- Highly diastereoselective one-pot synthesis of spiro{cyclopenta[a]indene-2, 2′-indene}diones from 1-indanones and aromatic aldehydes
-
Treatment of 1-indanones with aromatic aldehydes and NaOEt in THF affords complex spiropolycyclic compounds through a four-component reaction in which two molecules of each starting compound are combined with formation of four new carbon-carbon bonds, leading to the elaboration of a new five-membered ring that bears five contiguous stereogenic centers with a well-defined relative configuration. Different amounts of a minor epimer of the main product are also formed. The presence of methoxy substituents in the indanone component and the use of aldehydes derived from π-excedent heterocycles make the dimerization step a slower transformation. In these cases, better yields of spirodimers are obtained starting from the preformed enones. The reaction seems to take place by cross-aldol condensation, dehydration, and dimerization of the thus formed enones. The molecular mechanism of the dimerization reaction of enone 5g has been studied using DFT methods at the B3LYP/6-31G* level. The dimerization takes place through a process involving a Michael addition of a carbanion, obtained by deprotonation of 5g at the 3-position, to a second molecule of 5g, followed by an intramolecular Michael addition in the corresponding intermediate. The final protonation of the resulting anion accounts for the formation of the cis-fused pentacyclic system.
- Camps, Pelayo,Domingo, Luis R.,Formosa, Xavier,Galdeano, Carles,Gonzalez, Diana,Munoz-Torrero, Diego,Segales, Silvia,Font-Bardia, Merce,Solans, Xavier
-
-
Read Online
- Iridium-catalyzed chemoselective transfer hydrogenation of α, β-unsaturated ketones to saturated ketones in water
-
A chemoselective iridium-catalyzed transfer hydrogenation of α, β-unsaturated ketones was realized in water. The C[dbnd]C double bonds of 2-benzylidene indanones and analogues were hydrogenated exclusively catalyzed by an iridium complex (0.1 mol%) bearin
- Chen, Jinxun,Chen, Yongsheng,Cui, Xiaofeng,Jiang, Xiaolan,Liu, Qixing,Zhou, Haifeng
-
supporting information
(2022/01/24)
-
- Iron-catalyzed chemoselective hydride transfer reactions
-
A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.
- Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc
-
supporting information
(2021/06/07)
-
- Tetralone derivatives are MIF tautomerase inhibitors and attenuate macrophage activation and amplify the hypothermic response in endotoxemic mice
-
Macrophage migration inhibitory factor (MIF) is a pro-inflammatory cytokine playing crucial role in immunity. MIF exerts a unique tautomerase enzymatic activity that has relevance concerning its multiple functions and its small molecule inhibitors have been proven to block its pro-inflammatory effects. Here we demonstrate that some of the E-2-arylmethylene-1-tetralones and their heteroanalogues efficiently bind to MIF’s active site and inhibit MIF tautomeric (enolase, ketolase activity) functions. A small set of the synthesised derivatives, namely compounds (4), (23), (24), (26) and (32), reduced inflammatory macrophage activation. Two of the selected compounds (24) and (26), however, markedly inhibited ROS and nitrite production, NF-κB activation, TNF-α, IL-6 and CCL-2 cytokine expression. Pre-treatment of mice with compound (24) exaggerated the hypothermic response to high dose of bacterial endotoxin. Our experiments suggest that tetralones and their derivatives inhibit MIF’s tautomeric functions and regulate macrophage activation and thermal changes in severe forms of systemic inflammation.
- ?rfi, László,Bagóné Vántus, Viola,Garai, János,Garami, András,Jakus, Péter Balázs,Kéringer, Patrik,Kovács, Dominika,Krekó, Marcell,Lóránd, Tamás,Radnai, Balázs,Rumbus, Zoltán,Vámos, Eszter
-
p. 1357 - 1369
(2021/07/22)
-
- Green, rapid, and highly efficient syntheses of α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones as potentially biologic compounds via solvent-free microwave-assisted Claisen–Schmidt condensation catalyzed by MoCl5
-
A new, green, and highly efficient protocol for the expeditious preparation of some α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones via a simple microwave-assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent-free conditions, simple operation, use of a very inexpensive and available catalyst, low catalyst loading, short reaction times, high yields of the pure products, no harmful by-products, easy workup, and also the applicability of microwave irradiation as a clean source of energy. Furthermore, a gram-scale reaction was successfully conducted, proving the scalability of this current Claisen–Schmidt condensation reaction.
