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Multicomponent Reaction

Li-Zhu Wu, Tao Lei, Chao Zhou, Xiang-Zhu Wei, Bing Yang, Bin Chen, Chen-Ho Tung
Photo[2+2]cycloaddition of two olefins is general to assemble the core scaffold, cyclobutane, found in numerous bioactive molecules. We report here a new approach to synthesize cyclobutanes via multicomponent cascade reactions by merging aldol reaction and Witting reaction with visible light induced [2+2] cycloaddition, respectively. An array of cyclobutanes with high selectivity have been achieved from commercially available aldehydes, ketones (or phosphorus ylide) and olefins with visible light irradiation of a catalytic amount of Ir(ppy)3 at room temperature...
October 13, 2018: Chemistry: a European Journal
Xiaoge Gao, Lanqi Cen, Fangyuan Li, Ren Wen, Hongru Yan, Hong Yao, Songlei Zhu
Development of an effective and safe anti-cancer drug is an urgent request for hepatocellular carcinoma (HCC). In this study, we synthesized a series of novel indole substituted dihydropyrido[2,3-d]pyrimidines through the multicomponent reactions to connect pyrido[2,3-d]pyrimidine and indole moities via an one-pot three-component reaction of 3-cyanoacetyl indoles 1, various aromatic aldehyde 2, and 2,6-diaminopyrimidin-4(3H)-one 3. Subsequently, we screened their cytotoxicity via CCK-8 assay in HepG2 cells, a human hepatoma cell line and chose compound 4p that showed the lowest dosage of IC50 to study the antitumor activities to HCC...
October 4, 2018: Biochemical and Biophysical Research Communications
Chengjie Feng, Yifei Li, Xinyao Sheng, Ling Pan, Qun Liu
A novel multicomponent reaction of p-(trifluoromethyl)- p-quinolsilyl ethers, ketones, and nitriles was developed for the efficient synthesis of p-trifluoromethylated N-benzylamides. The key step of the reaction involves the formation of an unstable condensation precursor in situ generated form the condensation of p-(trifluoromethyl)- p-quinolsilyl ethers with ketones. This work provides a significant expansion to the Ritter-type reaction, and the reaction can proceed under mild reaction conditions and tolerate various nitriles including both aryl and aliphatic nitriles...
October 5, 2018: Organic Letters
Maryam Khalesi, Azim Ziyaei Halimehjani, Max Franz, Marc Schmidtmann, Jürgen Martens
Consecutive multicomponent reactions have been applied for the synthesis of novel pseudo-peptides bearing dithiocarbamate and N,X-heterocyclic groups (X = S, O) in only one structure. The first multicomponent reaction includes the synthesis of dithiocarbamates using an amine or amino acid, CS2 and an electrophile. The second MCR is synthesis of Asinger imines using 2-chloroisobutyraldehyde, NaXH (X = S, O), ketone and ammonia. The final MCR is Ugi reaction to afford the corresponding three-dimensional pseudo-peptides...
October 4, 2018: Amino Acids
Vinicius Vendrusculo, Vanessa P de Souza, Luiz Antônio M Fontoura, Marcelo G M D'Oca, Thais P Banzato, Paula A Monteiro, Ronaldo A Pilli, João Ernesto de Carvalho, Dennis Russowsky
A series of fifteen novel dihydropyrimidinone hybrid compounds were synthesized in good yields via a multicomponent reaction combined with the Huisgen reaction. The antiproliferative activity was investigated against nine tumor cell lines, and four hybrid compounds (TGI < 10 μM) showed promising antiproliferative activity against the tumor cell lines OVCAR-3 (ovarian), UACC-62 (melanoma) and U251 (glioma). Several hybrid compounds assayed have high TGI values (TGI 147.92-507.82) for the human keratinocyte cell line (HaCat), which reveals selectivity to cancer cells...
September 1, 2018: MedChemComm
Konstantina Karypidou, Sergio R Ribone, Mario A Quevedo, Leentje Persoons, Christophe Pannecouque, Christine Helsen, Frank Claessens, Wim Dehaen
Synthesis and biological evaluation of a novel library of fused 1,2,3-triazole derivatives are described. The in-house developed multicomponent reaction based on commercially available starting materials was applied and broad biological screening against various viruses was performed, showing promising antiviral properties for compounds 14d, 14n, 14q, 18f and 18i against human coronavirus 229E. Further in silico studies identified the key molecular interactions between those compounds and the 3-chymotrypsin-like protease, which is essential to the intracellular replication of the virus, supporting the hypothesis that the protease is the target molecule of the potential antiviral derivatives...
