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Indole Derivatives: Synthesis and Application II
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Indole Derivatives: Synthesis and Application II

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

Deadline for manuscript submissions: closed (31 July 2021) | Viewed by 18765

Special Issue Editors

Prof. Dr. David StC Black

E-Mail Website
Guest Editor
School of Chemistry, University of New South Wales (UNSW Sydney), Sydney, NSW 2052, Australia
Interests: heterocyclic chemistry; synthetic organic chemistry; natural products chemistry; new indole-based scaffolds; synthetic methodologies
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Naresh Kumar

E-Mail Website
Guest Editor
School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia
Interests: biologically active molecules; medicinal chemistry; organic chemical synthesis; peptidomimetics; novel antimicrobials; biomaterials
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Indoles continue to generate new chemistry as a result of their potential for reactivity and also for their central role in biological chemistry through the involvement of tryptophan. This Special Issue therefore seeks to cover a broad range of interests that include new reactivity patterns, new methods for indole transformations, the synthesis of indoles with additional fused rings, new synthetic routes to the indole framework, indole metal complexes, and aspects of medicinal chemistry incorporating indole systems. The aim of the Special Issue is to be inclusive and especially to document new and unusual features of indole chemistry.

Prof. Dr. David StC Black
Prof. Dr. Naresh Kumar
Guest Editors

Manuscript Submission Information

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Keywords

  • Organic synthesis
  • Natural products
  • Heterocyclic compounds
  • Ring cyclisations
  • Metal complexes
  • Organometallic compounds
  • Polymers
  • Molecular rearrangements
  • Biological activity

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Related Special Issue

Published Papers (6 papers)