- Bakhshi, Reza,Zeynizadeh, Behzad,Mousavi, Hossein
-
p. 623 - 637
(2019/08/26)
-
- Selective fluorometric “Turn-off” sensing for Hg2+ with pyrazoline compound and its application in real water sample analysis
-
In this study, a new pyrazoline derivative (4-(3-phenyl-3a,4-dihydroindeno[1,2-c]pyrazol-2(3H)-yl)benzenesulfonamide, K1) was described as fluorescent probe for fluorometric detection of Hg2+. This fluorescence probe had a high selectivity only
- Bozkurt, Ebru,Gul, Halise Inci
-
-
- Radical C?N Borylation of Aromatic Amines Enabled by a Pyrylium Reagent
-
Herein, we report a radical borylation of aromatic amines through a homolytic C(sp2)?N bond cleavage. This method capitalizes on a simple and mild activation via a pyrylium reagent (ScPyry-OTf) thus priming the amino group for reacti
- Chabbra, Sonia,Cornella, Josep,Leutzsch, Markus,Ma, Yuanhong,Niski, Jan,Pang, Yue,Reijerse, Edward J.,Schnegg, Alexander
-
supporting information
(2020/03/23)
-
- Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic addition of non-nucleophilic alkyls to alkynes
-
Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic cyclization of alkynes using non-nucleophilic alkyls as the nucleophile is reported. Upon photoexcitation, o-alkylphenyl alkynyl ketones can be transferred into (E)-photoenols. Thus, a nucleophilic methylene is formed from the non-nucleophilic alkyl. An AlCl3 catalyst can stabilize the (E)-photoenol intermediate and facilitate further intramolecular nucleophilic cyclization. DFT calculations indicated that the AlCl3-catalyzed cyclization is the regioselectivity determining step.
- Zhang, Yanbin,Jin, Ruiwen,Pan, Guangxing,Guo, Hao
-
supporting information
p. 11621 - 11624
(2020/10/19)
-
- I2/TBHP mediated diastereoselective synthesis of spiroaziridines
-
Eventhough spiroheterocycles are considered as emerging drug candidates, synthesis of spiroaziridines has not been well explored so far. Herein, we disclose an efficient I2/TBHP mediated diastereoselective synthesis of N-alkyl spiroaziridines from primary amines and easily accessible α,β-unsaturated ketones. The reaction is also compatible for the synthesis of 2-aroylaziridines.
- Ashitha, Kizhakkan Thiruthi,Vinaya, Puthiya Purayil,Krishna, Ajay,Vincent, Deepthy Cheeran,Jalaja, Renjitha,Varughese, Sunil,Somappa, Sasidhar Balappa
-
supporting information
p. 1588 - 1593
(2020/03/06)
-
- Tuning the Product Selectivity of the α-Alkylation of Ketones with Primary Alcohols using Oxidized Titanium Nitride Photocatalysts and Visible Light
-
The direct α-alkylation of ketones with alcohol to synthesize important α-alkylated ketones and enones is an attractive procedure for C-C bond formation. High reaction temperatures are always needed for heterogeneous catalysis using non-noble metals, and switching product selectivity in one catalysis system remains a great challenge. In the present study, a visible-light-driven procedure for this reaction is proposed, using oxidized TiN photocatalysts under mild conditions, whereby the product selectivity can be well-tuned. Oxidized TiN photocatalysts with tunable surface N/O ratios were successfully synthesized through the facile and flexible thermal oxidation treatment of low-cost TiN nanopowder. The α-alkylation of acetophenone with benzyl alcohol to form the two important compounds chalcone and dihydrochalcone occurred even at room temperature and almost complete conversion was achieved at 100 °C under visible light. The proportion of the two products can be well-tuned by switching the surface N/O ratio of the synthesized photocatalysts. Visible light is demonstrated to affect the surface N/O ratio of the photocatalysts and contribute to tuning the product selectivity. Light intensity and action spectrum study proves that the generation of energetic charge carriers results in the observed activities under visible light, based on interband transitions of TiN or the ligand-to-metal charge transfer (LMCT) effect of the surface complex formed on TiO2. Thermal energy can be coupled with light energy within this photocatalytic system, which will facilitate the full use of solar energy. Different sequential reaction mechanisms on TiN and TiO2 are proposed to be responsible for the tunable product selectivity. The wide reaction scope, the fine conversion at a low light intensity, and the favorable reusability of photocatalysts prove the great application potential of this visible-light-driven procedure for the α-alkylation of ketones with primary alcohols.
- Li, Peifeng,Su, Haijia,Xiao, Gang,Zhao, Yilin
-
p. 3640 - 3649
(2020/04/09)
-
- In vitro Anti-Trypanosomal Activities of Indanone-Based Chalcones
-
Human African trypanosomiasis is a neglected infectious disease that affects mostly people living in the rural areas of Africa. Current treatment options are limited to just four drugs that have been in use of four to nine decades. The life-threatening to
- Beteck, Richard M.,Legoabe, Lesetje J.,Isaacs, Michelle,Hoppe, Heinrich C.