September 22, 2018: Bioorganic & Medicinal Chemistry Letters
Renjie Chen, Yu Liu, Sunliang Cui
A novel 1,4-conjugate addition/esterification of ortho-quinone methides in a multicomponent reaction has been developed. In this protocol, numerous carboxylic acids, ynamides and in situ generated ortho-quinone methides could assemble rapidly to constitute this process for the synthesis of functionalized 3,3-diarylpropanamides with sufficient structural diversity. Furthermore, the products could be transformed to an array of compounds.
October 25, 2018: Chemical Communications: Chem Comm
Tania Mirza, Zubair Anwar, Muhammad Ahsan Ejaz, Sofia Ahmed, Muhammad Ali Sheraz, Iqbal Ahmad
The simultaneous assay of carboxymethylflavin (CMF), an intermediate in the photolysis of riboflavin, and its hydrolytic side-chain cleavage products, lumichrome (LC) (acid solution) and LC and lumiflavin (LF) as well as isoalloxazine ring cleavage products, 1,2-dihydro-1-methyl-2-keto-3-quinoxaline carboxylic acid (KA) and 1,2,3,4-tetrahydro-1-methyl-2,3-dioxo-quinoxaline (DQ) (alkaline solution) has been carried out by a multicomponent spectrofluorimetric method. The method is based on the adjustment of pH of the degraded solutions to 2...
September 27, 2018: Luminescence: the Journal of Biological and Chemical Luminescence
Aaron Trowbridge, Dominik Reich, Matthew J Gaunt
There is evidence to suggest that increasing the level of saturation (that is, the number of sp3 -hybridized carbon atoms) of small molecules can increase their likelihood of success in the drug discovery pipeline1 . Owing to their favourable physical properties, alkylamines have become ubiquitous among pharmaceutical agents, small-molecule biological probes and pre-clinical candidates2 . Despite their importance, the synthesis of amines is still dominated by two methods: N-alkylation and carbonyl reductive amination3 ...
September 2018: Nature
Shiying Fan, Xinyong Li, Libin Zeng, Mingmei Zhang, Zhifan Yin, Tingting Lian, Aicheng Chen
Rational design and fabrication of high quality complex multicomponent spinel ferrite with specific microstructures and solar light harvestings towards CO2 reduction and antibiotic degradation to future energetic and catalytic applications are highly desirable. In this study, novel Copper-Zinc-Iron multinary spinel hierarchical nano-microspheres (MSHMs) with different internal structures (solid nano-microspheres, yolk-shell hollow nano-microspheres, and double-shelled hollow nano-microspheres) have been successfully developed by a facile self-templated solvothermal strategy...
September 25, 2018: ACS Applied Materials & Interfaces
Jana Wiemann, Lucie Fischer Née Heller, Jacqueline Kessler, Dieter Ströhl, René Csuk
Isocyanide-based multicomponent reactions - especially the standard four component Ugi reaction - provide an easy and powerful access to compounds with an auspicious pharmacological potential. Therefore, a set of 16 novel derivatives of the diterpene dehydroabietylamine was synthesized by the Ugi-4CR. The subsequent screening of the synthesized α-acylamino carboxamides in colorimetric sulforhodamine B assays revealed an in vitro cytotoxicity towards several human tumor cell lines. Particularly, the rhodamine B conjugates 14-16 showed a remarkable cytotoxic activity, characterized by EC50 values in a low three-digit nanomolar range...
September 11, 2018: Bioorganic Chemistry
Sandeep V H S Bhaskaruni, Kranthi Kumar Gangu, Suresh Maddila, Sreekantha B Jonnalagadda
This personal account mainly introduces and reviews our recent contributions in developing different catalyst materials involving mixed oxides and their scope as renewable catalysts in multicomponent reactions to synthesize various novel heterocyclic scaffolds under green conditions. The application of various mixed oxides and their composites in the organic synthesis is emphasized through this review, in order to reveal the versatility, scope and importance of mixed oxides and their interactions during the reaction...
September 20, 2018: Chemical Record: An Official Publication of the Chemical Society of Japan ... [et Al.]
Lisa Moni, Fabio De Moliner, Silvia Garbarino, Jörn Saupe, Christian Mang, Andrea Basso
An Ugi multicomponent reaction with chiral cyclic amino acids, benzyl isocyanide and cyclic ketones (or acetone) has been exploited as key step for the generation of peptidomimetics. After a straightforward set of elaborations, the peptidomimetics were converted into polycyclic scaffolds displaying two orthogonally protected secondary amines. Libraries of compounds were obtained decorating the molecules through acylation/reductive amination reactions on these functional groups.
