Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
6.7
4.6
Journals
Molecules
Special Issues
Old and New Multicomponent Reactions and Their Applications in Different...
molecules-logo
Submit to Molecules Review for Molecules Propose a Special Issue

Journal Menu

► Journal Menu

Journal Browser

► Journal Browser
share announcement

Old and New Multicomponent Reactions and Their Applications in Different Fields

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

Deadline for manuscript submissions: closed (30 September 2020) | Viewed by 28590

Special Issue Editors

Prof. Dr. Gian Cesare Tron

E-Mail Website
Guest Editor
Università degli Studi del Piemonte Orientale Amedeo Avogadro, Novara, Italy
Interests: medicinal chemistry; discovery of novel multicomponent reactions; anticancer research
Prof. Dr. Tracey Pirali

E-Mail Website
Guest Editor
Università degli Studi del Piemonte Orientale Amedeo Avogadro, Novara, Italy
Interests: drug discovery; multicomponent reactions; orphan drugs
Dr. Mariateresa Giustiniano

E-Mail Website
Guest Editor
Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131 Naples, Italy
Interests: medicinal chemistry; anticancer research; development of green synthetic methodologies
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The last decades of the twentieth century witnessed the explosion of multicomponent reactions (MCRs), which are now recognized by the entire chemist community as privileged reactions in drug discovery programs. Old multicomponent reactions such as Hantschz, Biginelli, and Bargellini have been used to discover nifedipine, monastrol, and fenofibrate, respectively. “Younger” reactions, such as Ugi, Gewald, and Petasis, have been exploited to re-synthesize, in a green fashion, old drugs such as lidocaine, olanzepin, clopidogrel, praziquantel, carfentanil, and to prepare novel scaffolds endowed with potent biological activity. Recently, even a nondrug-like transformation, the Passerini reaction, has been transformed into a potent weapon into medicinal chemists’ hands to prepare soft drugs. Overall, the MCRs discovered to date have allowed us to increase the accessible chemical space covered by these fascinating transformations, and to reach a number that is much larger than that of the currently known two-component reactions. In 2011, John Andraos counted more than 90 primary MCR types.1 However, this number skyrocketed when taking into consideration all the possible reported variations for each individual type, confirming MCRs as a useful tool for the identification of bioactive molecules in medicinal chemistry programs. It is worth noting that the MCR field is still growing, highlighting the uncovered potential for this concise and efficient synthetic tool.

The ambitious goal of this Special Issue is to show how the use of old and new multicomponent reactions in medicinal chemistry programs can play an important role, both for the lead discovery and the lead optimization stages, either in academic or industrial settings. Manuscripts in which molecules obtained with MCRs are able to perturb biological systems are welcomed in this Special Issue, as well as review articles where bioactive molecules derived by a named MCR are gathered and critically discussed.

1. John Andraos “The algebra of organic synthesis” 2011, CRC Press

Prof. Gian Cesare Tron
Prof. Tracey Pirali
Dr. Mariateresa Giustiniano
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

  • Multicomponent reactions
  • Medicinal chemistry
  • Biological activity
  • Drug discovery
  • Domino reactions

Published Papers (5 papers)

Download All Papers
Order results
Result details
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:

Research

Jump to: Review

15 pages, 4789 KiB  
Article
A One-Pot Three-Component Synthesis and Investigation of the In Vitro Mechanistic Anticancer Activity of Highly Functionalized Spirooxindole-Pyrrolidine Heterocyclic Hybrids
by Raju Suresh Kumar, Dhaifallah M. Al-thamili, Abdulrahman I. Almansour, Natarajan Arumugam and Faruq Mohammad
Molecules 2020, 25(23), 5581; https://doi.org/10.3390/molecules25235581 - 27 Nov 2020
Cited by 5 | Viewed by 1627
Abstract
With an aim to develop more effective and affordable anticancer agents possessing a unique mechanism of action, we designed and synthesized derivatives of spirooxindole-pyrrolidine heterocyclic hybrids in good yields through a one-pot three-component (3+2) cycloaddition strategy. The synthesized compounds were characterized thoroughly for [...] Read more.
With an aim to develop more effective and affordable anticancer agents possessing a unique mechanism of action, we designed and synthesized derivatives of spirooxindole-pyrrolidine heterocyclic hybrids in good yields through a one-pot three-component (3+2) cycloaddition strategy. The synthesized compounds were characterized thoroughly for the physicochemical properties by making use of FT-IR, NMR spectroscopy, and mass spectrometry. Further, these compounds have been evaluated for the influence of anticancer activity against HepG2 cells up to 200 µg/mL concentration. The highly active molecular scaffold was tested for the in-depth mechanistic studies, and it was found that the major pathway of cell death is apoptosis which occurs through the induction of reactive oxygen species followed by the involvement of caspases. Full article
(This article belongs to the Special Issue Old and New Multicomponent Reactions and Their Applications in Different Fields)
►▼ Show Figures

