scholarly journals Breaking thiacalix[4]arene into pieces – a novel synthetic approach to higher calixarenes bearing mixed (–S–, –CH2–) bridges

RSC Advances ◽  
2021 ◽  
Vol 11 (58) ◽  
pp. 36934-36941
Author(s):  
Lukáš Kaiser ◽  
Tomáš Landovský ◽  
Karolína Salvadori ◽  
Václav Eigner ◽  
Hana Dvořáková ◽  
...  
Keyword(s):  
Building Block ◽  
Quantitative Yield ◽  
Synthetic Approach ◽  
Novel Approach

A novel approach is based on the cleavage of thiacalix[4]arene monosulfoxide with BuLi providing a linear tetramer in an essentially quantitative yield which is used as a building block for further cyclization.

Novel Synthetic Approach to Nine-Membered Diallylic Amides: Stereochemical Behavior and Utility as Chiral Building Block

Synlett ◽  
2008 ◽  
Vol 2008 (16) ◽  
pp. 2518-2522 ◽  
Author(s):  
Katsuhiko Tomooka ◽  
Masaki Suzuki ◽  
Kazuhiro Uehara ◽  
Maki Shimada ◽  
Toshiyuki Akiyama
Keyword(s):  
Building Block ◽  
Synthetic Approach ◽  
Chiral Building Block

OPTIMIZATION OF THE TECHNOLOGY OF BINDING COMPONENT PREPARATION FOR CATIONIC LIPOSOMES IN GENE THERAPY

2020 ◽  
pp. 169-171
Author(s):  
D. Egorov ◽  
M. Maslov
Keyword(s):  
Gene Therapy ◽  
Nucleic Acid ◽  
Cationic Liposomes ◽  
Mitsunobu Reaction ◽  
Synthetic Approach ◽  
Nucleic Acid Delivery ◽  
Novel Approach ◽  
Binding Component

Cationic liposomes for nucleic acid delivery were prepared from dimeric polycationic amphiphile. Novel synthetic approach was developed for that. Comparison of both novel approach based on Mitsunobu reaction and previous one is provided.

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO), a Versatile Precursor for Trifluoromethyl-Substituted Heteroarenes – a Short Synthesis of Celebrex® (Celecoxib)

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 121-125 ◽  
Author(s):  
Andreas Kirschning ◽  
Heiko Sommer ◽  
Max Braun ◽  
Benjamin Schröder
Keyword(s):  
Building Block ◽  
Synthetic Approach ◽  
Elimination Reaction ◽  
Stetter Reaction ◽  
Inflammatory Drug ◽  
Short Synthesis ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Key Steps

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted thiophenes, furans, pyrrols, and piperazines. Key steps are an addition–elimination reaction to ETFBO followed by the thiazolium-catalyzed Stetter reaction. The scope of this chemistry was demonstrated in a new synthetic approach towards the COX-2 selective, nonsteroidal anti-inflammatory drug Celebrex® (celecoxib).

scholarly journals Modular solid-phase synthesis, catalytic application and efficient recycling of supported phosphine–phosphite ligand libraries

2016 ◽  
Vol 45 (5) ◽  
pp. 2116-2123 ◽  
Author(s):  
Frank J. L. Heutz ◽  
Paul C. J. Kamer
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Quantitative Yield ◽  
Synthetic Approach ◽  
Phase Synthesis ◽  
Catalytic Application ◽  
Phosphite Ligands ◽  
Minimal Work ◽  
Work Up

A highly modular solid-phase synthetic approach is presented which provides facile access to libraries of recyclable phosphine–phosphite ligands in quantitative yield requiring only minimal work-up.

scholarly journals Synthesis, Stability, and Antidiabetic Activity Evaluation of (−)-Epigallocatechin Gallate (EGCG) Palmitate Derived from Natural Tea Polyphenols

