Synthesis and biological evaluation of 2-(5-substituted-1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-N-substituted-hydrazinecarbothioamides
Identifieur interne : 001761 ( Ncbi/Merge ); précédent : 001760; suivant : 001762Synthesis and biological evaluation of 2-(5-substituted-1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-N-substituted-hydrazinecarbothioamides
Auteurs : Subhas S. Karki ; Amol A. Kulkarni ; Sujeet Kumar ; Suresh Kumar Veliyath ; Erik De Clercq [Belgique] ; Jan Balzarini [Belgique]Source :
- Medicinal Chemistry Research [ 1054-2523 ] ; 2012.
Abstract
Various 5-substituted-2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (
Derivative
Url:
DOI: 10.1007/s00044-012-0184-x
PubMed: NONE
PubMed Central: 7079969
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Karki</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.411053.2</institution-id><institution-id institution-id-type="ISNI">0000 0001 1889 7360</institution-id><institution>Department of Pharmaceutical Chemistry,</institution><institution>KLE University’s College of Pharmacy,</institution></institution-wrap>Rajajinagar, Bangalore, 560010 Karnataka India</nlm:aff><wicri:noCountry code="subfield">560010 Karnataka India</wicri:noCountry></affiliation></author><author><name sortKey="Kulkarni, Amol A" sort="Kulkarni, Amol A" uniqKey="Kulkarni A" first="Amol A." last="Kulkarni">Amol A. Kulkarni</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.411053.2</institution-id><institution-id institution-id-type="ISNI">0000 0001 1889 7360</institution-id><institution>Department of Pharmaceutical Chemistry,</institution><institution>KLE University’s College of Pharmacy,</institution></institution-wrap>Rajajinagar, Bangalore, 560010 Karnataka India</nlm:aff><wicri:noCountry code="subfield">560010 Karnataka India</wicri:noCountry></affiliation></author><author><name sortKey="Kumar, Sujeet" sort="Kumar, Sujeet" uniqKey="Kumar S" first="Sujeet" last="Kumar">Sujeet Kumar</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.411053.2</institution-id><institution-id institution-id-type="ISNI">0000 0001 1889 7360</institution-id><institution>Department of Pharmaceutical Chemistry,</institution><institution>KLE University’s College of Pharmacy,</institution></institution-wrap>Rajajinagar, Bangalore, 560010 Karnataka India</nlm:aff><wicri:noCountry code="subfield">560010 Karnataka India</wicri:noCountry></affiliation></author><author><name sortKey="Veliyath, Suresh Kumar" sort="Veliyath, Suresh Kumar" uniqKey="Veliyath S" first="Suresh Kumar" last="Veliyath">Suresh Kumar Veliyath</name><affiliation><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.411053.2</institution-id><institution-id institution-id-type="ISNI">0000 0001 1889 7360</institution-id><institution>Department of Pharmaceutical Chemistry,</institution><institution>KLE University’s College of Pharmacy,</institution></institution-wrap>Rajajinagar, Bangalore, 560010 Karnataka India</nlm:aff><wicri:noCountry code="subfield">560010 Karnataka India</wicri:noCountry></affiliation></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><affiliation wicri:level="3"><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="GRID">grid.5596.f</institution-id><institution-id institution-id-type="ISNI">0000000106687884</institution-id><institution>Rega Institute for Medical Research,</institution><institution>KU Leuven,</institution></institution-wrap>Minderbroedersstraat 10, 3000 Leuven, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Minderbroedersstraat 10, 3000 Leuven</wicri:regionArea><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName></affiliation></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><affiliation wicri:level="3"><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="GRID">grid.5596.f</institution-id><institution-id institution-id-type="ISNI">0000000106687884</institution-id><institution>Rega Institute for Medical Research,</institution><institution>KU Leuven,</institution></institution-wrap>Minderbroedersstraat 10, 3000 Leuven, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Minderbroedersstraat 10, 3000 Leuven</wicri:regionArea><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName></affiliation></author></analytic><series><title level="j">Medicinal Chemistry Research</title><idno type="ISSN">1054-2523</idno><idno type="eISSN">1554-8120</idno><imprint><date when="2012">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><sec><title>Abstract</title><p>Various 