- Selective catalysis for the reductive amination of furfural toward furfurylamine by graphene-co-shelled cobalt nanoparticles
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Amines with functional groups are widely used in the manufacture of pharmaceuticals, agricultural chemicals, and polymers but most of them are still prepared through petrochemical routes. The sustainable production of amines from renewable resources, such as biomass, is thus necessary. For this reason, we developed an eco-friendly, simplified, and highly effective procedure for the preparation of a non-toxic heterogeneous catalyst based on earth-abundant metals, whose catalytic activity on the reductive amination of furfural or other derivatives (more than 24 examples) proved to be broadly available. More surprisingly, the cobalt-supported catalyst was found to be magnetically recoverable and reusable up to eight times with an excellent catalytic activity; on the other hand, the gram-scale tests catalyzed by the same catalyst exhibited the similar yield of the target products in comparison to its smaller scale, which was comparable to the commercial noble-based catalysts. Further results from a series of analytical technologies involving XRD, XPS, TEM/mapping, and in situ FTIR revealed that the structural features of the catalyst are closely in relation to its catalytic mechanisms. In simple terms, the outer graphitic shell is activated by the electronic interaction as well as the induced charge redistribution, enabling the easy substitution of the –NH2 moiety toward functionalized and structurally diverse molecules, even under very mild industrially viable and scalable conditions. Overall, this newly developed catalyst introduces the synthesis of amines from biomass-derived platforms with satisfactory selectivity and carbon balance, providing cost-effective and sustainable access to the wide applications of reductive amination.
- Liu, Jianguo,Ma, Longlong,Zhong, Shurong,Zhuang, Xiuzheng
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p. 271 - 284
(2022/01/19)
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- Design and synthesis of heteroaromatic-based benzenesulfonamide derivatives as potent inhibitors of H5N1 influenza A virus
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Influenza A virus is an enveloped negative single-stranded RNA virus that causes febrile respiratory infection and represents a clinically challenging threat to human health and even lives worldwide. Even more alarming is the emergence of highly pathogenic avian influenza (HPAI) strains such as H5N1, which possess much higher mortality rate (60%) than seasonal influenza strains in human infection. In this study, a novel series of heteroaromatic-based benzenesulfonamide derivatives were identified as M2 proton channel inhibitors. A systematic investigation of the structure-activity relationships and a molecular docking study demonstrated that the sulfonamide moiety and 2,5-dimethyl-substituted thiophene as the core structure played significant roles in the anti-influenza activity. Among the derivatives, compound 11k exhibited excellent antiviral activity against H5N1 virus with an EC50 value of 0.47 μM and selectivity index of 119.9, which are comparable to those of the reference drug amantadine.
- Yu, Yongshi,Tazeem,Xu, Zhichao,Du, Liaoqi,Jin, Mengyu,Dong, Chune,Zhou, Hai-Bing,Wu, Shuwen
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- Cobalt-based nanoparticles prepared from MOF-carbon templates as efficient hydrogenation catalysts
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The development of efficient and selective nanostructured catalysts for industrially relevant hydrogenation reactions continues to be an actual goal of chemical research. In particular, the hydrogenation of nitriles and nitroarenes is of importance for the production of primary amines, which constitute essential feedstocks and key intermediates for advanced chemicals, life science molecules and materials. Herein, we report the preparation of graphene shell encapsulated Co3O4- and Co-nanoparticles supported on carbon by the template synthesis of cobalt-terephthalic acid MOF on carbon and subsequent pyrolysis. The resulting nanoparticles create stable and reusable catalysts for selective hydrogenation of functionalized and structurally diverse aromatic, heterocyclic and aliphatic nitriles, and as well as nitro compounds to primary amines (>65 examples). The synthetic and practical utility of this novel non-noble metal-based hydrogenation protocol is demonstrated by upscaling several reactions to multigram-scale and recycling of the catalyst.
- Murugesan, Kathiravan,Senthamarai, Thirusangumurugan,Sohail, Manzar,Alshammari, Ahmad S.,Pohl, Marga-Martina,Beller, Matthias,Jagadeesh, Rajenahally V.
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p. 8553 - 8560
(2018/11/30)
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- A general and environmentally benign catalytic reduction of nitriles to primary amines
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An easily accessible in situ catalyst composed of [Ru(cod)methylallyl 2] and DPPF was developed for the environmentally benign hydrogenation of various nitriles to give primary amines. A solution of benzonitrile in toluene was transferred by syringe into an autoclave that contained argon and KOtBu. The catalyst was generated in situ by stirring [Ru(cod)methylallyl2] and DPPF in toluene for 10 min and transferring the solution by syringe into the autoclave. the reaction mixture was filtered through a short plug of silica gel and the yield was measured by GC. A superior catalyst activity with a TOF of up to 5783 h-1 is achieved in the model reaction under optimized conditions. The results also show that [Ru(cod)methylallyl2]/DPPF catalyst system exhibit a broad functional group tolerance.
