- Anxiolytic- and antidepressant-like effects of new phenylpiperazine derivative LQFM005 and its hydroxylated metabolite in mice
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The current treatments available for anxiety and depression are only palliative. Full remission has remained elusive, characterizing unmet medical needs. In the scope of an academic drug discovery program, we describe here the design, synthesis, in vitro metabolism prediction and pharmacological characterization of a new piperazine compound, 1-(4-methoxyphenyl)?4-((1-phenyl-1H-pyrazol-4-yl)methyl)piperazine (LQFM005), and of its main putative metabolite, 4-(4-((4-(4-methoxyphenyl)piperazin-1-yl)methyl)? 1H-pyrazol-1-yl)phenol (LQFM235). The production of the metabolite was initially performed by in vitro biotransformation of LQFM005 using Aspergillus candidus and then by chemical synthesis. Oral administration of either 12 or 24 μmol/kg LQFM005 to mice did not affect spontaneous locomotor activity but increased the time spent in the center of the open field. Both LQFM005 and LQFM235 (24 μmol/kg) increased the time spent by the mice in the open arms of the elevated plus maze (EPM), a good indication of anxiolytic-like effect, and decreased the immobility time in the forced swimming test (FST), suggesting an antidepressant-like effect. The previous administration of WAY-100635 (a 5-HT1A antagonist) abolished the effects of LQFM005 in both EPM and FST. Binding experiments showed that LQFM005 and its metabolite bind to the 5-HT1A receptor with a moderate affinity (Ki around 5–9 μM). The two compounds are relatively safe, as indicated by cytotoxic assessment using the 3T3 fibroblast cell line and estimated LD50 around 600 mg/kg. In conclusion, oral administration of the newly synthesized phenylpiperazines produced anxiolytic- and antidepressant-like effects in behavioral tests, putatively in part through the activation of 5-HT1A receptors.
- Moreira, Lorrane Kelle da Silva,Silva, Rafaela Ribeiro,da Silva, Dayane Moreira,Mendes, Mirella Andrade Silva,de Brito, Adriane Ferreira,de Carvalho, Flávio Souza,Sanz, Germán,Rodrigues, Marcella Ferreira,da Silva, Artur Christian Garcia,Thomaz, Douglas Vieira,de Oliveira, Valéria,Vaz, Boniek Gontijo,Li?o, Luciano Morais,Valadares, Marize Campos,Gil, Eric de Souza,Costa, Elson Alves,No?l, Fran?ois,Menegatti, Ricardo
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- NOVEL COMPOUND AS MTOR INHIBITOR AND USE THEREOF
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The present invention relates to a novel compound as an mTOR inhibitor and a use thereof and, more specifically, to a novel compound represented by formula 1 that exhibits mTOR inhibitory activity and a pharmaceutical composition comprising same as an act
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Paragraph 0063; 0096
(2021/03/04)
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- Unveiling Potent Photooxidation Behavior of Catalytic Photoreductants
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We describe a photocatalytic system that reveals latent photooxidant behavior from one of the most reducing conventional photoredox catalysts, N-phenylphenothiazine (PTH). This aerobic photochemical reaction engages difficult to oxidize feedstocks, such as benzene, in C(sp2)-N coupling reactions through direct oxidation. Mechanistic studies are consistent with activation of PTH via photooxidation and with Lewis acid cocatalysts scavenging inhibitors inextricably formed in this process.
- Targos, Karina,Williams, Oliver P.,Wickens, Zachary K.
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supporting information
p. 4125 - 4132
(2021/04/07)
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- Electrophotocatalytic SNAr Reactions of Unactivated Aryl Fluorides at Ambient Temperature and Without Base
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The electrophotocatalytic SNAr reaction of unactivated aryl fluorides at ambient temperature without strong base is demonstrated.
- Huang, He,Lambert, Tristan H.
