- RECYCLIZATION OF 4-METHYL(PHENYL)-2,3-DIHYDRO-1H-1,5-BENZODIAZEPIN-2-ONES
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Depending on the reaction conditions, the hydrazinolysis of 4-(acetyl-methylene)-1,2,3,5-tetrahydro-1,5-benzodiazepin-2-one affords N-(2-aminophenyl)-5-methyl-3-pyrazolylacetamide or 2-benzimidazo-5-methyl-3-pyrazolylmethane.In the presence of phenylhydrazine, 3,4,5-trimethyl-1,5-benzodiazepine is recyclized to 3,4,5-trimethyl-1-phenyl-2-pyrazole.
- Gaponov, A. A.,Solomko, Z. F.,Bozhanova, N. Ya.,Pantyukh, E. I.
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- 2-(3-Methyl-1-phenyl-1 H-pyrazol-4-yl)-3-phenylthiazolidin-4-ones as potent antioxidant and antidiabetic agent
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A series of 2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-phenylthiazolidin-4-ones (7a-7j) were synthesized by intramolecular cyclization of imines (6a-6j) with thioglycolic acid in the presence of acid catalyst. The Schiff bases were obtained upon reaction between electrophilic carbon atom of 3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (4) and nucleophilic nitrogen atom of substituted aromatic amines. in vitro Antioxidant activity was determined by DPPH redical scavenging assay mehod using ascorbic acid as standard. The antidiabetic activity was carried out by streptazocine induced diabetic method using rosiglitazone as standard drug on wister rats. From the study it were found that 3-(4-chlorophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7a), 3-(4-bromophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7b), 3-(3,4-dichlorophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7d ), 3-(3,4-difluorophenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)thiazolidin-4-one (7f) 2-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-(4-(trifluoromethyl) phenyl) thiazolidin-4-one (7h), 3-(4-methoxyphenyl)-2-(3-methyl-1-phenyl-1H-pyrazol-4-yl) thiazolidin-4-one (7j) shown more IC50compare to standard. Where as compound 7a, 7b, 7h, 7j show more significant antidiabetic effect against hyperglycemic rats compare to standard drugs at the dose of 5 mg/kg after 21 days of treatment.
- Sen, Sandip,De, Biplab,Easwari
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- Design and Synthesis of Fused and Spiro Pyrazole Derivatives
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Abstract: Condensation of 5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with p-hydroxybenzaldehyde in alcoholic sodium hydroxide yielded (Z)-4-(4-hydroxybenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one which was treated with acetylacetone, hydrazine hydrate, ethyl cyanoacetate, and ethyl acetoacetate to afford pyranopyrazole, pyrazolopyrazole, pyrazolopyridine, and 6-aminopyrazolopyridine derivatives, respectively. 5-Methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one was also reacted at the enamino carbon atom with 2,4-dichlorobenzoyl isothiocyanate, thiosemicarbazide, and hydrazine hydrate to produce pyrazolooxazine, pyrazolopyrazole, and spiro[pyrazole-3,3′-pyrazolo[3,4-c]pyrazole] derivatives.
- Abdelrahman, E. F.,Assy, M. G.,Shehta, W.
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- Structures and chemical equilibria of some N-heterocycles containing amide linkages
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Structures and chemical equilibria of 5-carboxy-2-thiouracil (1), 5,6-diphenyl-3-hydroxy-1,2,4-triazine (2), 1-phenyl-3-methyl-5-pyrazolone (3) and 2-mercapto-4,6-dimethylpyrimidine hydrochloride (4) are reported. Their electronic transitions are assigned and pK values are evaluated and discussed.
- Masoud,Abd El Zaher Mostafa,Ahmed,Abd El Moneim
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- Synthesis of Pyrano, Pyrido, Oxazino, and Spiro Pyrazole Derivatives and Their Antimicrobial Activity
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Abstract: Condensation of 5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with 4-hydroxybenzaldhyde in alcoholic sodium hydroxide yielded 4-(4-hydroxybenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and treatment of the latter with acetylacetone, hydrazine hydrate, ethyl cyanoacetate, and ethyl acetoacetate gave pyranopyrazole, pyrazolopyrazole, and pyrazolopyridine derivatives. 5-Methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one was reacted with 2,4-dichlorobenzoyl isothiocyanate, thiosemicarbazide, and hydrazine hydrate to afford pyrazolooxazine, pyrazolopyrazole, and spiro[pyrazole-3,3′-pyrazolo[3,4-c]pyrazole] derivatives. Some of the newly synthesized compounds showed high antimicrobial activity against three microbial strains (S. aureus, E. coli, C. albicans).