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 393
Author(s):  
Bingbing Liu ◽  
Zhengzhong Kang ◽  
Weidong Yan
Keyword(s):  
Synthesis Method ◽  
Epigallocatechin Gallate ◽  
Antidiabetic Activity ◽  
Molar Ratio ◽  
Synthetic Approach ◽  
Vitro Assay ◽  
Docking Simulations ◽  
Palmitoyl Chloride ◽  
Novel Approach

This work describes a novel approach for the synthesis of (−)-epigallocatechin gallate (EGCG) palmitate by a chemical-synthesis method, where the elevated stability of the EGCG derivative is achieved. Various parameters affecting the acylation process, such as the base, solvent, as well as the molar ratio of palmitoyl chloride, have been studied to optimize the acylation procedure. The optimized reaction condition was set as follows: EGCG/palmitoyl chloride/sodium acetate was under a molar ratio of 1:2:2, with acetone as the solvent, and the reaction temperature was 40 °C. Under the optimized condition, the yield reached 90.6%. The EGCG palmitate (PEGCG) was isolated and identified as 4′-O-palmitoyl EGCG. Moreover, the stability of PEGCG under different conditions was proved significantly superior to EGCG. Finally, PEGCG showed better inhibition towards α-amylase and α-glucosidase, which was 4.5 and 52 times of EGCG, respectively. Molecular docking simulations confirmed the in vitro assay results. This study set a novel and practical synthetic approach for the derivatization of EGCG, and suggest that PEGCG may act as an antidiabetic agent.

scholarly journals Two Complementary Synthetic Approaches to the Enantiomeric Forms of the Chiral Building Block (2,6,6-Trimethyltetrahydro-2H-pyran-2-yl)methanol: Application to the Stereospecific Preparation of the Natural Flavor Linaloyl Oxide

Catalysts ◽  
2018 ◽  
Vol 8 (9) ◽  
pp. 362 ◽  
Author(s):  
Stefano Serra ◽  
Davide De Simeis
Keyword(s):  
Fractional Crystallization ◽  
Building Block ◽  
Large Scale ◽  
Stereoselective Synthesis ◽  
Optical Purity ◽  
Building Blocks ◽  
Synthetic Approach ◽  
Racemic Form ◽  
Chiral Building Block ◽  
Synthetic Approaches

The enantiomeric forms of the alcohol (2,6,6-trimethyltetrahydro-2H-pyran-2-yl)methanol are potential chiral building blocks for the stereoselective synthesis of different natural terpenes. Here, we describe their preparation by means of two different synthetic approaches. The first is based on the stereospecific (+)-10-camphorsulfonic acid (CSA)-catalyzed cyclization of (R)- and (S)-2-methyl-5-(2-methyloxiran-2-yl)pentan-2-ol, which were in turn synthesized from (R)- and (S)-linalool, respectively. The latter monoterpenes are easily available from the chiral pool, with different optical purity. As our synthesis makes use of the intermediate 2,6-dimethyloct-7-ene-2,6-diol, whose enantiopurity can be improved through fractional crystallization, we obtained (2,6,6-trimethyltetrahydro-2H-pyran-2-yl)methanol enantiomers in an almost enantiopure form. The second synthetic approach is based on the lipase-mediated resolution of the aforementioned tetrahydropyranyl alcohol, which was prepared in racemic form starting from the industrial intermediate, dehydrolinalool. In this work, we report a large-scale resolution procedure that exploits the opposite enantioselectivity of Novozym® 435 lipase and lipase AK in the acetylation reaction of (2,6,6-trimethyltetrahydro-2H-pyran-2-yl)methanol. The two enantiomeric forms of the latter alcohol were employed for the first stereoselective synthesis of both enantiomers of the flavor, linaloyl oxide (2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran).

scholarly journals Polymer-Supported Synthesis of Various Pteridinones and Pyrimidodiazepinones

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1603
Author(s):  
Jan Chasák ◽  
Lucie Brulíková
Keyword(s):  
Building Block ◽  
Solid Phase ◽  
Structure Activity Relationship ◽  
Synthetic Methods ◽  
Activity Relationship ◽  
Synthetic Approach ◽  
Sar Studies ◽  
Structure Activity ◽  
Pharmacokinetic Properties ◽  
Polymer Supported