5-substituted-2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (<bold>4a</bold>, <bold>b</bold>) and 5-substituted-2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-<italic>N</italic>-(phenyl-4-substituted)hydrazinecarbothioamide (<bold>5a</bold>–<bold>h</bold>) derivatives were synthesized. The compounds were screened for cytotoxicity against human HeLa and CEM T-lymphocytes as well as murine L1210 cells. The compounds were also screened for β-lactamase inhibitory activity, antiviral, antibacterial, and antifungal activity against various strains of microorganisms. Several of these compounds were endowed with low micromolar 50 %-cytostatic concentration (IC<sub>50</sub>) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells (L1210) were also the most inhibitory against human T-lymphocyte (CEM) tumor cells. Derivative 2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-<italic>N</italic>-(4-methoxyphenyl)hydrazinecarbothioamide <bold>5c</bold> emerged as the most potent cytostatic compound among the tested compounds. Derivatives <bold>4b</bold>, <bold>5a</bold>, <bold>5b</bold>, and <bold>5d</bold> showed antiviral activity against HEL cell cultures (IC<sub>50</sub> 11–20 μM). Moderate antimicrobial activity was observed for all derivatives. The encouraging cytostatic and antiviral activity data provide an adequate rationale for further modification of these molecular scaffolds.</p></sec><sec><title>Graphical abstract</title><p>Derivative <bold>5c</bold> (1.9–4.4 μM) emerged as the most potent cytostatic compound among the tested compounds. Derivatives <bold>4b</bold>, <bold>5a</bold>, <bold>5b</bold>, and <bold>5d</bold> showed antiviral activity against HEL cell cultures (IC<sub>50</sub> 11–20 μM). <graphic position="anchor" xlink:href="44_2012_184_Figa_HTML" id="MO1"></graphic></p></sec></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Andreani, A" uniqKey="Andreani A">A Andreani</name></author><author><name sortKey="Bellini, S" uniqKey="Bellini S">S Bellini</name></author><author><name sortKey="Burnelli, S" uniqKey="Burnelli S">S Burnelli</name></author><author><name sortKey="Granaiola, M" uniqKey="Granaiola M">M Granaiola</name></author><author><name sortKey="Leoni, A" uniqKey="Leoni A">A Leoni</name></author><author><name sortKey="Locatelli, A" uniqKey="Locatelli A">A Locatelli</name></author><author><name sortKey="Morigi, R" uniqKey="Morigi R">R Morigi</name></author><author><name sortKey="Rambaldi, M" uniqKey="Rambaldi M">M Rambaldi</name></author><author><name 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Med Chem Res</journal-id><journal-id journal-id-type="iso-abbrev">Med Chem Res</journal-id><journal-title-group><journal-title>Medicinal Chemistry Research</journal-title></journal-title-group><issn pub-type="ppub">1054-2523</issn><issn pub-type="epub">1554-8120</issn><publisher><publisher-name>Springer-Verlag</publisher-name><publisher-loc>New York</publisher-loc></publisher></journal-meta><article-meta><article-id pub-id-type="pmc">7079969</article-id><article-id pub-id-type="publisher-id">184</article-id><article-id pub-id-type="doi">10.1007/s00044-012-0184-x</article-id><article-categories><subj-group subj-group-type="heading"><subject>Original Research</subject></subj-group></article-categories><title-group><article-title>Synthesis and biological evaluation of 2-(5-substituted-1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-<italic>N</italic>-substituted-hydrazinecarbothioamides</article-title></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><name><surname>Karki</surname><given-names>Subhas S.</given-names></name><address><phone>+91-80-23325611</phone><fax>+91-80-23425373</fax><email>subhasskarki@gmail.com</email></address><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>Kulkarni</surname><given-names>Amol A.</given-names></name><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>Kumar</surname><given-names>Sujeet</given-names></name><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>Veliyath</surname><given-names>Suresh Kumar</given-names></name><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>De Clercq</surname><given-names>Erik</given-names></name><xref ref-type="aff" rid="Aff2">2</xref></contrib><contrib contrib-type="author"><name><surname>Balzarini</surname><given-names>Jan</given-names></name><xref ref-type="aff" rid="Aff2">2</xref></contrib><aff id="Aff1"><label>1</label><institution-wrap><institution-id institution-id-type="GRID">grid.411053.2</institution-id><institution-id