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Research

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13 pages, 2238 KiB  
Article
Design, Synthesis, and In Vitro Evaluation of Novel Indolyl DiHydropyrazole Derivatives as Potential Anticancer Agents
by Katharigatta N. Venugopala, Mohammed Habeebuddin, Bandar E. Aldhubiab and Afzal Haq Asif
Molecules 2021, 26(17), 5235; https://doi.org/10.3390/molecules26175235 - 29 Aug 2021
Cited by 5 | Viewed by 2083
Abstract
Indoles derived from both natural sources or artificial synthetic methods have been known to interact with aryl hydrocarbon receptors (AhR), and exhibit anticancer activity. In light of these attractive properties, a series of hybrid molecules with structural features of indoles, i.e., those bearing [...] Read more.
Indoles derived from both natural sources or artificial synthetic methods have been known to interact with aryl hydrocarbon receptors (AhR), and exhibit anticancer activity. In light of these attractive properties, a series of hybrid molecules with structural features of indoles, i.e., those bearing a pyrazoline nucleus, were evaluated for their enhanced anticancer activity. The designed molecules were subjected to molecular docking in order to screen for potential AhR interacting compounds, and the identified indolyl dihydropyrazole derivatives were synthesized. The synthesized compounds were characterized, and their cytotoxicity was evaluated against four human cancer cell lines using the MTT assay. Based on the Glide g-score, H-bonding interactions and bonding energy of 20 candidate molecules were selected for further analysis from the 64 initially designed molecules. These candidate molecules have shown promising anti-proliferative activity against the cell lines tested. Among these candidate molecules, the compounds with hydroxy phenyl substitution on the pyrazoline ring have shown potent activity across all the tested cell lines. The designed scaffold was proven effective for screening potential candidate molecules with anticancer properties, and may be further optimized structurally for yielding the ideal anti-tumorigenic compound for the treatment of various cancers. Full article
(This article belongs to the Special Issue Indole Derivatives: Synthesis and Application II)
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31 pages, 2709 KiB  
Article
Synthesis and Antiplasmodial Activity of Bisindolylcyclobutenediones
by Duc Hoàng Lande, Abed Nasereddin, Arne Alder, Tim W. Gilberger, Ron Dzikowski, Johann Grünefeld and Conrad Kunick
Molecules 2021, 26(16), 4739; https://doi.org/10.3390/molecules26164739 - 5 Aug 2021
Cited by 5 | Viewed by 2686
Abstract
Malaria is one of the most dangerous infectious diseases. Because the causative Plasmodium parasites have developed resistances against virtually all established antimalarial drugs, novel antiplasmodial agents are required. In order to target plasmodial kinases, novel N-unsubstituted bisindolylcyclobutenediones were designed as analogs to [...] Read more.
Malaria is one of the most dangerous infectious diseases. Because the causative Plasmodium parasites have developed resistances against virtually all established antimalarial drugs, novel antiplasmodial agents are required. In order to target plasmodial kinases, novel N-unsubstituted bisindolylcyclobutenediones were designed as analogs to the kinase inhibitory bisindolylmaleimides. Molecular docking experiments produced favorable poses of the unsubstituted bisindolylcyclobutenedione in the ATP binding pocket of various plasmodial protein kinases. The synthesis of the title compounds was accomplished by sequential Friedel-Crafts acylation procedures. In vitro screening of the new compounds against transgenic NF54-luc P. falciparum parasites revealed a set of derivatives with submicromolar activity, of which some displayed a reasonable selectivity profile against a human cell line. Although the molecular docking studies suggested the plasmodial protein kinase PfGSK-3 as the putative biological target, the title compounds failed to inhibit the isolated enzyme in vitro. As selective submicromolar antiplasmodial agents, the N-unsubstituted bisindolylcyclobutenediones are promising starting structures in the search for antimalarial drugs, albeit for a rational development, the biological target addressed by these compounds has yet to be identified. Full article
(This article belongs to the Special Issue Indole Derivatives: Synthesis and Application II)
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13 pages, 1068 KiB  
Article
Design, Synthesis, and Antimicrobial Activity of Certain New Indole-1,2,4 Triazole Conjugates
by Reem I. Al-Wabli, Mona A. Alsulami, Sarah I. Bukhari, Nadine M. S. Moubayed, Maha S. Al-Mutairi and Mohamed I. Attia
Molecules 2021, 26(8), 2292; https://doi.org/10.3390/molecules26082292 - 15 Apr 2021
Cited by 20 | Viewed by 2728
Abstract
The increasing prevalence of microbial infections and the emergence of resistance to the currently available antimicrobial drugs urged the development of potent new chemical entities with eminent pharmacokinetic and/or pharmacodynamic profiles. Thus, a series of new indole-triazole conjugates 6a-u was designed and synthesized [...] Read more.
The increasing prevalence of microbial infections and the emergence of resistance to the currently available antimicrobial drugs urged the development of potent new chemical entities with eminent pharmacokinetic and/or pharmacodynamic profiles. Thus, a series of new indole-triazole conjugates 6a-u was designed and synthesized to be assessed as new antimicrobial candidates using the diameter of the inhibition zone and minimum inhibitory concentration assays against certain microbial strains. Their in vitro antibacterial evaluation revealed good to moderate activity against most of the tested Gram-negative strains with diameter of the inhibition zone (DIZ) values in the range of 11–15 mm and minimum inhibition concentration (MIC) values around 250 µg/mL. Meanwhile, their in vitro antifungal evaluation demonstrated a potent activity against Candida tropicalis with MIC value as low as 2 µg/mL for most of the tested compounds. Moreover, compound 6f is the most potent congener with an MIC value of 2 µg/mL against Candida albicans. Full article