-
p. 337 - 341
(2019/06/10)
-
- Synthesis of benzylidenecycloalkan-1-ones and 1,5-diketones under Claisen–Schmidt reaction: Influence of the temperature and electronic nature of arylaldehydes
-
Herein, we present the results of the influence of reaction temperature and the electronic nature of arylaldehydes in the reactions of benzocycloalkan-1-ones and arylaldehydes under classical Claisen–Schmidt condensation conditions. The products obtained, 2-arylidene derivatives of benzocycloalkan-1-ones and/or spiropolycyclic-1,5-diketones through multicomponent reactions, depended on the electronic nature of arylaldehyde and the reaction temperature. Besides, under identical conditions, 2-arylideneindan-1-ones afforded bis-indane-1,5-diketones through a process that involves Michael addition reaction, which is also dependent on the temperature. Theoretical studies using density-functional theory allowed understanding the chemical reactivity and the site selectivity of α,β-enones used in this work through the calculation of global and local electrophilicity on C–β. Both the electrophilicity of C-β and the temperature led the course of reaction toward the formation of aldol condensation, aldol condensation/Michael addition, and aldol condensation/dimerization products. This work is the first to perform the structural and configurational assignments of bis-indane-1,5-diketones.
- Lanta?o, Beatriz,Aguirre, José M.,Drago, Eleonora V.,Bollini, Mariela,de la Faba, Diego J.,Mufato, Jorge D.
-
supporting information
p. 2202 - 2214
(2017/11/20)
-
- Novel 2-aryl-4-(4′-hydroxyphenyl)-5H-indeno[1,2-b]pyridines as potent DNA non-intercalative topoisomerase catalytic inhibitors
-
On the basis of previous reports on the importance of thienyl, furyl or phenol group substitution on 5H-indeno[1,2-b]pyridine skeleton, a new series of rigid 2-aryl-4-(4′-hydroxyphenyl)-5H-indeno[1,2-b]pyridine derivatives were systematically designed and
- Park, Seojeong,Kadayat, Tara Man,Jun, Kyu-Yeon,Thapa Magar, Til Bahadur,Bist, Ganesh,Shrestha, Aarajana,Lee, Eung-Seok,Kwon, Youngjoo
-
-
- Discovery and structure-activity relationship studies of 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives as a novel class of potential therapeutics for inflammatory bowel disease
-
To develop effective therapeutics for inflammatory bowel disease (IBD), 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives, were designed and synthesized and their structure-activity relationships (SAR) were investigated. Compounds 7, 25, 26, 32, 39, 41, 52, 54, and 55 showed potent inhibitory effect (>70%) on the TNF-α-induced adhesion of monocytes to colon epithelial cells, which is one of the hallmark events leading to IBD. Such inhibitory activity of the compounds correlated with their suppressive activities against the TNF-α-induced production of ROS; ICAM-1 and MCP-1 expression, critical molecules involved in monocyte-epithelial adhesion; and NF-κB transcriptional activity. In addition, compounds 41 and 55 significantly suppressed the lipopolysaccharide (LPS)-induced expression of the TNF-α gene, with compound 55 showing better efficacy. This inhibition of TNF-α expression by compounds 41 and 55 corresponded to their additional inhibitory activity against AP-1 transcriptional activity, which is another transcription factor required for high level TNF-α expression. The strong inhibitory activity of compound 55 against an in vivo colitis model was confirmed by its dose-dependent inhibitory activity in a rat model of 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis, demonstrating compound 55 as a new potential candidate for the development of therapeutics against IBD.
- Kadayat, Tara Man,Banskota, Suhrid,Gurung, Pallavi,Bist, Ganesh,Thapa Magar, Til Bahadur,Shrestha, Aarajana,Kim, Jung-Ae,Lee, Eung-Seok
-
supporting information
p. 575 - 597
(2017/06/23)
-
- Design, synthesis, and structure-activity relationship study of halogen containing 2-benzylidene-1-indanone derivatives for inhibition of LPS-stimulated ROS production in RAW 264.7 macrophages
-
As a continuous effort to discover new potential anti-inflammatory agents, we systematically designed and synthesized sixty-one 2-benzylidene-1-indanone derivatives with structural modification of chalcone, and evaluated their inhibitory activity on LPS-stimulated ROS production in RAW 264.7 macrophages. Systematic structure-activity relationship study revealed that hydroxyl group in C-5, C-6, or C-7 position of indanone moiety, and ortho-, meta-, or para-fluorine, trifluoromethyl, trifluoromethoxy, and bromine functionalities in phenyl ring are important for inhibition of ROS production in LPS-stimulated RAW 264.7 macrophages. Among all the tested compounds, 6-hydroxy-2-(2-(trifluoromethoxy) benzylidene)-2,3-dihydro-1H-inden-1-one (compound 44) showed the strongest inhibitory activity of ROS production. Further studies on the mode of action revealed that compound 44 potently suppressed LPS-stimulated ROS production via modulation of NADPH oxidase. The findings of this work could be useful to design 2-benzylidene-indanone based lead compounds as novel anti-inflammatory agents.