- Abdelrahman, E. F.,Assy, M. G. M.,Farhan, M. E.,Shehta, W.
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- Ligand based design and synthesis of pyrazole based derivatives as selective COX-2 inhibitors
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The design and synthesis of novel pyrazole based derivatives has been carried out using the ligand based approach like pharmacophore and QSAR modelling of reported pyrazoles from the available literature to investigate the chemical features that are essential for the design of selective and potent COX-2 inhibitors. Both pharmacophore and QSAR models with good statistical parameters were selected for the design of the lead molecule. Also by exploiting the chemical structures of selective and marketed COX-2 inhibitors, celecoxib and SC-558 were used in designing the molecules which are used in the treatment of inflammation and related disorders. The therapeutic action of the Non-Steroidal Anti-inflammatory Agents (NSAIDs) is based primarily on the COX-2 inhibition. With this background we have synthesized some azomethine derivatives of 3-methyl-1-substituted-4-phenyl-6-[{(1E)-phenylmethylene}amino]-1,4-dihydro pyrano[2,3-c]pyrazole-5-carbonitrile 6(a-o) and were characterized by 1HNMR, 13CNMR and Mass spectral techniques. All the synthesized pyrazole derivatives were tested for in vitro membrane stability property in both COX-1 & COX-2 inhibition studies and in vivo anti-inflammatory activity by carrageenan induced rat paw edema model. Among them, compound 6k showed very good activity by in vivo anti-inflammatory activity with 0.8575 mmol/kg as ED50. Similarly compounds 6m, 6o, 6i and 6h exhibited comparable anti-inflammatory activity to standard drugs. Also the active compounds were further screened for ulcerogenic activity and were found be safer with less ulcer index compared to the marketed drugs like aspirin, ibuprofen and celecoxib.
- Murahari, Manikanta,Mahajan, Vivek,Neeladri, Sreenivasulu,Kumar, Maushmi S.,Mayur
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p. 583 - 597
(2019/02/24)
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- Copper-catalyzed convenient synthesis and SAR studies of substituted-1,2,3-triazole as antimicrobial agents
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Background: A novel copper-catalyzed synthesis of substituted-1,2,3-triazole derivatives has been developed and performed by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The reaction is one-pot multicomponent. Objective: We state the advancement and execution of a methodology allowing for the synthesis of some new substituted 1,2,3-triazole analogues with antimicrobial activity. Methods: A series of triazole derivatives was synthesized by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The structures of the synthesized compounds were elucidated and confirmed by1H NMR, IR, MS and elemental analysis. All the synthesized compounds were tested for their antimicrobial activity against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus nigar for antifungal activity, respectively. Results and Conclusion: From the antimicrobial data, it was observed that all the newly synthesized compounds showed good to moderate level of antibacterial and antifungal activity.
- Sarkate, Aniket P.,Karnik, Kshipra S.,Wakte, Pravin S.,Sarkate, Ajinkya P.,Izankar, Ashwini V.,Shinde, Devanand B.
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- Efficient Synthesis of Five Types of Heterocyclic Compounds via Intramolecular Elimination Using Ultrasound-Static Heating Technique
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An experimental technique, ultrasound-static heating, has been developed for the efficient synthesis of heterocyclic compounds. The technique involves ultrasonic irradiation and static heating processes. First, the ultrasonic irradiation process is performed to form an intermediate of the heterocyclic compound under mild conditions and the subsequent static heating process (heating the intermediate under solvent-free conditions without stirring) produces the target heterocyclic compounds via intramolecular elimination.
