- Synthesis and Biological Screening of Novel 5-(5-Aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole Derivatives
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A new series of 5-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole (6a-o) have been synthesized by a cyclocondensation reaction of ethyl 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate (3a-c) with aryl imidoxime (5a-e). The newly synthesize
- Agrawal, Brijmohan R.,Farooqui, Mazahar,Khandebharad, Amol U.,Kulkarni, Pravin S.,Sarda, Swapnil R.
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p. 209 - 215
(2022/01/06)
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- La(OTf)3-catalysed one-pot synthesis of pyrazole tethered imidazo[1,2-: A] azine derivatives and evaluation of their light emitting properties
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A facile and efficient protocol has been unfolded towards the diversity-oriented synthesis of highly fluorescent pyrazole C-3(5) tethered imidazo[1,2-a]azines via an La(OTf)3 catalysed one-pot multicomponent assembly of pyrazole carbaldehydes, 2-aminoazines and isonitriles. This present protocol offers several advantages such as multiple bond formation in a single step, low catalyst loading, short reaction time, appreciable atom economy, good functional group tolerance, scalability and easy to perform reaction conditions. The optical properties of pyrazolyl imidazo[1,2-a]azines were also studied, and they exhibited an excellent fluorescence quantum yield (ΦF up to 83%).
- Sharma, Shubham,Paul, Avijit Kumar,Singh, Virender
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supporting information
p. 684 - 694
(2020/01/31)
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- Discovery of 1,5-Diphenylpyrazole-3-Carboxamide Derivatives as Potent, Reversible, and Selective Monoacylglycerol Lipase (MAGL) Inhibitors
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Monoacylglycerol lipase (MAGL) is a serine hydrolase that plays an important role in the degradation of the endocannabinoid neurotransmitter 2-arachidonoylglycerol, which is implicated in many physiological processes. Beyond the possible utilization of MA
- Aghazadeh Tabrizi, Mojgan,Baraldi, Pier Giovanni,Baraldi, Stefania,Ruggiero, Emanuela,De Stefano, Lucia,Rizzolio, Flavio,Di Cesare Mannelli, Lorenzo,Ghelardini, Carla,Chicca, Andrea,Lapillo, Margherita,Gertsch, Jürg,Manera, Clementina,Macchia, Marco,Martinelli, Adriano,Granchi, Carlotta,Minutolo, Filippo,Tuccinardi, Tiziano
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p. 1340 - 1354
(2018/02/17)
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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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- A new efficient synthesis of pyrazoles from hydrazonoyl halides and β-oxophosphonates
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A new practical and efficient synthesis of 1,3,5-trisubstituted pyrazoles has been developed by reacting of hydrazonoyl halides with β-oxophosphonates under mild conditions in good yields with excellent regioselectivity. This process employs an addition-elimination sequence. Wide scope, functional group compatibility has been established.
- Sun, Aixue,Ye, Jia-Hai,Yu, Haitao,Zhang, Wenchao,Wang, Xiaolong
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supporting information
p. 889 - 892
(2015/03/03)
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- HISTONE DEACETYLASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF
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Provided are certain histone deacetylase (HDAC) inhibitors of Formula I, compositions thereof, and methods of their use.
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Paragraph 00169
(2014/10/15)
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- A new efficient synthesis of pyrazoles from hydrazonoyl halides and β-oxophosphonates
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A new practical and efficient synthesis of 1,3,5-trisubstituted pyrazoles has been developed by reacting of hydrazonoyl halides with β- oxophosphonates under mild conditions in good yields with excellent regioselectivity. This process employs an addition-elimination sequence. Wide scope, functional group compatibility has been established.
- Sun, Aixue,Ye, Jia-Hai,Yu, Haitao,Zhang, Wenchao,Wang, Xiaolong
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supporting information
p. 889 - 892
(2014/02/14)
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- 'One-pot' synthesis of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates via lithium tert-butoxide-mediated sterically hindered Claisen condensation and Knorr reaction
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A concise 'one-pot' synthesis of a variety of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates has been developed in moderate to good yields with excellent regioselectivity. Less cost lithium tert-butoxide has been identified as a base for sterically hindered Claisen condensation to efficiently generate the labile 3-substituted 4-aryl-2,4-diketoesters. Furthermore, extensive studies lead to a 'one-pot' process by combination of the Claisen condensation and the Knorr reaction for the synthesis of highly valuable 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates.