- Shrestha, Aarajana,Jin Oh, Hye,Kim, Mi Jin,Pun, Nirmala Tilija,Magar, Til Bahadur Thapa,Bist, Ganesh,Choi, Hongseok,Park, Pil-Hoon,Lee, Eung-Seok
-
p. 121 - 138
(2017/04/07)
-
- α-Unsubstituted Pyrroles by NHC-Catalyzed Three-Component Coupling: Direct Synthesis of a Versatile Atorvastatin Derivative
-
A practical one-pot cascade reaction protocol provides direct access to valuable 1,2,4-trisubstituted pyrroles. The process involves an N-heterocyclic carbene (NHC)-catalyzed Stetter-type hydroformylation using glycolaldehyde dimer as a novel C1 building-block, followed by a Paal-Knorr condensation with primary amines. The reaction makes use of simple and commercially available starting-materials and catalyst, an important feature regarding applicability and utility. Low catalyst loading under mild reaction conditions afforded a variety of 1,2,4-substituted pyrroles in a transition-metal-free reaction with high step economy and good yields. This methodology is applied in the synthesis of a versatile Atorvastatin precursor, in which a variety of modifications at the pyrrole core structure are possible.
- Fleige, Mirco,Glorius, Frank
-
supporting information
p. 10773 - 10776
(2017/08/22)
-
- Novel 2,4-diaryl-indenopyridine derivatives or pharmaceutically acceptable salts thereof, preparation method thereof, and pharmaceutical composition containing the same for preventing or treating cancer as active ingredients
-
The present invention relates to a novel 2,4-diaryl-indenopyridine derivative or a pharmaceutically acceptable salt thereof, a preparation method thereof, and a pharmaceutical composition comprising the same as an active component for preventing and treat
- -
-
Paragraph 0099; 0100
(2016/11/17)
-
- Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides
-
A series of new 4-(3-(4-substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides (7–12) was synthesized starting from 2-(4-substitutedbenzylidene)-2,3-dihydro-1H-inden-1-one (1–6) and 4-hydrazinobenzenesulfonamide. The substituted
- Gul, Halise Inci,Tugrak, Mehtap,Sakagami, Hiroshi,Taslimi, Parham,Gulcin, Ilhami,Supuran, Claudiu T.
-
p. 1619 - 1624
(2016/10/09)
-
- 2-Benzylidene-1-indanone derivatives as inhibitors of monoamine oxidase
-
In the present study, a series of twenty-two 2-benzylidene-1-indanone derivatives were synthesised and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. The 2-benzylidene-1-indanone derivatives are structurally related to a series of benzylideneindanone derivatives which has previously been found to be MAO-B inhibitors. This study finds that the 2-benzylidene-1-indanones are MAO-B specific inhibitors with IC50values 50?50?=?0.131?μM). An analysis of the structure–activity relationships for MAO-B inhibition show that substitution on the A-ring with a 5-hydroxy group and on the B-ring with halogens and the methyl group yield high potency inhibition. It may therefore be concluded that 2-benzylidene-1-indanone analogues are promising leads for design of therapies for disorders such as Parkinson's disease.
- Nel, Magdalena S.,Petzer, Anél,Petzer, Jacobus P.,Legoabe, Lesetja J.
-
supporting information
p. 4599 - 4605
(2016/09/13)
-
- Catalytic enantioselective cascade Michael/cyclization reaction of 3-isothiocyanato oxindoles with exocyclic α,β-unsaturated ketones: En route to 3,2′-pyrrolidinyl bispirooxindoles
-
Cascade Michael/cyclization reactions between 3-isothiocyanato oxindoles and exocyclic α,β-unsaturated ketones are shown to proceed efficiently in the presence of a quinine-derived tertiary amino-squaramide catalyst and furnish 3,2′-pyrrolidinyl bispirooxindoles containing two spiro-quaternary and three contiguous stereocenters as a single diastereomer with excellent enantioselectivities (up to 99:1 er).
