michael addition/condensation strategy, the use of an aldehyde to generate a suitable hydrazone derivative of the hydrazine was found to be key for curtailing background reactivity and tuning the catalyst-controlled enantioselectivity. The new synthetic method is easy to perform, uses a new and readily prepared cinchona-derived bifunctional catalyst, is broad in scope, and tolerates a range of functionalities with high enantioselectivity (up to >99:1 e.r.). The significant scalability of this methodology was demonstrated with the synthesis of more than 80 grams of a pyrazoline product with 89 % catalyst recovery.
- Thomson, Connor J.,Barber, David M.,Dixon, Darren J.
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supporting information
p. 2469 - 2473
(2019/02/01)
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- PROCESS FOR THE MANUFACTURE OF IMINIUM COMPOUNDS AND THEIR APPLICATION IN THE MANUFACTURE OF PYRAZOLE DERIVATIVES
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Process for the manufacture of iminium compounds and their application in the manufacture of pyrazole derivatives The present invention concerns processes for the manufacture of iminium compounds and their application in the manufacture of pyrazole derivatives, in particular in processes for the manufacture of pharmaceutically or agrochemically active compounds.
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Page/Page column 15
(2019/07/13)
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- SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS
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The present application relates to substituted fused heteroaryl and heterocyclic compounds, useful as nicotinamide adenine dinucleotide phosphate oxidase inhibitors (NADPH oxidase inhibitors), processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by NADPH oxidase. (Formula I)
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Page/Page column 107-108
(2018/12/03)
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- Mechanistic Studies on the Michael Addition of Amines and Hydrazines to Nitrostyrenes: Nitroalkane Elimination via a Retro-aza-Henry-Type Process
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In this article we report on the mechanistic studies of the Michael addition of amines and hydrazines to nitrostyrenes. Under the present conditions, the corresponding N-alkyl/aryl substituted benzyl imines and N-methyl/phenyl substituted benzyl hydrazones were observed via a retro-aza-Henry-type process. By combining organic synthesis and characterization experiments with computational chemistry calculations, we reveal that this reaction proceeds via a protic solvent-mediated mechanism. Experiments in deuterated methanol CD3OD reveal the synthesis and isolation of the corresponding deuterated intermediated Michael adduct, results that support the proposed slovent-mediated pathway. From the synthetic point of view, the reaction occurs under mild, noncatalytic conditions and can be used as a useful platform to yield the biologically important N-methyl pyrazoles in a one-pot manner, simple starting with the corresponding nitrostyrenes and the methylhydrazine.
- Kallitsakis, Michael G.,Tancini, Peter D.,Dixit, Mudit,Mpourmpakis, Giannis,Lykakis, Ioannis N.
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p. 1176 - 1184
(2018/02/09)
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- Preparation of 5-Aryl-2-Alkyltetrazoles with Aromatic Aldehydes, Alkylhydrazine, Di-tert-butyl Azodicarboxylate, and [Bis(trifluoroacetoxy)iodo]benzene
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A variety of 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles were directly prepared in good to moderate yields by the reaction of aromatic aldehydes with methylhydrazine and benzylhydrazine, followed by treatment with di-tert-butyl azodicarboxylate and [bis(trifluoroacetoxy)iodo]benzene in a mixture of dichloromethane and 2,2,2-trifluoroethanol at room temperature. The present method is a novel one-pot preparation of 5-aryl-2-methyltetrazoles and 5-aryl-2-benzyltetrazoles through a [2N + 2N] combination under transition metal-free and mild conditions.
- Imai, Taro,Harigae, Ryo,Moriyama, Katsuhiko,Togo, Hideo
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p. 3975 - 3980
(2016/05/24)
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- Radical Addition of Hydrazones by α-Bromo Ketones to Prepare 1,3,5-Trisubstituted Pyrazoles via Visible Light Catalysis
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A novel efficient tandem reaction of hydrazones and α-bromo ketones is reported for the preparation of 1,3,5-trisubstituted pyrazoles by visible light catalysis. In this system, the monosubstituted hydrazones show wonderful reaction activity with alkyl radicals, generated from α-bromo ketones. A radical addition followed by intramolecular cyclization affords the important pyrazole skeleton in good to excellent yields. This efficient strategy under mild conditions with wide group tolerance provides a potential approach to the 1,3,5-trisubstituted pyrazoles.
