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      Synthesis, Spectroscopic and Theoretical Studies of New Quasi-Podands from Bile Acid Derivatives Linked by 1,2,3-Triazole Rings

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          Abstract

          A novel method for the synthesis of bile acid derivatives has been developed using “click chemistry”. Intermolecular 1,3-dipolar cycloaddition of the propargyl ester of bile acids and azide groups of 1,3,5-tris(azidomethyl)benzene gave a new quasi-podands with 1,2,3-triazole rings. The structures of the products were confirmed by spectral ( 1H-NMR, 13C-NMR, and FT-IR) analysis, mass spectrometry and PM5 semiempirical methods. Estimation of the pharmacotherapeutic potential has been accomplished for synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS).

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          Optimization of parameters for semiempirical methods I. Method

          James J. P. Stewart (1989)
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            “On Water”: Unique Reactivity of Organic Compounds in Aqueous Suspension

            Sridhar Narayan, John Muldoon, M Finn … (2005)
            Article 0 comments Cited 225 times – based on 0 reviews     Review now
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              Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes.

              Gian Cesare Tron, Tracey Pirali, Richard Billington … (2008)
              In recent years, there has been an ever-increasing need for rapid reactions that meet the three main criteria of an ideal synthesis: efficiency, versatility, and selectivity. Such reactions would allow medicinal chemistry to keep pace with the multitude of information derived from modern biological screening techniques. The present review describes one of these reactions, the 1,3-dipolar cycloaddition ("click-reaction") between azides and alkynes catalyzed by copper (I) salts. The simplicity of this reaction and the ease of purification of the resulting products have opened new opportunities in generating vast arrays of compounds with biological potential. The present review will outline the accomplishments of this strategy achieved so far and outline some of medicinal chemistry applications in which click-chemistry might be relevant in the future. (c) 2007 Wiley Periodicals, Inc.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 24 February 2014
                Publication date Collection: February 2014
                Volume: 19
                Issue: 2
                Pages: 2557-2570
                Affiliations
                Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland; E-Mails: koenig@ 123456amu.edu.pl (H.K.); iwkow@ 123456amu.edu.pl (I.K.)
                Author notes
                [* ]Authors to whom correspondence should be addressed; E-Mail: tposp@ 123456amu.edu.pl (T.P.); brycki@ 123456amu.edu.pl (B.B.); Tel.: +48-61-829-1307 (T.P.); +48-61-829-1314 (B.B.).
                Article
                Publisher ID: molecules-19-02557
                DOI: 10.3390/molecules19022557
                PMC ID: 6270822
                PubMed ID: 24566321
                SO-VID: 31cb9fad-1d60-4eca-933c-078f44723f7d
                Copyright © © 2014 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                Date received : 17 December 2013
                Date revision received : 19 February 2014
                Date accepted : 20 February 2014
                Categories
                Subject: Article

                Keywords: bile acids,podands,click chemistry,1,2,3-triazole ring,pm5 calculations
                Data availability:
                Keywords: bile acids, podands, click chemistry, 1,2,3-triazole ring, pm5 calculations

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