- Kayal, Satavisha,Mukherjee, Santanu
-
supporting information
p. 10175 - 10179
(2016/11/17)
-
- BF3·Et2O mediated one-step synthesis of N-substituted-1,2-dihydropyridines, indenopyridines and 5,6-dihydroisoquinolines
-
A simple and efficient one-pot synthesis of N-substituted-1,2-dihydropyridines, indenopyridines and 5,6-dihydroisoquinolines by a BF3·Et2O mediated novel methodology, from easily available α,β-unsaturated ketones/arylidene ketones, phenyl acetylenes and substituted nitriles, has been described. This novel annulation provides quick access to complex polycyclic frameworks with an excellent substrate scope.
- Fathimath Salfeena,Ashitha,Sasidhar
-
supporting information
p. 10165 - 10169
(2016/11/17)
-
- Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity
-
For the development of potential anticancer agents, we designed and synthesized 30 new 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives containing aryl moiety such as furyl, thienyl, pyridyl, and phenyl at 2- and 4-position of 5H-indeno[1,2-b]pyridine. The
- Kadayat, Tara Man,Park, Chanmi,Jun, Kyu-Yeon,Magar, Til Bahadur Thapa,Bist, Ganesh,Yoo, Han Young,Kwon, Youngjoo,Lee, Eung-Seok
-
p. 160 - 173
(2015/02/19)
-
- An efficient synthesis and antimicrobial screening of new hybrid molecules containing coumarin and indenopyridine moiety
-
A novel series of hitherto unknown 3-(4-aryl-5H-indeno[1,2-b]pyridin-2-yl)coumarin derivatives 3a-r have been synthesized by the reaction of 3-coumarinyl methyl pyridinium salts 1a-c with appropriate 2-arylidene-1-indanones 2a-f under Krohnke's reaction c
- Brahmbhatt, Dinkar I.,Patel, Chirag V.,Bhila, Varun G.,Patel, Niraj H.,Patel, Apoorva A.
-
p. 1596 - 1606
(2015/04/21)
-
- Modified Pyridine-Substituted Coumarins: A New Class of Antimicrobial and Antitubercular Agents
-
Some new biologically potent coumarin derivatives 7a-f, 8a-f, and 9a-f bearing modified pyridine moieties (indeno[1,2-b]pyridine, 4-azaphenanthrene and benzofuro [3,2-b]pyridine) at the sixth position were designed and synthesized. All the synthesized com
- Giri, Rakesh R.,Lad, Hemali B.,Bhila, Varun G.,Patel, Chirag V.,Brahmbhatt
-
p. 363 - 375
(2015/10/29)
-
- Free radical-mediated chemoselective reduction of enones
-
A novel methodology has been devised for the chemoselective reduction of enones involving the use of nBu3SnH and azobisisobutyronitrile. The 1,4-reduction of variously substituted ,β-unsaturated cyclic and acyclic enones has been successfully c
- Sultan, Aeysha,Raza, Abdul Rauf,Tahir, Muhammad Nawaz
-
supporting information
p. 267 - 274
(2013/12/04)
-
- In vivo structure-activity relationship studies support allosteric targeting of a dual specificity phosphatase
-
Dual specificity phosphatase 6 (DUSP6) functions as a feedback attenuator of fibroblast growth factor signaling during development. In vitro high throughput chemical screening attempts to discover DUSP6 inhibitors have yielded limited success. However, in
- Korotchenko, Vasiliy N.,Saydmohammed, Manush,Vollmer, Laura L.,Bakan, Ahmet,Sheetz, Kyle,Debiec, Karl T.,Greene, Kristina A.,Agliori, Christine S.,Bahar, Ivet,Day, Billy W.,Vogt, Andreas,Tsang, Michael
-
p. 1436 - 1445
(2014/07/21)
-
- Synthesis of highly functionalised dispiropyrrolidine derivatives as novel acetylcholinesterase inhibitors
-
In the effort of finding novel acetyl cholinesterase (AChE) inhibitors to improve the efficacy of Alzheimer's disease (AD) treatment, series of substituted aryl-1′-methyldispiro[indan-2,2′ pyrrolidine-3′, 2"-indan]-1,3,1′-trione and substituted 7′-aryl-5′, 6′,7′,7a′-tetrahydrodispiro-[indane-2,5′-pyrrolo[1,2-c] [1,3]thiazole-6′,2"-indan]-1,3,1"-trione analogues were synthesized using [3+2]-cycloaddition reactions. These newly synthesized pyrrolidine compounds were assayed for their biological activity using Ellman's method. The structural elucidation of the compounds was performed by using 1H-NMR, 13C-NMR, ESI-MS spectra and elemental analyses. Eight out of twenty synthesized compounds showed more than 50% inhibition at concentration of 10 μM. Compound 2e, 2i and 3e were among the most active one, giving IC50 value as 3.3 μM for 2e, 3.7 μM for 2i and 5.5 μM for 3e, respectively. Lineweaver-Burk plot indicated that 2i inhibits AChE in a competitive manner. Molecular modelling study was performed to disclose the binding interaction of these compounds with the active site of AChE.