(This article belongs to the Special Issue Indole Derivatives: Synthesis and Application II)
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16 pages, 9444 KiB  
Article
Bimetallic Iron–Palladium Catalyst System as a Lewis-Acid for the Synthesis of Novel Pharmacophores Based Indole Scaffold as Anticancer Agents
by Mohammad Shahidul Islam, M. Ali, Abdullah Mohammed Al-Majid, Abdullah Saleh Alamary, Saeed Alshahrani, Sammer Yousuf, Muhammad Iqbal Choudhary and Assem Barakat
Molecules 2021, 26(8), 2212; https://doi.org/10.3390/molecules26082212 - 12 Apr 2021
Cited by 5 | Viewed by 2281
Abstract
The Friedel–Crafts reaction between substituted indoles as nucleophiles with chalcones-based benzofuran and benzothiophene scaffolds was carried out by employing a highly efficient bimetallic iron–palladium catalyst system. This catalytic approach produced the desired bis-heteroaryl products with low catalyst loading, a simple procedure, and [...] Read more.
The Friedel–Crafts reaction between substituted indoles as nucleophiles with chalcones-based benzofuran and benzothiophene scaffolds was carried out by employing a highly efficient bimetallic iron–palladium catalyst system. This catalytic approach produced the desired bis-heteroaryl products with low catalyst loading, a simple procedure, and with acceptable yield. All synthesized indole scaffolds 3a–3s were initially evaluated for their cytotoxic effect against human fibroblast BJ cell lines and appeared to be non-cytotoxic. All non-cytotoxic compounds 3a–3s were then evaluated for their anticancer activities against cervical cancer HeLa, prostate cancer PC3, and breast cancer MCF-7 cell lines, in comparison to standard drug doxorubicin, with IC50 values 1.9 ± 0.4 µM, 0.9 ± 0.14 µM and 0.79 ± 0.05 µM, respectively, and appeared to be moderate to weak anticancer agents. Fluoro-substituted chalcone moiety-containing compounds, 3b appeared to be the most active member of the series against cervical HeLa (IC50 = 8.2 ± 0.2 µM) and breast MCF-7 cancer cell line (IC50 = 12.3 ± 0.04 µM), whereas 6-fluroindol-4-bromophenyl chalcone-containing compound 3e (IC50 = 7.8 ± 0.4 µM) appeared to be more active against PC3 prostate cancer cell line. Full article
(This article belongs to the Special Issue Indole Derivatives: Synthesis and Application II)
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8 pages, 769 KiB  
Article
Grindstone Chemistry: Design, One-Pot Synthesis, and Promising Anticancer Activity of Spiro[acridine-9,2′-indoline]-1,3,8-trione Derivatives against the MCF-7 Cancer Cell Line
by Perumal Gobinath, Ponnusamy Packialakshmi, Ali Daoud, Saud Alarifi, Akbar Idhayadhulla and Surendrakumar Radhakrishnan
Molecules 2020, 25(24), 5862; https://doi.org/10.3390/molecules25245862 - 11 Dec 2020
Cited by 11 | Viewed by 2648 | Correction
Abstract
In this study, the synthesis of one-pot 10-phenyl-3,4,6,7-tetrahydro-1H-spiro [acridine-9,2′-indoline]-1,3,8-trione derivatives was achieved via a four-component cyclocondensation reaction, which was carried out in solvent-free conditions, and using p-toluenesulfonic acid (p-TSA) as a catalyst. The product was confirmed by FT-IR, 1H-NMR, 13 [...] Read more.
In this study, the synthesis of one-pot 10-phenyl-3,4,6,7-tetrahydro-1H-spiro [acridine-9,2′-indoline]-1,3,8-trione derivatives was achieved via a four-component cyclocondensation reaction, which was carried out in solvent-free conditions, and using p-toluenesulfonic acid (p-TSA) as a catalyst. The product was confirmed by FT-IR, 1H-NMR, 13C-NMR, mass spectra, and elemental analysis. Furthermore, the anticancer activity was screened for all compounds. Among these compounds, compound 1c was more effective (GI50 0.01 µm) against MCF-7 cancer cell lines than standard and other compounds. Therefore, the objective of this study was achieved with a few promising molecules having been demonstrated to be potential anticancer agents. Full article
(This article belongs to the Special Issue Indole Derivatives: Synthesis and Application II)
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Review

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42 pages, 10432 KiB  
Review
Recent Progress Concerning the N-Arylation of Indoles
by Petr Oeser, Jakub Koudelka, Artem Petrenko and Tomáš Tobrman
Molecules 2021, 26(16), 5079; https://doi.org/10.3390/molecules26165079 - 22 Aug 2021
Cited by 16 | Viewed by 4919
Abstract
This review summarizes the current state-of-the-art procedures in terms of the preparation of N-arylindoles. After a short introduction, the transition-metal-free procedures available for the N-arylation of indoles are briefly discussed. Then, the nickel-catalyzed and palladium-catalyzed N-arylation of indoles are both [...] Read more.
This review summarizes the current state-of-the-art procedures in terms of the preparation of N-arylindoles. After a short introduction, the transition-metal-free procedures available for the N-arylation of indoles are briefly discussed. Then, the nickel-catalyzed and palladium-catalyzed N-arylation of indoles are both discussed. In the next section, copper-catalyzed procedures for the N-arylation of indoles are described. The final section focuses on recent findings in the field of biologically active N-arylindoles. Full article
(This article belongs to the Special Issue Indole Derivatives: Synthesis and Application II)
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