- Fan, Xiu-Wei,Lei, Tao,Zhou, Chao,Meng, Qing-Yuan,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
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p. 7127 - 7133
(2016/08/30)
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- Synthesis of o -(dimethylamino)aryl ketones, acridones, acridinium salts, and 1 H -indazoles by the reaction of hydrazones and arynes
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A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
- Dubrovskiy, Anton V.,Larock, Richard C.
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p. 11232 - 11256
(2013/02/23)
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- Method for preparing 1,3,4-substituted pyrazol compounds
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The invention provides an Ethernet bridge or router comprising a network fabric adapted to provide interconnectivity to a plurality of Ethernet ports, each of the Ethernet ports being adapted to receive and/or transmit Ethernet frames, and wherein the Ethernet bridge or router further comprises an encapsulator connected to receive Ethernet Protocol Data Units from the Ethernet ports, wherein the encapsulator is operable to generate a Fabric Protocol Data Unit from a received Ethernet Protocol Data Unit, the Fabric Protocol Data Unit comprising a header portion, and a payload portion which comprises the Ethernet Protocol Data Unit concerned, and wherein the encapsulator is operable to transform Ethernet destination address information from the Ethernet Protocol Data Unit into a routing definition for the network fabric, and to include this routing definition in the header portion of the Fabric Protocol Data Unit. Also provided is a method of data delivery across a network.
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Page/Page column 10
(2011/08/03)
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- The significance of 2-furyl ring substitution with a 2-(para -substituted) aryl group in a new series of pyrazolo-triazolo-pyrimidines as potent and highly selective hA3 adenosine receptors antagonists: New insights into structure-affinity relationship and receptor-antagonist recognition
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Among the heterocyclic structures identified as potent human A3 (hA3) adenosine receptor's antagonists, we have demonstrated that the new pyrazolo-triazolo-pyrimidines, bearing an aryl group in replacement of the C2-furyl ring, not only confer a good pharmacological profile (with significantly enhanced selectivity against other adenosine receptor subytpes) but also overcome the metabolic transformation of the furan ring into toxic intermediates. All the synthesized [2-(para-substituted) phenyl]-pyrazolo- triazolo-pyrimidines showed affinity at the hA3 receptor in the low nanomolar range. The most potent derivative of the series presented better affinity and excellent selectivity (compound 31, Ki hA3 = 0.108 nM; hA1/hA3 = 5200; hA2A/hA3 = 7200), in comparison to the C2-furyl counterpart. A receptor-driven molecular modeling investigation, based on a recently proposed model of A 3 receptor derived from the crystallographic structure of human A2A receptor, has been carried out in order to support the experimental binding data and to justify the enhanced selectivity against the other receptor subtypes.
- Cheong, Siew Lee,Dolzhenko, Anna,Kachler, Sonja,Paoletta, Silvia,Federico, Stephanie,Cacciari, Barbara,Dolzhenko, Anton,Klotz, Karl-Norbert,Moro, Stefano,Spalluto, Giampiero,Pastorin, Giorgia
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scheme or table
p. 3361 - 3375
(2010/09/05)
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- A new route to substituted pyrimido[5,4-e]-l,2,4-triazine-5,7(1H,6H)-diones and facile extension to 5,7(6H,8H) isomers
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A new route to substituted pyrimido[5,4-e]-l,2,4-triazine-5,7(lH,6H)-diones is outlined. The synthesis proceeds via preformed hydrazone intermediates, which are then condensed with an activated chlorouracil to build up the entire molecular framework, foll
- Turbiak, Anjanette J.,Showalter, H. D. Hollis
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experimental part
p. 4022 - 4026
(2010/03/30)
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- Facile method for conversion of 2-(Chloroseleno)benzoyl chloride into 2-substituted 3-hydroxybenzo[b]selenophenes
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The easily accessible 2-(chloroseleno)benzoyl chloride has broad application in the synthesis of benzizoselenazol-3(2H)-ones and benzo[b]selenophen-3(2H)-ones. Treatment of 2-acylbenzo[b]selenophen-3(2H)-ones with nitrogen nucleophiles such as hydrazines
- Lisiak, Rafal,Mochowski, Jacek
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experimental part
p. 4271 - 4281
(2009/12/31)
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- 3,4,5-Trisubstituted isoxazoles as novel PPARδ agonists. Part 2
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A series of PPARδ-selective agonists was investigated and optimized for a favorable in vivo pharmacokinetic profile. Isoxazole LCI765 (17d) was found to be a potent and selective PPARδ agonist with good in vivo PK properties in mouse (Cmax = 5.1 μM, t1/2 = 3.1 h). LCI765 regulated expression of genes involved in energy homeostasis in relevant tissues when dosed orally in C57BL6 mice. A co-crystal structure of compound LCI765 and the LBD of PPARδ is discussed.
