- A facile one pot synthesis of pyrano[2,3-c]pyrazole derivatives under microwave irradiation
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A series of substituted pyrano[2,3-c]pyrazole derivatives were synthesized by the one pot reaction of aromatic aldehydes, malononitrile and 3-methyl-1-phenyl-2-pyrazolin-5-one under microwave irradiation in good yields.
- Zhou, Jian-Feng,Tu, Shu-Jiang,Zhu, Hui-Qin,Zhi, San-Jun
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- HClO4-sio2 nanoparticles: An efficient and versatile catalyst for synthesis of 1,4-dihydropyrano[2,3-c]pyrazoles
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The reaction between aromatic aldehydes, malononitrile and 3-methyl-1-phenyl-2-pyrazoline-5-one catalysed by silica supported perchloric acid nanoparticles (HClO4-sio2 nanoparticles) in solvent H2O under reflux provided a
- Sadeghi, Bahareh,Shirkhani, Mona,Hassanabadi, Alireza
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Read Online
- Synthesis and biological activities of some new phosphorus compounds containing pyranopyrazole moiety
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A simple method for construction of functionalized pyranopyrazoles containing phosphoramide and phosphonate groups via one-pot reaction was achieved. The methodology depended on the reaction of 6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazol
- Abdel-Monem, Wafaa R.,Abed-Kariem, Somaia M.,Alfaifi, Mohammad Y.,Ali, Tarik E.,Assiri, Mohammed A.,EL-Edfawy, Somaya M.,El-Shaaer, Hafez M.,Elbehairi, Serag Eldin I.,Hassanin, Noha M.,Shati, Ali A.
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p. 1119 - 1137
(2021/06/21)
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- Synthesis and in vitro antimicrobial, antioxidant, and antiproliferative activities of some new pyrano[2,3-c]pyrazoles containing 1,2-azaphospholes, 1,3,2-diazaphosphinines and phosphonate moieties
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New 1,2-azaphosphole, 1,3,2-diazaphosphinine, and phosphonate derivatives containing pyrano[2,3-c]pyrazole moiety were achieved. The synthetic pathways depended on the reaction of 6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile with some phosphorus reagents such as diethyl phosphite, phosphorus sulfides, and phenyl phosphorus halides under different conditions. Compounds 6 and 7 recorded potent antibacterial and antifungal activities with lower toxicity, while compounds 4 and 6 displayed promising antioxidative properties. Further, compounds 4 and 9 exhibited potent cytotoxic effects against MCF-7, HepG-2, and HCT-116 cancer cells. The early apoptotic cell death was observed by the compounds in all types of the treated cells. Compounds 3, 5, 7, 10, and 14 recorded low to moderate percentages of necrosis and late apoptosis toward all treated cells.
- Ali, Tarik E.,Assiri, Mohammed A.,El-Shaaer, Hafez M.,Abdel-Kariem, Somaia M.,Abdel-Monem, Wafaa R.,El-Edfawy, Somaya M.,Hassanin, Noha M.,Shati, Ali A.,Alfaifi, Mohammad Y.,Elbehairi, Serag Eldin I.
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supporting information
p. 2478 - 2497
(2021/06/30)
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- Catalyst-free UV365-assisted synthesis of pyran annulated heterocyclic scaffolds and evaluation of their antibacterial activities
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A convenient and eco-friendly, one-pot synthetic protocol for pharmaceutically important pyran-based heterocyclic compounds is repeated herein. The reactions were carried out at room temperature in a water–ethanol solvent mixture under direct irradiation
- Dutta, Arup,Rahman, Noimur,Kumar, John Elisa,Rabha, Jintu,Phukan, Tridip,Nongkhlaw, Rishanlang
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supporting information
p. 263 - 278
(2020/11/03)
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- Zn (II)-Schiff base covalently anchored to CaO@SiO2: A hybrid nanocatalyst for green synthesis of 4H-pyrans
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In this study, the Zn (II)-Schiff base covalently anchored onto the surface of CaO@SiO2 nanoparticles. The structure of this hybrid nanomaterial (CaO@SiO2-NH2-Sal-Zn) was characterized using the analytical techniques such
- Sameri, Fatemeh,Bodaghifard, Mohammad Ali,Mobinikhaledi, Akbar
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- Tungstic acid (H4WO5) immobilized on magnetic-based zirconium amino acid metal–organic framework: An efficient heterogeneous Br?nsted acid catalyst for l-(4-phenyl)-2,4-dihydropyrano[2,3c]pyrazole derivatives preparation
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A new magnetic nanocatalyst based on the immobilization of tungstic acid onto new design robust, cost-effective, green, and scalable zirconium-L-aspartate amino acid metal–organic framework (MOF)-grafted L-(+)-tartaric acid stabilized magnetite nanopartic
- Khademi, Shima,Zahmatkesh, Saeed,Aghili, Alireza,Badri, Rashid
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- Sugarcane Bagasse Ash-Based Silica-Supported Boric Acid (SBA-SiO2-H3BO3): A Versatile and Reusable Catalyst for the Synthesis of 1,4Dihydropyrano[2,3c]pyrazole Derivatives
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Abstract: A simple, green, and efficient protocol has been developed for the synthesis of biologically active 1,4dihydropyrano[2,3c]pyrazole derivatives via one-pot four-component reaction of various substituted benzaldehydes, hydrazine hydrate or phenylh
- Kumar, A.,Pandey, A. K.,Shrivastava, S. C.
