- Novel benzenesulfonamide-bearing pyrazoles and 1,2,4-thiadiazoles as selective carbonic anhydrase inhibitors
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Two series comprising 20 novel benzenesulfonamides bearing thioureido-linked pyrazole 8 and amino-1,2,4-thiadiazole 10 were synthesized and assayed as human carbonic anhydrase (hCA) inhibitors against isoforms I and II as well as the tumor-associated isof
- Kumar, Rajiv,Kumar, Amit,Ram, Sita,Angeli, Andrea,Bonardi, Alessandro,Nocentini, Alessio,Gratteri, Paola,Supuran, Claudiu T.,Sharma, Pawan K.
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- Base-Promoted Intermolecular Cyclization of Substituted 3-Aryl(Heteroaryl)-3-chloroacrylaldehydes and Tetrahydroisoquinolines: An Approach to Access Pyrrolo[2,1-a]isoquinolines
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We have developed a new base-promoted intermolecular cascade cyclization reaction of substituted 3-aryl(heteroaryl)-3-chloroacrylaldehydes and tetrahydroisoquinolines in one pot. The reaction provides a facile and practical synthesis of pyrrolo[2,1-a]isoquinolines. A number of pyrrolo[2,1-a]isoquinolines were synthesized in moderate to high yields (up to 97%).
- Yang, Ziqi,Lu, Ning,Wei, Zhonglin,Cao, Jungang,Liang, Dapeng,Duan, Haifeng,Lin, Yingjie
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p. 11950 - 11955
(2016/12/09)
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- Unexpected tandem reaction of new type moritabaylis- Hillman adducts promoted by [HMIM]HSO4/NANO3 system
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A tandem reaction of new type Baylis-Hillman adducts 1 was prompted by ionic liquid [Hmim]HSO4/NaNO3 system and the unexpected products 6-aryl-2H-pyran-3-carboxylates 2 and imidazolium salts 3 were efficiently formed via the rearrang
- Zhong, Weihui,Wang, Guan,Chen, Kai
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scheme or table
p. 43 - 56
(2012/02/02)
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- Synthesis of biaryl derivatives by using ruthenium-mediated [2+2+2] cyclotrimerization and Suzuki-Miyaura cross-coupling as key steps
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Functionalized biaryl derivatives have been prepared by applying [2+2+2] cyclotrimerization with the aid of Grubbs first-generation catalyst (G-I). The trimerized products were subjected to the Suzuki-Miyaura cross-coupling reaction sequence to generate h
- Kotha, Sambasivarao,Seema, Vittal,Mobin, Shaikh M.
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scheme or table
p. 1581 - 1586
(2011/06/25)
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- Synthesis, biological evaluation and in silico study of β-chloro vinyl chalcones as inhibitors of the TNF-α, IL-6 with anticancer and antioxidant activity
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A series of novel β-chloro vinyl chalcones have been synthesized from substituted (Z)-3-chloro-3-phenylacraldehydes with 1-(3-bromo-2-hydroxyl-4,6- dimethoxyphenyl)ethanone by Claisen-Schmidt condensation reaction. Compounds were screened for anti-inflammatory, anticancer and antioxidant activity. Compounds 6a, 6d and 6f revealed promising anti-inflammatory activity (87-99 %) with less cytotoxicity (4-9 %) at 10 μM. Compounds 6a, 6d, 6e and 6f having significant anticancer activity (71-83 %). Bioavailability of compounds were checked by in vitro cytotoxicity and confirmed to be nontoxic. Structure activity relationship and in silico drug relevant properties of compounds revealed as potential candidates for future drug discovery study.
- Bandgar, Babasaheb P.,Hote, Baliram S.,Nile, Shivraj H.
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body text
p. 725 - 732
(2012/05/05)
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- Synthesis and biological screening of a combinatorial library of β-chlorovinyl chalcones as anticancer, anti-inflammatory and antimicrobial agents
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A combinatorial library of β-chlorovinyl chalcones (4) were synthesized by Claisen-Schmidt condensation reaction. Catalytic reaction of substituted 3-chloro-3-phenyl-propenal (2) and 1-(2,4-dimethoxy-phenyl)-ethanone or 1-(4-methoxy-phenyl)-ethanone (3) i
- Bandgar, Babasaheb P.,Gawande, Shrikant S.