In this report, we employed the solid-phase synthetic approach to prepare variously substituted dihydropteridinones, tetrahydropyrrolopteridinones, and pyrimidodiazepinones, using a versatile building block-4,6-dichloro-5-nitropyrimidine. All these compounds are pharmacologically significant scaffolds of the great importance of medicinal chemists. The fast and efficient synthetic methodology is highly desirable for defining their structure-activity relationship (SAR) and optimizing pharmacokinetic properties. Our research efforts utilize simple synthetic methods to generate a library of analogues for future SAR studies. The efficiency of our approach was exemplified in various pteridinones as well as pyrimidodiazepinones.

1,5-Anhydro-d-fructose as Chiral Building Block: A Novel Approach to 1-Deoxymannojirimycin

Synthesis ◽  
2006 ◽  
Vol 2006 (05) ◽  
pp. 827-830
Author(s):  
Inge Lundt ◽  
Peter Maier ◽  
Søren Møller Andersen
Keyword(s):  
Building Block ◽  
Novel Approach ◽  
Chiral Building Block

scholarly journals Delineation of the third antigenic site of lysozyme by application of a novel ‘surface-simulation’ synthetic approach directly linking the conformationally adjacent residues forming the site

1976 ◽  
Vol 159 (1) ◽  
pp. 89-93 ◽  
Author(s):  
C L Lee ◽  
M Z Atassi
Keyword(s):  
Chemical Reactivity ◽  
Antigenic Site ◽  
Surface Region ◽  
Synthetic Approach ◽  
The Novel ◽  
Disulphide Bridge ◽  
Native Proteins ◽  
Novel Approach ◽  
Peptide Linkage ◽  
Imaginary Line

We have previously shown that an antigenic site in native lysozyme resides around the disulphide bridge 30-115 and incorporates Lys-33 and Lys-116 and one or both of Tyr-20 and Tyr-23. These residues fall in an imaginary line circumscribing part of the surface of the molecule and passing through the spatially adjacent residues Tyr-20, Arg-21, Tyr-23, Lys-116, Asn-113, Arg-114, Phe-34 and Lys-33. The identity of the site was confirmed by demonstrating that the synthetic peptide Tyr-Arg-Tyr-Gly-Lys-Asn-Arg-Gly-Phe-Lys (which does not exist in lysozyme but simulates a surface region of it), and an analogue in which glycine replaced Tyr-23, possessed remarkable immuno-chemical reactivity that accounted entirely for the expected reactivity of the site in native lysozyme. Tyr-23 is not part of the site, and its contribution was satisfied by a glycine spacer. The novel approach presents a powerful technique for the delineation of antigenic (and other binding) sites in native proteins and confirms that these need not always comprise residues in direct peptide linkage.

Synthesis of glycerol carbonate from glycerol and dimethyl carbonate in basic ionic liquids

2011 ◽  
Vol 84 (3) ◽  
pp. 755-762 ◽  
Author(s):  
Cinzia Chiappe ◽  
Sunita Rajamani
Keyword(s):  
Ionic Liquids ◽  
Process Optimization ◽  
Building Block ◽  
Dimethyl Carbonate ◽  
Quantitative Yield ◽  
Glycerol Carbonate ◽  
Renewable Materials ◽  
Conversion Yield ◽  
Solvent Additive ◽  
Fold Excess

Glycerol carbonate is a key multifunctional compound used as solvent, additive, and building block in alternative chlorine-free processes. Here, we report the synthesis of glycerol carbonate from renewable materials (glycerol and dimethyl carbonate, DMC) using basic ionic liquids (ILs) as catalysts. After process optimization, it has been possible to isolate pure glycerol carbonate in quantitative yield using a three-fold excess of DMC and ca. 15 % of IL. The IL could be reused at least four times without any significant reduction in the conversion yield.

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