Imidazo[4,5‐b]pyridine derivatives of potential tuberculostatic activity, II: Synthesis and bioactivity of designed and some other 2‐cyanomethylimidazo[4,5‐b]pyridine derivatives
Identifieur interne : 000A57 ( Istex/Corpus ); précédent : 000A56; suivant : 000A58Imidazo[4,5‐b]pyridine derivatives of potential tuberculostatic activity, II: Synthesis and bioactivity of designed and some other 2‐cyanomethylimidazo[4,5‐b]pyridine derivatives
Auteurs : Ludwik Bukowski ; Roman KaliszanSource :
- Archiv der Pharmazie [ 0365-6233 ] ; 1991-09.
English descriptors
- Teeft :
- Active congeners, Antibacterial activity, Bacterial strain, Bioactivity, Bioactivity data, Bukowski, Derivative, Etheric solution, Medical academy, Mycobacterium, Mycobacterium tuberculosis, Pyridine derivatives, Qsar, Qsar analysis, Qsar equation, Recrystallized, Room temp, Small portions, Weinheim.
Abstract
Based on the analysis of Quantitative Structure ‐ Activity Relationships (QSAR) three representatives of imidazo[4,5‐b]pyridine derivatives of predicted high antibacterial activity against Mycobacterium tuberculosis were synthetized and tested bacteriologically. Excellent agreement of the predicted and experimentally observed bioactivity was noted. Additional new derivatives of 4‐methyl‐4H‐2‐cyanomethylimidazo[4,5‐b]pyridine (7) and 2‐(α‐methylcyanomethyl)imidazo[4,5‐b]pyridine (22) were also synthesized and some of them were tested for tuberculostatic activity. The compounds synthesized according to a standard “trial and error” approach appeared generally inactive.
Imidazo[4,5‐b]pyridin‐Derivate mit potentiell tuberkulostatischer Wirkung, 2. Mitt: Synthese und Bioaktivität einiger 2‐Cyanomethylimidazo[4,5‐b]pyridin‐Derivate Auf Grund der Analyse von Quantitativen Struktur‐Wirkung‐Beziehungen (QSAR), die in der 1. Mitt, beschrieben wurden, wurden drei Imidazo[4,5‐b] pyridin‐Derivate mit der vorhergesehenen hohen antibakteriellen Aktivität gegen Mycobacterium tuberculosis entworten, synthetisiert und bakteriologisch geprüft. Ausgezeichnete übereinstimmung wurde zwischen der vorhergesehenen und experimentellen Bioaktivität festgestellt. Nachträglich wurden auch neue Derivate von 4‐Methyl‐4H‐2‐Cyanomethylimidazo[4,5‐b] pyridin 7 und 2‐(α‐Methylcyanomethyl)imidazo[4,5‐b]pyridin 22 synthetisiert und manche von ihnen wurden auf tuberkulostatische Wirkung geprüft. Die Verbindungen, die nach der “Versuch und Fehler” Methode synthetisiert wurden, stellten sich als inaktiv heraus.
Url:
DOI: 10.1002/ardp.2503240903
Links to Exploration step
ISTEX:70A4BDC63479704B77637986CD8F48EDE2334E68Le document en format XML
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Excellent agreement of the predicted and experimentally observed bioactivity was noted. Additional new derivatives of 4‐methyl‐4H‐2‐cyanomethylimidazo[4,5‐b]pyridine (7) and 2‐(α‐methylcyanomethyl)imidazo[4,5‐b]pyridine (22) were also synthesized and some of them were tested for tuberculostatic activity. The compounds synthesized according to a standard “trial and error” approach appeared generally inactive.</div><div type="abstract" xml:lang="de">Imidazo[4,5‐b]pyridin‐Derivate mit potentiell tuberkulostatischer Wirkung, 2. Mitt: Synthese und Bioaktivität einiger 2‐Cyanomethylimidazo[4,5‐b]pyridin‐Derivate Auf Grund der Analyse von Quantitativen Struktur‐Wirkung‐Beziehungen (QSAR), die in der 1. Mitt, beschrieben wurden, wurden drei Imidazo[4,5‐b] pyridin‐Derivate mit der vorhergesehenen hohen antibakteriellen Aktivität gegen Mycobacterium tuberculosis entworten, synthetisiert und bakteriologisch geprüft. Ausgezeichnete übereinstimmung wurde zwischen der vorhergesehenen und experimentellen Bioaktivität festgestellt. Nachträglich wurden auch neue Derivate von 4‐Methyl‐4H‐2‐Cyanomethylimidazo[4,5‐b] pyridin 7 und 2‐(α‐Methylcyanomethyl)imidazo[4,5‐b]pyridin 22 synthetisiert und manche von ihnen wurden auf tuberkulostatische Wirkung geprüft. 