Organocatalytic Polymerization of Furfuryl Methacrylate and Post-Diels-Alder Click Reaction to Cross-Linked Materials

2015 ◽  
Vol 216 (13) ◽  
pp. 1421-1430 ◽  
Author(s):  
Shuo Kelvin Feng ◽  
Meghan Schmitt ◽  
Eugene Y.-X. Chen
Keyword(s):  
Click Reaction ◽  
Diels Alder ◽  
Organocatalytic Polymerization

Near-infrared light-responsive, diselenide containing core-cross-linked micelles prepared by the Diels–Alder click reaction for photocontrollable drug release application

2018 ◽  
Vol 9 (39) ◽  
pp. 4813-4823 ◽  
Author(s):  
Sabrina Aufar Salma ◽  
Maheshkumar Prakash Patil ◽  
Dong Woo Kim ◽  
Cuong Minh Quoc Le ◽  
Byung-Hyun Ahn ◽  
...  
Keyword(s):  
Drug Release ◽  
Near Infrared ◽  
Click Reaction ◽  
Diels Alder ◽  
Infrared Light ◽  
Near Infrared Light ◽  
Micelle System ◽  
Drug Vehicle

We report a facile and efficient preparation of a NIR-triggered micelle system for a drug vehicle.

scholarly journals Bio-orthogonal “click-and-release” donation of caged carbonyl sulfide (COS) and hydrogen sulfide (H2S)

2017 ◽  
Vol 53 (8) ◽  
pp. 1378-1380 ◽  
Author(s):  
Andrea K. Steiger ◽  
Yang Yang ◽  
Maksim Royzen ◽  
Michael D. Pluth
Keyword(s):  
Hydrogen Sulfide ◽  
Click Reaction ◽  
Carbonyl Sulfide ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
New Strategy ◽  
Electron Demand

The inverse-electron demand Diels–Alder (IEDDA) click reaction between thiocarbamate-functionalized trans-cyclooctenes and tetrazines provides a new strategy for bio-orthogonal COS/H2S delivery.

Diels-alder click reaction for the preparation of polycarbonate block copolymers

2013 ◽  
Vol 51 (10) ◽  
pp. 2252-2259 ◽  
Author(s):  
Pinar Sinem Omurtag ◽  
Ufuk Saim Gunay ◽  
Aydan Dag ◽  
Hakan Durmaz ◽  
Gurkan Hizal ◽  
...  
Keyword(s):  
Block Copolymers ◽  
Click Reaction ◽  
Diels Alder

scholarly journals Alkynes as Privileged Synthons in Selected Organic Name Reactions

2019 ◽  
Vol 16 (2) ◽  
pp. 205-243 ◽  
Author(s):  
Majid M. Heravi ◽  
Mahzad Dehghani ◽  
Vahideh Zadsirjan ◽  
Manijheh Ghanbarian
Keyword(s):  
Organic Chemistry ◽  
Click Reaction ◽  
Alder Reaction ◽  
Unsaturated Hydrocarbon ◽  
Diels Alder ◽  
Biologically Active ◽  
Organic Reactions ◽  
Sonogashira Reaction ◽  
High Status ◽  
Diels Alder Reaction

Background:Alkynes are actually basic chemicals, serving as privileged synthons for planning new organic reactions for assemblage of a reactive motif, which easily undergoes a further desirable transformation. Name reactions, in organic chemistry are referred to those reactions which are well-recognized and reached to such status for being called as their explorers, discoverers or developers. Alkynes have been used in various name reactions. In this review, we try to underscore the applications of alkynes as privileged synthons in prevalent name reactions such as Huisgen 1,3-dipolar cycloaddtion via Click reaction, Sonogashira reaction, and Hetero Diels-Alder reaction.Objective:In this review, we try to underscore the applications of alkynes as privileged synthons in the formation of heterocycles, focused on the selected reactions of alkynes as a synthon or impending utilization in synthetic organic chemistry, which have reached such high status for being included in the list of name reactions in organic chemistry.Conclusion:Alkynes (including acetylene) are an unsaturated hydrocarbon bearing one or more triple C-C bond. Remarkably, alkynes and their derivatives are frequently being used as molecular scaffolds for planning new organic reactions and installing reactive functional group for further reaction. It is worth mentioning that in general, the terminal alkynes are more useful and more frequently being used in the art of organic synthesis. Remarkably, alkynes have found different applications in pharmacology, nanotechnology, as well as being known as appropriate starting precursors for the total synthesis of natural products and biologically active complex compounds. They are predominantly applied in various name reactions such as Sonogashira, Glaser reaction, Friedel-crafts reaction, Castro-Stephens coupling, Huisgen 1.3-dipolar cycloaddtion reaction via Click reaction, Sonogashira reaction, hetero-Diels-Alder reaction. In this review, we tried to impress the readers by presenting selected name reactions, which use the alkynes as either stating materials or precursors. We disclosed the applications of alkynes as a privileged synthons in several popular reactions, which reached to such high status being classified as name reactions. They are thriving and well known and established name reactions in organic chemistry such as Regioselective, 1,3-dipolar Huisgen cycloaddtion reaction via Click reaction, Sonogashira reaction and Diels-Alder reaction.