- Jiang, Jian-An,Huang, Wei-Bin,Zhai, Jiao-Jiao,Liu, Hong-Wei,Cai, Qi,Xu, Liu-Xin,Wang, Wei,Ji, Ya-Fei
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p. 627 - 635
(2013/07/25)
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- Novel antiobesity agents: Synthesis and pharmacological evaluation of analogues of Rimonabant and of LH21
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Searching for novel antiobesity agents, a series of cannabinoid LH21 and of Rimonabant-fatty acid amide analogues have been prepared. Synthesis of pyrazoles 2a-2c was achieved by a two steps simple methodology via α,β-unsaturated ketones. Carboxamides 8a-8h were obtained in good yields from esters 7a-7c by a one-pot procedure which takes place under mild conditions. New compounds have been evaluated in vivo as anorectic agents. Some of them showed interesting properties reducing food intake in rats by a mechanism which does not involve the endocannabinoid system.
- Alvarado, Mario,Decara, Juan,Luque, María Jesús,Hernandez-Folgado, Laura,Gómez-Ca?as, María,Gómez-Ruiz, María,Fernández-Ruiz, Javier,Elguero, José,Jagerovic, Nadine,Serrano, Antonia,Goya, Pilar,De Fonseca, Fernando Rodríguez
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p. 1708 - 1716
(2013/05/09)
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- Synthesis of bromodifluoromethyl substituted pyrazoles and isoxazoles
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Bromodifluoromethyl substituted β-diketone 3a-3d, prepared from corresponding ketones and ethyl bromodifluoroactate in the presence of sodium methoxide, reacted with aryl hydrazine derivatives affording bromodifluoromethyl substituted pyrazoles in high re
- Yang, Xueyan,Shui, Shengxia,Chen, Xi,He, Hai'ou,Wu, Fanhong
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experimental part
p. 426 - 432
(2010/04/23)
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- Cross coupling of bromo sydnones: Development of a flexible route toward functionalized pyrazoles
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(Chemical Equation Presented) The application of a Suzuki cross coupling approach to a range of C-4 substituted sydnones from a 4-bromosydnone is described. Moreover, the potential of this approach to prepare a diverse range of pyrazoles is demonstrated.
- Browne, Duncan L.,Taylor, John B.,Plant, Andrew,Harrity, Joseph P. A.
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supporting information; experimental part
p. 396 - 400
(2009/04/07)
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- Synthesis of N-methoxy-N-methyl-β-enaminoketoesters: New synthetic precursors for the regioselective synthesis of heterocyclic compounds
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Weinreb amides react with the lithium or sodium acetylide of ethyl propynoate in a hitherto unexplored acyl substitution-conjugate addition sequence to furnish (E)-N-methoxy-N-methyl-β-enaminoketoesters. This approach provides a diverse entry to densely functionalized heterocyclic compounds, including pyrazoles through regioselective cyclocondensations with hydrazines in a microwave-assisted reaction.
- Persson, Tobias,Nielsen, John
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p. 3219 - 3222
(2007/10/03)
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- New COX-2/5-LOX inhibitors: Apoptosis-inducing agents potentially useful in prostate cancer chemotherapy
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The arachidonic acid metabolizing enzymes cyclooxygenase-2 (COX-2) and lipoxygenases (LOXs) have been found to be implicated in a variety of cancers, including prostate cancer. To develop new therapeutic treatments, it therefore seemed interesting to design dual COX-2/5-LOX inhibitors. We report here the synthesis and in vitro pharmacological properties of diarylpyrazole derivatives that have in their structure key pharmacophoric elements to obtain optimal interaction with subsites of active pockets in both enzyme systems. Using a molecular modeling approach, a set of SAR data is proposed, highlighting the importance of the sulfonyl group of one of the aryl moieties in terms of proliferation inhibition and/or apoptosis induction.
