- Design and synthesis of pyridine-pyrazole-sulfonate derivatives as potential anti-HBV agents
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Hepatitis B virus (HBV) is an infectious disease, which can cause acute and chronic infections. Every year, over 7.5 million persons die due to HBV. No effective drug exists for the treatment of HBV. Thus, we designed and synthesized 16 new pyridine-pyraz
- Chuang, Hong,Huang, Lin-Chiang Sherlock,Kapoor, Mohit,Liao, Yi-Jen,Yang, Cheng-Lin,Chang, Chia-Ching,Wu, Chun-Yi,Hwu, Jih Ru,Huang, Tsurng-Juhn,Hsu, Ming-Hua
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Read Online
- Compound, luminescent layer guest material, organic electroluminescent device and display device
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The invention provides a compound as shown in a general formula (I). The compoundcan be used for an organic electroluminescent device as a guest material of a luminescent layer. The compound comprises a natural heterocyclic ring and iridium (Ir) coordinated structure, and the light emitting wavelength of the compound can be effectively regulated and controlled. When the compound is used as a guest material of a light-emitting layer, the light-emitting efficiency and the light stability of the organic electroluminescent device can be improved. In addition, the compound provided by the invention is small in molecular weight, is applied to a light-emitting layer, is relatively low in evaporation temperature, and is beneficial to processing. The invention also provides a luminescent layer guest material containing the compound shown in the general formula (I), an organic electroluminescent device and a display device.
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Paragraph 0099-0103; 0112-0116; 0127-0131
(2021/06/22)
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- Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl N2-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis
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Alkyl N-aryl 1,2,3-triazole-carboxylates are important molecules or intermediates in medicinal chemistry, but the synthesis of N2-aryl counterparts remains elusive. Herein, we describe a Cu-mediated annulation reaction of alkyl 3-aminoacrylates with aryldiazonium salts, both of which are readily available substrates. Furthermore, alkyl 2-aminoacrylates are also viable substrates. Diverse alkyl N2-aryl 1,2,3-triazole-carboxylates and their analogues can be rapidly prepared under mild conditions. Especially, this protocol allows one to access several druglike variants of carbonic anhydrase inhibitors and celecoxib.
- Liu, Hao-Nan,Cao, Hao-Qiang,Cheung, Chi Wai,Ma, Jun-An
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supporting information
p. 1396 - 1401
(2020/02/22)
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- 6-AMINO-2,4-DIHYDROPYRANO [2,3-C] PYRAZOLES AND METHODS OF USE
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The present invention generally relates to 6-amino-2,4-dihydropyrano [2,3-c] pyrazoles as a ubiquitin specific protease 7 (USP7) inhibitor useful for the treatment of diseases mediated by malfunction of USP7, such as inflammation, cancer, and immunological disorders. The invention described herein also pertains to pharmaceutical compositions and methods for treating diseases mediated by malfunction of USP7, in mammals using compounds disclosed herein.
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Paragraph 0097-0099; 0101
(2018/10/25)
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- Reformatsky and Blaise reactions in flow as a tool for drug discovery. One pot diversity oriented synthesis of valuable intermediates and heterocycles
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The application of Reformatsky and Blaise reactions for the preparation of a diverse set of valuable intermediates and heterocycles in a one-pot protocol is described. To achieve this goal, a greener activation protocol for zinc in flow conditions has been developed to introduce this metal efficiently into α-bromoacetates. The organozinc compounds were added to a diverse set of ketones and nitriles to obtain a wide range of functional groups and heterocyclic systems.
- Huck,Berton,De La Hoz,Díaz-Ortiz,Alcázar
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supporting information
p. 1420 - 1424
(2017/05/12)
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- The synthesis and evaluation of triazolopyrimidines as anti-tubercular agents
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We identified a di-substituted triazolopyrimidine with anti-tubercular activity against Mycobacterium tuberculosis. Three segments of the scaffold were examined rationally to establish a structure-activity relationship with the goal of improving potency and maintaining good physicochemical properties. A number of compounds displayed sub-micromolar activity against Mycobacterium tuberculosis with no cytotoxicity against eukaryotic cells. Non-substituted aromatic rings at C5 and a two-carbon chain connecting a terminal aromatic at C7 were preferred features; the presence of NH at C7 and a lack of substituent at C2 were essential for potency. We identified compounds with acceptable metabolic stability in rodent and human liver microsomes. Our findings suggest that the easily-synthesized triazolopyrimidines are a promising class of potent anti-tubercular agents and warrant further investigation in our search for new drugs to fight tuberculosis.
