883-38-5Relevant academic research and scientific papers
New hydrazone derivatives of pyrazole-4-carboxaldehydes exhibited anti-inflammatory properties
Chen, Qiuyan,Deng, Xianqing,He, Shihui,Li, Sifan,Liang, Yuqiu,Liu, Bing,Song, Mingxia,Yu, Shengwang
, p. 501 - 510 (2020/04/17)
Background: Several series of hydrazone derivatives of pyrazole-4-carboxaldehydes (4-11) were designed and synthesized to screen their inflammatory activity. Methods: The products were characterized by1H NMR,13C NMR and HRMS. In vitro LPS-induced TNF-α model and in vivo xylene-induced ear-edema model were used to evaluate their anti-inflammatory activity. Results and Conclusion: Bioassays indicated that most of the compounds markedly inhibited the expression of TNF-α at the concentration of 10 μg/mL. Compounds 7b and 11c, two of the most potent compounds, exhibited TNF-α inhibitory ability in a dose-dependent manner with IC50 values of 5.56 and 3.69 μM, respectively. In vivo, intraperitoneal administration with 7b and 11c markedly inhibited the ear edema at the doses of 20 and 50 mg/kg. Compound 11c, inhibited edema by 49.59 % at the dose of 20 mg/kg, was comparable to the reference drug dexamethasone at the same dose (with an inhibition of 50.49 %). To understand the binding pattern, molecular docking of representa-tive 7b and 11c was performed, which demonstrated that both compounds have a forceful binding with the TNF-α, and that the phenyl and hydrazide moieties of them play a significant role in binding with the target site.
Synthesis of poly-functionalized pyrazoles under Vilsmeier-Haack reaction conditions
Popov, Aleksandr V.,Kobelevskaya, Valentina A.,Larina, Ludmila I.,Rozentsveig, Igor B.
, p. 1 - 14 (2019/11/11)
Synthesis of 1,3-disubstituted 5-chloro-1H-pyrazole-4-carbaldehydes was achieved by formylation of the corresponding 5-chloro-1H-pyrazoles under Vilsmeier-Haack conditions.
Synthesis and evaluation of anticonvulsant activities of pyrazol semicarbazones. Part II
Song, Ming-Xia,Wu, Yi,Deng, Xian-Qing
, p. 800 - 808 (2016/09/23)
A series of 2-((5-aryloxy-1-methyl-3-methyl-1H-pyrazol-4-yl)methylene) hydrazinecarboxamides (6a-6l) and 2-((5-aryloxy-1-methyl-3-phenyl-1H-pyrazol-4-yl)methylene) hydrazinecarboxamides (7a-7l) were designed and synthesized. The maximal electroshock shock (MES) and subcutaneous pentylenetetrazole (sc-PTZ) seizure models in mice were used to evaluate the antiepileptic effect of compounds synthesized. Further, the acute neurotoxicity profile was also studied via the rotarod test. The results of sc-PTZ test indicate that a majority of compounds possessed anticonvulsant activity with long duration of protection effects. Among of them, compound 6k was found to be the most promising one, with an ED50 value of 20.4 mg/kg (in sc-PTZ model) and a PI value of 10.8, possessing higher anti-PTZ activity and wider safety margin than valproate and ethosuximide.
Synthesis and antitumor activity of some pyrazole derivatives
El-Baih, Fatma E.M.,Al-Hazimi, Hassan M.
experimental part, p. 1309 - 1313 (2011/12/16)
Vilsmeier-Haack chloroformylation of 1a-e using DMF and an excess of POCl3 yielded the corresponding pyrazole-4-carbaldehydes 2a-e. Reaction of 2a,c with o-bromophenol and KOH in DMF gave the target compound 5-phenoxypyrazole-4- carbaldehydes 3a,b which in turn gave the corresponding oximes 4a,b by oximation of 3a,b with hydroxylamine. Condensation of 2b,c with 1,2-diaminobenzene and 2-aminothiophenol was carried out to give tetrahydrobenzo[b]pyrazolo[3,4-e][1,4] diazepine derivatives 5a,b and benzo[b]pyrazolo[4,3- f][1,4]thiazepine derivatives 6a,b, respectively. Some of the prepared compounds was examined as cytotoxic agents. The compounds 3a, 4a, 5a and 6a were proved to be less or more active than the standared doxorubicin depending on the cell lines.
Influence of chromophore dipole moments in parameterts of organic light emitting devices based on phenyl and methyl modified pyrazoloquinoline
Gondek,Nizio?,Danel,Szlachcic,Pluciński,Sanetra,Kityk
experimental part, p. 1501 - 1505 (2010/06/20)
Absorption, photo- and electroluminescence spectra of some trityl substituted 1H-pyrazolo[3,4-b]quinolines derivatives (methyl- and phenyl substituted) and fabrication of the single layered organic light emitting diodes are reported. The bulky trityl substituent was introduced to prevent aggregation and crystallization of the dopant in polymer matrix. Role of ground state dipole moments in the observed red Stokes shift, electroluminescent features and photocarrier transport is explored. The maximally achieved brightness about 50 Cd/m2 is observed in the spectral range extending from 443 nm up to 462 nm. The voltage threshold was varied from 7.8 V up to 10 V. The brightness-current dependences show an existence of at least two types of carrier injections.
5-((1H-Pyrazol-4-yl)methylene)-2-thioxothiazolidin-4-one inhibitors of ADAMTS-5
Gilbert, Adam M.,Bursavich, Matthew G.,Lombardi, Sabrina,Georgiadis, Katy E.,Reifenberg, Erica,Flannery, Carl R.,Morris, Elisabeth A.
, p. 1189 - 1192 (2007/10/03)
A series of 5-((1H-pyrazol-4-yl)methylene)-2-thioxothiazolidin-4-one inhibitors of ADAMTS-5 (aggrecanase-2) is described. These compounds show μM functional inhibition of ADAMTS-5, and represent a new class of agents with the potential of inhibiting degradation of aggrecan, a major component of cartilage which is lost in osteoporosis. Compound 12 is noteworthy in that it has an ADAMTS-5 IC50: 1.1 μM and shows >40-fold functional selectivity over ADAMTS-4 (aggrecanase-1).
Reaction of 4-Hydroxy-5-oximino-3-thiophenecarboxylates with Hydrazines. Formation of Pyrazolylthiohydroxamic Acids
Robey,Alt,Van Meter
, p. 413 - 428 (2007/10/03)
The reactions of 4-hydroxy-5-oximino-3-thiophenecarboxylates with hydrazine and substituted hydrazines have been investigated. The products of the reactions have been shown to be pyrazole-3- or 5-thiohydroxamic acids rather than the hydrazones previously described by Benary and Silberstrom. Two alternate mechanisms are proposed which account for the regiochemical outcome. The structures of the pyrazole-3- and 5-thiohydroxamic acids and corresponding nitriles have been proven by independent synthesis, comparison to known compounds, and by proton and carbon magnetic resonance and long range HETCOR experiments.
Azide Ring-Opening-Ring-Closure Reactions and Tele-substitutions in Vicinal Azidopyrazole-, Pyrrole- and Indolecarboxaldehydes
Becher, Jan,Joergensen, Per Lauge,Pluta, Krystian,Krake, Niels J.,Faelt-Hansen, Birgitte
, p. 2127 - 2134 (2007/10/02)
5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3.Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields.Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields.In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.