- Pommery, Nicole,Taverne, Thierry,Telliez, Aurélie,Goossens, Laurence,Charlier, Caroline,Pommery, Jean,Goossens, Jean-Fran?ois,Houssin, Raymond,Durant, Fran?ois,Hénichart, Jean-Pierre
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p. 6195 - 6206
(2007/10/03)
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- Synthesis, central and peripheral benzodiazepine receptor affinity of pyrazole and pyrazole-containing polycyclic derivatives
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A series of new pyrazole-condensed 6,5,5 tricyclic compounds were synthesized and tested to evaluate their binding affinities at both central (CBR) and peripheral (PBR) benzodiazepine receptors. Some 1-aryl-5- phenylpyrazole derivatives were also prepared and tested for comparison with their corresponding rigid tricyclic analogs. Among the newly synthesized 1-aryl-1,4-dihydro-indeno[1,2-c]pyrazoles bearing both an ethoxycarbonyl group at position 3 and a carbonyl function at the position 4, compound 4b emerged as a new potent (IC50 = 26.4 nM) and selective CBR ligand. The 4-oxo-1-aryl-1,4-dihydro-indeno[1,2-c]pyrazole diethylamide derivative 14a was instead identified as a relatively potent (IC50 = 124 nM) but highly selective PBR ligand.
- Campagna, Francesco,Palluotto, Fausta,Carotti, Angelo,Maciocco, Elisabetta
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p. 849 - 856
(2007/10/03)
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- New pyrazolium-carboxylates as structural analogues of the pseudo-cross-conjugated betainic alkaloid nigellicine
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Pyrazolium-3-carboxylates were examined as relatives of the betainic alkaloid Nigellicine and as new examples of the sparsely populated class 16 of heterocyclic pseudo-cross-conjugated mesomeric betaines (PCCMB). The title compounds were prepared in a 4-step procedure starting from β-diketo compounds 8 which were cyclized with substituted hydrazines. The resulting isomeric pyrazole esters 9 and 10 were separated and subsequently quaternized with dimethyl sulfate in the presence of nitrobenzene to pyrazolium esters 11 and 12. Saponification was best accomplished in diluted sulfuric acid, which resulted in the formation of the pseudo-cross-conjugated mesomeric betaines 13 and 14 in one step. Protonation to the corresponding carboxylic acids required the treatment of the betaines with tetrafluoroboric acid in dichloromethane. The effect of negative solvatochromism proves the charge separation in the ground state of the molecules. X-ray crystallographic analyses, semiempirical calculations, and ESI mass spectrometric measurements were performed to gain knowledge about the phenomenon of pseudo-cross-conjugation.
- Schmidt, Andreas,Habeck, Tobias,Kindermann, Markus Karl,Nieger, Martin
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p. 5977 - 5982
(2007/10/03)
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- Haloacetylated enol ethers. 11 [16]. Synthesis of 1-methyl- and 1- phenyl pyrazole-3(5)-ethyl esters. A one-pot procedure
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A one-pot synthesis of 1-methyl- and 1-phenylpyrazole-3(5)-ethyl esters 2,3a-e by the cyclocondensation of β-alkoxyvinyl trichloromethyl ketones 1a- e with methyl and phenyl hydrazine hydrochloride under mild conditions, is reported. A study using compounds la-e with different substituents proved that these are versatile building blocks for the synthesis of pyrazole derivatives, having a 3(5)-ethoxycarbonyl substituent in good yields (60- 89%). The hydrazine and β-alkoxyvinyl trichloromethyl ketone substituent effects on the reaction regiochemistry on the formation of the 1,3- and 1,5- isomer were observed.
- Martins, Marcos A. P.,Freitag, Rogerio A.,Da Rosa, Adriano,Flores, Alex F. C.,Zanatta, Nilo,Bonacorso, Helio G.
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p. 217 - 220
(2007/10/03)
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- (13)C Chemical Shifts and (1)H - (13)C Coupling Constants of N-Phenyl-, N-p-Fluorophenyl- and N-o-Nitrophenylpyrazoles
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The (13)C chemical shifts and some (1)H - (13)C coupling constants of twelve N-arylpyrazoles are reported.The assignments were made by using the effects of a fluorine substituent and two-dimensional techniques. Key words: (13)C chemical shifts, (1)H - (13
- Begtrup, Mikael,Vedso, Per,Cabildo, Pilar,Claramunt, Rosa Maria,Elguero, Jose,Meutermans, Wim
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p. 455 - 459
(2007/10/02)
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