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experimental part
p. 2060 - 2065
(2010/06/12)
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- Synthesis and biological evaluation of β-chloro vinyl chalcones as inhibitors of TNF-α and IL-6 with antimicrobial activity
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A series of β-chloro vinyl chalcones have been synthesized by Claisen-Schmidt condensation. β-chloro vinyl aldehyde has been synthesized by the Vilsmayer-Hack formylation reaction. The structures of the newly synthesized compounds were confirmed by 1H NMR, IR and Mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-α and IL-6) and antimicrobial (antibacterial and antifungal) activity. Compounds 5a, 5d, 5e, 5g and 5i exhibited promising activity against IL-6 with 58-83% inhibition at 10 μM concentration. None of the compound was found to be cytotoxic in CCK-8 cells at 10 μM concentration. Whereas compounds 5b, 5d, 5e and 5i showed very good antibacterial activity and compounds 5a, 5b, 5e and 5i showed good antifungal activity.
- Bandgar, Babasaheb P.,Patil, Sachin A.,Korbad, Balaji L.,Nile, Shivraj H.,Khobragade, Chandrahase N.
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scheme or table
p. 2629 - 2633
(2010/07/09)
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- Synthesis of a novel series of thieno[3,2-d]pyrimidin-4-(3H)-ones
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2-Aminothieno[3,2-d]pyrimidin-4-ones were synthesized in one step by condensation of 3-amino(benzo)thiophene car-boxylate with chloroformamidine hydrochloride. Georg Thieme Verlag Stuttgart.
- Abdillahi, Ismail,Kirsch, Gilbert
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scheme or table
p. 1428 - 1430
(2010/10/03)
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- The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones
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Studies directed at the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)- ones from (Z)-3-aryl-3-haloenoic acids are described. The successful strategy relies on the preparation of (Z)-3-aryl-3-haloenoic acids from acetophenones through the corresponding
- Gupton, John T.,Telang, Nakul,Banner, Edith J.,Kluball, Emily J.,Hall, Kayleigh E.,Finzel, Kara L.,Jia, Xin,Bates, Spencer R.,Welden, R. Scott,Giglio, Benjamin C.,Eaton, James E.,Barelli, Peter J.,Firich, Lauren T.,Stafford, John A.,Coppock, Matthew B.,Worrall, Eric F.,Kanters, Rene P.F.,Keertikar, Kerry,Osterman, Rebecca
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experimental part
p. 9113 - 9122
(2011/01/12)
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- Efficient synthesis of a new type of baylis-hillman adducts and their stereoselective bromination
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A new type of Baylis-Hillman adducts derived from chlorovinyl aldehydes were prepared via Vilsmeier reaction of ketones with a bis(trichloromethyl) carbonate (BTC)/DMF system to construct chlorovinyl aldehydes, followed by sonochemical Baylis-Hillman reaction under solvent-free conditions. The stereoselective bromination of these new compounds with a Br2-Ph3P system has been achieved efficiently with good to excellent yields under mild conditions. Copyright Taylor & Francis Group, LLC.
- Zhong, Weihui,Jiang, Lingbo,Guo, Baoming,Wu, Yaotiao,Hong, Lingjuan,Chen, Yanhui
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experimental part
p. 2441 - 2456
(2010/09/05)
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- One-pot synthesis of new type aza- Baylis-Hillman adducts from chlorovinyl aldehydes under solvent-free condition
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A series of new type aza- Baylis-Hillman adducts were prepared in moderate yields by one-pot treatment of chlorovinyl aldehydes, benzenesulfonamides and activated olefi ns under solvent-free condition. The chlorovinyl aldehydes were obtained via chlorofor
- Zhong, Weihui,Chen, Yanhui,Wang, Guan
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body text
p. 44 - 49
(2010/07/03)
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- Synthesis of selenophene analogues of the tacrine series: Comparison of classical route and microwave irradiation
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New 3-amino-2-selenophenecarbonitriles condensed with cyclanones to afford, in one step, analogues of Tacrine. A comparison between classical heating and microwave irradiation for the Friedlaender condensation is presented. Georg Thieme Verlag Stuttgart.
