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      A Facile Synthesis of N-H- and N-Substituted Acridine-1,8-diones under Sonic Condition

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      Author(s): , *
      Publication date (Electronic):
      Journal: The Scientific World Journal
      Publisher: Hindawi Publishing Corporation

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          Abstract

          Synthesis of an assembly of structurally important N-H- and N-substituted acridine-1,8-diones by CAN (ceric ammonium nitrate) catalysed one-pot four-component reaction of electron-deficient and electron-rich aromatic aldehydes and aromatic amines or ammonium acetate and dimedone or cyclohexyl-1,3-diones at 26°C under sonic condition is reported. The method is clean and energy efficient as it uses a greener method and an eco-friendly catalyst.

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          Most cited references35

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          Ultrasound in synthetic organic chemistry

          Timothy Mason (1997)
          Article 0 comments Cited 73 times – based on 0 reviews     Review now
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            Discovery of dual function acridones as a new antimalarial chemotype.

            Aaron Janowsky, Michael Winter, Sergio Wittlin … (2009)
            Preventing and delaying the emergence of drug resistance is an essential goal of antimalarial drug development. Monotherapy and highly mutable drug targets have each facilitated resistance, and both are undesirable in effective long-term strategies against multi-drug-resistant malaria. Haem remains an immutable and vulnerable target, because it is not parasite-encoded and its detoxification during haemoglobin degradation, critical to parasite survival, can be subverted by drug-haem interaction as in the case of quinolines and many other drugs. Here we describe a new antimalarial chemotype that combines the haem-targeting character of acridones, together with a chemosensitizing component that counteracts resistance to quinoline antimalarial drugs. Beyond the essential intrinsic characteristics common to deserving candidate antimalarials (high potency in vitro against pan-sensitive and multi-drug-resistant Plasmodium falciparum, efficacy and safety in vivo after oral administration, inexpensive synthesis and favourable physicochemical properties), our initial lead, T3.5 (3-chloro-6-(2-diethylamino-ethoxy)-10-(2-diethylamino-ethyl)-acridone), demonstrates unique synergistic properties. In addition to 'verapamil-like' chemosensitization to chloroquine and amodiaquine against quinoline-resistant parasites, T3.5 also results in an apparently mechanistically distinct synergism with quinine and with piperaquine. This synergy, evident in both quinoline-sensitive and quinoline-resistant parasites, has been demonstrated both in vitro and in vivo. In summary, this innovative acridone design merges intrinsic potency and resistance-counteracting functions in one molecule, and represents a new strategy to expand, enhance and sustain effective antimalarial drug combinations.
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              Interest of acridine derivatives in the anticancer chemotherapy.

              M Demeunynck, A Martelli, F Charmantray (2001)
              DNA is considered as one of the main targets for anticancer drug design. The planar structure of acridines confers to the molecules the ability to bind DNA by intercalation and therefore to interfere with metabolic processes. A large number of natural alkaloids and synthetic acridine derivatives have been tested as anticancer agents. So far, a few molecules have entered clinical trials and have been approved for chemotherapy. The mechanisms of action are not fully understood. Cytotoxicity may be related to potent enzyme inhibition. Topoisomerase and telomerase activities may be strongly affected by acridines. The affinity of acridines for DNA has also been used to design new active compounds in which a DNA modifying group is tethered to the acridine nucleus. Acridine derivatives display other pharmacological properties such as antibacterial and antimalarial activities. They are also tested for Alzheimer's disease.
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                Author and article information

                Journal
                Journal ID (nlm-ta): ScientificWorldJournal
                Journal ID (iso-abbrev): ScientificWorldJournal
                Journal ID (publisher-id): TSWJ
                Title: The Scientific World Journal
                Publisher: Hindawi Publishing Corporation
                ISSN (Electronic): 1537-744X
                Publication date Collection: 2013
                Publication date (Electronic): 31 December 2013
                Volume: 2013
                Electronic Location Identifier: 930787
                Affiliations
                Department of Studies in Chemistry, Bangalore University, Central College Campus, Palace Road, Bengaluru-560001, India
                Author notes

                Academic Editors: B. I. Kharisov, A. Sirit, and A. Tarraga

                Article
                DOI: 10.1155/2013/930787
                PMC ID: 3899711
                SO-VID: e9e737f6-d279-4736-8a40-5af06d8cdeef
                Copyright © Copyright © 2013 S. Sudha and M. A. Pasha.
                License:

                This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                History
                Date received : 16 August 2013
                Date accepted : 3 October 2013
                Funding
                Funded by: http://dx.doi.org/10.13039/501100001501 University Grants Commission
                Award ID: 37-71/2009(SR)
                Categories
                Subject: Research Article

                ScienceOpen disciplines: Uncategorized
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