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p. 653 - 660
(2021/06/02)
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- Synthesis of some novel antimicrobial and antioxidant agents of functionalized pyrazolo[4',3':5,6]pyrano[3,2-d]-[1,2]azaphospholes and pyrazolo[4',3':5,6]pyrano[2,3-d]-[1,3,2]diazaphosphinines
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We have demonstrated facile synthetic approach for some novel functionalized pyrazolo[4',3':5,6]pyrano[3,2-d][1,2]azaphospholes and pyrazolo-[4',3':5,6]pyrano[2,3-d][1,3,2]diazaphosphinines via treatment of 6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[
- Abdel-Kariem, Somaia M.,Abdel-Monem, Wafaa R.,Ali, Tarik E.,El-Edfawy, Somaya M.,El-Shaaer, Hafez M.,Hassanin, Noha M.
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p. 1902 - 1913
(2020/11/19)
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- Synthesis, characterization and application of Fe3O4@SiO2@CPTMO@DEA-SO3H nanoparticles supported on bentonite nanoclay as a magnetic catalyst for the synthesis of 1,4-dihydropyrano[2,3-c]pyrazoles
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Fe3O4 nanoparticles were prepared and decorated on the surface of nanobentonite (NB), and subsequently modified by the organic and inorganic linkers and then sulfonic acid immobilization on the nanoparticles. The NB-Fe3Os
- Eftekhari far, Behrouz,Nasr-Esfahani, Masoud
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- Sulfonic acid-functionalized Fe3O4-supported magnetized graphene oxide quantum dots: A novel organic-inorganic nanocomposite as an efficient and recyclable nanocatalyst for the synthesis of dihydropyrano[2,3-c]pyrazole and 4H-chromen
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In this research, the main emphasis has been focused on the preparation of a novel Fe3O4-supported propane-1-sulfonic acid-grafted graphene oxide quantum dots (Fe3O4@GOQD-O-(propane-1-sulfonic acid)) that it was
- Khaleghi Abbasabadi, Masoud,Azarifar, Davood,Esmaili Zand, Hamid Reza
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- Synthesis and characterization of Fe3O4@THAM-SO3H as a highly reusable nanocatalyst and its application for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives
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In this work, a new, green and beneficial nanomagnetic catalyst was easily fabricated using sulfuric acid as an acidic group on Fe3O4 nanoparticles coated with tris (hydroxymethyl) aminomethane (THAM). The synthesized catalyst was characterized by FT-IR, TGA/DTG, XRD, TEM, EDS, VSM, and SEM analyses. Next, its catalytic activity was studied for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives. This catalyst has advantages such as high catalytic activity, non-toxicity, easy separation from the reaction mixture using an external magnet and reuses for several times without significantly reducing in its catalytic activity.