- Enthaler, Stephan,Addis, Daniele,Junge, Kathrin,Erre, Giulia,Beller, Matthias
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experimental part
p. 9491 - 9494
(2009/10/14)
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- PYRAZOLOPYRIMIDINES AS CYCLIN-DEPENDENT KINASE INHIBITORS
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In its many embodiments, the present invention provides a novel class of pyrazolo[1,5-a]pyrimidine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.
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- Design, synthesis, and biological evaluation of new inhibitors of the endocannabinoid uptake: Comparison with effects on fatty acid amidohydrolase
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A new series of arachidonic acid derivatives were synthesized and evaluated as inhibitors of the endocannabinoid uptake. Most of them are able to inhibit anandamide uptake with IC50 values in the low micromolar range (IC50 = 0.8-24 μM). ln general, the compounds had only weak effects upon CB1, CB2, and VR1 receptors (Ki > 1000-10000 nM). In addition, there was no obvious relationship between the abilities of the compounds to affect anandamide uptake and to inhibit anandamide metabolism by fatty acid amidohydrolase (FAAH; IC50 = 30-113 μM). This indicates that the compounds do not exert their effects secondarily to FAAH inhibition. It is hoped that these compounds, particularly the most potent in this series (compound 5, UCM707, with IC50 values for anandamide uptake and FAAH of 0.8 and 30 μM, respectively), will provide useful tools for the elucidation of the role of the anandamide transporter system in vivo.
- López-Rodríguez, María L.,Viso, Alma,Ortega-Gutiérrez, Silvia,Fowler, Christopher J.,Tiger, Gunnar,De Lago, Eva,Fernández-Ruiz, Javier,Ramos, José A.
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p. 1512 - 1522
(2007/10/03)
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- Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors
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In the present work, we have designed and synthesized a series of arachidonic acid derivatives of general structure I which have been characterized as highly potent and selective inhibitors of anandamide transporter (IC50 = 24-0.8 μM, Ki > 1000-5000 nM for CB1 and CB2 cannabinoid receptors and vanilloid VR1 receptor). Among them, N-(3-furylmethyl)eicosa-5,8,11,14-tetraenamide deserves special attention as being the most potent endocannabinoid transporter inhibitor (IC50 = 0.8 μM) described to date.
- López-Rodríguez,Viso,Ortega-Gutiérrez,Lastres-Becker,González,Fernández-Ruiz,Ramos
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p. 4505 - 4508
(2007/10/03)
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- Anti-Helicobacter pylori agents. 3. 2-[(Arylalkyl)guanidino]-4- furylthiazoles
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A series of 2-[(arylalkyl)guanidino]-4-[(5-acetamidomethyl)furan-2- yl]thiazoles and some 4-acetamidomethyl positional isomers were synthesized and evaluated for antimicrobial activity against Helicobacter pylori. Among the compounds that had potent antim
- Katsura, Yousuke,Nishino, Shigetaka,Ohno, Mitsuko,Sakane, Kazuo,Matsumoto, Yoshimi,Morinaga, Chizu,Ishikawa, Hirohumi,Takasugi, Hisashi
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p. 2920 - 2926
(2007/10/03)
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- Acid cleavable compounds, their preparation and use as bifunctional acid-labile crosslinking agents
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Novel compounds, their preparation and their use as bifunctional acid-labile crosslinking agents which are cleavable in an acid environment at a pH of below about 5.0 allowing for the controlled release of nucleophilic groups attached thereto are disclosed.
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- Quinazoline derivatives possessing anti-tumor activity
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The invention relates to quinazoline derivatives, or pharmaceutically-acceptable salts thereof, which possess anti-tumor activity; to processes for their manufacture; and to pharmaceutical compositions containing them. The invention provides a quinazoline of the formula: STR1 wherein R1 is hydrogen or amino, or alkyl or alkoxy each of up to 6 carbon atoms; or R1 is substituted alkyl or alkoxy each of up to 3 carbon atoms; R2 is hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, halogenoalkyl or cyanoalkyl each of up to 6 carbon atoms; Ar is phenylene or heterocyclene; L is a group of the formula --CO.NH--, --NH.CO--, --CO.NR3 --, --NR3. CO--, --CH=CH--, --CH2 O--, --OCH2, --CH2 S--, --SCH2 --, --CO.CH2 --, --CH2.CO-- or --CO.O--, wherein R3 is alkyl of up to 6 carbon atoms; and Y is aryl or heteroaryl or a hydrogenated derivative thereof: or Y is a group of the formula --A--Y1 in which A is alkylene, cycloalkylene, alkenylene or alkynylene each of up to 6 carbon atoms and Y1 is aryl or heteroaryl or a hydrogenated derivative thereof; or a pharmaceutically-acceptable salt thereof.
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