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<ref target="http://www.tei-c.org/">We use TEI</ref></desc></application></appInfo></encodingDesc><profileDesc><abstract xml:lang="en" style="main"><head>Abstract</head><p>Based on the analysis of Quantitative Structure ‐ Activity Relationships (QSAR) three representatives of imidazo[4,5‐<hi rend="italic">b</hi>]pyridine derivatives of predicted high antibacterial activity against <hi rend="italic">Mycobacterium tuberculosis</hi> were synthetized and tested bacteriologically. Excellent agreement of the predicted and experimentally observed bioactivity was noted. Additional new derivatives of 4‐methyl‐4<hi rend="italic">H</hi>‐2‐cyanomethylimidazo[4,5‐<hi rend="italic">b</hi>]pyridine (7) and 2‐(α‐methylcyanomethyl)imidazo[4,5‐<hi rend="italic">b</hi>]pyridine (22) were also synthesized and some of them were tested for tuberculostatic activity. The compounds synthesized according to a standard “trial and error” approach appeared generally inactive.</p></abstract><abstract xml:lang="de" style="main"><p>Imidazo[4,5‐<hi rend="italic">b</hi>]pyridin‐Derivate mit potentiell tuberkulostatischer Wirkung, 2. Mitt: Synthese und Bioaktivität einiger 2‐Cyanomethylimidazo[4,5‐<hi rend="italic">b</hi>]pyridin‐Derivate</p><p>Auf Grund der Analyse von Quantitativen Struktur‐Wirkung‐Beziehungen (QSAR), die in der 1. Mitt, beschrieben wurden, wurden drei Imidazo[4,5‐<hi rend="italic">b</hi>] pyridin‐Derivate mit der vorhergesehenen hohen antibakteriellen Aktivität gegen <hi rend="italic">Mycobacterium tuberculosis</hi> entworten, synthetisiert und bakteriologisch geprüft. Ausgezeichnete übereinstimmung wurde zwischen der vorhergesehenen und experimentellen Bioaktivität festgestellt. Nachträglich wurden auch neue Derivate von 4‐Methyl‐4<hi rend="italic">H</hi>‐2‐Cyanomethylimidazo[4,5‐<hi rend="italic">b</hi>] pyridin 7 und 2‐(α‐Methylcyanomethyl)imidazo[4,5‐<hi rend="italic">b</hi>]pyridin 22 synthetisiert und manche von ihnen wurden auf tuberkulostatische Wirkung geprüft. 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Excellent agreement of the predicted and experimentally observed bioactivity was noted. Additional new derivatives of 4‐methyl‐4<i>H</i>‐2‐cyanomethylimidazo[4,5‐<i>b</i>]pyridine (7) and 2‐(α‐methylcyanomethyl)imidazo[4,5‐<i>b</i>]pyridine (22) were also synthesized and some of them were tested for tuberculostatic activity. The compounds synthesized according to a standard “trial and error” approach appeared generally inactive.</p></abstract><abstract type="main" xml:lang="de"><p>Imidazo[4,5‐<i>b</i>]pyridin‐Derivate mit potentiell tuberkulostatischer Wirkung, 2. Mitt: Synthese und Bioaktivität einiger 2‐Cyanomethylimidazo[4,5‐<i>b</i>]pyridin‐Derivate</p><p>Auf Grund der Analyse von Quantitativen Struktur‐Wirkung‐Beziehungen (QSAR), die in der 1. Mitt, beschrieben wurden, wurden drei Imidazo[4,5‐<i>b</i>] pyridin‐Derivate mit der vorhergesehenen hohen antibakteriellen Aktivität gegen <i>Mycobacterium tuberculosis</i> entworten, synthetisiert und bakteriologisch geprüft. Ausgezeichnete übereinstimmung wurde zwischen der vorhergesehenen und experimentellen Bioaktivität festgestellt. Nachträglich wurden auch neue Derivate von 4‐Methyl‐4<i>H</i>‐2‐Cyanomethylimidazo[4,5‐<i>b</i>] pyridin 7 und 2‐(α‐Methylcyanomethyl)imidazo[4,5‐<i>b</i>]pyridin 22 synthetisiert und manche von ihnen wurden auf tuberkulostatische Wirkung geprüft. Die Verbindungen, die nach der “Versuch und Fehler” Methode synthetisiert wurden, stellten sich als inaktiv heraus.</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Imidazo[4,5‐b]pyridine derivatives of potential tuberculostatic activity, II: Synthesis and bioactivity of designed and some other 2‐cyanomethylimidazo[4,5‐b]pyridine derivatives</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Imidazo[4,5‐b]Pyridine</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Imidazo[4,5‐b]pyridine derivatives of potential tuberculostatic activity, II: Synthesis and bioactivity of designed and some other 2‐cyanomethylimidazo[4,5‐b]pyridine derivatives</title></titleInfo><name type="personal"><namePart type="given">Ludwik</namePart><namePart type="family">Bukowski</namePart><affiliation>Department of Organic Chemistry and Department of Biopharmaceutics and Pharmacodynamics, Medical