institution-id-type="ISNI">0000 0001 1889 7360</institution-id><institution>Department of Pharmaceutical Chemistry,</institution><institution>KLE University’s College of Pharmacy,</institution></institution-wrap>Rajajinagar, Bangalore, 560010 Karnataka India</aff><aff id="Aff2"><label>2</label><institution-wrap><institution-id institution-id-type="GRID">grid.5596.f</institution-id><institution-id institution-id-type="ISNI">0000000106687884</institution-id><institution>Rega Institute for Medical Research,</institution><institution>KU Leuven,</institution></institution-wrap>Minderbroedersstraat 10, 3000 Leuven, Belgium</aff></contrib-group><pub-date pub-type="epub"><day>26</day><month>8</month><year>2012</year></pub-date><pub-date pub-type="ppub"><year>2013</year></pub-date><volume>22</volume><issue>4</issue><fpage>2014</fpage><lpage>2022</lpage><history><date date-type="received"><day>11</day><month>4</month><year>2012</year></date><date date-type="accepted"><day>25</day><month>7</month><year>2012</year></date></history><permissions><copyright-statement>© Springer Science+Business Media, LLC 2012</copyright-statement><license><license-p>This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.</license-p></license></permissions><abstract id="Abs1"><sec><title>Abstract</title><p>Various 5-substituted-2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (<bold>4a</bold>, <bold>b</bold>) and 5-substituted-2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-<italic>N</italic>-(phenyl-4-substituted)hydrazinecarbothioamide (<bold>5a</bold>–<bold>h</bold>) derivatives were synthesized. The compounds were screened for cytotoxicity against human HeLa and CEM T-lymphocytes as well as murine L1210 cells. The compounds were also screened for β-lactamase inhibitory activity, antiviral, antibacterial, and antifungal activity against various strains of microorganisms. Several of these compounds were endowed with low micromolar 50 %-cytostatic concentration (IC<sub>50</sub>) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells (L1210) were also the most inhibitory against human T-lymphocyte (CEM) tumor cells. Derivative 2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-<italic>N</italic>-(4-methoxyphenyl)hydrazinecarbothioamide <bold>5c</bold> emerged as the most potent cytostatic compound among the tested compounds. Derivatives <bold>4b</bold>, <bold>5a</bold>, <bold>5b</bold>, and <bold>5d</bold> showed antiviral activity against HEL cell cultures (IC<sub>50</sub> 11–20 μM). Moderate antimicrobial activity was observed for all derivatives. The encouraging cytostatic and antiviral activity data provide an adequate rationale for further modification of these molecular scaffolds.</p></sec><sec><title>Graphical abstract</title><p>Derivative <bold>5c</bold> (1.9–4.4 μM) emerged as the most potent cytostatic compound among the tested compounds. Derivatives <bold>4b</bold>, <bold>5a</bold>, <bold>5b</bold>, and <bold>5d</bold> showed antiviral activity against HEL cell cultures (IC<sub>50</sub> 11–20 μM). <graphic position="anchor" xlink:href="44_2012_184_Figa_HTML" id="MO1"></graphic></p></sec></abstract><kwd-group xml:lang="en"><title>Keywords</title><kwd>2,3-Dioxo-2,3-dihydroindole</kwd><kwd>Thiosemicarbazones</kwd><kwd>Cytotoxicity assay</kwd><kwd>Antiviral activity</kwd><kwd>Antimicrobial activity</kwd></kwd-group><custom-meta-group><custom-meta><meta-name>issue-copyright-statement</meta-name><meta-value>© Springer Science+Business Media New York 2013</meta-value></custom-meta></custom-meta-group></article-meta></front></pmc><affiliations><list><country><li>Belgique</li></country><region><li>Province du Brabant flamand</li></region><settlement><li>Louvain</li></settlement></list><tree><noCountry><name sortKey="Karki, Subhas S" sort="Karki, Subhas S" uniqKey="Karki S" first="Subhas S." last="Karki">Subhas S. Karki</name><name sortKey="Kulkarni, Amol A" sort="Kulkarni, Amol A" uniqKey="Kulkarni A" first="Amol A." last="Kulkarni">Amol A. Kulkarni</name><name sortKey="Kumar, Sujeet" sort="Kumar, Sujeet" uniqKey="Kumar S" first="Sujeet" last="Kumar">Sujeet Kumar</name><name sortKey="Veliyath, Suresh Kumar" sort="Veliyath, Suresh Kumar" uniqKey="Veliyath S" first="Suresh Kumar" last="Veliyath">Suresh Kumar Veliyath</name></noCountry><country name="Belgique"><region name="Province du Brabant flamand"><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name></region><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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