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supporting information
p. 658 - 662
(2019/11/28)
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- Design, synthesis and pharmacological assessment of new pyrazole compounds
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Aims: This study investigated the antinociceptive and anti-inflammatory effects of new pyrazole compounds LQFM011(5), LQFM043(6) and LQFM044(7) as well as the mechanisms of action and acute in vitro toxicity. Main methods: The antinociceptive activity was evaluated using the acetic acid-induced abdominal writhing test, formalin-induced pain test and the Randall–Selitto test. The anti-inflammatory activity was evaluated using models of paw oedema and pleurisy induced by carrageenan; cell migration, the levels of tumour necrosis factor α (TNF-α) and myeloperoxidase (MPO) enzyme activity were evaluated. In addition, the ability to inhibit phospholipase A2 (PLA2) in vitro and docking in PLA2 were used. Acute oral systemic toxicity in mice was evaluated through the neutral red uptake assay. Key findings: The synthesised compounds (5–7), delivered via gavage (p.o.) at 70, 140 or 280 μmol/kg, decreased the number of writhings induced by acetic acid; the three compounds (280 μmol/kg p.o.) reduced the paw licking time in the first and second phase of the formalin test and decreased the nociceptive threshold variation in the Randall–Selitto test. Furthermore, this dose reduced oedema formation, leucocyte migration (specifically through reduction in polymorphonuclear cell movement) and increased mononuclear cells. MPO activity and the levels of pro-inflammatory cytokines TNF-α were decreased. Evaluation of PLA2 inhibition via the docking simulation revealed more interactions of LQFM043R(6) and LQFM044(7), data that corroborated the half-maximal inhibitory concentration (IC50) of PLA2 inhibition in vitro. Therefore, LQFM011(5), LQFM043(6) and LQFM044(7) were classified with the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) as category 4.
- Costa, Elson A.,Florentino, Iziara F.,Li?o, Luciano M.,Menegatti, Ricardo,Oliveria, Jordana C.,Pazini, Francine,Sanz, Germán,Silva, Daiany P. B.,Valadares, Marize C.,Vaz, Boniek G.,Verli, Hugo,Villavicencio, Bianca,da Silva, Lidya C.,de Carvalho, Flávio S.,dos Santos, Fernanda Cristina Alcantara,dos Santos, Thaís Rosa Marques
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p. 915 - 928
(2020/07/21)
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- Anti-inflammatory and antinociceptive activity profile of a new lead compound – LQFM219
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LQFM219 is a molecule designed from celecoxibe (COX-2 inhibitor) and darbufelone (inhibitor of COX-2 and 5-LOX) lead compounds through a molecular hybridisation strategy. Therefore, this work aimed to investigate the antinociceptive and anti-inflammatory activities of this new hybrid compound. The acute oral systemic toxicity of LQFM219 was evaluated via the neutral red uptake assay. Acetic acid-induced abdominal writhing and CFA-induced mechanical hyperalgesia were performed to evaluate the antinociceptive activity, and the anti-oedematogenic activity was studied by CFA-induced paw oedema and croton oil-induced ear oedema. Moreover, the acute anti-inflammatory activity was determined by carrageenan-induced pleurisy. In addition, cell migration, myeloperoxidase enzyme activity, and TNF-α and IL-1β levels were determined in pleural exudate. Moreover, a redox assay was conducted using electroanalytical and DPPH methods. The results demonstrated that LQFM219 was classified as GHS category 4, and it showed better free radical scavenger activity compared to BHT. Besides, LQFM219 decreased the number of writhings induced by acetic acid and the response to the mechanical stimulus in the CFA-induced mechanical hyperalgesia test. Furthermore, LQFM219 reduced oedema formation, cell migration, and IL-1β and TNF-α levels in the pleural cavity and inhibited myeloperoxidase enzyme activity. Thus, our study provides that the new pyrazole derivative, LQFM219, demonstrated low toxicity, antinociceptive and anti-inflammatory potential in vitro and in vivo.
- Cardoso, Carina S.,Costa, Elson A.,Florentino, Iziara F.,Leite, Jacqueline A.,Menegatti, Ricardo,Silva, Andreia L. P.,Valadares, Marize C.,Vaz, Boniek G.,da Silva, Artur C. G.,da Silva, Daiany P. B.,de S. Gil, Eric,Galv?o, Gustavo M.,Li?o, Luciano M.,Sabino, José R.,Sanz, Germán
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- Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication
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Visible-light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron transfer (SET), resulting in C?H/N?H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the cis-2,6-dimethylpiperidine moieties.
- Huang, He,Strater, Zack M.,Rauch, Michael,Shee, James,Sisto, Thomas J.,Nuckolls, Colin,Lambert, Tristan H.