- Faroughi Niya, Homayoun,Hazeri, Nourallah,Maghsoodlou, Malek Taher
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- Preparation, characterization and catalytic application of molybdenum Schiff-base complex immobilized on silica-coated Fe3O4 as a reusable catalyst for the synthesis of pyranopyrazole derivatives
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A recoverable molybdenum Schiff-base complex immobilized on silica-coated Fe3O4 nanoparticles was prepared and characterized. This superparamagntic nanocatalyst, which is separable using an external magnet, can be used as an efficien
- Hamrahian, Seyedeh Aghigh,Salehzadeh, Sadegh,Rakhtshah, Jamshid,Haji babaei, Farshid,Karami, Niloofar
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- Fe3O4-supported N-pyridin-4-amine-grafted graphene oxide as efficient and magnetically separable novel nanocatalyst for green synthesis of 4H-chromenes and dihydropyrano[2,3-c]pyrazole derivatives in water
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Abstract: Fe3O4-magnetized N-pyridin-4-amine-functionalized graphene oxide [Fe3O4@GO-N-(pyridin-4-amine)] was readily prepared via a three-step procedure. The synthesized nanofilms were characterized by scanning
- Azarifar, Davood,Khaleghi-Abbasabadi, Masoud
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p. 199 - 222
(2018/10/15)
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- A concise route for the one-pot multi-component synthesis of 4,6-disubstituted 2-aminopyridine-3-carbonitriles and pyranopyrazoles using cobalt (II) nitrate hexahydrate as catalyst
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Three facile and efficient routes for one-pot, cobalt (II) nitrate hexahydrate catalyzed multi-component synthesis of 2-amino-3-cyanopyridine and pyranopyrazole derivatives have been developed. The present protocols offer the products in good yields from the simple and readily available starting materials. The other salient features of these protocols are operational simplicity, easy isolation of product without the need of column chromatographic purification, and the use of cobalt (II) nitrate hexahydrate as an efficient catalyst.
- Pejman, Hamed,Hazeri, Nourallah,Fatahpour, Maryam,Faroughi Niya, Homayoun
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p. 241 - 247
(2019/07/31)
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- Zn(L-proline)2 as an efficient and reusable catalyst for the multi-component synthesis of pyran-annulated heterocyclic compounds
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We have developed a simple, straightforward and highly efficient multi-component one-pot synthesis of 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocyclic compounds. Zn(L-proline)2 has been utilized as a mild and efficient Lewis acid cata
- Tahmassebi, Daryoush,Blevins, John E.,Gerardot, Shori S.
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- Environmentally benign synthesis of pyranopyrazole derivatives by cobalt Schiff-base complexes immobilized on magnetic iron oxide nanoparticles
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In this work, an efficient and straight procedure has been described for one-pot three-component synthesis of pyranopyrazole derivatives in the presence of a new cobalt Schiff-base complex immobilized on silica-coated Fe3O4 nanoparti
- Shaabani, Behrouz,Maleki, Hossein,Rakhtshah, Jamshid
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p. 139 - 147
(2019/07/10)
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- A highly efficient and reusable catalyst for the synthesis of 4H-benzo[b]pyran derivatives
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A series of substituted 4H-pyrans derivatives were synthesized by a one-pot, multi-component reaction of aromatic aldehydes, malononitrile, and pyrazolone derivatives or active methylene carbonyl compounds such as dimedone, in the presence of 1,3-dimethyl
- Redouane, Mohamed Abdenour,Khiri-Meribout, Naima,Benzerka, Saida,Debache, Abdelmadjid
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p. 167 - 179
(2020/02/27)
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- Application of Yttrium Iron Garnet as a Powerful and Recyclable Nanocatalyst for One-Pot Synthesis of Pyrano[2,3-c]pyrazole Derivatives under Solvent-Free Conditions
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The application of yttrium iron garnet (YIG) superparamagnetic nanoparticles as a new recyclable and highly efficient heterogeneous magnetic catalyst for one-pot synthesis of pyrano[2,3-c]pyrazole derivatives under solvent-free conditions, as well as etherification and esterification reactions are described. The advantages of the proposed method include the lack of organic solvents, clean reaction, rapid removal of the catalyst, short reaction times, excellent yields, and recyclability of the catalyst.
- Sedighinia,Badri,Kiasat
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p. 1755 - 1763
(2020/01/11)
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- An Eco-friendly Catalytic System for One-pot Multicomponent Synthesis of Diverse and Densely Functionalized Pyranopyrazole and Benzochromene Derivatives
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An external base-free, efficient, cost-effective, and environmentally benign protocol has been developed for the one-pot multicomponent synthesis of highly functionalized pyranopyrazoles and benzochromenes using water extract of Agave americana (century p
- Patil,Patil, Rupesh C.,Patil, Suresh S.
