CuI NPs Facilitated Click Chemistry for the Late-Stage Diversification of Bioactive Complex Small Molecules

2019 ◽  
Author(s):  
rahul upadhyay ◽  
Rahul Kumar ◽  
Rohit Rana ◽  
Onkar S. Nayal ◽  
Sushil K. Maurya
Keyword(s):  
Small Molecules ◽  
Click Chemistry ◽  
Late Stage

scholarly journals A Model for Late-Stage Modification of Polyurethane Dendrimers Using Thiol-Ene Click Chemistry

2021 ◽  
Author(s):  
Dhruba Poudel ◽  
Richard Taylor
Keyword(s):  
Click Chemistry ◽  
Late Stage ◽  
Click Reaction ◽  
Synthetic Approach ◽  
Protecting Group ◽  
One Pot ◽  
The Core ◽  
Curtius Reaction

Protecting group free, one-pot multicomponent Curtius reaction was utilized to afford diurethane G-1 dendron. In our synthetic approach, G-1 dendron can undergo late-stage modification using thiol-ene click reaction, which was then attached to the core to furnish a dendrimer. In another approach, the G-1 dendron was attached to the core and so formed dendrimer was surface functionalized using thiol-ene click chemistry. Either way, we can synthesize the dendrimer.

One pot conjugation of small molecules to RNA using click chemistry

2012 ◽  
Vol 53 (50) ◽  
pp. 6747-6750 ◽  
Author(s):  
Wei Wang ◽  
Ke Chen ◽  
Dezhong Qu ◽  
Weilin Chi ◽  
Wei Xiong ◽  
...  
Keyword(s):  
Small Molecules ◽  
Click Chemistry ◽  
One Pot

scholarly journals Light-induced primary amines and o-nitrobenzyl alcohols cyclization as a versatile photoclick reaction for modular conjugation

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
An-Di Guo ◽  
Dan Wei ◽  
Hui-Jun Nie ◽  
Hao Hu ◽  
Chengyuan Peng ◽  
...  
Keyword(s):  
Small Molecules ◽  
Click Chemistry ◽  
Chemical Biology ◽  
Materials Science ◽  
Primary Amines ◽  
Mild Conditions ◽  
Native Proteins ◽  
Good Biocompatibility ◽  
Operational Simplicity

Abstract The advent of click chemistry has had a profound impact on many fields and fueled a need for reliable reactions to expand the click chemistry toolkit. However, developing new systems to fulfill the click chemistry criteria remains highly desirable yet challenging. Here, we report the development of light-induced primary amines and o-nitrobenzyl alcohols cyclization (PANAC) as a photoclick reaction via primary amines as direct click handle, to rapid and modular functionalization of diverse small molecules and native biomolecules. With intrinsic advantages of temporal control, good biocompatibility, reliable chemoselectivity, excellent efficiency, readily accessible reactants, operational simplicity and mild conditions, the PANAC photoclick is robust for direct diversification of pharmaceuticals and biorelevant molecules, lysine-specific modifications of unprotected peptides and native proteins in vitro, temporal profiling of endogenous kinases and organelle-targeted labeling in living systems. This strategy provides a versatile platform for organic synthesis, bioconjugation, medicinal chemistry, chemical biology and materials science.

Versatile Site-Specific Conjugation of Small Molecules to siRNA Using Click Chemistry

2011 ◽  
Vol 76 (5) ◽  
pp. 1198-1211 ◽  
Author(s):  
Takeshi Yamada ◽  
Chang Geng Peng ◽  
Shigeo Matsuda ◽  
Haripriya Addepalli ◽  
K. Narayanannair Jayaprakash ◽  
...  
Keyword(s):  
Small Molecules ◽  
Click Chemistry ◽  
Site Specific

scholarly journals SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization

2018 ◽  
Vol 140 (8) ◽  
pp. 2919-2925 ◽  
Author(s):  
Zilei Liu ◽  
Jie Li ◽  
Suhua Li ◽  
Gencheng Li ◽  
K. Barry Sharpless ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Late Stage

F-Based Small Group Decoration of Heteroarenes via C-H Activation: Medicinal Chemistry Rationale and late-stage Synthetic Methods

2021 ◽  
Vol 25 ◽  
Author(s):  
Paolo Ronchi ◽  
Sara Guariento ◽  
Daniele Pala ◽  
Daniela Pizzirani ◽  
Claudio Fiorelli ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Small Molecules ◽  
Small Group ◽  
Small Groups ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Synthetic Methods ◽  
Type Reaction ◽  
Approved Drugs ◽  
Chemistry Community

