scholarly journals Extendable stapling of unprotected peptides by crosslinking two amines with o-phthalaldehyde

2022 ◽  
Vol 13 (1) ◽  
Author(s):  
Bo Li ◽  
Lan Wang ◽  
Xiangxiang Chen ◽  
Xin Chu ◽  
Hong Tang ◽  
...  
Keyword(s):  
Condensation Reaction ◽  
Cysteine Residue ◽  
Amino Groups ◽  
One Pot ◽  
Peptide Substrates ◽  
Peptide Chemistry ◽  
Peptide Modification ◽  
Wide Range ◽  
Sequential Addition ◽  
Aqueous Conditions

AbstractPeptide modification methods that do not rely on the cysteine residue are underdeveloped, and their development could greatly expand the current toolbox for peptide chemistry. During the course of preliminary investigations into the classical ortho-phthalaldehyde (OPA)-amine-thiol condensation reaction, we found that in the absence of thiol, OPA readily condenses with two primary alkyl amines to form a class of underexplored isoindolin-1-imine compounds under mild aqueous conditions. From the intramolecular version of this OPA-2amines reaction, an efficient and selective methodology using mild reaction conditions has been developed for stapling unprotected peptides via crosslinking of two amino groups in both an end-to-side and side-to-side fashion. The stapling method is superfast and broadly applicable for various peptide substrates with the reacting amino groups separated by a wide range of different amino acid units. The macrocyclization reactions of selected substrates are completed within 10 seconds at 5 mM concentration and within 2 minutes at 50 μM concentration. Importantly, the resulting cyclized peptides with an isoindolinimine linkage can be extended in a one-pot sequential addition manner with several different electron-deficient π electrophiles, thereby generating more complex structures.

Knoevenagel Condensation of Phosphinoylacetic Acids with Aldehydes: An Efficient One-Pot Strategy for the Synthesis of P-Functionalized Alkenyl Compounds

Synthesis ◽  
2021 ◽  
Author(s):  
Kamil Dziuba ◽  
Katarzyna Szwaczko ◽  
Sławomir Frynas
Keyword(s):  
Efficient Method ◽  
Knoevenagel Condensation ◽  
Condensation Reaction ◽  
Environmentally Friendly ◽  
Phosphine Oxides ◽  
One Pot ◽  
Practical Procedure ◽  
Synthesis Strategy ◽  
Wide Range ◽  
Knoevenagel Condensation Reaction

AbstractA wide range of commercially available aldehydes have been applied to Knoevenagel condensation reaction to give E-alkenylphosphine oxides and vinylphosphine oxides. The readily available phosphinoylacetic acids derived from P(O)–H compounds were used as the starting materials in the reaction, providing a highly stereoselective and efficient method for constructing α,β-unsaturated phosphine oxides. Moreover, this simple and practical procedure provides an alternative and more environmentally friendly synthesis strategy for this type of P-functionalized alkenyl compounds.

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

2020 ◽  
Author(s):  
Birgit Meindl ◽  
Katharina Pfennigbauer ◽  
Berthold Stöger ◽  
Martin Heeney ◽  
Florian Glöcklhofer
Keyword(s):  
Wittig Reaction ◽  
Condensation Reaction ◽  
Synthetic Methods ◽  
Anthracene Derivative ◽  
Double Ring ◽  
Mild Conditions ◽  
Wide Range ◽  
Anthracene Derivatives

Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions followed by a deprotection and intramolecular double ring-closing condensation reaction. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach.<br>

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

Chalcones: As potent α-amylase enzyme inhibitors; synthesis, in vitro, and in silico studies

2020 ◽  
Vol 16 ◽  
Author(s):  
Mahboob Ali ◽  
Momin Khan ◽  
Khair Zaman ◽  
Abdul Wadood ◽  
Maryam Iqbal ◽  
...  
Keyword(s):  
In Silico ◽  
Enzyme Inhibitors ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Type Ii Diabetes Mellitus ◽  
Spectroscopic Techniques ◽  
Chalcone Derivatives ◽  
In Silico Studies ◽  
Wide Range

: Background: The inhibition of α-amylase enzyme is one of the best therapeutic approach for the management of type II diabetes mellitus. Chalcone possesses a wide range of biological activities. Objective: In the current study chalcone derivatives (1-17) were synthesized and evaluated their inhibitory potential against α-amylase enzyme. Method: For that purpose, a library of substituted (E)-1-(naphthalene-2-yl)-3-phenylprop-2-en-1-ones was synthesized by ClaisenSchmidt condensation reaction of 2-acetonaphthanone and substituted aryl benzaldehyde in the presence of base and characterized via different spectroscopic techniques such as EI-MS, HREI-MS, 1H-, and 13C-NMR. Results: Sixteen synthetic chalcones were evaluated for in vitro porcine pancreatic α-amylase inhibition. All the chalcones demonstrated good inhibitory activities in the range of IC50 = 1.25 ± 1.05 to 2.40 ± 0.09 μM as compared to the standard commercial drug acarbose (IC50 = 1.34 ± 0.3 μM). Conclusion: Chalcone derivatives (1-17) were synthesized, characterized, and evaluated for their α-amylase inhibition. SAR revealed that electron donating groups in the phenyl ring have more influence on enzyme inhibition. However, to insight the participation of different substituents in the chalcones on the binding interactions with the α-amylase enzyme, in silico (computer simulation) molecular modeling analyses were carried out.