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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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- NaF-catalyzed efficient one-pot synthesis of dihydropyrano[2,3-c]pyrazoles under ultrasonic irradiation via MCR approach
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Sodium fluoride was identified as an efficient catalyst for the preparation of series of dihydropyrano [2,3-c]pyrazoles (4a–l) by the three-component condensation of 3-Methyl-1-phenyl-2-pyrazoline-5-one (1), aromatic aldehydes (2) and malononitrile (3) in
- Konakanchi, Ramaiah,Gondru, Ramesh,Nishtala, Venkata Bharat,Kotha, Laxma Reddy
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p. 1994 - 2001
(2018/07/03)
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- Synthesis and antimicrobial screening of pyrimidine annulated dihydropyrano[2, 3-c] pyrazole derivatives
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A series of pyrimidine annulated dihydropyrano[2, 3-c]pyrazole derivatives were synthesized and screened for their antimicrobial activity. The precursor, dihydropyrano[2, 3-c]pyrazole was synthesised under catalyst free condition using PEG-400 as reaction
- Hegde, Hemant,Ahn, Chuljin,Waribam, Preeti,Shetty, Nitinkumar S.
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- Amino acid ionic liquid-based titanomagnetite nanoparticles: An efficient and green nanocatalyst for the synthesis of 1,4-dihydropyrano[2,3-c]pyrazoles
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The amino acid ionic liquid tetrabutylammonium asparaginate (TBAAsp) was immobilized on titanomagnetite (Fe3?xTixO4) nanoparticles in a facile one-pot process using an organosilane compound (TMSP) as spacer. The modified F
- Azarifar, Davood,Badalkhani, Omolbanin,Abbasi, Younes
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- Tungstic acid-functionalized Fe3O4@TiO2: preparation, characterization and its application for the synthesis of pyrano[2,3-c]pyrazole derivatives as a reusable magnetic nanocatalyst
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A new magnetic nanocatalyst based on the immobilization of tungstic acid onto 3-chloropropyl-grafted TiO2-coated Fe3O4 nanoparticles (Fe3O4@TiO2@(CH2)3OWO3H
- Gholtash, Jamileh Etemad,Farahi, Mahnaz
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p. 40962 - 40967
(2019/01/03)
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- γ-Fe2O3@Cu3Al-LDH-TUD as a new Amphoteric, Highly Efficient and Recyclable Heterogeneous Catalyst for the Solvent-free Synthesis of Dihydropyrano[3,2-c]pyrazoles and dihydropyrano[3,2-c]chromens
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Thiourea dioxide was immobilized on γ-Fe2O3@Cu3Al-LDH magnetic nanoparticles to prepare the γ-Fe2O3@Cu3Al-LDH-TUD MNPs. The structure and properties of these magnetic nanoparticles were est
- Azarifar, Davood,Tadayoni, Mehrdad,Ghaemi, Masoumeh
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- One-pot three-component process for the synthesis of substituted pyrano[2,3-c]pyrazoles catalyzed by nanostructured FSM-16-SO3H
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A three-component process for the one-pot synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles by the reaction of aldehydes, 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, and malononitrile in the presence of FSM-16-SO3/s
- Hashemi-Uderji, Somayeh,Abdollahi-Alibeik, Mohammad
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p. 1709 - 1719
(2018/07/06)
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- Zn(ANA)2Cl2 complex as efficient catalyst for the synthesis of dihydropyrano[2,3-c]pyrazoles in aqueous medium via one-pot multicomponent reaction: a green approach
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The first example of recyclable Zn(ANA)2Cl2 catalyzed tandem one-pot three-component protocol reaction between aromatic aldehydes, malononitrile, and phenylmethylpyrazolone to furnish 4-substituted-1,4-dihydropyrano[2,3-c]pyrazole-5-
- Konakanchi, Ramaiah,Nishtala, Venkata Bharat,Kankala, Shravankumar,Kotha, Laxma Reddy
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supporting information
p. 2642 - 2651
(2018/11/26)
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- SBA-Pr-NH2 catalyzed preparation of pyrano[2, 3-c]pyrazoles under solvent-free conditions
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This report provides a description of an efficient and simple procedure for the synthesis of pyrano[2, 3-c]pyrazole derivatives via a one-pot three-component reaction of arylmethylidene malononitrile, ethylacetoacetate and phenylhydrazine in the presence of amino-functionalized SBA-15 as a highly effective heterogeneous solid basic catalyst under solvent-free conditions. The remarkable advantages are the simplicity of the experimental procedures, high yields, short reaction times, and reusability of the catalyst.
