- Asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives: Which possesses the highest activity to protect DNA or scavenge radical?
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A series of asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives were synthesized. Their antioxidant abilities in protecting DNA against 2,2′-azobis(2-amidinopropane hydrochloride)-induced oxidation and scavenging 2,2′-azinobis(3-ethylbenzothiazoline-6- sulfonate) cationic radical (ABTS) radical were evaluated. In synthesis, the Michael addition reactions between phenylhydrazine and asymmetrical ferrocenylidene curcumin derivatives exhibit evident regioselectivity. The direction of addition depends on whether the benzene ring is substituted or not. The antioxidant abilities of compounds will increase when the ferrocenyl group is introduced. Moreover, such improvement derived from ferrocenyl group is also related to other substituent groups in molecule, not independent. Interestingly, p-dimethylamino group which is never considered as an active group, however, exhibits the best activity in protecting DNA and scavenging ABTS radical.
- Li, Pei-Ze,Liu, Zai-Qun
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- Some 1,3,5-trisubstituted pyrazoline derivatives targeting breast cancer: Design, synthesis, cytotoxic activity, EGFR inhibition and molecular docking
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Different 1,3,5-trisubstituted pyrazoline derivatives 2a-c, 3-c, 4a-f, 6a-c, 7a-f and 8a-d were prepared via condensation reaction of the appropriate chalcone 1a-c or 5a-c with various hydrazine derivatives. All compounds were screened for their cytotoxicity against breast MCF-7 cancer cell line and the normal fibroblasts WI-38. Thirteen compounds 2a, 3a, 3c, 4a-d, 6c, 7d, 7e, 8b, 8d and 8f revealed promising cytotoxicity against MCF-7 compared to the reference standard staurosporine and they were safe to the normal fibroblasts WI-38. In addition, compounds 3c, 6c, 7d, 8b and 8d elicited higher cytotoxicity than erlotinib and exhibited promising EGFR inhibitory activity at submicromolar level comparable to that of erlotinib except for compound 8b that may exert its cytotoxicity via another mechanism besides EGFR inhibition. Molecular docking of 3c, 6c, 7d, 8b and 8d in the active site of EGFR confirmed the obtained results.
- El Kerdawy, Ahmed M.,El-Ansary, Dina Y.,George, Riham F.,Kandeel, Manal
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- Second harmonic generation in pyrazoline derivatives of dibenzylideneacetones and chalcone: A combined experimental and theoretical approach
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In this work, we investigate theoretically and experimentally second harmonic generation (SHG) in three pyrazoline compounds, being two derivatives of dibenzylideneacetone (DBA) (C23H20N2 and C25H24N2O2) and one derivative of chalcone (C21H18N2). The compounds were synthesized after two steps employing a Claisen-Schmidt condensation followed by an addition-elimination reaction with phenylhydrazine. All compounds were characterized using NMR, FT-IR, UV-Vis, and XRD. We calculated the first-order hyperpolarizabilities of these molecules using program packages based on the time-dependent Hartree-Fock (TDHF) and density functional theory (DFT). SHG was characterized by Kurtz and Perry's powder method. We observed that these organic crystals present SHG efficiencies up to 5 times larger than the KDP, and we associated these values to their molecular structure and crystalline arrangements. The values obtained experimentally and theoretically evidence that these compounds have good potential for application in electronic devices based on second-order nonlinear responses.
