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The Design and Synthesis of Indole Derivatives and Their Metal Complexes

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

Deadline for manuscript submissions: 31 October 2024 | Viewed by 3807

Special Issue Editor

Dr. Barbara Morzyk-Ociepa

E-Mail Website
Guest Editor
Institute of Chemistry, Faculty of Science and Technology, Jan Dlugosz University, Armii Krajowej 13/15, 42-200 Czestochowa, Poland
Interests: coordination chemistry; structural chemistry; spectroscopy, in particular vibrational spectroscopy; computational chemistry; heterocycles as ligands
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Indoles are widely distributed in nature. These heterocycles, depending on the type of substituent and its position in the indole rings, can display different properties and applications. Therefore, the design and synthesis of indole derivatives and their metal complexes are constantly discussed by researchers.

This Special Issue aims to showcase new research and review works developed in the field of title compounds, with the aim of making an important contribution to the community. Studies on both indole derivatives, their metal complexes, and DFT calculations, also including the potential application of these compounds, are welcome.

Dr. Barbara Morzyk-Ociepa
Guest Editor

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

  • heterocyclic compounds
  • indole
  • synthetic method
  • natural product
  • biological activity
  • metal complex
  • DFT calculations

Published Papers (4 papers)

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Research

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15 pages, 3050 KiB  
Article
Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-ray Diffraction, Infrared Spectroscopy, and DFT Calculations
by Julia Polak, Julia Bąkowicz and Barbara Morzyk-Ociepa
Molecules 2024, 29(10), 2201; https://doi.org/10.3390/molecules29102201 - 8 May 2024
Viewed by 468
Abstract
This study presents a new 5-methoxy-1H-indole-2-carboxylic acid (MI2CA) polymorph investigated by single-crystal X-ray diffraction, infrared spectroscopy, and density functional theory (ωB97X-D) calculations employing two basis sets (6-31++G(d,p) and aug-cc-pVTZ). The compound crystallizes in the monoclinic system, space group P21/c [...] Read more.
This study presents a new 5-methoxy-1H-indole-2-carboxylic acid (MI2CA) polymorph investigated by single-crystal X-ray diffraction, infrared spectroscopy, and density functional theory (ωB97X-D) calculations employing two basis sets (6-31++G(d,p) and aug-cc-pVTZ). The compound crystallizes in the monoclinic system, space group P21/c (a = 4.0305(2) Å, b = 13.0346(6) Å, c = 17.2042(9) Å, β = 91.871(5)°, Z = 4). In the crystalline structure, the formation of cyclic dimers via double hydrogen bonds O−H⋯O between MI2CA molecules was observed. Interactions between the NH groups of the indole rings and the adjacent methoxy groups, as well as C–H⋯O contacts, significantly influence the spatial arrangement of molecules. The results from DFT calculations, including dimeric and trimeric structures, agree well with the experimental structural and spectroscopic data. Analysis of the infrared spectra confirms the conclusions drawn from X-ray diffraction studies and reveals differences between the IR spectra of the newly obtained polymorph and that reported earlier in the literature. This comprehensive study sheds some light on the MI2CA polymorphism and is important for a potential pharmacological applications of this compound. Full article
(This article belongs to the Special Issue The Design and Synthesis of Indole Derivatives and Their Metal Complexes)
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14 pages, 5454 KiB  
Communication
An Operationally Simple Approach to Indole Derivatives from 2-Alkenylanilines Utilizing an Oxidation–Intramolecular Cyclization–Elimination Sequence
by Lauren N. Hines, Jacob R. King, Alex C. Atwood, Rachel M. Chapman, Matthew B. Griffey, Christine R. Tutwiler and Christopher Jon Monceaux
Molecules 2023, 28(24), 7968; https://doi.org/10.3390/molecules28247968 - 6 Dec 2023
Viewed by 661
Abstract
Herein we describe a novel route to indole derivatives from a variety of N-substituted 2-alkenylanilines. This route features three operationally simple steps: (1) oxidation to convert N-substituted 2-alkenylanilines into epoxide intermediates, (2) intramolecular cyclization, and (3) the acid-catalyzed elimination of water. Full article
(This article belongs to the Special Issue The Design and Synthesis of Indole Derivatives and Their Metal Complexes)
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12 pages, 1301 KiB  
Article
Base-Catalyzed Nucleophilic Addition Reaction of Indoles with Vinylene Carbonate: An Approach to Synthesize 4-Indolyl-1,3-dioxolanones
by Xia Chen, Xiao-Yu Zhou and Ming Bao
Molecules 2023, 28(21), 7450; https://doi.org/10.3390/molecules28217450 - 6 Nov 2023
Viewed by 951
Abstract
The N-functionalized indole is a privileged structural framework in a wide range of bioactive molecules. The nucleophilic addition between indoles with vinylene carbonate proceeded smoothly in the presence of K2CO3 as the catalyst to produce novel indolyl-containing skeletons and [...] Read more.
The N-functionalized indole is a privileged structural framework in a wide range of bioactive molecules. The nucleophilic addition between indoles with vinylene carbonate proceeded smoothly in the presence of K2CO3 as the catalyst to produce novel indolyl-containing skeletons and 4-indolyl-1,3-dioxolanones in satisfactory to excellent yields (up to >97% yield). Various synthetically useful functional groups, such as halogen atoms, cyano, nitro, and methoxycarbonyl groups, remained intact during the regioselective N-H addition reactions. The developed catalytic system also could accommodate 2-naphthalenol to achieve the target O-H additive product in good yield. Full article
(This article belongs to the Special Issue The Design and Synthesis of Indole Derivatives and Their Metal Complexes)
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Review

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34 pages, 15183 KiB  
Review
Indole-Containing Metal Complexes and Their Medicinal Applications
by Zahra Kazemi, Hadi Amiri Rudbari, Nakisa Moini, Fariborz Momenbeik, Federica Carnamucio and Nicola Micale
Molecules 2024, 29(2), 484; https://doi.org/10.3390/molecules29020484 - 18 Jan 2024
Cited by 1 | Viewed by 1163
Abstract
Indole is an important element of many natural and synthetic molecules with significant biological activity. Nonetheless, the co-presence of transitional metals in organic scaffold may represent an important factor in the development of effective medicinal agents. This review covers some of the latest [...] Read more.
Indole is an important element of many natural and synthetic molecules with significant biological activity. Nonetheless, the co-presence of transitional metals in organic scaffold may represent an important factor in the development of effective medicinal agents. This review covers some of the latest and most relevant achievements in the biological and pharmacological activity of important indole-containing metal complexes in the area of drug discovery. Full article
(This article belongs to the Special Issue The Design and Synthesis of Indole Derivatives and Their Metal Complexes)
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: Indole-based metal complexes and their medicinal applications
Authors: Zahra Kazem; Hadi Amiri Rudbari; Fariborz Momenbeik; Nakisa Moini; Federica Carnamucio; Nicola Micale
Affiliation: University of Isfahan, Iran; University of Alzahra, Iran; University of Messina, Italy
Abstract: The indole nucleus is an important element of many natural and synthetic molecules with significant biological activity. Nonetheless, the co-presence of transitional metals in organic scaffold may represent an important factor in the development of effective medicinal agents. This review covers some of the relevant and recent achievements in the biological, chemical and pharmacological activity of important indole-based metal complexes in the areas of drug discovery.

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