- Zuniga, Edison S.,Korkegian, Aaron,Mullen, Steven,Hembre, Erik J.,Ornstein, Paul L.,Cortez, Guillermo,Biswas, Kallolmay,Kumar, Naresh,Cramer, Jeffrey,Masquelin, Thierry,Hipskind, Philip A.,Odingo, Joshua,Parish, Tanya
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p. 3922 - 3946
(2017/07/05)
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- Facile and short synthesis of (±) 1-hydroxy indolizidine and (±) coniceine from picolinic acid ethyl ester via cross claisen condensation
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New short synthesis of (±) 1-hydroxy indolizidine (4) and (±) coniceine (5) are described starting from picolinic acid ethyl ester (6). The key steps are the conversion of the picolinic acid ethyl ester into β-keto ester 7 via cross Claisen condensation and hydrogenation of the β-keto ester in to hydroxy bicyclic amide (8) using PtO2/H2.
- Veeraswamy,Anjaiah,Yennam, Satyanarayana,Jayashree
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p. 1667 - 1670
(2015/03/04)
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- New Pyrazolecarboxylic compd., its manufacturing method and pest control agents
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PROBLEM TO BE SOLVED: To provide a new pyrazole compound capable of showing excellent biological activity to not only spider mites but also Nematoda. SOLUTION: It is found that a new pyrazole compound having a nitrogen-containing hetero ring in a first position of a pyrazole ring and a sulfonate group in a fifth position shows excellent biological activity to not only the spider mites but also the Nematoda. COPYRIGHT: (C)2012,JPOandINPIT
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Paragraph 0129; 0130; 0131
(2018/05/03)
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- Novel Substituted Imidazopyrimidines as Gpbar1 Receptor Modulators
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The present invention relates to novel substituted imidazo[1,2-a]pyrimidine compounds of formula (I), their pharmaceutically acceptable salts, and their isomers, stereoisomers, conformers, tautomers, polymorphs, hydrates and solvates. The present inventio
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Paragraph 0115; 0116; 0117; 0133
(2015/05/13)
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- Synthesis of pyridyl substituted pyrazolo[4,3-c]pyridines as potential inhibitors of protein kinases
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A synthetic route towards 3-(2-pyridyl)-6-(hetero)aryl-1H-pyrazolo[4,3-c] pyridines is described. The key step consists of a microwave-assisted multi-component reaction, including a Sonogashira type cross-coupling of appropriate 5-chloropyrazole-4-carbaldehydes with alkynyl- (hetero)arenes followed by pyridine ring formation of the coupling products in the presence of tert-butylamine, directly affording the title compounds. A congener without substituent at N-1 was accessed via cleavage of a tert-butyl protecting group. Detailed NMR spectroscopic studies (1H, 13C and 15N) were undertaken with the obtained compounds. Selected representatives were evaluated for their potential as inhibitors of protein kinases.
- Vilkauskaite, Gyte,Schaaf, Patricia,Saekus, Algirdas,Krystof, Vladimir,Holzer, Wolfgang
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p. 135 - 149
(2014/03/21)
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- Access to β-keto esters by palladium-catalyzed carbonylative coupling of aryl halides with monoester potassium malonates
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New tricks for an old dog: The Pd-catalyzed carbonylative α-arylation of monoethyl potassium malonates with aryl bromides and reactive aryl chlorides provides a simple and direct route to aryl β-ketoesters. Because only stoichiometric amounts of carbon monoxide are employed, the method is ideal for the introduction of carbon isotopes into more complex structures. Copyright
- Korsager, Signe,Nielsen, Dennis U.,Taaning, Rolf H.,Skrydstrup, Troels
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supporting information
p. 9763 - 9766
(2013/09/23)
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- Tert-BuOK-Catalyzed condensation of ethyl diazoacetate to aldehydes and palladium-catalyzed 1,2-hydrogen migration for the synthesis of β-ketoesters under solvent-free conditions
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A mild and convenient method for the condensation of ethyl diazoacetate (EDA) with aldehydes catalyzed by tert-BuOK under solvent-free conditions was developed. The corresponding α-diazo-β-hydroxy esters were further converted into β-ketoesters through palladium-catalyzed 1,2-hydrogen migration under neat conditions. The two-step transformation exemplifies a simple method for the efficient and green synthesis of β-ketoesters. The Royal Society of Chemistry 2013.