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supporting information
p. 13318 - 13322
(2019/08/12)
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- Novel choline analog 2-(4-((1-phenyl-1H-pyrazol-4-yl)methyl)piperazin-1-yl)ethan-1-ol produces sympathoinhibition, hypotension, and antihypertensive effects
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The search for new drugs remains an important focus for the safe and effective treatment of cardiovascular diseases. Previous evidence has shown that choline analogs can offer therapeutic benefit for cardiovascular complications. The current study investigates the effects of 2-(4-((1-phenyl-1H-pyrazol-4-yl)methyl)piperazin-1-yl)ethan-1-ol (LQFM032) on cardiovascular function and cholinergic-nitric oxide signaling. Synthesized LQFM032 (0.3, 0.6, or 1.2?mg/kg) was administered by intravenous and intracerebroventricular routes to evaluate the potential alteration of mean arterial pressure, heart rate, and renal sympathetic nerve activity of normotensive and hypertensive rats. Vascular function was further evaluated in isolated vessels, while pharmacological antagonists and computational studies of nitric oxide synthase and muscarinic receptors were performed to assess possible mechanisms of LQFM032 activity. The intravenous and intracerebroventricular administration of LQFM032 elicited a temporal reduction in mean arterial pressure, heart rate, and renal sympathetic nerve activity of rats. The cumulative addition of LQFM032 to isolated endothelium-intact aortic rings reduced vascular tension and elicited a concentration-dependent relaxation. Intravenous pretreatment with L-NAME (nitric oxide synthase inhibitor), atropine (nonselective muscarinic receptor antagonist), pirenzepine, and 4-DAMP (muscarinic M1 and M3 subtype receptor antagonist, respectively) attenuated the cardiovascular effects of LQFM032. These changes may be due to a direct regulation of muscarinic signaling as docking data shows an interaction of choline analog with M1 and M3 but not nitric oxide synthase. Together, these findings demonstrate sympathoinhibitory, hypotensive, and antihypertensive effects of LQFM032 and suggest the involvement of muscarinic receptors.
- Menegatti, Ricardo,Carvalho, Flávio S.,Li?o, Luciano M.,Villavicencio, Bianca,Verli, Hugo,Mour?o, Aline A.,Xavier, Carlos H.,Castro, Carlos H.,Pedrino, Gustavo R.,Franco, Octavio L.,Oliveira-Silva, Iransé,Ashpole, Nicole M.,Silva, Osmar Nascimento,Costa, Elson A.,Fajemiroye, James O.
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p. 1071 - 1083
(2019/05/15)
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- Anti-inflammatory effect of a new piperazine derivative: (4-methylpiperazin-1-yl)(1-phenyl-1H-pyrazol-4-yl)methanone
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Aims: This study investigates the anti-nociceptive and anti-inflammatory effects of new piperazine compound (LQFM182) as well as the toxicity acute in vitro. Main methods: To evaluate the anti-nociceptive activity, the acetic acid-induced abdominal writhing test, tail flick test and formalin-induced pain test were used. The anti-inflammatory activity was evaluated using the models of paw oedema and pleurisy induced by carrageenan and some inflammatory parameters were evaluated, including cell migration, myeloperoxidase enzyme activity and the levels of TNF-α and IL-1β cytokines in pleural exudate. The acute oral systemic toxicity of LQFM182 in mice was evaluated through the neutral red uptake (nru) assay. Key findings: LQFM182 (50, 100 or 200?mg/kg, p.o.) decreased the number of writhings induced by acetic acid in a dose-dependent manner, and an intermediate dose (100?mg/kg, p.o.) reduced the paw licking time of animals in the second phase of the formalin test. Furthermore, LQFM182 (100?mg/kg, p.o.) reduced oedema formation at all hours of the paw oedema induced by carrageenan test and in pleurisy test reduced cell migration from the reduction of polymorphonuclear cells, myeloperoxidase enzyme activity and the levels of pro-inflammatory cytokines IL-1β and TNF-α. Therefore, it was classified in GHS category 300?50??2000?mg/kg. Significance: Reduction of the TNF-α and IL-1β levels.