- de Araújo, Raiane Sodré,de Alcantara, Aline Moreira,Abeg?o, Luis M.G.,de Souza, Yago Pereira,Brand?o Silva, Ant?nio Carlos,Machado, Rogério,Joatan Rodrigues, José,Rodriguez Pliego, Josefredo,d'Errico, Francesco,Siqueira Valle, Marcelo,de Alencar, Márcio André Rodrigues Cavalcanti
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- Direct N-heterocyclization of hydrazines to access styrylated pyrazoles: synthesis of 1,3,5-trisubstituted pyrazoles and dihydropyrazoles
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A microwave-assisted method has been developed for the synthesis of tri-substituted pyrazoles via direct N-heterocyclization of hydrazines with metal-acetylacetonate and -dibenzylideneacetonate without using any base or additives. Most importantly, the synthesis of 1-aryl-5-phenyl-3-styryl-1H-pyrazoles was achieved in a single step using hydrochloride salt of various phenylhydrazines and this is the first report for direct construction of these molecules. The reaction medium and microwave conditions play a critical role for their selective product formation during the reaction. The present reaction explored the usage of metal-diketonic complexes as reaction substrates providing acetylacetone and dibenzylideneacetone moieties to directly participate in cyclization with hydrazines to form the corresponding pyrazoles in excellent yields. The present protocol introduces the important N-heterocyclic moieties in the final structures, giving the reaction great applications from a medicinal chemistry perspective, particularly in the late stage modification strategies in drug discovery.
- Venkateswarlu, Vunnam,Kour, Jaspreet,Kumar, K. A. Aravinda,Verma, Praveen Kumar,Reddy, G. Lakshma,Hussain, Yaseen,Tabassum, Aliya,Balgotra, Shilpi,Gupta, Sorav,Hudwekar, Abhinandan D.,Vishwakarma, Ram A.,Sawant, Sanghapal D.
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p. 26523 - 26527
(2018/08/07)
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- TfOH mediated intermolecular electrocyclization for the synthesis of pyrazolines and its application in alkaloid synthesis
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TfOH mediated easy access to interesting pyrazolines starting from an aldehyde, phenylhydrazine and styrene has been developed. The scope of this synthetic methodology has been explored by synthesizing various 1,3,5-trisubstituted pyrazolines in very good yields with very high regioselectivity. The origin of regioselectivity has been explained by comparing the stability of possible intermediate carbocations. The synthetic utility of a green solvent has been explored by synthesizing some of pyrazolines in a DES medium. The synthetic application of the present methodology is employed in the synthesis of a pyrazoline alkaloid.
- Annes, Sesuraj Babiola,Vairaprakash, Pothiappan,Ramesh, Subburethinam
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p. 30071 - 30075
(2018/09/11)
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- Cellulose sulfonic acid as a green, efficient, and reusable catalyst for Nazarov cyclization of unactivated dienones and pyrazoline synthesis
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A high yielding, eco-friendly and simple procedure for the synthesis of five membered carbo- and heterocycles through cellulose sulfonic acid (CSA) mediated electrocyclization processes has been developed. Cellulose sulfonic acid (CSA) not only was able to induce the cyclization of "unactivated" dienones generating cyclopentenoids; it was also able to trigger the cyclization of α,β-unsaturated hydrazones giving rise to pyrazolines in excellent yields under green reaction conditions. The ease of catalyst recovery and reusability, short reaction time, simple experimental and work-up procedure; compared to the conventional methods, makes this protocol practical, environmentally friendly and economically desirable. The cellulose-SO3H (CSA) was characterized by FT-IR spectroscopy, powder X-ray diffraction (XRD) and Scanning Electron Microscopy (SEM) analyses, and catalyst stability was judged by thermogravimetry/differential thermal analysis (TG/DTA). The catalyst can be recycled several times without significant loss of catalytic activity.
- Daneshfar, Zahra,Rostami, Ali
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p. 104695 - 104707
(2015/12/30)
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- Synthesis, characterization and biological activity studies of some substituted pyrimidine derivatives
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A new series of substituted 1-phenyl-3-styryl-4,5-dihydo-1H-pyrazoles (TP1-TP9) has been synthesized by the cyclisation of chalcones with phenyl hydrazine and glacial acetic acid and substituted 4-styryl-pyrimidin-2-ols (LP1-LP9) have been synthesized by the condensation of chalcones with urea in the presence of 40% NaOH as a base. The intermediate substituted 1,5-diphenylpenta-2,4-dien-1-ones were synthesized by condensing cinnamaldehyde with various substituted aromatic ketones in presence of 20% NaOH. The title compounds obtained were characterized by IR, 1H NMR, mass spectral data and were screened for antimicrobial, anticancer and antitubercular activity.