- Chen, Shufeng,Yuan, Fang,Zhao, Haiying,Li, Baoguo
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p. 12616 - 12620
(2013/08/23)
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- NOVEL SUBSTITUTED IMIDAZOPYRIMIDINES AS GPBAR1 RECEPTOR MODULATORS
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The present invention relates to novel substituted imidazo[1,2-a]pyrimidine compounds of formula (I), their pharmaceutically acceptable salts, and their isomers, stereoisomers, conformers, tautomers, polymorphs, hydrates and solvates. The present inventio
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Page/Page column 42
(2013/05/09)
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- Simple, fast and efficient synthesis of β-keto esters from the esters of heteroaryl compounds, its antimicrobial study and cytotoxicity towards various cancer cell lines
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A series of β-keto esters were synthesized from heteroaryl esters and ethyl acetate using LiHMDS as base at -50 to -30 °C. The increase in yields of cross condensed product were observed and the percentage of self condensed product was reduced drastically by applying the suitable base (LiHMDS), solvent and the minimum amount of ethyl acetate. All these β-keto esters were characterized using 1H NMR, 13C NMR and mass spectral data. A plausible mechanism is also depicted to prove the formation of trans-esterified products. All the synthesized compounds were subjected to test for their cytotoxicity towards various cancer cell lines and also tested for their antimicrobial activity towards various bacterial and fungal strains and some of them were found to have promising activity.
- Venkat Ragavan,Vijayakumar,Rajesh,Palakshi Reddy,Karthikeyan,Suchetha Kumari
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supporting information; experimental part
p. 4193 - 4197
(2012/07/14)
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- Efficient one-pot selective reduction of esters in β-ketoesters using LiHMDS and lithium aluminium hydride
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The ester functionality in β-keto esters is selectively reduced in one-pot, first by enolization using LiHMDS and then reduced with lithium aluminium hydride. This method produces β-hydroxyl ketones from the corresponding β-keto esters in high yield.
- Sivagurunathan,Raja Mohamed Kamil,Syed Shafi,Liakth Ali Khan,Ragavan, R. Venkat
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experimental part
p. 1205 - 1207
(2011/03/21)
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- Molybdenum(VI) dichloride dioxide catalyzed synthesis of β-keto esters by C-H insertion of ethyl diazoacetate into aldehydes
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Synthesis of β-keto esters by condensing various aldehydes with ethyl diazoacetate is achieved by using molybdenum(VI) dichloride dioxide. Aromatic, aliphatic, and heterocyclic aldehydes are successfully condensed with ethyl diazoacetate to obtain corresponding β-keto esters in high yields at room temperature.
- Jeyakumar, Kandasamy,Chand, Dillip Kumar
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p. 1685 - 1687
(2008/12/21)
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- Selective synthesis of α-substituted β-keto esters from aldehydes and diazoesters on mesoporous silica catalysts
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The titled reactions are effectively catalyzed on mesoporous silica MCM-41 but not on amorphous silica prepared from the same starting materials as those of MCM-41. The ordered porous structure was essential to generate the acid catalysis. Planting of Al or Ti ion improved not only the catalytic activity but also the tolerance to basic functional groups of substrates. The catalytic activity of Al- or Ti-MCM-41 was better than that of SnCl2 and NbCl5 in the homogeneous phase. In particular, Al (or Ti)-MCM-41 was characteristically active for the reaction of aldehydes with α-substituted diazoesters to give 2-substituted-3-oxo propionic acid esters.
