scholarly journals Chiral Diamine in Small Molecule Biomimetic Asymmetric Catalysis

2021 ◽  
Author(s):  
Fanyun Zeng ◽  
Chen Chen ◽  
Liu Liu ◽  
Yifan Li ◽  
Bo Li ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Enzymatic Reaction ◽  
Addition Reactions ◽  
Broad Application ◽  
Design And Synthesis ◽  
Chiral Diamine ◽  
Commodity Chemicals ◽  
Great Progress ◽  
Further Development ◽  
Environmentally Friendly Approach

Enzymatic reaction, as an environmentally friendly approach, has made great progress producing commodity chemicals comparing to the conventional metallo/organo catalysis. However, the reaction compatibility is not satisfactory. The development of biomimetic catalysis balancing both strategies for the green and broad application in synthesis is desirable. Here, we report the design and synthesis of a chiral diamine catalyst fulfilling this requirement. Asymmetric addition reactions using this ligand in water were demonstrated and the corresponding products were produced in excellent yields and enantiomeric ratios. This pluripotent ligand has also shown good reactivity/enantioselectivity on a number of representative reactions in both green and organic solvents. We anticipate that the ligand would allow further development of other catalysts for important yet challenging green stereoselective transformations.

scholarly journals Computational Insight into the Rope-Skipping Isomerization of Diarylether Cyclophanes

Symmetry ◽  
2021 ◽  
Vol 13 (11) ◽  
pp. 2127
Author(s):  
Thomas J. Summers ◽  
Hrishikesh Tupkar ◽  
Tyler M. Ozvat ◽  
Zoë Tregillus ◽  
Kenneth A. Miller ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Room Temperature ◽  
Chemical Bonds ◽  
Chiral Molecules ◽  
Free Energies ◽  
Design And Synthesis ◽  
The Impact ◽  
Rope Skipping ◽  
Temperature Factors ◽  
Insight Into

The restricted rotation of chemical bonds may lead to the formation of stable, conformationally chiral molecules. While the asymmetry in chiral molecules is generally observed in the presence of one or more stereocenters, asymmetry exhibited by conformational chirality in compounds lacking stereocenters, called atropisomerism, depends on structural and temperature factors that are still not fully understood. This atropisomerism is observed in natural diarylether heptanoids where the length of the intramolecular tether constrains the compounds to isolable enantiomers at room temperature. In this work, we examine the impact tether length has on the activation free energies to isomerization of a diarylether cyclophane substructure with a tether ranging from 6 to 14 carbons. Racemization activation energies are observed to decay from 48 kcal/mol for a 7-carbon tether to 9.2 kcal/mol for a 14-carbon tether. Synthetic efforts to experimentally test these constraints are also presented. This work will likely guide the design and synthesis of novel asymmetric cyclophanes that will be of interest in the catalysis community given the importance of atropisomeric ligands in the field of asymmetric catalysis.

scholarly journals Design and synthesis of thiamine analogues to study their binding to the ECF transporter for thiamine in bacteria

MedChemComm ◽  
2016 ◽  
Vol 7 (5) ◽  
pp. 966-971 ◽  
Author(s):  
L. Monjas ◽  
L. J. Y. M. Swier ◽  
A. R. de Voogd ◽  
R. C. Oudshoorn ◽  
A. K. H. Hirsch ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Substrate Specificity ◽  
Small Molecules ◽  
Energy Coupling ◽  
Coupling Factor ◽  
Design And Synthesis ◽  
Further Development ◽  
Thiamine Analogues

This work presents new small molecules that bind to the protein ThiT, which confers substrate specificity to the Energy-Coupling Factor (ECF) transporter for thiamine. Further development of the molecules may lead to compounds with antimicrobial activity.