- We, Ang Chee,Ali, Mohamed Ashraf,Yoon, Yeong Keng,Ismail, Rusli,Choon, Tan Soo,Khaw, Kooi-Yeong,Murugaiyah, Vikneswaran,Lakshmipathi, Venu Sanjeevi
-
p. 156 - 161
(2014/03/21)
-
- Design, synthesis and in vitro cytotoxicity evaluation of new 3',4'-bis (3,4,5-trisubstituted)-4'H-spiro[indene-2,5'-isoxazol]-1(3H)-one derivatives as promising anticancer agents
-
A new series of 3',4'-bis(3,4,5-trimethoxyphenyl)-4'H-spiro[indene-2,5'-isoxazol]-1(3H)-one derivatives was designed and synthesized. The cytotoxic effects of the synthesized compounds were evaluated on several different human cancer cells. Among them, compound 9e displayed the most potent in vitro antiproliferative activity with IC50 values of 0.07±0.01 μM on T47D cells. Another potent derivative 9h displayed an IC50 value of 0.12±0.07 μM against T47D cells, comparable to that of the positive controls (Colchicine' Cisplatin' Vincristine' Vinblastine' Doxorubicin' Celecoxib). The structure-activity relationships were discussed and both anti-tubulin and COX-2 inhibitory effects were proposed for the developed compounds
- Abolhasani, Hoda,Zarghi, Afshin,Abolhasani, Ahmad,Hamzeh-Mivehroud, Maryam,Bargahi, Nasrin,Notash, Behrouz,Mojarrad, Javid Shahbazi,Dastmalchi, Siavoush
-
p. 1149 - 1161
(2015/03/31)
-
- Dehydrogenation and oxidative coupling of alcohol and amines catalyzed by organosilicon-supported TiO2@PMHSIPN
-
The catalytic dehydrogenation and tandem transformation of aromatic alcohols, including oxidative coupling of alcohols and amines, were achieved successfully using a catalytic amount of organosilicon-supported titania (TiO2@PMHSIPN), which enables the efficient synthesis of aromatic aldehydes, imines, and benzimidazoles in good to excellent yields. This journal is the Partner Organisations 2014.
- Wang, Hu,Zhang, Jin,Cui, Yu-Ming,Yang, Ke-Fang,Zheng, Zhan-Jiang,Xu, Li-Wen
-
p. 34681 - 34686
(2014/11/08)
-
- Evaluation of silica-H2SO4 as an efficient heterogeneous catalyst for the synthesis of chalcones
-
We report an efficient silica-H2SO4 mediated synthesis of a variety of chalcones that afforded the targeted compounds in very good yield compared to base catalyzed solvent free conditions as well as acid or base catalyzed refluxing conditions.
- Sultan, Aeysha,Raza, Abdul Rauf,Abbas, Muhammad,Khan, Khalid Mohammed,Tahir, Muhammad Nawaz,Saari, Nazamid
-
p. 10081 - 10094
(2013/09/23)
-
- A facile three-component [3+2]-cycloaddition for the regioselective synthesis of highly functionalised dispiropyrrolidines acting as antimycobacterial agents
-
A series of fourteen dispiropyrrolidines were synthesized using [3+2]-cycloaddition reactions and were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv in HTS (High Throughput Screen). Most of the compounds showed moderate to good activity with MIC of less than 20 μM. Compound 4′-(4-bromophenyl)-1′- methyldispiro[acenaphthylene-1,2′-pyrrolidine-3′,2″-indane]-2, 1″(1H)-dione (4c) was found to be the most active with MIC of 12.50 μM.