- Thomae, David,Kirsch, Gilbert,Seck, Pierre
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scheme or table
p. 1600 - 1606
(2009/04/03)
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- Design, synthesis, and biological evaluation of thiophene analogues of chalcones
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Chalcones are characterized by possessing an enone moiety between two aromatic rings. A series of chalcone-like agents, in which the double bond of the enone system is embedded within a thiophene ring, were synthesized and evaluated for antiproliferative
- Romagnoli, Romeo,Baraldi, Pier Giovanni,Carrion, Maria Dora,Cara, Carlota Lopez,Cruz-Lopez, Olga,Preti, Delia,Tolomeo, Manlio,Grimaudo, Stefania,Cristina, Antonella Di,Zonta, Nicola,Balzarini, Jan,Brancale, Andrea,Sarkar, Taradas,Hamel, Ernest
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p. 5367 - 5376
(2008/12/20)
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- Synthesis of thiophene analogues of the tacrine series
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3-Amino-2-cyanothiophenes condensed with cyclanones and afforded analogues of Velnacrine in two or three steps. Condensation under Friedlander's conditions gave tacrine analogues in one step. Georg Thieme Verlag Stuttgart.
- Thomae, David,Kirsch, Gilbert,Seck, Pierre
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p. 1027 - 1032
(2008/02/02)
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- Synthesis and antifungal activity of novel 3,6-diaryl-5H-[1,2,4]triazolo[4, 3-b][1,2,4]triazepines
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(Chemical Equation Presented) 5-Aryl-3,4-diamino-1,2,4-triazoles 5 on treatment with β-chlorocinnamaldehydes 7 in the presence of catalytic amount of p-TsOH and N,N-dimethylformamide as an energy transfer medium under microwave irradiation and as solvent with oil-bath heating at 80°C affords novel 3,6-diaryl-5H-[1,2,4]triazolo[4,3-b]-1,2,4]triazepines 8. The structures of the synthesized compounds were established on the basis of 1H NMR, IR, mass spectral data and elemental analysis.
- Gupta, Monika
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p. 1023 - 1027
(2008/03/29)
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- Reactions of (Z)-3-aryl-3-chloropropenals with nucleophiles: Stereoselective formation of (E)-vinylogous esters, (E)-vinylogous amides, and vinamidinium salts
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The highly stereoselective conversions of (Z)-3-aryl-3-chloropropenals to (E)-3-alkoxy-3-arylpropenals, to (E)-3-aryl-3-morphorlinopropenals, and to vinamidinium salts are reported. The stereochemical assignments were based on 2D-NMR experiments.
- Clough, Stuart,Gupton, John,Ligali, Adepeju,Roberts, Matthew,Driscoll, David,Annett, Scott,Hewitt, Alisa,Hudson, Matthew,Jackson, Edward,Miller, Robert,Norwood, Bradley,Kanters, Rene,Wyre, Hadley,Petruzzi, Heather
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p. 7554 - 7561
(2007/10/03)
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- Vilsmeier reagent for formylation in solvent-free conditions using microwaves
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POCl3-DMF over silica gel has been used for the synthesis of β-chlorovinylaldehydes (1-5), 2-aryl-3-formylindoles (6-8), 2-chloro-3-formylquinolines (9-13) and other aromatic aldehydes (14-20) using solvent-free conditions and microwave irradiation.
- Paul,Gupta,Gupta
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p. 1115 - 1118
(2007/10/03)
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- Synthesis and stereochemistry of β-aryl-β-haloacroleins: Useful intermediates for the preparation of (Z) and (E)-2-en-4-ynecarbaldehydes and for the synthesis of rubrolides
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The synthesis of α-substituted β-aryl-β-haloacroleins by two different pathways is presented. The determination of their stereochemistry by NOE experiments is reported for the first time. Furthermore, we describe the preparation of 2-en-4-ynecarbaldehydes
- Prim, Damien,Fuss, Alexia,Kirsch, Gilbert,Silva, Artur M. S.
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p. 1175 - 1180
(2007/10/03)
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- SYNTHESIS OF NEW 2,5-DIARYL SELENOPHENES
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A synthesis of 2,5-parasubstituted diaryl selenophenes is described. β-Aryl-β-chloro acroleins, easily prepared from substituted acetophenones and Vilsmaier-Haack reagent, are condensed with appropriate benzylbromide derivatives to give the title compound
- Prim, Damien,Joseph, Delphine,Kirsch, Gilbert
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p. 137 - 144
(2007/10/02)
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- New Thiophene Derivatives as Potential Materials for Non Linear Optics
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A method of synthesis of unsymmetrical 2,5-diarylthiophenes is described using β-chloroacroleins, prepared from acetophenones, and their condensation with sodium sulfide and various benzyl bromides.
- Kirsch, Gilbert,Prim, Damien,Leising, Frederic,Mignani, Gerard
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p. 1005 - 1010
(2007/10/02)
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