- Jiang, Hongfei,Dong, Xueyang,Jin, Xin,Zhu, Danyang,Yin, Ruijuan,Yu, Rilei,Wan, Shengbiao,Zhang, Lijuan,Jiang, Tao
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p. 2009 - 2013
(2018/07/31)
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- Cobalt doped ZnS nanoparticles as a recyclable catalyst for solvent-free synthesis of heterocyclic privileged medicinal scaffolds under infrared irradiation
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This paper reports preparation and characterization of cobalt doped ZnS NPs and their catalytic application in the synthesis of heterocyclic privileged medicinal scaffolds involving pyrazolones (with excellent regioselectivity) and 1,3-oxathiolan-5-one frameworks under infrared irradiation. Nanoparticles have been prepared at room temperature by a wet chemical method. The heterogeneous catalysts were fully characterized by XRD, TEM, EDAX, ICP-AES and UV/Vis. Under infrared radiation (IR), the catalytic activity of Co doped ZnS NPs was about 40-fold higher under IR as compared to the conventional method. Nanocatalyst plays a dual role of catalyst as well as susceptor, and enhances the overall capacity to absorb IR in the reaction mixture. Doping by Co promotes the activity and selectivity of ZnS NPs as indicated by their high TOF value, providing the products with good to excellent yields. The surface acidity of NPs was measured by FTIR spectra of chemisorbed pyridine. The present method does not involve any hazardous organic solvent or catalyst. The introduction of nanocatalyst in an IR system offers promising features for the reaction response such as the shorter reaction time, simple work-up procedure, and purification of products by non-chromatographic methods. The catalyst was reused up to four runs without an appreciable loss of catalytic activity.
- Dandia, Anshu,Parewa, Vijay,Gupta, Shyam L.,Rathore, Kuldeep S.
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- Synthesis and biological evaluation of substituted pyrazoles as blockers of divalent metal transporter 1 (DMT1)
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Three distinct series of substituted pyrazole blockers of divalent metal transporter 1 (DMT1) were elaborated from the high-throughput screening pyrazolone hit 1. Preliminary hit-to-lead efforts revealed a preference for electron-withdrawing substituents in the 4-amido-5-hydroxypyrazole series 6a-l. In turn, this preference was more pronounced in a series of 4-aryl-5- hydroxypyrazoles 8a-j. The representative analogs 6f and 12f were found to be efficacious in a rodent model of acute iron hyperabsorption. These three series represent promising starting points for lead optimization efforts aimed at the discovery of DMT1 blockers as iron overload therapeutics.
- Cadieux, Jay A.,Zhang, Zaihui,Mattice, Maryanne,Brownlie-Cutts, Alison,Fu, Jianmin,Ratkay, Laszlo G.,Kwan, Rainbow,Thompson, Jay,Sanghara, Joseph,Zhong, Jing,Goldberg, Y. Paul
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scheme or table
p. 90 - 95
(2012/02/16)
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- Intramolecular diels-alder reaction in ionic liquids: Effect of ion-specific solvent friction
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(Chemical Equation Presented) The present work aims at understanding the role of viscosity or solvent friction in ionic liquids for an intramolecular Diels-Alder (IMDA) reaction of (E)-1-phenyl-4-[2-(3-methyl-2-butenyloxy) benzylidene]-5-pyrazolone (1). The results have been analyzed on the basis of the current theoretical models, and their failure to account for the observed trends is discussed in terms of "effective" viscosity or microviscosity. The rates of the reaction decrease with the increasing viscosity of the ionic liquids. As evident from the anionic effect, the solute-solvent specific interactions play a role in governing the kinetics of the reaction. The lower viscosities of the bistrifluoromethanesulfonimide [NTf2] - based ionic liquids as compared to those based on tetrafluoroborate [BF4]- anion fail to result in a corresponding acceleration in the rates of the reaction. These contradictory results indicate that solvent microviscosity, rather than the bulk macroscopic viscosity, should be the criteria for selecting the ionic liquids as reaction media.
- Tiwari, Shraeddha,Khupse, Nageshwar,Kumar, Anil
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supporting information; experimental part
p. 9075 - 9083
(2009/04/06)
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- Pyrazolone methylamino piperidine derivatives as novel CCR3 antagonists
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The discovery and optimization of a novel class of potent CCR3 antagonists is described. Details of synthesis and SAR are given together with some ADME properties of selected compounds. An optimal balance between activities, physicochemical properties, and in vitro metabolic stability was reached by the proper choice of substituents.