- Wei, Ang Chee,Ali, Mohamed Ashraf,Yoon, Yeong Keng,Ismail, Rusli,Choon, Tan Soo,Kumar, Raju Suresh
-
supporting information
p. 1383 - 1386
(2013/03/14)
-
- Synthesis of 2,3-dihydro-1H-inden-1-one derivatives via Ni-catalyzed intramolecular hydroacylation
-
An efficient synthetic method for the formation of 2,3-dihydro-1H-inden-1- one derivatives through a Ni-catalyzed intramolecular hydroacylation of 2-(prop-2-ynyl)benzaldehydes has been developed. Examination of various nickel and other transition metal catalysts and phosphine ligands showed that the use of Ni(COD)2 catalyst combined with P(i-Pr)3 ligand was the best choice to the success of the present intramolecular hydroacylation. A wide range of functional groups were tolerated, affording the corresponding substituted α-lidene-2,3-dihydro-1H-inden-1-ones in good to high yields with a sole E-selectivity under present reaction conditions.
- Yang, Fan,Jin, Tienan,Yamamoto, Yoshinori
-
supporting information; experimental part
p. 5223 - 5228
(2012/08/07)
-
- Antimycobacterial activity: A facile three-component [3+2]-cycloaddition for the regioselective synthesis of highly functionalised dispiropyrrolidines
-
A series of twelve dispiropyrrolidines were synthesized using [3+2]-cycloaddition reactions. The synthesized compounds were screened for their antimycobacterial activity against M. tuberculosis H37Rv and INH resistant M. tuberculosis strains using agar dilution method, four of them showed good activity with MIC of less than 1 μM. Compound 4′-[5-(4-fluorophenyl)pyridin-3-yl]-1′-methyldispiro[indan-2, 2′ pyrrolidine-3′,2″-indan]-1,3,1″-trione (4b) was found to be the most active with MIC of 0.1215 and 5.121 μM, respectively.
- Wei, Ang Chee,Ali, Mohamed Ashraf,Yoon, Yeong Keng,Ismail, Rusli,Choon, Tan Soo,Kumar, Raju Suresh,Arumugam, Natarajan,Almansour, Abdulrahman I.,Osman, Hasnah
-
scheme or table
p. 4930 - 4933
(2012/09/07)
-
- Palladium-catalyzed cyclocarbonylation of arynes with methyl allyl carbonates: Selective synthesis of 1 H -inden-1-ones
-
A selective protocol for the synthesis of 2-methylene-3-substituted-2,3- dihydro-1H-inden-1-ones and 2-benzylidene-2,3-dihydro-1H-inden-1-ones has been developed via palladium-catalyzed cyclocarbonylation reactions of arynes with allyl carbonates and carbon monooxide (CO). It is noteworthy that the selectivity of this new route is depended on both substrates and ligands.
- Pi, Shao-Feng,Yang, Xu-Heng,Huang, Xiao-Cheng,Liang, Yun,Yang, Guan-Nan,Zhang, Xiao-Hong,Li, Jin-Heng
-
supporting information; experimental part
p. 3484 - 3487
(2010/08/05)
-
- SMALL MOLECULE INHIBITORS OF DUSP6 AND USES THEREFOR
-
Compounds that stimulate fibroblast growth factor production, and thus cell growth are provided. Also provided are compositions comprising the compounds and methods of using the compounds. The compounds can be used to treat wounds, to expand cell populations, such as hematopoietic cells, or to grow tissue in vitro, among other uses.
- -
-
Page/Page column 24
(2010/10/03)
-
- Chloride ion pairs as catalysts for the alkylation of aldehydes and ketones with C-H acidic compounds
-
Chloride anions associated with various soft cations (like tetraalkyl ammoniums, alkyl imidazoliums or pyridiniums) were shown to be able to promote the alkylation of carbonyl derivatives with acidic compounds, as exemplified on Knoevenagel and aldol condensations under relatively mild conditions. This activity was attributed to an enhanced nucleophilicity of the chlorine anion, originating from a softness/hardness mismatch between the anion and the cation.
- Carrignon, Camille,Makowski, Philippe,Antonietti, Markus,Goettmann, Frédéric
-
supporting information; experimental part
p. 4833 - 4837
(2009/10/26)
-
- Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles
-
(Chemical Equation Presented) Catalytic variant: Allyl silanes and silyl enol ethers 1 are good substrates for the catalytic highly enantioselective fluorodesilylation using a combination of a biscinchona alkaloid, N-fluorobenzenesulfonimide (NFSI), and base (see scheme). Pharmaceutically attractive 3-aryl-3-fluorooxindoles such as 3 can also be synthesized with high enantioselectivity.