- Batista, Daniel C.,Silva, Daiany P. B.,Florentino, Iziara F.,Cardoso, Carina S.,Gon?alves, Merita P.,Valadares, Marize C.,Li?o, Luciano M.,Sanz, Germán,Vaz, Boniek G.,Costa, Elson A.,Menegatti, Ricardo
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p. 217 - 226
(2017/10/06)
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- Pyridazinone compounds and use thereof (by machine translation)
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The invention discloses a pyridazinone compounds, structure such as formula I shown: In the type of each substituent is as defined in the specification. The compounds of this invention have broad-spectrum antibacterial, insecticidal or acaricidal activity, the cucumber downy mildew, wheat powdery mildew, corn rust, rice blast, cucumber anthracnose and has excellent control effect. (by machine translation)
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Paragraph 0498
(2018/05/07)
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- Anxiolytic-like effect of 2-(4-((1-phenyl-1H-pyrazol-4-yl)methyl)piperazin-1-yl)ethan-1-ol is mediated through the benzodiazepine and nicotinic pathways
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In this study, we proposed the design, synthesis of a new compound 2-(4-((1-phenyl-1H-pyrazol-4-yl)methyl)piperazin-1-yl)ethan-1-ol (LQFM032), and pharmacological evaluation of its anxiolytic-like effect. This new compound was subjected to pharmacological screening referred to as Irwin test, prior to sodium pentobarbital-induced sleep, open-field and wire tests. The anxiolytic-like effect of this compound was evaluated using elevated plus maze and light–dark box tests. In addition, the mnemonic activity was evaluated through step-down test. In sodium pentobarbital-induced sleep test, LQFM032 decreased latency and increased duration of sleep. In the open-field test, LQFM032 altered behavioral parameter, that suggested anxiolytic-like activity, as increased in crossings and time spent at the center of open field. In the plus maze test and light–dark box test, the LQFM032 showed anxiolytic-like activity, increased entries and time spent on open arms, and increased in number of transitions and time spent on light area, respectively. Those effects was antagonized by flumazenil but not with 1-(2-Methoxyphenyl)-4-(4-phthalimidobutyl)piperazine (NAN-190). The LQFM032 did not alter mnemonic activity. Moreover, the anxiolytic-like activity of LQFM032 was antagonized by mecamylamine. In summary, LQFM032 showed benzodiazepine and nicotinic pathways mediated anxiolytic-like activity without altering the mnemonic activity.
- Brito, Adriane F.,Fajemiroye, James O.,Neri, Hiasmin F. S.,Silva, Dayane M.,Silva, Daiany P. B.,Sanz, Germán,Vaz, Boniek G.,de Carvalho, Flávio S.,Ghedini, Paulo C.,Li?o, Luciano M.,Menegatti, Ricardo,Costa, Elson A.
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p. 432 - 442
(2017/08/08)
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- HERBICIDAL SUBSTITUTED PYRIMIDINYLOXY BENZENE COMPOUNDS
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Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, (INSERT FORMULA 1 HERE) wherein each Y1, Y2, Y3, Y4, Z, R2, m and R3 are as defined in the di
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Page/Page column 44
(2015/06/25)
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- Chemoselective and regiospecific formylation of 1-phenyl-1H-pyrazoles through the duff reaction
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The synthesis of formylated 1-phenyl-1H-pyrazole derivatives under the Duff reaction conditions is reported. Our results indicate that 1-phenyl-1H-pyrazole systems containing electron-withdrawing and electron-donating substituents at the phenyl moiety rea
- De Oliveira,Mairink,Pazini,Liao,De Oliveira,Viegas Jr.,De Oliveira,Cunha,Oliveira,Paz Jr.,Eberlin,Menegatti, Ricardo
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supporting information
p. 1633 - 1639
(2013/05/22)
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- Central pharmacological activity of a new piperazine derivative: 4-(1-Phenyl-1h-pyrazol-4-ylmethyl)-piperazine-1-carboxylic acid ethyl ester
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Aims: Our study focuses on the design and synthesis of a new piperazinic derivate, 4-(1-phenyl-1h-Pyrazol-4-Ylmethyl)-Piperazine-1-Carboxylic Acid Ethyl ester (LQFM008), and evaluation of its anxiolytic-like profile in Swiss mice. Main methods: LQFM008 was evaluated in a screening test of the central nervous system including the rota-rod, sodium pentobarbital-induced sleep, open field, elevated plus maze and light-dark box tests. Key findings: LQFM008 induced convulsions at the dose of 1.1 mmol/kg (i.p., s.c. or p.o.). LQFM008 up to 400 μmol/kg had no effect in the rota rod test. In the open field test, LQFM008 increased the number of crossings and the time spent at the central area as well as the sleeping time in sodium pentobarbital-induced sleep. In the elevated plus maze and light-dark box tests, this compound showed an anxiolytic-like activity. This anxiolytic-like activity was antagonized by NAN-190 (5-HT 1A antagonist) but not by flumazenil (benzodiazepine antagonist). Significance: The compound LQFM008 showed anxiolytic-like activity which may involve serotonergic pathway.