- Zainali, Mahnaz,Amrollahi, Mohammad A.
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- A ternary hybrid system based on combination of mesoporous silica, heteropolyacid and double-layered clay: an efficient catalyst for the synthesis of 2,4-dihydro-3H-pyrazol-3-ones and pyranopyrazoles in aqueous medium: studying the effect of the synthetic
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SBA/hydrotalcite/heteropolyacid nanocomposite is synthesized via a novel procedure in which the as-prepared heteropolyacid-loaded SBA-15 was impregnated with calcined hydrotalcite. The ternary hybrid system was characterized by using SEM/EDS, XRD, BET, TP
- Sadjadi, Samahe,Heravi, Majid M.,Zadsirjan, Vahideh,Farzaneh, Vahid
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p. 6765 - 6785
(2018/07/13)
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- Amberlite-supported L-prolinate: A novel heterogeneous organocatalyst for the three-component synthesis of 4H-pyrano[2,3-c]pyrazole derivatives
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This report describes a new and convenient procedure for heterogenization of L-proline organocatalyst, which is based on non-covalent immobilization of L-proline on the surface of anion-exchange resin amberlite IRA900OH (AmbIRA900OH) as an efficient, chea
- Nazari,Keshavarz
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p. 539 - 545
(2017/05/01)
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- Application of a biological-based nanomagnetic catalyst in the synthesis of bis-pyrazols and pyrano[3,2-c]pyrazoles
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{Fe3O4@SiO2@(CH2)3-thiourea dioxide-SO3H/HCl}, a newly reported nanomagnetic core–shell supported solid acid catalyst, was successfully employed in the preparation of 4,4′-(arylmethylene)bi
- Zolfigol, Mohammad Ali,Navazeni, Mahdiyeh,Yarie, Meysam,Ayazi-Nasrabadi, Roya
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- Synthesis of Novel Tacrine Analogs as Acetylcholinesterase Inhibitors
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In this work, a wide range of novel pyrazolo[4′,3′:5,6]pyrano[2,3-b]quinolin-5-amines were synthesized as tacrine analogs. At first, reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, aromatic aldehydes, and malononitrile gave 6-amino-4-aryl-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles. Then, reaction of the latter compounds with cyclohexanone led to the formation of the title compounds. Also, they were evaluated for their in vitro acetylcholinesterase and butyrylcholinesterase inhibitory activities. Interestingly, most of them showed good inhibitory activity comparing with rivastigmine as the reference drug.
- Mahdavi, Mohammad,Saeedi, Mina,Gholamnia, Laleh,Jeddi, Seyed Amir Behzad,Sabourian, Reyhaneh,Shafiee, Abbas,Foroumadi, Alireza,Akbarzadeh, Tahmineh
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p. 384 - 390
(2017/02/05)
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- Ag/Tio2 nano thin films catalyzed efficient synthesis of 6-amino-4-aryl-3-methyl-1,4-dihydropyrano[2,3-C] pyrazole-5-carbonitriles at green conditions
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Ag/TiO2 nano thin films was found to be efficient and green heterogeneous catalyst for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives via a one-pot three-component reaction between 3-methyl-1H-pyrazol-5(4H)-one or 3-methyl-1(phenyl)-
- Irani, Sharmin,Maghsoodlou, Malek Taher,Hadavi, M. Saeed,Hazeri, Nourallah,Lashkari, Mojtaba
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p. 814 - 820
(2017/05/26)
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- Synthesis of pyrano[2,3-c]pyrazoles by ionic liquids under green and eco-safe conditions
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Optimization of a green approach to the synthesis of pyrano[2,3-c]pyrazoles based on the one-pot, four-component condensation via a domino Knoevenagel/Michael/cyclization sequence was investigated. This method involved the evaluation of the activity of se
- Zakeri, Masoumeh,Nasef, Mohamed Mahmoud,Kargaran, Tina,Ahmad, Arshad,Abouzari-Lotf, Ebrahim,Asadi, Jahanbakhsh
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p. 717 - 728
(2017/02/10)
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- Piperidine-Promoted Three-Component Condensation: Synthesis of Chromene Heterocycles and Pyrazolotriazoles
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Chromenes, the oxygen-containing heterocyclic compounds, have a “special” place in biologically active natural products and in synthetic chemistry and in the fields of medicinal, agrochemical, cosmetic, and pigment industries. In this work, piperidine was used as a base catalyst for the convenient synthesis of 1,4-dihydropyrano[2,3-c]pyrazole, 5,10-dihydro-4H-benzo[g]chromene, and pyrazolo[1,2-a] [1,2,4]triazole derivatives at ambient temperature. This methodology has several advantages including the use of easily accessible and inexpensive catalysts, short reaction times, high yields, convenient work-up, and not needing column chromatography.