- Ishimaru, Takehisa,Shibata, Norio,Horikawa, Takao,Yasuda, Naomi,Nakamura, Shuichi,Toru, Takeshi,Shiro, Motoo
-
supporting information; experimental part
p. 4157 - 4161
(2009/03/11)
-
- Studies on the chemistry of 2-(2-oxo-3-phenylpropyl)-benzaldehydes: Novel total synthesis of 3-phenylnaphthalen-2-ols and 2-hydroxy-3-phenyl-1,4- naphthoquinones
-
We describe the first studies on the chemistry of 2-(2-oxo-3-phenylpropyl) benzaldehydes, which were converted into 3-benzylisochromen-1-ones via the corresponding 2-(2-oxo-3-phenylpropyl)benzoic acid. The 2-(2-oxo-3-phenylpropyl) benzaldehydes proved to be convenient starting materials for the synthesis of 3-phenyl-2-naphthols. Oxidation of the latter compounds resulted in a novel, efficient synthesis of 3-phenyl-1,2-naphthoquinones, which were efficiently transformed into 2-hydroxy-3-phenyl-1,4-naphthoquinones.
- Martínez, Ana,Fernández, Marcos,Estévez, Juan C.,Estévez, Ramón J.,Castedo, Luis
-
p. 485 - 492
(2007/10/03)
-
- Iodotrimethylsilane-Mediated Cross-Aldol Condensation: A Facile Synthesis of α,α′-Bis(substituted benzylidene)cycloalkanones
-
A facile and efficient method for the preparation of α, α′-bis(substituted benzylidene)cycloalkanones is described for the first time using iodotrimethylsilane generated in situ from chlorotrimethylsilane and sodium iodide in acetonitrile. The reaction proceeds rapidly at room temperature, giving high yields of products.
- Sabitha, Gowravaram,Reddy, G. S. Kiran Kumar,Reddy, K. Bhaska,Yadav
-
p. 263 - 266
(2007/10/03)
-
- One-pot inter- and intramolecular Friedel-Crafts reactions in Baylis-Hillman chemistry: A novel facile synthesis of (E)-2-arylideneindan-1-ones
-
A simple one-pot stereoselective transformation of tert-butyl 3-aryl-3-hydroxy-2-methylenepropanoates, the Baylis-Hillman adducts obtained from t-butyl acrylate, into (E)-2-arylideneindan-1-ones involving one inter- and one intramolecular Friedel-Crafts r
- Basavaiah, Deevi,Reddy, Ravi Mallikarjuna
-
p. 3025 - 3027
(2007/10/03)
-
- Aldol condensation of cycloalkanones with aromatic aldehydes catalysed with TiCi3(SO3CF3)
-
Efficient cross-aldol condensation of cyclopentanone, cyclohexanone and 1-indanone with various aromatic aldehydes is catalysed with TiCl3(SO3CF3) at room temperature in excellent yields.
- Iranpoor,Zeynizadeh,Aghapour
-
p. 554 - 555
(2007/10/03)
-
- Studies on the Dimerization of 2-Benzylidene-1-indanone
-
It has been observed that 2-(-E)-benzylidene-1-indanone (1) undergoes dimerization under basic conditions. The reaction is highly stereoselective and provides almost exclusively dimer 2b using NaHCO3/DMF, guanidine carbonate/DMF, or Cs2CO3/CH3CN. The structure and the relative stereochemistry of compound 2b were initially established on the basis of COSY, HMQC, HMBC, and NOESY NMR correlation techniques. The structure and the stereochemistry were then confirmed by X-ray crystallographic analysis. Two other stereoisomers were obtained, in minor proportions, by varying the experimental conditions. A fourth isomer was also produced using 2-(Z)-benzylidene-1-indanone as the starting material.
- Berthelette, Carl,McCooye, Chris,Leblanc, Yves,Trimble, Laird A.,Tsou, Nancy N.
-
p. 4339 - 4342
(2007/10/03)
-
- REACTION DE DIELS ALDER DE L'ISOPRENE ET DU DIMETHYL-2,3 BUTADIENE AVEC QUELQUES ARYLIDENE-2 INDANONES
-
The Diels Alder reaction of isoprene and 2,3-dimethylbutadiene with some 2-arylidene indanones is studied.The structure of the adducts are assigned and the conformation discussed by the use of 1H and 13C NMR and X ray diffraction.
- Titouani, S. Lafquih,Soufiaoui, M.,Toupet, L.,Carrie, R.
-
p. 3869 - 3878
(2007/10/02)
-
- Heterocycles. 14. Synthesis of 5H-Indenopyrimidines
-
1-Indanone (I) was reacted with aryl aldehydes (II) to give the corresponding 2-arylidene-1-indanones (III).Condensation of the chalcones III with guanidine revealed the formation of the corresponding 5H-2-amino-4-arylidenopyrimidines (V).The structures of all products were substantiated by chemical and spectroscopic methods.
- El-Rayyes, Nizar,Al-Qatami, Sheekha,Edun, Mustafa
-
p. 481 - 483
(2007/10/02)
-