- Pegurier, Cecile,Collart, Philippe,Danhaive, Pierre,Defays, Sabine,Gillard, Michel,Gilson, Frederic,Kogej, Thierry,Pasau, Patrick,Van Houtvin, Nathalie,Van Thuyne, Marc,van Keulen, BerendJan
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p. 4228 - 4231
(2008/02/09)
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- De novo design and synthesis of HIV-1 integrase inhibitors
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Existing AIDS therapies are out of reach for most HIV-infected people in developing countries and, where available, they are limited by their toxicity and their cost. New anti-HIV agents are needed urgently to combat emerging viral resistance and reduce the side effects associated with currently available drugs. Toward this end, LeapFrog, a de novo drug design program was used to design novel, potent, and selective inhibitors of HIV-1 integrase. The designed compounds were synthesized and tested for in vitro inhibition of HIV-1 integrase. Out of the 25 compounds that were designed, and synthesized, four molecules (compounds 23, 26, 43, and 59) showed moderate to low inhibition of HIV-1 integrase for 3′-processing and 3′- strand transfer activities. Nonetheless, these compounds possess structural features not seen in known HIV-1 integrase inhibitors and thus can serve as excellent leads for further optimization of anti-HIV-1 integrase activity.
- Makhija, Mahindra T.,Kasliwal, Rajesh T.,Kulkarni, Vithal M.,Neamati, Nouri
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p. 2317 - 2333
(2007/10/03)
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- NOVEL UREIDO - AND AMIDO-PYRAZOLONE DERIVATIVES
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The present invention provides compounds of formula (I); wherein each of R1 to R4 is independently selected from hydrogen, a halogen, a substituted or unsubstituted cyclic and heterocyclic moiety, substituted or unsubstituted, linear or branched alkyl, alkyloxy, alkylcarbonyl, alkyloxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl, alkynyloxycarbonyl, aryl, benzyl, arlyoxy, arylcarbonyl, aryloxycarbonyl and sulphur equivalents of said oxy, carbonyl and oxycarbonyl moieties, and A is NH, or (CH2)n, where n is preferably 0, 1 or 2. The invention also relates to methods for preparing the compounds and their uses as CCK receptor ligands and CCK antagonists.
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- Disazo pyrazolone pigment compositions
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Disazo pyrazolone pigments are provided which have improved properties achieved by incorporating certain azomethine compounds. The pigment is prepared by reacting a primary amine terminated alkylene oxide polymer and acetoacetanilide or substituted acetoacetanilide to form an azomethine coupler, and subsequently co-reacting the azomethine coupler and a pyrazolone coupler with tetrazotized 3,3'-dichlorobenzidine or tetrazotized o-dianisidine. The pigment is useful in printing ink, plastics and paints.
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- Mechanisms of Heterocycle Ring Formation. Part 5. A Carbon-13 Nuclear Magnetic Resonance Study of Pyrazolinone Synthesis by the Reaction of β-Ketoesters with Substituted Hydrazines
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The 16 reactions between each of four hydrazines and four β-ketoesters have been followed by 13C n.m.r. spectroscopy.Peaks were assigned to starting materials, intermediates, and products, and reaction mechanisms determined and rationalized.Most rections proceed by attack of the least hindered hydrazine nitrogen atom on the keto carbon group of the ketoester.Relative rates of nucleophilic attack determine the build-up of intermediate and in some cases the nature of the products formed.
- Katrizky, Alan R.,Barczynski, Piotr,Ostercamp, Daryl L.
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p. 969 - 976
(2007/10/02)
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- 1H-N.M.R., 13C-N.M.R., and I.R.-Investigations Concerning Tautomerism of 15N-Labeled 3-Methyl-1-phenyl-Δ2-pyrazolin-5-one
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The behaviour of the 15N-mono and dilabeled compound in dependence on temperature and solvent polarity is described.Chemical shifts, nJ(15N-13C) coupling constants (n = 1 - 3) have been determined.In the cases of 2,2,2-trifluoroethanole and hexafluoroisopropanole the Δ4-pyrazolin-3-one is stabilized and detected by 3J(15N-2-H-4) = 3 Hz, 1J(13C-3-15N-2) = 11,0 Hz and δ(13C-5).In HMPT the 5-hydroxypyrazole form predominates and is characterized by 3J(15N-1-H-4) = 5,1 Hz and δ (13C-5).Coupling constants 3J(15N-2-H-4) and J(13C-3-15N-2) could not be observed in this solvent.In accordance with 1H- and 13C-n.m.r.-parameters i.r. measurements in dependence on temperature lead to the conclusion that in DMSO and THF for instance all three tautomers are present and variation of temperature does not change the equilibrium between the tautomers.A good relationship between the content of the CH2, OH and NH forms and the Donor Numbers (DN) and Acceptor Numbers (AN) by Gutmann has been found.
- Freyer, Wolfgang,Koeppel, Hubert,Radeglia, Reiner,Malewski, Guenter
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p. 238 - 250
(2007/10/02)
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