Design and synthesis of tetraazachlorins, tetraazabacteriochlorins and tetraazaisobacteriochlorins

2009 ◽  
Vol 13 (02) ◽  
pp. 188-202 ◽  
Author(s):  
Elena A. Makarova ◽  
Evgeny A. Lukyanets
Keyword(s):  
Dicarboxylic Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Azomethine Ylides ◽  
Addition Reactions ◽  
Dipolar Cycloadditions ◽  
Design And Synthesis ◽  
Diels Alder Reaction ◽  
Oxidation Resistant ◽  
Derivatives Of

Three approaches to the synthesis of reduced derivatives of tetraazaporphine such as tetraazachlorin, tetraazabacteriochlorin, and tetraazaisobacteriochlorin are reviewed. The first synthesis of alkyl-substituted tetraazachlorins was achieved by the catalytic hydrogenation of magnesium complexes of tetraazaporphines. Two other synthesis approaches for reduced tetraazaporphines based on the mixed condensation of the precursors with different hydrogenation levels and β–β addition reactions have been developed in the last decade. The use of tetramethylsuccinonitrile as the saturated component in the mixed condensation with derivatives of aromatic and heteroaromatic dicarboxylic acids enable the synthesis of oxidation-resistant benzo-; 1,2- and 2,3-naphtho-; pyrazino-; 2,3- and 3,4-pyridino-fused tetraazachlorins, tetraazabacteriochlorins, and tetraazaisobacteriochlorins. Fullerene conjugates of reduced tetraazaporphine derivatives were obtained using 1,2-dicyanofullerene as the source of the hydrogenated sites. Tetraazaporphine can act as dienophile in Diels-Alder reaction with dienes of the anthracene and cyclopentadiene series and also as dipolarophile in 1,3-dipolar cycloadditions with azomethine ylides and nitrones. In addition, the effect of the reduction of peripheral double bonds in tetraazaporphine macrocycle alone, and in combination with annelation of benzene or heterocyclic rings on the absorption spectra is discussed.

scholarly journals Chirality transfer in metal-catalysed intermolecular addition reactions involving allenes

2016 ◽  
Vol 3 (9) ◽  
pp. 1186-1204 ◽  
Author(s):  
José Miguel Alonso ◽  
María Teresa Quirós ◽  
María Paz Muñoz
Keyword(s):  
Asymmetric Catalysis ◽  
Addition Reactions ◽  
Chirality Transfer

This review covers chirality transfer in metal-catalysed intermolecular addition reactions involving allenes, including axial-to-central chirality transfer, asymmetric catalysis and racemization.

The Design and Synthesis of Planar Chiral Ligands and Their Application to Asymmetric Catalysis

Synlett ◽  
2014 ◽  
Vol 25 (05) ◽  
pp. 615-630 ◽  
Author(s):  
Wanbin Zhang ◽  
Nicholas Butt ◽  
Delong Liu
Keyword(s):  
Asymmetric Catalysis ◽  
Chiral Ligands ◽  
Design And Synthesis

scholarly journals Recent Progress in Constructing Plasmonic Metal/Semiconductor Hetero-Nanomaterials for Improved Photocatalysis

2018 ◽  
Author(s):  
Liang Ma ◽  
Shuang Chen ◽  
You-Long Chen ◽  
Mo-Xi Liu ◽  
Hai-Xia Li ◽  
...  
Keyword(s):  
Photocatalytic Activity ◽  
Hydrogen Production ◽  
Recent Progress ◽  
Physical Mechanism ◽  
Co2 Reduction ◽  
Future Perspectives ◽  
Design And Synthesis ◽  
Semiconductor Nanomaterials ◽  
Further Development ◽  
Photocatalytic Applications

Hetero-nanomaterials constructed by plasmonic metals and functional semiconductors show enormous potential in photocatalytic applications, such as water splitting, hydrogen production, CO2 reduction, pollutants treatment. Their photocatalytic performances can be better regulated through adjusting structure, ingredient, and components arrangement. Therefore, the reasonable design and synthesis of metal/semiconductor hetero-nanostructures is of vital significance. In this article, we briefly review the recent progress in efficiently establishing metal/semiconductor nanomaterials for improved photocatalysis. The defined photocatalysts mainly include traditional binary hybrids, ternary multi-metals/semiconductor and metal/multi-semiconductors heterojunctions. The underlying physical mechanism for the improved photocatalytic activity of the established photocatalysts are highlighted. At the end of this article, a brief summary and possible future perspectives for further development in this field are demonstrated.