- De Brito, Adriane Ferreira,Martins, José Luís Rodrigues,Fajemiroye, James Oluwagbamigbe,Galdino, Pablinny Moreira,De Lima, Thereza Christina Monteiro,Menegatti, Ricardo,Costa, Elson Alves
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experimental part
p. 910 - 916
(2012/09/07)
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- Synthesis and antileishmanial activity of new 1-aryl-1H-pyrazole-4- carboximidamides derivatives
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Chemotherapy for leishmaniasis, diseases caused by protozoa of the genus Leishmania, remains inefficient in several treatments. So there is a need to search for new drugs. In this work, we have synthesized 1-aryl-1H-pyrazole-4- carboximidamides derivatives and evaluated antileishmanial activities in vitro, as well as cytotoxic effects. Structure-activity relationship (SAR) studies were carried out with all the compounds of the series. Compound 2 showed an activity profile that can be improved through medicinal chemistry strategies.
- Dos Santos, Mauri?cio S.,Gomes, Adriana O.,Bernardino, Alice M. R.,De Souza, Marcos C.,Khan, Misbahul A.,De Brito, Monique A.,Castro, Helena C.,Abreu, Paula A.,Rodrigues, Carlos R.,De Le?o, Rosa M. M.,Leon, Leonor L.,Canto-Cavalheirr, Marilene M.
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experimental part
p. 352 - 358
(2011/10/04)
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- Complete assignment of NMR data of 22 phenyl-1H-pyrazoles' derivatives
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Complete assignment of 1H and 13C NMR chemical shifts and J(1H/1H and 1H/19F) coupling constants for 22 1-phenyl-1H-pyrazoles' derivates were performed using the concerted application of 1H 1D and 1H, 13C 2D gs-HSQC and gs-HMBC experiments. All 1-phenyl-1H-pyrazoles' derivatives were synthesized as described by Finar and co-workers. The formylated 1-phenyl-1H-pyrazoles' derivatives were performed under Duff's conditions. Copyright
- De Oliveira, Aline Lima,Alves De Oliveira, Carlos Henrique,Mairink, Laura Maia,Pazini, Francine,Menegatti, Ricardo,Liao, Luciano Morais
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scheme or table
p. 537 - 542
(2011/10/09)
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- Synthesis, antichagasic in vitro evaluation, cytotoxicity assays, molecular modeling and SAR/QSAR studies of a 2-phenyl-3-(1-phenyl-1H-pyrazol-4-yl)-acrylic acid benzylidene-carbohydrazide series
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Chagas disease (American trypanosomiasis) is one of the most important parasitic diseases with serious social and economic impacts mainly on Latin America. This work reports the synthesis, in vitro trypanocidal evaluation, cytotoxicity assays, and molecular modeling and SAR/QSAR studies of a new series of N-phenylpyrazole benzylidene-carbohydrazides. The results pointed 6k (X = H, Y = p-NO2, pIC50 = 4.55 M) and 6l (X = F, Y = p-CN, pIC50 = 4.27 M) as the most potent derivatives compared to crystal violet (pIC50 = 3.77 M). The halogen-benzylidene-carbohydrazide presented the lowest potency whereas 6l showed the most promising profile with low toxicity (0% of cell death). The best equation from the 4D-QSAR analysis (Model 1) was able to explain 85% of the activity variability. The QSAR graphical representation revealed that bulky X-substituents decreased the potency whereas hydrophobic and hydrogen bond acceptor Y-substituents increased it.
- Vera-DiVaio, Maria A.F.,Freitas, Antonio C.C.,Castro, Helena C.,de Albuquerque, Sergio,Cabral, Lucio M.,Rodrigues, Carlos R.,Albuquerque, Magaly G.,Martins, Rita C.A.,Henriques, Maria G.M.O.,Dias, Luiza R.S.
