Synthesis and biological evaluation of 2-(5-substituted-1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-N-substituted-hydrazinecarbothioamides
Identifieur interne : 001761 ( Ncbi/Checkpoint ); 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
Affiliations:
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-substituted-hydrazinecarbothioamides</title>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Synthesis and biological evaluation of 2-(5-substituted-1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-<italic>N</italic>
-substituted-hydrazinecarbothioamides</title>
<author><name sortKey="Karki, Subhas S" sort="Karki, Subhas S" uniqKey="Karki S" first="Subhas S." last="Karki">Subhas S. Karki</name>
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<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>
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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>
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<institution>KLE University’s College of Pharmacy,</institution>
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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>
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<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>
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<author><name sortKey="Veliyath, Suresh Kumar" sort="Veliyath, Suresh Kumar" uniqKey="Veliyath S" first="Suresh Kumar" last="Veliyath">Suresh Kumar Veliyath</name>
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<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>
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<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>
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<institution-id institution-id-type="ISNI">0000000106687884</institution-id>
<institution>Rega Institute for Medical Research,</institution>
<institution>KU Leuven,</institution>
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Minderbroedersstraat 10, 3000 Leuven, Belgium</nlm:aff>
<country xml:lang="fr">Belgique</country>
<wicri:regionArea>Minderbroedersstraat 10, 3000 Leuven</wicri:regionArea>
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<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>
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<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>
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</div1>
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</TEI>
<affiliations><list><country><li>Belgique</li>
</country>
<region><li>Province du Brabant flamand</li>
</region>
<settlement><li>Louvain</li>
</settlement>
</list>
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<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>
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<name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name>
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</affiliations>
</record>
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