- Kangani, Mehrnoush,Hazeri, Nourallah,Yazdani-Elah-Abadi, Afshin,Maghsoodlou, Malek-Taher
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p. 1259 - 1269
(2017/10/18)
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- Synthesis and biological evaluation of dihydropyrano-[2,3-c]pyrazoles as a new class of PPAR? partial agonists
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Peroxisome proliferator-activated receptor ? (PPAR?) is a well-known target for thiazolidinedione antidiabetic drugs. In this paper, we present the synthesis and biological evaluation of a series of dihydropyrano[2,3-c]pyrazole derivatives as a novel family of PPAR? partial agonists. Two analogues were found to display high affinity for PPAR? with potencies in the micro molar range. Both of these hits were selective against PPAR?, since no activity was measured when tested against PPARα, PPAR? and RXRα. In addition, a novel modelling approach based on multiple individual flexible alignments was developed for the identification of ligand binding interactions in PPAR?. In combination with cell-based transactivation experiments, the flexible alignment model provides an excellent analytical tool to evaluate and visualize the effect of ligand chemical structure with respect to receptor binding mode and biological activity.
- Qvortrup, Katrine,Jensen, Jakob F.,S?rensen, Mikael S.,Kouskoumvekaki, Irene,Petersen, Rasmus K.,Taboureau, Olivier,Kristiansen, Karsten,Nielsen, Thomas E.
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- Spirocyclopropanes from Intramolecular Cyclopropanation of Pyranopyrazoles and Pyranopyrimidine-diones and Lewis Acid Mediated (3 + 2) Cycloadditions of Spirocyclopropylpyrazolones
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A robust intramolecular cyclopropanation reaction was first performed on pyranopyrazole and pyranopyrimidine-dione derivatives to obtain spirocyclopropylpyrazolones and barbiturates, using iodosylbenzene (PhIO) or the combination of iodobenzene diacetate (PIDA)/molecular iodine (I2), under mild reaction conditions. Syntheses of functionally and stereochemically diversified, novel spiropyrazolone fused 2-iminothiophene and spiropyrazolone fused pyrroline scaffolds were also demonstrated via Lewis acid catalyzed highly diastereoselective (3 + 2) cycloaddition reactions of the synthesized spiro-cyclopropyl pyrazolones with phenyl isothiocyanate and benzonitrile, respectively.
- Mukherjee, Prasun,Das, Asish R.
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p. 2794 - 2802
(2017/03/14)
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- Synthesis of functionalized chromene and spirochromenes using L-proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
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An efficient and recyclable homogeneous catalyst is developed using commercially cheap L-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, L-proline and melamine (3:1 ratio; 3 mol% on total weight) was found to be best catalyst to give the desired products with excellent yields (up to 99%) in very short times (1–15 min) at room temperature in DMSO as solvent. The catalyst was recovered by adding EtOAc and reused up to 5 cycles without losing the catalytic activity.
