1681-94-3Relevant academic research and scientific papers
Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects
Hall, Thomas H.,Adams, Hannah,Vyas, Vijyesh K.,Michael Chu,Wills, Martin
, (2020/12/07)
A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C[dbnd]O group reduce the level of C[dbnd]O reduction compared to C[dbnd]C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.
Zinc-coordinated aza-pyrrolidone optical diagnosis and treatment reagent with long-wave absorption characteristic as well as preparation and application thereof
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Paragraph 0042-0046, (2021/06/23)
The invention discloses a zinc-coordinated aza-pyrrolidone optical diagnosis and treatment reagent with a long-wave absorption characteristic as well as preparation and application thereof. The optical diagnosis and treatment reagent is composed of a metal center and an aza-pyrrolidone auxiliary ligand; the whole preparation process is simple, the prepared complex has a long absorption wavelength, and the absorption wavelength can be prolonged along with the change of the aza-pyrrolidone auxiliary ligand, so that the optical diagnosis and treatment reagent has a deep tissue penetration depth in the field of living body application; the complex can be excited by near-infrared light and can emit near-infrared light, so that the damage of an excitation light source to a biological sample can be weakened; and the complex can be used in the field of photodynamic and photothermal combined therapy guided by biological imaging, and has an important application prospect.
Iridium coordination aza-pyrrolidone optical diagnosis and treatment reagent as well as preparation method and application thereof
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Paragraph 0040-0043, (2020/08/26)
The invention discloses an iridium coordination aza-pyrrolidone optical diagnosis and treatment reagent as well as a preparation method and application thereof. The complex is composed of a cyclo-metal ligand, a metal center and an aza-pyrrolidone auxiliary ligand, the overall preparation process is simple, and the prepared complex has a long absorption wavelength, so that the complex has a deep tissue penetration depth in the field of living body application and is more suitable for biological imaging. The complex has strong absorption in an ultraviolet region and a near-infrared region, andcan be excited by near-infrared light, so that the damage of an excitation light source to a biological sample can be weakened; and the complex can be used in the field of photodynamic photo-thermal combined therapy guided by biological imaging, and has important application prospects.
Transition-Metal-Free Catalytic Formal Hydroacylation of Terminal Alkynes
Yatabe, Takafumi,Mizuno, Noritaka,Yamaguchi, Kazuya
, p. 11564 - 11569 (2018/11/23)
Although hydroacylation is a very useful reaction for producing ketones from aldehydes with 100% atom efficiency, classical Rh-catalyzed hydroacylation presents several problems, including the need for transition metal catalysts, unwanted decarbonylation of aldehydes, and difficulty in regioselectivity control. However, formal hydroacylation utilizing the nucleophilicity of terminal alkynes can avoid these problems. In this work, we have achieved transition-metal-free formal hydroacylation of terminal alkynes using an Mg3Al-CO3-layered double hydroxide as a heterogeneous catalyst. This system was applicable to the efficient synthesis of α,β-unsaturated ketones with various substituents, and the catalyst can be reused without a significant loss of catalytic performance.
Carbon-carbon bond formation in acid deep eutectic solvent: Chalcones synthesis: Via Claisen-Schmidt reaction
Tiecco, Matteo,Germani, Raimondo,Cardellini, Fabio
, p. 43740 - 43747 (2016/05/24)
One of the most studied properties of novel organic solvents is represented by their use as media for many chemical reactions. In this field Ionic Liquids (ILs) and more recently Deep Eutectic Solvents (DESs) have been playing significant roles for their smart properties. DESs are increasing their relevance thanks to their low toxicity, and because of their simple and cheap preparation that can be carried out by simply mixing two compounds. In this work we present the studies of the use of an acid DES obtained from 3-(cyclohexyldimethylammonio)propane-1-sulfonate and (1S)-(+)-10-camphorsulfonic acid (SB3-Cy/CSA) as reaction media and catalyst for carbon-carbon bond formation reaction via Claisen-Schmidt condensation. This powerful and widely used aldol condensation was performed without the use of any catalysts that are usually needed in this reaction, because of the presence of acid CSA in the DES components. We synthesised fourteen substituted chalcones from benzaldehydes and substituted benzaldehydes in combination with acetophenone and substituted acetophenones as probe reactions. The advantages of the use of this DES in this relevant reaction are represented by: the green properties of the media and its low toxicity; the absence of harmful acids to catalyse the aldol condensation because of the camphorsulfonic acid composing the DES mixture; the recycling and the re-use of the DES in subsequent reaction cycles; the mild conditions and the excellent conversions and yields observed.
A new solid acid catalyst FeCl3/bentonite for aldol condensation under solvent-free condition
Muthuvel,Dineshkumar,Thirumurthy,Rajasri,Thirunarayanan
, p. 252 - 260 (2017/01/18)
For the first time, a new solid acid catalyst has been used for the synthesis of aryl chalcones under solvent free conditions. A simple method (solid dispersion method) has been adopted for the synthesis of FeCl3/bentonite. The prepared catalyst has been characterized by different characterization techniques. A series of E-1-(substituted phenyl)-3-(1-pyrenyl)-2-propen-1-ones have been synthesized using FeCl3/bentonite under microwave-assisted solvent-free conditions. The yields are in the range from 80 to 88%. All the synthesized chalcones have been characterized by their physical constants, analytical, IR, 1H and 13C NMR spectral data. This catalyst can be reused for further runs (after fifth cycle) without decrease in activity. This catalyst gives excellent yields and is inexpensive and easily recyclable for this reaction.