- Ishwar Bhat,Kumar, Abhishek,Thara,Kumar, Pankaj
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p. 271 - 276
(2019/01/21)
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- Iron-catalyzed aerobic oxidative aromatization of 1,3,5-trisubstituted pyrazolines
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A simple and high yielding method for the synthesis of tri-substituted pyrazoles via iron(III) catalyzed aerobic oxidative aromatization of pyrazolines has been reported. The process demonstrates a variety of functional group tolerance.
- Ananthnag, Guddekoppa S.,Adhikari, Adithya,Balakrishna, Maravanji S.
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p. 240 - 243
(2013/12/04)
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- Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors
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A series of dibenzylideneacetones (A1-A12) and some of their pyrazolines (B1-B4) were synthesized and evaluated in vitro for blood stage antiplasmodial properties in Plasmodium falciparum culture using SYBR-green-I fluorescence assay. The compound (1E, 4E)-1,5-bis(3,4-dimethoxyphenyl)penta-1,4-dien-3-one (A9) was found to be the most active with IC50 of 1.97 μM against chloroquine-sensitive strain (3D7) and 1.69 μM against chloroquine-resistant field isolate (RKL9). The MTT based cytotoxicity assay on HeLa cell line has confirmed that A9 is selective in its action against malaria parasite (with a therapeutic index of 166). Our results revealed that these compounds exhibited promising antiplasmodial activities which can be further explored as potential leads for the development of cheaper, safe, effective and potent drugs against chloroquine-resistant malarial parasites.
- Aher, Rahul Balasaheb,Wanare, Gajanan,Kawathekar, Neha,Kumar, Ravi Ranjan,Kaushik, Naveen Kumar,Sahal, Dinkar,Chauhan, Virander Singh
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supporting information; experimental part
p. 3034 - 3036
(2011/06/24)
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- Synthesis of 1,5-diaryl-3-arylethenyl-2-pyrazolines under ultrasound irradiation
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Synthesis of 1,5-diaryl-3-arylethenyl-2-pyrazolines via the reaction of 1,5-diaryl-1,4-pentadien-3-one and phenyl hydrazine in glacial acetic acid was carried out in 32-80 % yields under ultrasound irradiation. This procedure has the advantages of mild conditions, short reaction time and high yield.
- Li, Ji-Tai,Zhai, Xin-Li,Meng, Xian-Tao
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experimental part
p. 589 - 592
(2010/10/03)
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- New reaction of photoaromatization of aryl- and hetarylpyrazolines
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Aryl- and hetarylpyrazolines smoothly undergo photoaromatization under irradiation with the visible light (λ > 400 nm) in the presence of carbon tetrachloride. The reaction is accompanied by an increase in the acidity of the medium and a change in the fluorescence. The structure of pyrazoline and solvent considerably affect the photoaromatization rate. The mechanism of the reaction was proposed, which agrees with the experimental data.
- Traven,Ivanov
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experimental part
p. 1063 - 1069
(2009/09/05)
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- KHSO4 · H2O/SiO2-catalyzed, one-pot, solvent-free synthesis of pyrazolines, tetrahydrocarbozoles and indoles using microwave irradiation
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A new high-yielding, operationally simple, solvent-free, and mild method for preparation of pyrazolines, tetrahydrocarbazoles, and indoles has been developed using KHSO4 · H2O impregnated on SiO 2. The reactions have been probed under microwave irradiation (MWI), and ultrasonic and thermal conditions, employing different solid supports. The data revealed that KHSO4 · H2O impregnated on SiO2 under MWI provides the best yields in a shorter time under solvent-free reaction conditions. Copyright Taylor & Francis Group, LLC.
- Kapoor, Kamal K.,Ganai, Bilal A.,Kumar, Satish,Andotra, Charanjeet S.