- Nagaraju, Sakkani,Paplal, Banoth,Sathish, Kota,Giri, Santanab,Kashinath, Dhurke
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supporting information
p. 4200 - 4204
(2017/10/06)
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- Method for preparing pyrano[2, 3-c]pyridine derivative through catalysis of basic ionic liquid
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The invention provides a method for preparing a pyrano[2, 3-c]pyridine derivative through catalysis of a basic ionic liquid, and belongs to the technical field of organic synthesis. The molar ratio of aromatic aldehyde, ethyl acetoacetate or ethyl benzoyl
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Paragraph 0055; 0056; 0057
(2017/08/22)
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- Aqua-mediated multicomponent synthesis of various 4H-pyran derivatives catalyzed by poly(4-vinylpyridine)-supported copper iodide nanoparticle catalyst
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A green and efficient approach for synthesis of some new 4H-pyran derivatives is reported, catalyzed by green recyclable poly(4-vinylpyridine)-supported copper iodide nanoparticle catalyst in water. This procedure has many advantages such as operational s
- Albadi, Jalal,Mansournezhad, Azam
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p. 5739 - 5752
(2016/06/01)
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- Green synthesis of tetrahydrobenzo[b] pyrans, pyrano[2,3-c] pyrazoles and spiro[indoline-3,4′-pyrano[2,3-c] pyrazoles catalyzed by nano-structured diphosphate in water
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A green and recoverable nano-structured diphosphate (Na2CaP2O7) was synthesized and fully characterized using FT-IR spectra, X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), and energy-dispersive X-ray
- Maleki, Behrooz,Nasiri, Negar,Tayebee, Reza,Khojastehnezhad, Amir,Akhlaghi, Hossien Ali
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p. 79128 - 79134
(2016/09/09)
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- Applications of a novel nano magnetic catalyst in the synthesis of 1,8-dioxo-octahydroxanthene and dihydropyrano[2,3-c]pyrazole derivatives
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Imidazole-based ionic liquid-stabilized on silica coated Fe3O4 magnetic nano particles [nano-Fe3O4SiO2(CH2)3-Imidazole-SO3H]Cl as a novel heterogeneous acidic catalyst
- Zolfigol, Mohammad Ali,Ayazi-Nasrabadi, Roya,Baghery, Saeed,Khakyzadeh, Vahid,Azizian, Saeid
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- Sulfonic acid–functionalized magnetic Fe3-xTixO4nanoparticles: New recyclable heterogeneous catalyst for one-pot synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[2,3-c]pyrazole derivatives
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In this work, titanomagnetite nanoparticles (Fe3-xTixO4) have been used as a novel suppport for the synthesis of a magnetic acidic catalyst. These nanoparticles were functionalized with sulfonic acid groups to prepare the
- Azarifar, Davood,Abbasi, Younes
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p. 745 - 758
(2016/07/06)
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- Ultrasound promoted facile one pot synthesis of highly substituted pyran derivatives catalyzed by silica-coated magnetic NiFe2O4 nanoparticle-supported H14[NaP5W30O110] under mild condition
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Silica-coated magnetic NiFe2O4 nanoparticle-supported Preyssler heteropolyacid (H14[NaP5W30O110]) catalyzed efficiently the synthesis of highly substituted pyran derivatives under ultrasoni
- Maleki, Behrooz,Baghayeri, Mehdi,Jannat Abadi, Sedigheh Ayazi,Tayebee, Reza,Khojastehnezhad, Amir
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p. 96644 - 96661
(2016/10/24)
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- Silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40; Synthesis, preparation, and application as an efficient, magnetic, green catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives
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A powerful, magnetic, supported, acid catalyst, NiFe2O4@SiO2-H3PW12O40, was prepared by chemical support of Keggin (H3PW12O40) heteropolyacid (HPA) on silica-coated NiFe2O4 magnetic nanoparticles. XRD, TEM, SEM, VSM, and FTIR confirmed that the keggin HPA is well dispersed on the surface of silica-coated NiFe2O4 magnetic nanoparticles. The magnetically recoverable catalyst could be easily recycled at least six times without significant loss of catalytic activity. After full characterization, its catalytic activity was investigated in the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives. Graphical Abstract: (1) Novel silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40 was fabricated and characterized. (2) Recyclability of the catalyst. (3) Avoiding use of corrosive acid catalysts. (4) Green chemistry.
- Maleki, Behrooz,Eshghi, Hossein,Barghamadi, Mohammad,Nasiri, Negar,Khojastehnezhad, Amir,Sedigh Ashrafi, Samaneh,Pourshiani, Omid
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p. 3071 - 3093
(2016/04/05)
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- ANTI-CANCER COMPOUNDS TARGET RAL GTPASES AND METHODS OF USING THE SAME
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Methods of inhibiting the growth or metastasis of a cancer in a subject by inhibiting a Ral GTPase in the subject, and small molecule inhibitors of Ral GTPases useful in the methods of the invention. Pharmaceutical compositions containing the compounds of the invention, and methods of using the same.