Effect of Donor-Acceptor Coupling on TICT Dynamics in the Excited States of Two Dimethylamine Substituted Chalcones
Ghosh, Rajib,Palit, Dipak K.
, p. 11128 - 11137 (2015/11/23)
Significant effect of coupling between the electron donor and acceptor groups in intramolecular charge transfer (ICT) dynamics has been demonstrated by comparing the photophysical properties of two isomeric N,N-dimethylaminochalcone derivatives (namely, DMAC-A and DMAC-B). In the case of the DMAC-B molecule, the distance between the donor (N,N-dimethylaniline or DMA) and the acceptor (carbonyl) groups is larger by one ethylene unit as compared to that in the case of DMAC-A. The excited singlet (S1) states of both the isomers have strong ICT character but their photophysical properties are remarkably different. In polar solvents, fluorescence quantum yields (and the lifetimes of the S1 state) of DMAC-A are more than 2 orders of magnitude lower (and shorter) than those of DMAC-B. Remarkable differences in the photophysical properties of these two isomers arise due to occurrence of the ultrafast twisting of the DMA group (or the TICT process) during the course of deactivation of the S1 state of the DMAC-A molecule, but not in the case of DMAC-B. In the later case, because of the presence of a large energy barrier along the twisting coordinate(s), TICT is not a feasible process, and hence, the S1 state of DMAC-B has the planar ICT structure. In the DMAC-A molecule, the strength of coupling between the donor and acceptor groups is relatively stronger because of a shorter distance between these groups. Femtosecond transient absorption spectroscopic measurements and DFT/TDDFT calculations have been adopted to establish the above aspects of the relaxation dynamics of the S1 states of these two isomeric chalcones.
Synthesis and biological evaluation of some new pyrazoline substituted benzenesulfonylurea/thiourea derivatives as anti-hyperglycaemic agents and aldose reductase inhibitors
Ovais, Syed,Pushpalatha,Reddy, G. Bhanuprakash,Rathore, Pooja,Bashir, Rafia,Yaseen, Shafiya,Dheyaa, Alhamza,Yaseen, Raed,Tanwar, Omprakash,Akthar, Mymoona,Samim, Mohammed,Javed, Kalim
, p. 209 - 217 (2014/05/20)
Seventeen new pyrazoline substituted benzenesulfonylurea/thiourea derivatives (2a-q) were synthesized and characterized by elemental analysis and various spectroscopic techniques viz; IR, 1H NMR, 13C NMR, and MS data. Thirteen compounds showed moderate to good anti-hyperglycaemic activity in glucose fed hyperglycaemic normal rats at the dose of 0.05 mM/kg b.w. On the basis of docking results nine compounds (2a, 2c, 2e, 2h, 2k, 2l, 2n, 2o and 2q) were evaluated for their ability to inhibit rat lens aldose reductase. Out of these six compounds (2h, 2k, 2l, 2n, 2o and 2q) were found more effective than the known ARI sorbinil. Five compounds (2h, 2k, 2l, 2n and 2o) showed significant dual action (anti-hyperglycaemic and aldose reductase inhibition).
Preheated fly-ash catalyzed aldol condensation: Efficient synthesis of chalcones and antimicrobial activities of some 3-thienyl chalcones
Arulkumaran, Ranganathan,Vijayakumar, Sambandhamoorthy,Sakthinathan, S. Pazhanivel,Kamalakkannan, Dakshnamoorthy,Ranganathan, Kaliyaperumal,Suresh, Ramamoorthy,Sundararajan, Rajasekaran,Vanangamudi, Ganesan,Thirunarayanan, Ganesamoorthy
, p. 1684 - 1690 (2013/09/24)
In the present study we have prepared a series of some chalcones using solvent - free Aldol - condensation by microwave irradiation. The yields of the ketones are more than 60%. The synthesised chalcones were characterized by their analytical, physical and spectral data. The antimicrobial activities of substituted styryl 3-thienyl ketones have been studied using Bauer-Kirby method.
Synthesis and anti-inflammatory activity of celecoxib like compounds
Ovais, Syed,Yaseen, Shafiya,Bashir, Rafia,Rathore, Pooja,Samim, Mohammed,Singh, Surender,Nair, Vinod,Javed, Kalim
, p. 1105 - 1112 (2013/10/01)
Nine novel 4-[3-(4-Dimethylamino-phenyl)-5-aryl-4,5-dihydro-pyrazol-1-yl]- benzenesulfonamides (2a-i) were synthesized and evaluated for their anti-inflammatory and antiproliferative activities. These compounds (2a-i) showed moderate to strong anti-inflammatory activity in carrageenan rat paw oedema test. Compounds 2b, 2d and 2g showing comparable anti-inflammatory activity to that of reference drug celecoxib were evaluated for their ulcerogenic and analgesic activities. The effect of 2b, 2d and 2g on the content of NO, TNF-α and PGE2 in exudates from rat paw stimulated by carrageenan was also evaluated. The compound 2c showed considerable antitumor activities against all 60 human tumor cell lines with effective GI50 (MG-MID) value of 3.63 μM. It exhibited maximum activity against melanoma (LOX IMVI and SK-MEL-5) cancer cell lines with GI50 value less than 2 μM.