: The use of F-based decorations in drug discovery started from the development of fluorocorticoids and fluorochinolones (1950s and 1980s, respectively), and has resulted in about 20% of approved drugs on the Market containing fluorine. From a medicinal chemistry perspective, the installation of F-based small groups (e.g., CF3, -CF2H, -OCF3, -OCF2H, -SCF3, -SCF2H) necessarily impacts on physicochemical, pharmacokinetics, pharmacodynamics and toxicological properties of small molecules. Accordingly, a huge interest in this topic is constantly arising in the medicinal chemistry community. Focusing on heteroarenes, the synthetic access to these substitutions is guaranteed by a number of effective reactions such as Minisci-type reaction, photochemistry or electrochemistry C-H activation. The aim of this work is to analyze the rationale in using these groups in medicinal chemistry and highlight the currently available synthetic toolbox of C-H activation for their introduction on heteroarenes of pharmaceutical interest. A particular focus has been given to those procedures amenable to the late-stage functionalisation process.

Backbone-Enabled Peptide Macrocyclization through Late-Stage Palladium-Catalyzed C–H Activation

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 199-204 ◽  
Author(s):  
Zengbing Bai ◽  
Huan Wang
Keyword(s):  
Natural Products ◽  
Small Molecules ◽  
Late Stage ◽  
Cyclic Peptides ◽  
Medicinal Chemistry ◽  
Materials Science ◽  
Three Dimensional ◽  
Chemical Methods ◽  
New Methods ◽  
Palladium Catalyzed

Peptide macrocycles are widely used in fields ranging from medicinal chemistry to materials science. Efficient chemical methods for the synthesis of cyclic peptides with novel three-dimensional structures are highly desired to facilitate the development of this unique class of compounds. However, the range of methods available for constructing peptide macrocycles is limited compared with that for small molecules. We recently developed new methods for synthesizing highly constrained cyclic peptides with C–C crosslinks through Pd-catalyzed C–H activation reactions. These methods use endogenous backbone amides as directing groups and, therefore, have the potential for use in late-stage functionalization of peptide natural products.

scholarly journals Stage-Specific and Selective Delivery of Caged Azidosugars into the Intracellular Parasite Toxoplasma gondii by Using an Esterase-Ester Pair Technique

mSphere ◽  
2019 ◽  
Vol 4 (3) ◽  
Author(s):  
Tadakimi Tomita ◽  
Hua Wang ◽  
Peng Wu ◽  
Louis M. Weiss
Keyword(s):  
Toxoplasma Gondii ◽  
Small Molecules ◽  
Click Chemistry ◽  
Cell Biology ◽  
Host Cells ◽  
Intracellular Parasite ◽  
Content Type ◽  
Intracellular Parasites ◽  
Specific Manner ◽  
Selective Delivery

ABSTRACT Toxoplasma gondii is an obligate intracellular parasite that chronically infects up to a third of the human population. The parasites persist in the form of cysts in the central nervous system and serve as a reservoir for the reactivation of toxoplasmic encephalitis. The cyst wall is known to have abundant O-linked N-acetylgalactosamine glycans, but the existing metabolic labeling methods do not allow selective labeling of intracellular parasite glycoproteins without labeling of host glycans. In this study, we have integrated Cu(I)-catalyzed bioorthogonal click chemistry with a specific esterase-ester pair system in order to selectively deliver azidosugars to the intracellular parasites. We demonstrated that α-cyclopropyl modified GalNAz was cleaved by porcine liver esterase produced in the parasites but not in the host cells. Our proof-of-concept study demonstrates the feasibility and potential of this esterase-ester click chemistry approach for the selective delivery of small molecules in a stage-specific manner. IMPORTANCE Selective delivery of small molecules into intracellular parasites is particularly problematic due to the presence of multiple membranes and surrounding host cells. We have devised a method that can deliver caged molecules into an intracellular parasite, Toxoplasma gondii, that express an uncaging enzyme in a stage-specific manner without affecting host cell biology. This system provides a valuable tool for studying many intracellular parasites.

scholarly journals A chemoselective strategy for late-stage functionalization of complex small molecules with polypeptides and proteins

2018 ◽  
Vol 11 (1) ◽  
pp. 78-85 ◽  
Author(s):  
Daniel T. Cohen ◽  
Chi Zhang ◽  
Colin M. Fadzen ◽  
Alexander J. Mijalis ◽  
Liana Hie ◽  
...  
Keyword(s):  
Small Molecules ◽  
Late Stage
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