Figure 1

18 pages, 6177 KiB  
Article
Three-Component Reaction of Diamines with Triethyl Orthoformate and Diethyl Phosphite and Anti-Proliferative and Antiosteoporotic Activities of the Products
by Patrycja Petruczynik, Paweł Kafarski, Mateusz Psurski, Joanna Wietrzyk, Zdzisław Kiełbowicz, Jan Kuryszko and Ewa Chmielewska
Molecules 2020, 25(6), 1424; https://doi.org/10.3390/molecules25061424 - 20 Mar 2020
Cited by 3 | Viewed by 3499
Abstract
A three-component reaction between diamines (diaminobenzenes, diaminocyclohexanes, and piperazines), triethyl orthoformate, and diethyl phosphite was studied in some detail. In the case of 1,3- and 1,4-diamines and piperazines, products of the substitution of two amino moieties—the corresponding tetraphosphonic acids—were obtained. In the cases [...] Read more.
A three-component reaction between diamines (diaminobenzenes, diaminocyclohexanes, and piperazines), triethyl orthoformate, and diethyl phosphite was studied in some detail. In the case of 1,3- and 1,4-diamines and piperazines, products of the substitution of two amino moieties—the corresponding tetraphosphonic acids—were obtained. In the cases of 1,2-diaminobenzene, 1,2-diaminocyclohexanes and 1,2-diaminocyclohexenes, only one amino group reacted. This is most likely the result of the formation of hydrogen bonding between the phosphonate oxygen and a hydrogen of the adjacent amino group, which caused a decrease in the reactivity of the amino group. Most of the obtained compounds inhibited the proliferation of RAW 264.7 macrophages, PC-3 human prostate cancer cells, and MCF-7 human breast cancer cells, with 1, trans-7, and 16 showing broad nonspecific activity, which makes these compounds especially interesting in the context of anti-osteolytic treatment and the blocking of interactions and mutual activation of osteoclasts and tumor metastatic cells. These compounds exhibit similar activity to zoledronic acid and higher activity than incadronic acid, which were used as controls. However, studies of sheep with induced osteoporosis carried out with compound trans-7 did not support this assumption. Full article
(This article belongs to the Special Issue Old and New Multicomponent Reactions and Their Applications in Different Fields)
►▼ Show Figures

Graphical abstract

Review

Jump to: Research

20 pages, 14627 KiB  
Review
The 115 Years Old Multicomponent Bargellini Reaction: Perspectives and New Applications
by Marta Serafini, Ilaria Murgia, Mariateresa Giustiniano, Tracey Pirali and Gian Cesare Tron
Molecules 2021, 26(3), 558; https://doi.org/10.3390/molecules26030558 - 21 Jan 2021
Cited by 11 | Viewed by 5845
Abstract
Despite its uniqueness, the Bargellini multicomponent reaction remains barely known by the most part of chemists. This can be ascribed to the fact that this transformation has not been adequately reviewed in the classic books of named reactions in organic chemistry. Nevertheless, several [...] Read more.
Despite its uniqueness, the Bargellini multicomponent reaction remains barely known by the most part of chemists. This can be ascribed to the fact that this transformation has not been adequately reviewed in the classic books of named reactions in organic chemistry. Nevertheless, several works on this reaction have been carried out over the years, many of them were written in Italian in the period 1929–1966. In this review article we extensively cover, in a chronological order, the most important applications of the Bargellini reaction reported to date, with the hope that this knowledge-sharing will help chemists to properly use this multicomponent transformation and imagine novel reactivities based on it. Full article
(This article belongs to the Special Issue Old and New Multicomponent Reactions and Their Applications in Different Fields)
►▼ Show Figures

Figure 1

52 pages, 16015 KiB  
Review
Recent Advances in Palladium-Catalyzed Isocyanide Insertions
by Jurriën W. Collet, Thomas R. Roose, Bram Weijers, Bert U. W. Maes, Eelco Ruijter and Romano V. A. Orru
Molecules 2020, 25(21), 4906; https://doi.org/10.3390/molecules25214906 - 23 Oct 2020
Cited by 43 | Viewed by 5354
Abstract
Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose [...] Read more.
Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review highlights the advances made in this field over the past eight years. Full article
(This article belongs to the Special Issue Old and New Multicomponent Reactions and Their Applications in Different Fields)
►▼ Show Figures

Figure 1

71 pages, 6797 KiB  
Review
Synthesis of Biologically Active Molecules through Multicomponent Reactions
by Daniel Insuasty, Juan Castillo, Diana Becerra, Hugo Rojas and Rodrigo Abonia
Molecules 2020, 25(3), 505; https://doi.org/10.3390/molecules25030505 - 24 Jan 2020
Cited by 122 | Viewed by 11569
Abstract
Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many [...] Read more.
Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review. Full article
(This article belongs to the Special Issue Old and New Multicomponent Reactions and Their Applications in Different Fields)
►▼ Show Figures

Figure 1

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying articles 1-5
Back to TopTop