- Murata, Hiroaki,Ishitani, Haruro,Iwamoto, Masakazu
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p. 4788 - 4791
(2008/12/22)
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- Therapeutic Compounds
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The invention provides a compound of formula I: wherein R1-R6, X, Y, and B have any of the values described herein, as well as salts of such compounds, compositions comprising such compounds, and therapeutic methods that comprise the administration of such compounds. The compounds are inhibitors of MAO-B enzyme function and are useful for improving cognitive function and for treating psychiatric disorders in animals.
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Page/Page column 54-55
(2010/11/28)
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- TGF-BETA INHIBITORS
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The present invention is directed to inhibitors of TGF-BETA of Formula (I).
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Page/Page column 17
(2008/06/13)
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- 3-‘4-HETEROCYCLYL -1,2,3,-TRIAZOL-1-YL!-N-ARYL-BENZAMIDES AS INHIBITORS OF THE CYTOKINES PRODUCTION FOR THE TREATMENT OF CHRONIC INFLAMMATORY DISEASES
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Disclosed compounds of formula (I), which inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.
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Page/Page column 128
(2008/06/13)
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- FUSED PYRAZOLE DERIVATIVES AS TGF-BETA SIGNAL TRANSDUCTION INHIBITORS FOR THE TREATMENT OF FIBROSIS AND NEOPLASMS
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The disclosed invention is directed to compounds of the formula: Formula (I) and methods of using these compounds.
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Page/Page column 22
(2010/02/14)
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- Ethyl 3-(2-pyridyl)-2H-azirine-2-carboxylate: Synthesis and reaction with dienes
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Ethyl 3-(2-pyridyl)-2H-azirine-2-carboxylate, the first example of an 3-heteroamatic 2H-azirine has been prepared. The reaction of ethyl 3-(2-pyridyl)-2H-azirine-2-carboxylate with conjugated 1,3-dienes, under mild conditions and in the absence of Lewis acid catalyst, afforded cycloadducts in good yield and high stereoselectivity.
- Alves, M. Jose,Fortes, A. Gil,Lemos, Americo,Martins, Cristina
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p. 555 - 558
(2007/10/03)
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- Niobium(V) chloride-catalyzed C-H insertion reactions of α-diazoesters: Synthesis of β-keto esters
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Aldehydes react readily with ethyl diazoacetate in the presence of 5 mol% of NbCl5 in dichloromethane to produce the corresponding β-keto esters in good yields with high selectivity. This method is very useful for the preparation of β-keto esters from both electron-rich as well as electron-deficient aromatic aldehydes under mild reaction conditions.
- Yadav,Subba Reddy,Eeshwaraiah,Reddy
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p. 875 - 878
(2007/10/03)
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- NOVEL COMPOUNDS AS PHARMACEUTICAL AGENTS
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The current invention relates to compounds of the formula:(Ia) and the pharmaceutically acceptable salts thereof and their use as TGF-beta signal transduction inhibitors for treating cancer and other diseases in a patient in need thereof by administration of said compounds.
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- Synthesis of tetrasubstituted pyridines by the acid-catalysed Bohlmann-Rahtz reaction
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New facile experimental procedures for the preparation of 2,3,4,6-tetrasubstituted pyridines in a single synthetic step have been developed. Thus, an enamino ester and alkynone react by Michael addition-cyclodehydration in a heterocyclisation process that is catalysed by acetic acid, Amberlyst 15 ion exchange resin, zinc(II) bromide or ytterbium(III) triflate. The new one-step Bronsted or Lewis acid-catalysed Bohlmann-Rahtz reaction is a simple, direct and highly expedient method for the synthesis of pyridines that proceeds at a lower reaction temperature and avoids the need to isolate reaction intermediates.
- Bagley, Mark C.,Brace, Christian,Dale, James W.,Ohnesorge, Maren,Phillips, Nathan G.,Xiong, Xin,Bower, Justin
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p. 1663 - 1671
(2007/10/03)
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- Phytotoxic 2-alkyl-5-(heterocyclic)-pyrrole-3,4-dicarboxylates
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Phytotoxic 2-methyl-5-(heterocyclic)-pyrrole-3,4-dicarboxylates.
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