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      A review on recent developments of indole-containing antiviral agents

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          Abstract

          Indole represents one of the most important privileged scaffolds in drug discovery. Indole derivatives have the unique property of mimicking the structure of peptides and to bind reversibly to enzymes, which provide tremendous opportunities to discover novel drugs with different modes of action. There are seven indole-containing commercial drugs in the Top-200 Best Selling Drugs by US Retail Sales in 2012. There are also an amazing number of approved indole-containing drugs in the market as well as compounds currently going through different clinical phases or registration statuses. This review focused on the recent development of indole derivatives as antiviral agents with the following objectives: 1) To present one of the most comprehensive listings of indole antiviral agents, drugs on market or compounds in clinical trials; 2) To focus on recent developments of indole compounds (including natural products) and their antiviral activities, summarize the structure property, hoping to inspire new and even more creative approaches; 3) To offer perspectives on how indole scaffolds as a privileged structure might be exploited in the future.

          Graphical abstract

          The recent developments of indole compounds for antiviral drug discovery were comprehensively reviewed.

          Highlights

          • •

            The recent development of indole derivatives as antiviral agents was reviewed.

          • •

            A comprehensive list of indole antiviral agents on market or in clinical trials was provided.

          • •

            The future of indole-based antiviral agents was prospected.

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          Most cited references114

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          The exploration of macrocycles for drug discovery--an underexploited structural class.

          Edward Driggers, Stephen Hale, Jinbo Lee … (2008)
          Macrocyclic natural products have evolved to fulfil numerous biochemical functions, and their profound pharmacological properties have led to their development as drugs. A macrocycle provides diverse functionality and stereochemical complexity in a conformationally pre-organized ring structure. This can result in high affinity and selectivity for protein targets, while preserving sufficient bioavailability to reach intracellular locations. Despite these valuable characteristics, and the proven success of more than 100 marketed macrocycle drugs derived from natural products, this structural class has been poorly explored within drug discovery. This is in part due to concerns about synthetic intractability and non-drug-like properties. This Review describes the growing body of data in favour of macrocyclic therapeutics, and demonstrates that this class of compounds can be both fully drug-like in its properties and readily prepared owing to recent advances in synthetic medicinal chemistry.
          Article 0 comments Cited 263 times – based on 0 reviews     Review now
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            Privileged scaffolds for library design and drug discovery.

            Matthew E Welsch, Scott A. Snyder, Brent Stockwell (2010)
            This review explores the concept of using privileged scaffolds to identify biologically active compounds through building chemical libraries. We hope to accomplish three main objectives: to provide one of the most comprehensive listings of privileged scaffolds; to reveal through four selected examples the present state of the art in privileged scaffold library synthesis (in hopes of inspiring new and even more creative approaches); and also to offer some thoughts on how new privileged scaffolds might be identified and exploited. Copyright 2010 Elsevier Ltd. All rights reserved.
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              Conversion of tryptophan to indole-3-acetic acid by TRYPTOPHAN AMINOTRANSFERASES OF ARABIDOPSIS and YUCCAs in Arabidopsis.

              Christina S Won, Xiangling Shen, Kiyoshi Mashiguchi … (2011)
              Auxin is an essential hormone, but its biosynthetic routes in plants have not been fully defined. In this paper, we show that the TRYPTOPHAN AMINOTRANSFERASE OF ARABIDOPSIS (TAA) family of amino transferases converts tryptophan to indole-3-pyruvate (IPA) and that the YUCCA (YUC) family of flavin monooxygenases participates in converting IPA to indole-3-acetic acid, the main auxin in plants. Both the YUCs and the TAAs have been shown to play essential roles in auxin biosynthesis, but it has been suggested that they participate in two independent pathways. Here, we show that all of the taa mutant phenotypes, including defects in shade avoidance, root resistance to ethylene and N-1-naphthylphthalamic acid (NPA), are phenocopied by inactivating YUC genes. On the other hand, we show that the taa mutants in several known auxin mutant backgrounds, including pid and npy1, mimic all of the well-characterized developmental defects caused by combining yuc mutants with the auxin mutants. Furthermore, we show that overexpression of YUC1 partially suppresses the shade avoidance defects of taa1 and the sterile phenotypes of the weak but not the strong taa mutants. In addition, we discovered that the auxin overproduction phenotypes of YUC overexpression lines are dependent on active TAA genes. Our genetic data show that YUC and TAA work in the same pathway and that YUC is downstream of TAA. The yuc mutants accumulate IPA, and the taa mutants are partially IPA-deficient, indicating that TAAs are responsible for converting tryptophan to IPA, whereas YUCs play an important role in converting IPA to indole-3-acetic acid.
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                Author and article information

                Contributors
                Qiong Chen
                Guang-Fu Yang
                Journal
                Journal ID (nlm-ta): Eur J Med Chem
                Journal ID (iso-abbrev): Eur J Med Chem
                Title: European Journal of Medicinal Chemistry
                Publisher: Elsevier Masson SAS.
                ISSN (Print): 0223-5234
                ISSN (Electronic): 1768-3254
                Publication date PMC-release: 23 October 2014
                Publication date (Print): 7 January 2015
                Publication date (Electronic): 23 October 2014
                Volume: 89
                Pages: 421-441
                Affiliations
                [a ]Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR China
                [b ]Collaborative Innovation Center of Chemical Science and Engineering, Tianjing 30071, PR China
                Author notes
                [∗ ]Corresponding authors. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR China. qchen@ 123456mail.ccnu.edu.cn gfyang@ 123456mail.ccnu.edu.cn
                Article
                Publisher ID: S0223-5234(14)00993-3
                DOI: 10.1016/j.ejmech.2014.10.065
                PMC ID: 7115707
                PubMed ID: 25462257
                SO-VID: 67646fa1-111c-488e-98b6-72fab00ce01e
                Copyright © Copyright © 2014 Elsevier Masson SAS. All rights reserved.
                License:

                Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.

                History
                Date received : 7 September 2014
                Date revision received : 20 October 2014
                Date accepted : 22 October 2014
                Categories
                Subject: Article

                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: indole,antiviral activity,entry and fusion inhibitor,reverse transcriptase inhibitor,integrase inhibitor,protease inhibitor,polymerase inhibitor,natural product
                Data availability:
                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: indole, antiviral activity, entry and fusion inhibitor, reverse transcriptase inhibitor, integrase inhibitor, protease inhibitor, polymerase inhibitor, natural product

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