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Click Chemistry in Organic Synthesis
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Click Chemistry in Organic Synthesis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 January 2023) | Viewed by 9171

Special Issue Editors

Dr. Sergey Timofeev

E-Mail Website
Guest Editor
A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russia
Interests: polyhedral boron hydrides; cobalt/iron bis(dicarbollide); closo-dodecaborate; nido-carborane; nucleosides and nucleotides; cholesterol; BNCT; click-chemistry
Dr. Anna A. Druzina

E-Mail Website
Guest Editor
A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russia
Interests: polyhedral boron hydrides; cobalt/iron bis(dicarbollide); closo-dodecaborate; nido-carborane; nucleosides and nucleotides; cholesterol; BNCT; click-chemistry

Special Issue Information

Dear Colleagues,

It is difficult to imagine the modern chemistry of organic and organoelement compounds without such a powerful and widespread chemical tool as the click reaction. Chemists today use click reactions in various fields—bioorganic and medical, polymer chemistry, molecular biology, surface chemistry, and materials science.

Click chemistry is a recent strategy that has been employed to functionalize chemical structures. Its described chemical processes are adapted for the rapid and reliable production of chemicals by combining individual building blocks with each other.

One-pot click reactions generate minimal, harmless byproducts. They are characterized by a high thermodynamic driving force that quickly and irreversibly leads to a high yield of a single reaction product, with reliable high reaction specificity and work in both small- and large-scale applications. This is particularly important because modern organic chemistry requires a redirection toward those main principles. The applications of click reactions in organic chemistry are numerous.

Thus, we invite chemists to publish their original results in this special Issue of Molecules titled “Click Chemistry in Organic Synthesis”. In this Special Issue, comprehensive reviews, original research articles, and short communications are presented that deal with the potential of click reactions in modern organic chemistry.

Dr. Sergey Timofeev
Dr. Anna A. Druzina
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • click chemistry
  • bioconjugation
  • cycloaddition
  • 1,2,3-triazole
  • modular synthesis
  • one-pot synthesis
  • stereoselective synthesis

Published Papers (5 papers)

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Research

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15 pages, 1151 KiB  
Article
Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity
by Sanami Numai, Risako Yoto, Masataka Kimura, Eric E. Simanek and Yoshikazu Kitano
Molecules 2023, 28(1), 131; https://doi.org/10.3390/molecules28010131 - 23 Dec 2022
Cited by 3 | Viewed by 1666
Abstract
Dendrimers are attractive macromolecules for a broad range of applications owing to their well-defined shapes and dimensions, highly branched and globular architectures, and opportunities for exploiting multivalency. Triazine dendrimers in particular offer advantages such as ease of synthesis, stability, well-defined spherical structure, multivalency, [...] Read more.
Dendrimers are attractive macromolecules for a broad range of applications owing to their well-defined shapes and dimensions, highly branched and globular architectures, and opportunities for exploiting multivalency. Triazine dendrimers in particular offer advantages such as ease of synthesis, stability, well-defined spherical structure, multivalency, potential to achieve acceptable drug loadings, and low polydispersity. In this study, the potential utility of alkyne-azide “click” cycloadditions of first-, second-, and third-generation triazine dendrimers containing three or six alkynyl groups with benzyl azide was examined using copper catalysts. “Click-and-grow” and “grow-then-click” strategies were employed. For the first- and second- generation dendrimers, the desired triazole derivatives were obtained in high yields and purified by simple reprecipitation without column chromatography; however, some difficulties were observed in the preparation of third-generation dendrimers. The desired reaction proceeded under microwave irradiation as well as with simple heating. This click chemistry can be utilized for various melamine dendrimers that are fabricated with other amine linkers. Full article
(This article belongs to the Special Issue Click Chemistry in Organic Synthesis)
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Scheme 1