- Epple, Robert,Azimioara, Mihai,Russo, Ross,Xie, Yongping,Wang, Xing,Cow, Christopher,Wityak, John,Karanewsky, Don,Bursulaya, Badry,Kreusch, Andreas,Tuntland, Tove,Gerken, Andrea,Iskandar, Maya,Saez, Enrique,Martin Seidel,Tian, Shin-Shay
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p. 5488 - 5492
(2007/10/03)
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- Method for treating multiple sclerosis
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Provided is a method of treating multiple sclerosis employing certain aryl-substituted rhodanines.
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- EVIDENCIA A FAVOR DE IONES DIPOLARES COMO PRIMEROS INTERMEDIARIOS EN LA OXIDACION DE AZINAS E HIDRAZONAS CON AGENTES DE TRANSFERENCIA DE OXIGENO
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Experimental evidence is present in favor of dipolar ions R2C(O-)-N=N+=CR2 and R2C(O-)-N=N+R2 as the first intermediates formed in the oxidation of azines R2C=N-N=CR2 and hydrazones R2C=N-NR2 with oxygen transfer agents.Keywords: oxidacion de azinas, oxidacion de hidrazonas, agentes de transferencia de oxigeno
- Paredes, R.,Chavez, A. L.,Dolbier, W. R.,Burkholder, C. B.
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p. 217 - 219
(2007/10/02)
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- Aryl-substituted rhodanine derivatives
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Provided are certain aryl-substituted rhodanine derivatives, treatment methods and pharmaceutical formulations thereof.
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- Method of treating inflammatory bowel disease
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Provided is a method of treating inflammatory bowel disease in mammals utilizing certain benzyl-substituted rhodanine derivatives. Also provided are novel benzyl-substituted rhodanine derivatives and pharmaceutical compositions thereof, as well as a novel process for selectively isolating in substantially pure enantiomeric form the enantiomers of certain racemic benzyl-substituted rhodanine derivatives.
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- Method of treating type I diabetes
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Provided is a method for treating Type I diabetes in mammals utilizing certain aryl-substituted rhodanine derivatives.
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- In the Search for New Anticancer Drugs, III. Phosphorylated Diaziridine Derivatives
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Several N-diethoxyphosphoryl derivatives 7 of various diaziridines, and compounds 12, 15a, 15b, 18 and 20, structurally related to TEPA (1a) and spin labeled Thio-TEPA (1c) were synthesized. In three cases, attempts to synthesize phosphorylated
- Sosnovsky, George,Lukszo, Jan
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p. 884 - 894
(2007/10/02)
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- Cationic dyestuffs
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Cationic dyestuffs of the formula STR1 WHEREIN R represents an alkyl, alkenyl, cycloalkyl, aralkyl, aryl or heteryl radical or an alkylene radical bonded to A or to a ring fusted with A, R1 represents hydrogen, an alkyl, aralkyl, aryl or heteryl or nitrile, R2 represents hydrogen, alkyl, aralkyl or aryl, R3 represents alkyl, R4 represents hydrogen, alkyl, aralkyl, aryl, heteryl or alkylene or arylene bonded to R5, R5 represents a five- or six-membered aromatic ring, A represents the remaining members of a heterocyclic 5-membered or 6-membered ring and An- represents an anion, A process for their preparation and their use for dyeing, printing and bulk dyeing of natural and synthetic materials.
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