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p. 2727 - 2735
(2007/10/03)
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- Oxidative addition of N-aminophthalimide to alkenyl-4,5-dihydropyrazoles and alkenylpyrazoles. Synthesis of aziridinylpyrazoles
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Oxidation of N-aminophthalimide with lead tetraacetate in the presence of 1,5-diaryl-3-[(E)-2-arylethenyl]-1H-pyrazoles, as well as of 1,3-diphenyl-5-[(E)-2-phenylethenyl]-1H-pyrazole, gives adducts at the exocyclic C=C bond, the corresponding phthalimidoaziridinylpyrazoles. From 1,5-diphenyl-3-[(1E,3E)-4-phenyl-1,3-butadienyl]-1H-pyrazole, only product of addition at both exocyclic C=C bonds was obtained. In the reaction with 1-phenyl-3-[(1E,3E)-4-phenyl-1,3-butadienyl]-5-[(E)-2-phenylethenyl] -1H-pyrazole, the adduct at the styryl C=C bond was isolated. Analogous 4,5-dihydropyrazoles, 1,5-diphenyl-3-[(1E,3E)-4-phenyl-1,3-butadienyl]-4,5- dihydro-1H-pyrazole and 1-phenyl-3-[(1E,3E)-4-phenyl-1,3-butadienyl]-5-[(E)-2- phenylethenyl]-4,5-dihydro-1H-pyrazole, turned out to be inert in oxidative addition of N-aminophthalimide.
- Ignatenko,Blandov,Kuznetsov
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p. 1793 - 1801
(2007/10/03)
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- Reaction of 1,5-Diphenyl-1,4-pentadien-3-one and 1,5-Diphenyl-1-penten-4-yn-3-one with monosubstituted hydrazines
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Phenyl-and isopropylhydrazines react with 1,5-diphenyl-1,4-pentadien-3-one to give 4,5,6,7-tetrahydroindazole derivatives instead of the expected 4,5-dihydropyrazoles. The reaction of phenylhydrazine with 1,5-diphenyl-1-penten-4-yn-3-one leads to formation of 1,5-diphenyl-3-phenylethynyl-4,5-dihydropyrazole. 2,4-Dinitrophenylhydrazine reacts with 1,5-diphenyl-1-penten-4-yn-3-one, affording the corresponding unsaturated hydrazone rather than pyrazole derivative.
- Botvinnik,Blandov,Kuznetsov
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p. 421 - 425
(2007/10/03)
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- Antibacterials and antimycotics: Part 1: Synthesis and activity of 2- pyrazoline derivatives
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A series of 3-styryl-1,5-diphenyl and 5-styryl-1,3-diphenyl 2- pyrazolines of different substitutions has been synthesized by condensation of substituted α,β-unsaturated ketones with phenylhydrazine hydrochloride in presence of catalytic amount of concentrated HCl. Compounds in the 3- styryl series had OMe, NMe2, NO2, OH and isopropyl substituents and those in the 5-styryl series had OMe, NMe2 and NO(s). The 3-styryl-1,5-diphenyl compounds showed little variation in antibacterial activity towards gram- positive and gram-negative bacteria in terms of geometric mean minimum inhibitory concentrations (MIC). The 4',4-NMe2, 4',4-NO2 and 4',4-OMe compounds were found to possess the highest activity in the series. The 5- styryl-1,3-diphenyl series showed lower activities than the 3-styryl series. The in vitro antimycotic activity of the 4',4-OH and 2',2-OH substituted compounds showed good activity than the other molecules in the two series.
- Nauduri, Dhananjaya,Reddy, Gopu Bala Show
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p. 1254 - 1260
(2007/10/03)
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- ACTIVATED Ba(OH)2 AS CATALYST IN ORGANIC SYNTHESIS
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Several barium hydroxide catalysts have been prepared.Of these, the one called C-200 has been shown to be the most active.It has been used in several organic reactions: aldol and Claisen-Schmidt condensations, ester hydrolysis, esterification of acid chlorides, Williamson's ether synthesis, benzil-benzilic acid rearrangement and the synthesis of Δ2-pyrazolines.
- Garcia-Raso, Angel,Sinisterra, Jose V.,Marinas, Jose M.
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p. 1435 - 1445
(2007/10/02)
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