Academy, 80‐416 Gdansk, Poland</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Roman</namePart><namePart type="family">Kaliszan</namePart><affiliation>Department of Organic Chemistry and Department of Biopharmaceutics and Pharmacodynamics, Medical Academy, 80‐416 Gdansk, Poland</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Hannover</placeTerm></place><dateIssued encoding="w3cdtf">1991-09</dateIssued><dateCaptured encoding="w3cdtf">1990-07-10</dateCaptured><copyrightDate encoding="w3cdtf">1991</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">0</extent><extent unit="tables">2</extent><extent unit="references">7</extent></physicalDescription><abstract lang="en">Based on the analysis of Quantitative Structure ‐ Activity Relationships (QSAR) three representatives of imidazo[4,5‐b]pyridine derivatives of predicted high antibacterial activity against Mycobacterium tuberculosis were synthetized and tested bacteriologically. Excellent agreement of the predicted and experimentally observed bioactivity was noted. Additional new derivatives of 4‐methyl‐4H‐2‐cyanomethylimidazo[4,5‐b]pyridine (7) and 2‐(α‐methylcyanomethyl)imidazo[4,5‐b]pyridine (22) were also synthesized and some of them were tested for tuberculostatic activity. The compounds synthesized according to a standard “trial and error” approach appeared generally inactive.</abstract><abstract lang="de">Imidazo[4,5‐b]pyridin‐Derivate mit potentiell tuberkulostatischer Wirkung, 2. Mitt: Synthese und Bioaktivität einiger 2‐Cyanomethylimidazo[4,5‐b]pyridin‐Derivate Auf Grund der Analyse von Quantitativen Struktur‐Wirkung‐Beziehungen (QSAR), die in der 1. Mitt, beschrieben wurden, wurden drei Imidazo[4,5‐b] pyridin‐Derivate mit der vorhergesehenen hohen antibakteriellen Aktivität gegen Mycobacterium tuberculosis entworten, synthetisiert und bakteriologisch geprüft. Ausgezeichnete übereinstimmung wurde zwischen der vorhergesehenen und experimentellen Bioaktivität festgestellt. Nachträglich wurden auch neue Derivate von 4‐Methyl‐4H‐2‐Cyanomethylimidazo[4,5‐b] pyridin 7 und 2‐(α‐Methylcyanomethyl)imidazo[4,5‐b]pyridin 22 synthetisiert und manche von ihnen wurden auf tuberkulostatische Wirkung geprüft. Die Verbindungen, die nach der “Versuch und Fehler” Methode synthetisiert wurden, stellten sich als inaktiv heraus.</abstract><relatedItem type="host"><titleInfo><title>Archiv der Pharmazie</title></titleInfo><titleInfo type="abbreviated"><title>Arch. Pharm. Pharm. Med. Chem.</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><subject><genre>article-category</genre><topic>Article</topic><topic>Articles</topic></subject><identifier type="ISSN">0365-6233</identifier><identifier type="eISSN">1521-4184</identifier><identifier type="DOI">10.1002/(ISSN)1521-4184</identifier><identifier type="PublisherID">ARDP</identifier><part><date>1991</date><detail type="volume"><caption>vol.</caption><number>324</number></detail><detail type="issue"><caption>no.</caption><number>9</number></detail><extent unit="pages"><start>537</start><end>542</end><total>6</total></extent></part></relatedItem><relatedItem type="references" displayLabel="cit1"><titleInfo><title>Arch. Pharm. (Weinheim)</title></titleInfo><genre>journal-article</genre><note type="citation/reference">L. Bukowski and R. Kaliszan, Arch. Pharm. (Weinheim) 324, 121 (1991).</note><name type="personal"><namePart type="given">L.</namePart><namePart type="family">Bukowski</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">R.</namePart><namePart type="family">Kaliszan</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1991</date><detail type="volume"><caption>vol.</caption><number>324</number></detail><extent unit="pages"><start>121</start></extent></part></relatedItem><relatedItem type="references" displayLabel="cit2"><titleInfo><title>Pol. J. Pharmacol. Pharm.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">L. Bukowski, Pol. J. Pharmacol. Pharm. 38, 91 (1986);</note><name type="personal"><namePart type="given">L.</namePart><namePart type="family">Bukowski</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1986</date><detail type="volume"><caption>vol.