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experimental part
p. 295 - 302
(2011/02/26)
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- NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
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The present invention relates to piperidine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
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Page/Page column 72
(2009/10/01)
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- Inhibitors of 15-hydroxyprostaglandin dehydrogenase for stimulating pigmentation of the skin or skin appendages
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Inhibitors of 15-hydroxyprostaglandin dehydrogenase (15-PGDH), for example tetrazole, styrylpyrazole, phenylfuran, phenylthiophene, phenylpyrrazole, pyrazolecarboxamide, 2-thioacetamide and azo compounds, are useful for promoting or stimulating pigmentati
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Page/Page column 62
(2010/10/19)
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- A2B ADENOSINE RECEPTOR ANTAGONISTS
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Disclosed are novel compounds that are A2B adenosine receptor antagonists having the following structure (I) wherein R1 and R2 are independently chosen from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, and optionally substituted heteroaryl, and R4 is an optionally substituted heteroaryl moiety. The compounds of the invention are useful for treating various disease states, including asthma, chronic obstructive pulmonary disorder, pulmonary inflammation, emphysema, diabetic disorders, inflammatory gastrointestinal tract disorders, immunological/inflammatory disorders, cardiovascular diseases, neurological disorders, and diseases related to angiogenesis.
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Page/Page column 43
(2008/06/13)
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- Solvent-free preparation of tris-pyrazolyl-1,3,5-triazines
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Tris-pyrazolyl-1,3,5-triazines have been prepared by cyclotrimerization of aromatic nitriles in solvent-free conditions. The interesting structures of these compounds make them candidates for application in coordination chemistry and crystal engineering.
- De La Hoz, Antonio,Díaz-Ortiz, Angel,Elguero, José,Martínez, Luis J.,Moreno, Andrés,Sánchez-Migallón, Ana
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p. 4397 - 4403
(2007/10/03)
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- Synthesis of new benzylic ethers of oximes derived from 1-phenyl- pyrazole compounds
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In the scope of a research program aiming at the synthesis and pharmacological evaluation of new antithrombotic agents via rational molecular design, we describe in this paper the synthesis of benzyl ethers of aryl-pyrazolic oxime derivatives. Ethers' (2a-2c) and (3a-3c) are derived from 4-formyl-1-N-phenylpyrazole (4) in good yield. Designed as interphenylenic analogues of the ridogrel (1), one expects these compounds to present dual properties, i.e., thromboxane A2 receptors antagonism and thromboxane synthetase inhibition.
- Muri, Estela M. F.,Barreiro, Eliezer J.,Fraga, Carlos A. M.
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p. 1299 - 1321
(2007/10/03)
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- Research in the Azole Series. Synthesis and 13C NMR Study of Pyrazole-4-carboxaldehydes
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Ten new pyrazoles have been prepared and their 13C nmr chemical shifts compared with those of twelve other pyrazoles, some of them prepared purposely for this study.The chemical shifts are discussed statistically assuming that they are additive.A formyl group in the position 4 of the pyrazole ring produces a large effect on carbon C4 (SCS = 17.3 ppm) and medium effects on carbons C3 (SCS = 1.9 ppm) and C5 (SCS = 3.8 ppm).The azines derived from pyrazole-4-carboxaldehydes are of the E,E-configuration.
- Echevarria, Aurea,Elguero, Jose,Meutermans, Wim
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p. 957 - 960
(2007/10/02)
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- DIRECT SYNTHESIS OF 2-SUBSTITUTED 5-FORMYLPYRIMIDINES AND RING TRANSFORMATION OF THEIR PHENYLHYDRAZONES INTO 4-FORMYL-1-PHENYLPYRAZOLE
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Triformylmethane (1) reacted with benzamidine, guanidine and S-methylisothiourea to give 2-substituted 5-formylpyrimidines (2a-c), whose phenylhydrazones (3a-c) readily underwent ring transformation into 4-formyl-1-phenylpyrazole (4) on heating in acidic methanol.
- Takagi, Kaname,Bajnati, Abdelilah,Hubert-Habart, Michel
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p. 1105 - 1109
(2007/10/02)
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- Direct syntheses of pyrazole-4-carbaldehydes and pyrimidine-5-carbaldehydes starting from triformylmethane.
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Triformylmethane is transformed into the pyrazole-4-carbaldehydes 2, 4, 6, 7, 9, 11 and the pyrazole-4-carbaldehydes 8, 10, 12 by corresponding hydrazines, and into the pyrimidine-5-carbaldehydes 13, 14, 15 by appropriate amidines.
- Takagi, K.,Bajnati, A.,Hubert-Habart, M.
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p. 660 - 666
(2007/10/02)
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