scholarly journals One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT

Crystals ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 117
Author(s):  
Yousef Hijji ◽  
Rajeesha Rajan ◽  
Hamdi Ben Yahia ◽  
Said Mansour ◽  
Abdelkader Zarrouk ◽  
...  
Keyword(s):  
Schiff Base ◽  
Molecular Orbital ◽  
Density Functional ◽  
Condensation Reaction ◽  
3D Structure ◽  
Water Soluble ◽  
Microwave Assisted Synthesis ◽  
One Pot ◽  
Microwave Assisted ◽  
Td Dft

The(3R,4R,6R)-3-(((E)-2-hydroxybenzylidene)amino)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol water-soluble Glucose amine Schiff base (GASB-1) product was made available by condensation of 2-hydroxybenzaldehyde with (3R,6R)-3-amino-6-(hydroxymethyl)-tetra-hydro-2H-pyran-2,4,5-triol under mono-mode microwave heating. A one-pot 5-minute microwave-assisted reaction was required to complete the condensation reaction with 90% yield and without having byproducts. The 3D structure of GASB-1 was solved from single crystal X-ray diffraction data and computed by DFT/6-311G(d,p). The Hirshfeld surface analysis (HSA), molecular electronic potential (MEP), Mulliken atomic charge (MAC), and natural population analysis (NPA) were performed. The IR and UV-Vis spectra were matched to their density functional theory (DFT) relatives and the thermal behavior was resolved in an open-room condition via thermogravimetry/Derivative thermogravimetry (TG/DTG) and differential scanning calorimetry (DSC). The highest occupied molecular orbital/lowest unoccupied molecular orbital (HOMO/LUMO), density of state (DOS), and time-dependence TD-DFT computations were correlated to the experimental electron transfer in water and acrylonitrile solvents.

scholarly journals Single particle dual plasmonic effect for efficient organic solar cells

2021 ◽  
Author(s):  
Adi Prasetio ◽  
Soyeon Kim ◽  
Muhammad Jahandar ◽  
Dong Chan Lim
Keyword(s):  
Solar Cells ◽  
Organic Solar Cells ◽  
Light Absorption ◽  
Resonance Effect ◽  
Localized Surface Plasmon ◽  
Main Role ◽  
Charge Generation ◽  
One Pot ◽  
Wide Range ◽  
Light Reflectance

AbstractIncorporating localized surface plasmon resonance (LSPR) into organic solar cells (OSCs) is a popular method for improving the power conversion efficiency (PCE) by introducing better light absorption. In this work, we designed a one-pot synthesis of Ag@SiO2@AuNPs dual plasmons and observed an immense increase in light absorption over a wide range of wavelengths. Ag@SiO2 plays the main role in enhancing light absorption near the ultraviolet band. The silica shell can also further enhance the LSP resonance effect and prevent recombination on the surface of AgNPs. The AuNPs on the Ag@SiO2 shell exhibited strong broad visible-light absorption due to LSP resonance and decreased light reflectance. By utilizing Ag@SiO2@AuNPs, we could enhance the light absorption and photoinduced charge generation, thereby increasing the device PCE to 8.57% and Jsc to 17.67 mA cm−2, which can be attributed to the enhanced optical properties. Meanwhile, devices without LSPR nanoparticles and Ag@SiO2 LSPR only showed PCEs of 7.36% and 8.18%, respectively.

scholarly journals A New Supported Manganese-Based Coordination Complex as a Nano-Catalyst for the Synthesis of Indazolophthalazinetriones and Investigation of Its Antibacterial Activity

Chemistry ◽  
2021 ◽  
Vol 3 (3) ◽  
pp. 783-799
Author(s):  
Maryam Ariannezhad ◽  
Davood Habibi ◽  
Somayyeh Heydari ◽  
Vahideh Khorramabadi
Keyword(s):  
Antibacterial Activity ◽  
Simple Procedure ◽  
Condensation Reaction ◽  
Antibacterial Properties ◽  
Coordination Complex ◽  
Bacterial Strains ◽  
One Pot ◽  
Nano Catalyst ◽  
Ft Ir ◽  
The One

A new magnetic supported manganese-based coordination complex (Fe3O4@SiO2@CPTMS@MBOL@ Mn) was prepared in consecutive stages and characterized via various techniques (VSM, SEM, TEM, XRD, FT-IR, EDX, TG-DTA, and ICP). To evaluate its application, it was used for synthesis of divers Indazolophthalazinetriones in a simple procedure via the one-pot three-component condensation reaction of aldehydes, dimedone, and phthalhydrazide in ethanol under reflux conditions. The Mn catalyst can be recycled without any noticeable loss in catalytic activity. Additionally, the antibacterial properties of the nano-catalyst were studied against some bacterial strains.

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