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Page/Page column 40
(2016/04/26)
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- Anti-cancer compounds targeting Ral GTPases and methods of using the same
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The invention provides methods of inhibiting the growth or metastasis of a cancer in a mammal by inhibiting a Ral GTPase in the mammal. The invention also provides small molecule inhibitors of Ral GTPases useful in the methods of the invention and pharmaceutical compositions containing the therapeutically effective compounds of the invention, and methods of using the same.
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Page/Page column 57; 67
(2016/06/28)
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- Synthesis of novel Ral inhibitors: An in vitro and in vivo study
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Chemical synthesis was performed to produce a series of 6-amino-1,3-disubstituted-4-phenyl-1,4-dihydro pyrano[2,3-c]pyrazole-5-carbonitrile compounds (14–57) which were characterized by1H NMR,13C NMR and LC/MS–MS. These compounds were assessed for their effect on the in vitro anchorage independent growth of human lung cancer cell line H2122 and IC50values calculated. Two of the more potent compounds, BQU057 40 and BQU082 57 also displayed a dose dependent effect on RalA and RalB activity in H2122 spheroids using the common RalBP1 pull-down assay. Mouse PK and tissue distribution studies on 40 and 57 were performed and demonstrated that parent drug was present in tumor 3.0 h post ip (50 mg/Kg) dose.
- Yan, Chao,Theodorescu, Dan,Miller, Bettina,Kumar, Amit,Kumar, Vijay,Ross, David,Wempe, Michael F.
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supporting information
p. 5815 - 5818
(2016/11/25)
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- Identification of benzochromene derivatives as a highly specific NorA efflux pump inhibitor to mitigate the drug resistant strains of s. aureus?
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Increased expression of efflux transport proteins confers the Multi Drug Resistant (MDR) phenotype to drug resistant bacteria, which can be mitigated by efflux pump inhibitors (EPI). EPI's have the dual advantage of restoring efficacy of antibiotics and retarding the evolution of drug resistant mutants. In this study, 17 heterocyclic derivatives synthesized by a polyethylenimine (PEI) catalyzed one-pot protocol were evaluated for their EPI potential. Based on in silico studies and in vitro studies, 5 benzochromene (BC) based compounds (among 17 heterocyclic derivatives), were observed to significantly potentiate the effect of ciprofloxacin (CPX) and displayed a best modulation factor of 32, against the NorA overexpressed mutant SA-1199B. Toxicity analyses using the zebrafish model showed that, from all the benzochromene compounds evaluated, BC9 exhibited low toxicity. BC9 inhibited the NorA efflux pump at a minimum effective concentration (MEC) of 2 mg ml1 (4.03 mM) and even at subinhibitory concentrations, and it was effective in reversing the CPX MIC of both the ATCC strain and a clinical isolate of MRSA by 128 and 4 fold respectively. Our results show that benzochromene derivative BC9 is a highly specific NorA inhibitor that can be employed to mitigate MDR strains of S. aureus that overexpress the NorA efflux pump.
- Ganesan, Asaithampi,Christena, Lowrence Rene,Subbarao, Himesh Makala Venkata,Venkatasubramanian, Ulaganathan,Thiagarajan, Raman,Sivaramakrishnan, Venkatabalasubramanian,Kasilingam, Kabilan,Saisubramanian, Nagarajan,Ganesan, Subramaniapillai Selva
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p. 30258 - 30267
(2018/04/26)
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- Four-Component Synthesis of pyrano[2,3-c]pyrazoles Catalyzed by Triphenylphosphine in Aqueous Medium
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Background: The pyrano[2,3-c]pyrazoles have various biological properties such as antiinflammatory, anti-cancer, antifongical, analgesics and have a potential inhibitor for human ChK1 kinase. For these reasons several synthetic methods are reported. For o
- Khodja, Imène Amine,Fisli, Amina,Lebhour, Oumeima,Boulcina, Raouf,Boumoud, Boudjemaa,Debache, Abdelmadjid
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- Morpholine triflate promoted one-pot, four-component synthesis of dihydropyrano[2,3-c]pyrazoles
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A one-pot, four-component reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile was discussed using Lewis acid catalyst morpholine triflate (MorT) to afford a series of dihydropyrano[2,3-c]pyrazoles, which were generally catalyze
- Zhou, Chen-Feng,Li, Jian-Jun,Su, Wei-Ke
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p. 1686 - 1690
(2016/11/11)
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