Injectable dual cross-linked adhesive hyaluronic acid multifunctional hydrogel scaffolds for potential applications in cartilage repair

2020 ◽  
Vol 11 (18) ◽  
pp. 3169-3178
Author(s):  
Chenxi Yu ◽  
Huichang Gao ◽  
Qingtao Li ◽  
Xiaodong Cao
Keyword(s):  
Hyaluronic Acid ◽  
Mechanical Strength ◽  
Cartilage Repair ◽  
Click Reaction ◽  
Diels Alder ◽  
Hydrogel Scaffolds ◽  
Potential Applications

A double crosslinked hydrogels was designed and prepared by combining the Diels–Alder click reaction and possessed good mechanical strength, injectability and adhesion.

scholarly journals Synthesis of Novel N-Heterocyclic Compounds Containing 1,2,3-Triazole Ring System via Domino, “Click” and RDA Reactions

Molecules ◽  
2019 ◽  
Vol 24 (4) ◽  
pp. 772 ◽  
Author(s):  
Márta Palkó ◽  
Mohamed El Haimer ◽  
Zsanett Kormányos ◽  
Ferenc Fülöp
Keyword(s):  
Heterocyclic Compounds ◽  
Click Reaction ◽  
Triazole Ring ◽  
Heterocyclic Ring ◽  
Ring System ◽  
Diels Alder ◽  
Ring Closure ◽  
Synthetic Route ◽  
13C Nuclear Magnetic Resonance ◽  
Nmr Methods

An uncomplicated, high-yielding synthetic route has been developed to constitute complicated heterocycles, applying domino, click and retro-Diels–Alder (RDA) reaction sequences. Starting from 2-aminocarboxamides, a new set of isoindolo[2,1-a]quinazolinones was synthesized with domino ring closure. A click reaction was performed to create the 1,2,3-triazole heterocyclic ring, followed by an RDA reaction resulting in dihydropyrimido[2,1-a]isoindole-2,6-diones. The absolute configuration, concluded by the norbornene structure that served as a chiral source, remained constant throughout the transformations. The structure of the synthesized compounds was examined by 1H and 13C Nuclear Magnetic Resonance (NMR) methods.

scholarly journals Side-by-Side Comparison of Five Chelators for 89Zr-Labeling of Biomolecules: Investigation of Chemical/Radiochemical Properties and Complex Stability

Cancers ◽  
2021 ◽  
Vol 13 (24) ◽  
pp. 6349
Author(s):  
Helen Damerow ◽  
Ralph Hübner ◽  
Benedikt Judmann ◽  
Ralf Schirrmacher ◽  
Björn Wängler ◽  
...  
Keyword(s):  
Density Functional ◽  
Chelating Agents ◽  
Click Reaction ◽  
Reaction Times ◽  
Diels Alder ◽  
Functional Theory ◽  
Inverse Electron Demand ◽  
Relative Kinetic ◽  
Small Model

In this work, five different chelating agents, namely DFO, CTH-36, DFO*, 3,4,3-(LI-1,2-HOPO) and DOTA-GA, were compared with regard to the relative kinetic inertness of their corresponding 89Zr complexes to evaluate their potential for in vivo application and stable 89Zr complexation. The chelators were identically functionalized with tetrazines, enabling a fully comparable, efficient, chemoselective and biorthogonal conjugation chemistry for the modification of any complementarily derivatized biomolecules of interest. A small model peptide of clinical relevance (TCO-c(RGDfK)) was derivatized via iEDDA click reaction with the developed chelating agents (TCO = trans-cyclooctene and iEDDA = inverse electron demand Diels-Alder). The bioconjugates were labeled with 89Zr4+, and their radiochemical properties (labeling conditions and efficiency), logD(7.4), as well as the relative kinetic inertness of the formed complexes, were compared. Furthermore, density functional theory (DFT) calculations were conducted to identify potential influences of chelator modification on complex formation and geometry. The results of the DFT studies showed—apart from the DOTA-GA derivative—no significant influence of chelator backbone functionalization or the conjugation of the chelator tetrazines by iEDDA. All tetrazines could be efficiently introduced into c(RGDfK), demonstrating the high suitability of the agents for efficient and chemoselective bioconjugation. The DFO-, CTH-36- and DFO*-modified c(RGDfK) peptides showed a high radiolabeling efficiency under mild reaction conditions and complete 89Zr incorporation within 1 h, yielding the 89Zr-labeled analogs as homogenous products. In contrast, 3,4,3-(LI-1,2-HOPO)-c(RGDfK) required considerably prolonged reaction times of 5 h for complete radiometal incorporation and yielded several different 89Zr-labeled species. The labeling of the DOTA-GA-modified peptide was not successful at all. Compared to [89Zr]Zr-DFO-, [89Zr]Zr-CTH-36- and [89Zr]Zr-DFO*-c(RGDfK), the corresponding [89Zr]Zr-3,4,3-(LI-1,2-HOPO) peptide showed a strongly increased lipophilicity. Finally, the relative stability of the 89Zr complexes against the EDTA challenge was investigated. The [89Zr]Zr-DFO complex showed—as expected—a low kinetic inertness. Unexpectedly, also, the [89Zr]Zr-CTH-36 complex demonstrated a high susceptibility against the challenge, limiting the usefulness of CTH-36 for stable 89Zr complexation. Only the [89Zr]Zr-DFO* and the [89Zr]Zr-3,4,3-(LI-1,2-HOPO) complexes demonstrated a high inertness, qualifying them for further comparative in vivo investigation to determine the most appropriate alternative to DFO for clinical application.

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