2018: Frontiers in Chemistry
A Gaston Orrillo, Andrea M Escalante, Maitena Martinez-Amezaga, Ignacio L E Cabezudo, Ricardo L E Furlan
Dynamic multilevel systems can be assembled from molecular building blocks through two or more reversible reactions that form covalent bonds. Molecular networks of dynamic multilevel systems can exhibit different connectivities between nodes. The design and creation of molecular networks in multilevel systems require to control the crossed reactivity of the functional groups (how to connect nodes) and the conditions of the reactions (when to connect nodes). In the recent years, the combination of orthogonal or communicating reactions, which can be simultaneous or individually activated, has produced a variety of systems which gave place to macrocycles and cages, as well as molecular motors and multicomponent architectures on surfaces...
September 19, 2018: Chemistry: a European Journal
Klaus Schaper, Thomas J J Müller
Thiophenes occur as important building blocks in natural products, pharmaceutical active compounds, and in materials for electronic and opto-electronic devices. Therefore, there is a considerable demand for efficient synthetic strategies for producing these compounds. This review focuses on ring-forming multicomponent reactions for synthesizing thiophenes and their derivatives.
September 17, 2018: Topics in Current Chemistry (Journal)
Max Franz, Timo Stalling, Henning Steinert, Jürgen Martens
The first trapping of N-acyliminium ions by in situ generated carbaminic acid (product of carbon dioxide (CO2) and amine) is reported. This catalyst-free reaction provides a convenient and feasible approach to prepare N-acyl thia- and oxazolidinyl carbamates with good functional-group compatibility and high efficiency under green conditions. Furthermore, the multicomponent method features a broad substrate scope, facile product diversification, smooth scale-up and notable potential for polymer applications.
September 26, 2018: Organic & Biomolecular Chemistry
Manijeh Nematpour, Elham Rezaee, Mehdi Jahani, Sayyed Abbas Tabatabai
A facile sonochemical route for the synthesis of benzo[1,3]thiazine derivatives via a one pot, multicomponent, intramolecular CH activation reaction from isocyanides, aniline and benzoyl (acetyl) isothiocyanate adduct catalyzed by copper (I) iodide in acetone at 30 °C have been reported. The advantages of the described method include using simple and readily available starting materials and performing under mild copper-catalytic reaction conditions and also obtaining pure product with high yield without applying column chromatography...
August 3, 2018: Ultrasonics Sonochemistry
Jacqueline Ferandin Honorio, Márcia Teresinha Veit, Pedro Yahico Ramos Suzaki, Priscila Ferri Coldebella, Eliane Sloboda Rigobello, Célia Regina Granhen Tavares
In the present study, the use of the rice husk biomass as an alternative biosorbent for treating the estrone, 17β-estradiol, and estriol hormones in monocomponent and multicomponent systems was investigated. The high-performance liquid chromatography technique (HPLC-UV) was applied in order to quantify the hormones, validating this method according to ANVISA and INMETRO. The biosorbent presented functional groups typical of cellulose, hemicellulose, lignin, and proteins, with an amorphous, fibrous, and porous surface...
September 10, 2018: Environmental Technology
Chad M Gilmer, Ned B Bowden
This article reports the fabrication of organic solvent nanofiltration membranes containing a labile disulfide bond, which is broken by reaction with a chemical stimulus. These membranes are a new generation of smart membranes that have tailored selectivities and flux that can be altered by reacting with a chemical stimulus. The selectivity and flux of chemicals through the membranes was controlled by varying the concentration of disulfide bonds in the membrane. When the disulfide bonds were cleaved, the pores in the membrane became larger and yielded different separation properties...
August 31, 2018: ACS Omega
Maryam Nourisefat, Farhad Panahi, Ali Khalafi-Nezhad
In this study, amino acids and peptides were used as reactants in a Hantzsch multicomponent reaction in order to synthesize new structurally diverse molecules containing these synthons. As well, an applicable strategy for modification of these natural molecules with heterocycle backbones such as pyrimidine, xanthene and acridine is introduced. Using this method, a set of new amino acid- and peptide-functionalized heterocycles were synthesized in good to excellent yields under mild conditions. Furthermore, carbohydrates were used as substrates in the synthesis of some derivatives...
September 5, 2018: Molecular Diversity
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