scholarly journals Rational Design and Synthesis of Naphthalene Diimide Linked Bis-Naphthalimides as DNA Interactive Agents

2021 ◽  
Vol 9 ◽  
Author(s):  
M. Shaheer Malik ◽  
Syed Farooq Adil ◽  
Ziad Moussa ◽  
Hatem M. Altass ◽  
Ismail I. Althagafi ◽  
...  
Keyword(s):  
Rational Design ◽  
Thermal Denaturation ◽  
Telomeric Dna ◽  
Docking Analysis ◽  
Design And Synthesis ◽  
Naphthalene Diimide ◽  
G Quadruplex ◽  
Further Development ◽  
Molecular Docking Analysis ◽  
Better Than

A molecular modeling assisted rational design and synthesis of naphthalene diimide linked bis-naphthalimides as potential DNA interactive agents is described. Chemical templates incorporating naphthalene diimide as a linker in bis-naphthalimide motif were subjected to molecular docking analysis at specific intercalation and telomeric DNA G-quadruplex sites. Excellent results were obtained, which were better than the standards. A short and convenient synthetic route was employed to access these hybrids experimentally, followed by evaluation of their ability to cause thermal denaturation of DNA and cytotoxic properties along with ADME predictions. The obtained results provided useful insights and two potential molecules were identified for further development.

scholarly journals Synthesis and Bioevaluation of 5-Chloro-4-(1,3-Oxazol-5-yl)-1Н-Pyrrole-3-Carboxyamides as Antimicrobial Agents

2020 ◽  
Vol 11 (3) ◽  
pp. 10595-10606
Keyword(s):  
Antimicrobial Agents ◽  
Ester Group ◽  
Alkyl Aryl ◽  
Design And Synthesis ◽  
Consecutive Reactions ◽  
Efficient Construction ◽  
Further Development ◽  
Hydrolysis Of ◽  
Derivatives Of ◽  
High Antifungal Activity

This investigation deals with the design and synthesis of new derivatives of pyrrole consisting of modifying atoms of chlorine, amide, and 1,3-oxazole fragments. These compounds can be interesting in the context of research of new antimicrobial agents. Ethyl 5-chloro-4-formyl-1H-pyrrole-3-carboxylates were used as a key substrate for further transformation into target compounds. This process was realized as a direct transformation of an aldehyde fragment into a 1,3-oxazole cycle by van Leusen’s reaction followed by hydrolysis of an ester group, which finally converted a reactant into the corresponding pyrrole-3-carboxylic acid. This acid has been found to be an efficient construction block for the further development of antimicrobial agents. The preparative potential of these compounds has been verified by way of their transformation into a series of carbamides through consecutive reactions with thionyl chloride and alkyl-, aryl, and heterylamines under mild reaction conditions. According to bio screening results, the following two compounds have been chosen as those exhibiting a high anti-staphylococcus activity: 1-butyl-5-chloro-2-methyl-4-(1,3-oxazol-5-yl)-N-[(1,3-thiazol-2-yl]-1H-pyrrole-3-carboxamide and 1-butyl-5-chloro-N-[(3-dimethylaminosulfonyl)phenyl]-2-methyl-4-(1,3-oxazol-5-yl)-1H-pyrrole-3-carboxamide (МІС=7.8 µg/ml), while another one – 5-сhloro-N-(4-chlorophenyl)-4-(1,3-oxazol-5-yl)-2-phenyl-1-propyl-1H-pyrrole-3-carboxamide was selected as a compound exhibiting high antifungal activity (МІС=7.8 µg/ml) against the reference strains Candida albiсans АТСС 885/653 and Aspergillus niger K9.

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