</caption><number>38</number></detail><extent unit="pages"><start>91</start></extent></part><titleInfo><title>C.A.</title></titleInfo><genre>journal-article</genre><note type="citation/reference">C.A. 106, 176258 m (1987).</note><part><date>1987</date><detail type="volume"><caption>vol.</caption><number>106</number></detail><extent unit="pages"><start>176258 m</start></extent></part></relatedItem><relatedItem type="references" displayLabel="cit4"><titleInfo><title>Pharmazie</title></titleInfo><genre>journal-article</genre><note type="citation/reference">L. Bukowski and M. Janowiec, Pharmazie 45, 904 (1990).</note><name type="personal"><namePart type="given">L.</namePart><namePart type="family">Bukowski</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M.</namePart><namePart type="family">Janowiec</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1990</date><detail type="volume"><caption>vol.</caption><number>45</number></detail><extent unit="pages"><start>904</start></extent></part></relatedItem><relatedItem type="references" displayLabel="cit5"><titleInfo><title>J. K. Seydel andK.‐J. Schaper,Chemische Struktur und Biologische Aktivität von Wirkstoffen, Methoden der Quantitativen Struktur‐Wirkung‐Analyse,Verlag Chemie, Weinheim, New York1979.</title></titleInfo><note type="citation/reference">J. K. Seydel and K.‐J. Schaper, Chemische Struktur und Biologische Aktivität von Wirkstoffen, Methoden der Quantitativen Struktur‐Wirkung‐Analyse, Verlag Chemie, Weinheim, New York 1979.</note><name type="personal"><namePart type="given">J. K.</namePart><namePart type="family">Seydel</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">K.‐J.</namePart><namePart type="family">Schaper</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>book</genre><originInfo><publisher>Verlag Chemie</publisher><place><placeTerm type="text">Weinheim, New York</placeTerm></place></originInfo><part><date>1979</date></part></relatedItem><relatedItem type="references" displayLabel="cit6"><titleInfo><title>R. Kaliszan,Quantitative Structure‐Chromatographic Retention Relationships,Wiley, New York1987.</title></titleInfo><note type="citation/reference">R. Kaliszan, Quantitative Structure‐Chromatographic Retention Relationships, Wiley, New York 1987.</note><name type="personal"><namePart type="given">R.</namePart><namePart type="family">Kaliszan</namePart><role><roleTerm type="text">author</roleTerm></role></name><genre>book</genre><originInfo><publisher>Wiley</publisher><place><placeTerm type="text">New York</placeTerm></place></originInfo><part><date>1987</date></part></relatedItem><relatedItem type="references" displayLabel="cit7"><titleInfo><title>Pharmazie</title></titleInfo><genre>journal-article</genre><note type="citation/reference">L. Bukowski and M. Janowiec, Pharmazie 44, 267 (1989).</note><name type="personal"><namePart type="given">L.</namePart><namePart type="family">Bukowski</namePart><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M.</namePart><namePart type="family">Janowiec</namePart><role><roleTerm type="text">author</roleTerm></role></name><part><date>1989</date><detail type="volume"><caption>vol.</caption><number>44</number></detail><extent unit="pages"><start>267</start></extent></part></relatedItem><relatedItem type="references" displayLabel="cit8"><titleInfo><title>Organicum.Organisch‐Chemisches Grundpraktikum,Berlin1967. [Ph846]</title></titleInfo><note type="citation/reference">Organicum. Organisch‐Chemisches Grundpraktikum, Berlin 1967. [Ph846]</note><genre>book</genre><originInfo><publisher>Organisch‐Chemisches Grundpraktikum</publisher><place><placeTerm type="text">Berlin</placeTerm></place></originInfo><part><date>1967</date></part></relatedItem><identifier type="istex">70A4BDC63479704B77637986CD8F48EDE2334E68</identifier><identifier type="ark">ark:/67375/WNG-NPLQS9NG-0</identifier><identifier type="DOI">10.1002/ardp.2503240903</identifier><identifier type="ArticleID">ARDP2503240903</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 1991 WILEY‐VCH Verlag GmbH & Co. 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