19 pages, 6562 KiB  
Article
Design, Synthesis and Biological Evaluation of New Carbohydrate-Based Coumarin Derivatives as Selective Carbonic Anhydrase IX Inhibitors via “Click” Reaction
by Naying Chu, Yitong Wang, Hao Jia, Jie Han, Xiaoyi Wang and Zhuang Hou
Molecules 2022, 27(17), 5464; https://doi.org/10.3390/molecules27175464 - 25 Aug 2022
Cited by 7 | Viewed by 1771
Abstract
In this work, we designed a series of new carbohydrate-based coumarin carbonic anhydrase IX inhibitors by using 1,2,3-triazoles as linker. Next, these designed compounds were synthesized by the optimized one-pot click chemistry reaction condition. Subsequently, these target compounds were assayed for the inhibition [...] Read more.
In this work, we designed a series of new carbohydrate-based coumarin carbonic anhydrase IX inhibitors by using 1,2,3-triazoles as linker. Next, these designed compounds were synthesized by the optimized one-pot click chemistry reaction condition. Subsequently, these target compounds were assayed for the inhibition of three carbonic anhydrase isoforms (CA I, CA II and CA IX). Intriguingly, all the compounds showed better CA IX inhibitory activity than initial coumarin fragments. Among them, compound 10a (IC50: 11 nM) possessed the most potent CA IX inhibitory activity, which was more potent than the reference drug acetazolamide (IC50: 30 nM). Notably, compound 10a showed 3018-fold, 1955-fold selectivity relative to CA I and CA II, respectively. Meanwhile, representative compounds could reduce tumor cell viability and the extracellular acidification in HT-29 and MDA-MB-231 cancer cell lines. Even more interestingly, our target compounds had no apparent cytotoxicity toward MCF-10A cell line. In addition, the in vitro stability assays also indicated our developed compounds possessed good liver microsomal metabolic stabilities and plasma stability. Furthermore, representative compounds revealed relatively low hERG cardiac toxicity and acute toxicity. Furthermore, docking studies were carried out to understand the interactions of our target compounds with the protein target CA IX. Collectively, our results suggest that compound 10a, as a selective CA IX inhibitor, could be an important lead compound for further optimization and development as an anticancer agent. Full article
(This article belongs to the Special Issue Click Chemistry in Organic Synthesis)
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14 pages, 3067 KiB  
Article
Optical Properties of New Third-Order Nonlinear Materials Modified by Click Chemistry
by Yuzhen Zhao, Zhenhua Li, Qing Li, Yang Zhao, Ruijuan Yao, Cheng Ma, Yongming Zhang and Dong Wang
Molecules 2022, 27(15), 5006; https://doi.org/10.3390/molecules27155006 - 6 Aug 2022
Cited by 4 | Viewed by 1506
Abstract
A high-yielding click reaction was used to synthesize a series of highly conjugated, symmetrical, as well as asymmetrical compounds with a benzene core. Cyclic voltammetry and ultraviolet/visible absorption spectroscopy were carried out, and proved that the side groups of the benzene derivatives played [...] Read more.
A high-yielding click reaction was used to synthesize a series of highly conjugated, symmetrical, as well as asymmetrical compounds with a benzene core. Cyclic voltammetry and ultraviolet/visible absorption spectroscopy were carried out, and proved that the side groups of the benzene derivatives played an important role in the energy gaps, and affected the third-order non-linear optical response. The maximum absorption wavelength of the series of benzene derivatives showed an obvious red-shift. Moreover, the addition of resilient electron-withdrawing groups significantly narrowed the energy levels as compared with precursors. The third-order nonlinear properties of this benzene derivative were tested by the Z-scan technique. The expected properties of this series of molecules were obtained, and it was found that the series of molecules undergoes a transition from reverse saturable absorption to saturable absorption, which has certain reference significance for a nonlinear optical field. Full article
(This article belongs to the Special Issue Click Chemistry in Organic Synthesis)
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Figure 1

17 pages, 2034 KiB  
Article
Regioselective One-Pot Synthesis, Biological Activity and Molecular Docking Studies of Novel Conjugates N-(p-Aryltriazolyl)-1,5-benzodiazepin-2-ones as Potent Antibacterial and Antifungal Agents
by Asma Nsira, Hasan Mtiraoui, Sami Chniti, Hanan Al-Ghulikah, Rafik Gharbi and Moncef Msaddek
Molecules 2022, 27(13), 4015; https://doi.org/10.3390/molecules27134015 - 22 Jun 2022
Cited by 4 | Viewed by 1509
Abstract
Novel 1,2,3-triazolo-linked-1,5-benzodiazepinones were designed and synthesized via a Cu(I)-catalyzed 1,3-dipolar alkyne-azide coupling reaction (CuAAC). The chemical structures of these compounds were confirmed by 1H NMR, 13C NMR, HMBC, HRMS, and elemental analysis. The compounds were screened for their in vitro antibacterial [...] Read more.
Novel 1,2,3-triazolo-linked-1,5-benzodiazepinones were designed and synthesized via a Cu(I)-catalyzed 1,3-dipolar alkyne-azide coupling reaction (CuAAC). The chemical structures of these compounds were confirmed by 1H NMR, 13C NMR, HMBC, HRMS, and elemental analysis. The compounds were screened for their in vitro antibacterial and antifungal activities. Several compounds exhibited good to moderate activities compared to those of established standard drugs. Furthermore, the binding interactions of these active analogs were confirmed through molecular docking. Full article
(This article belongs to the Special Issue Click Chemistry in Organic Synthesis)
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Review

Jump to: Research

20 pages, 4957 KiB  
Review
Advances in the Synthesis of Fused 1,2,3-Triazoles via a MCR-Intramolecular Azide-Alkyne Cycloaddition Approach
by Rahul P, Joice Thomas, Wim Dehaen and Jubi John
Molecules 2023, 28(1), 308; https://doi.org/10.3390/molecules28010308 - 30 Dec 2022
Cited by 6 | Viewed by 2026
Abstract
The present review narrates several reports which deal with the synthesis of fused 1,2,3-triazole containing scaffolds following a sequential multicomponent reaction (MCR)—intramolecular azide-alkyne cycloaddition (IAAC) approach. The reviewed reactions were cleverly designed so as to incorporate azide and alkyne functionalities in the MCR [...] Read more.
The present review narrates several reports which deal with the synthesis of fused 1,2,3-triazole containing scaffolds following a sequential multicomponent reaction (MCR)—intramolecular azide-alkyne cycloaddition (IAAC) approach. The reviewed reactions were cleverly designed so as to incorporate azide and alkyne functionalities in the MCR product which was then subjected to IAAC. The review is divided into two sections based on the number of components in the multicomponent reaction. We have aimed at a critical discussion and also have highlighted either advantages or disadvantages of each methodology. Full article
(This article belongs to the Special Issue Click Chemistry in Organic Synthesis)
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