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Synthesis and cytostatic evaluation of some 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide
Various substituted 2-(5-substituted-2-oxoindolin-3-ylidene)- N -substituted hydrazine carbothioamide 4a–g and 2-(5-substituted-1-(4-substituted benzyl)-2-oxoindolin-3-ylidene)- N -substituted hydrazine carbothioamide 5a–k were synthesized. The compounds were evaluated for their cytostatic activity...
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| Published in: | Medicinal chemistry research 2011-11, Vol.20 (8), p.1229-1234 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| container_title | Medicinal chemistry research |
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| creator | Karki, Subhas S. Kulkarni, Amol Teraiya, Nishith De Clercq, Erik Balzarini, Jan |
| description | Various substituted 2-(5-substituted-2-oxoindolin-3-ylidene)-
N
-substituted hydrazine carbothioamide
4a–g
and 2-(5-substituted-1-(4-substituted benzyl)-2-oxoindolin-3-ylidene)-
N
-substituted hydrazine carbothioamide
5a–k
were synthesized. The compounds were evaluated for their cytostatic activity against human Molt4/C8 and CEM T-lymphocytes as well as murine L1210 leukemia cells. Several of these compounds were endowed with low micromolar 50%-inhibitory concentration (IC
50
) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells were also most inhibitory against human T-lymphocyte tumor cells. 2-(5-fluoro-1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-
N
-
p
-tolylhydrazine carbothioamide (
5b
) emerged as the most potent cytostatic compound among the tested compounds. The encouraging cytostatic data provide an adequate rationale for further modification of these molecular scaffolds. |
| doi_str_mv | 10.1007/s00044-010-9458-3 |
| format | article |
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N
-substituted hydrazine carbothioamide
4a–g
and 2-(5-substituted-1-(4-substituted benzyl)-2-oxoindolin-3-ylidene)-
N
-substituted hydrazine carbothioamide
5a–k
were synthesized. The compounds were evaluated for their cytostatic activity against human Molt4/C8 and CEM T-lymphocytes as well as murine L1210 leukemia cells. Several of these compounds were endowed with low micromolar 50%-inhibitory concentration (IC
50
) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells were also most inhibitory against human T-lymphocyte tumor cells. 2-(5-fluoro-1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-
N
-
p
-tolylhydrazine carbothioamide (
5b
) emerged as the most potent cytostatic compound among the tested compounds. The encouraging cytostatic data provide an adequate rationale for further modification of these molecular scaffolds.</description><identifier>ISSN: 1054-2523</identifier><identifier>EISSN: 1554-8120</identifier><identifier>DOI: 10.1007/s00044-010-9458-3</identifier><language>eng</language><publisher>New York: Springer-Verlag</publisher><subject>Biochemistry ; Biomedical and Life Sciences ; Biomedicine ; Cell Biology ; Hydrazine ; Hydrazines ; Leukemia ; Lymphocytes ; Lymphocytes T ; Melphalan ; Original Research ; Pharmacology/Toxicology ; Substitutes ; Tumor cells</subject><ispartof>Medicinal chemistry research, 2011-11, Vol.20 (8), p.1229-1234</ispartof><rights>Springer Science+Business Media, LLC 2010</rights><rights>Springer Science+Business Media, LLC 2010.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c359t-b800c37300e0bf9b68e61a93124ea7366b44a5fd67b0d660d72b748c69867b963</citedby><cites>FETCH-LOGICAL-c359t-b800c37300e0bf9b68e61a93124ea7366b44a5fd67b0d660d72b748c69867b963</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Karki, Subhas S.</creatorcontrib><creatorcontrib>Kulkarni, Amol</creatorcontrib><creatorcontrib>Teraiya, Nishith</creatorcontrib><creatorcontrib>De Clercq, Erik</creatorcontrib><creatorcontrib>Balzarini, Jan</creatorcontrib><title>Synthesis and cytostatic evaluation of some 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide</title><title>Medicinal chemistry research</title><addtitle>Med Chem Res</addtitle><description>Various substituted 2-(5-substituted-2-oxoindolin-3-ylidene)-
N
-substituted hydrazine carbothioamide
4a–g
and 2-(5-substituted-1-(4-substituted benzyl)-2-oxoindolin-3-ylidene)-
N
-substituted hydrazine carbothioamide
5a–k
were synthesized. The compounds were evaluated for their cytostatic activity against human Molt4/C8 and CEM T-lymphocytes as well as murine L1210 leukemia cells. Several of these compounds were endowed with low micromolar 50%-inhibitory concentration (IC
50
) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells were also most inhibitory against human T-lymphocyte tumor cells. 2-(5-fluoro-1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-
N
-
p
-tolylhydrazine carbothioamide (
5b
) emerged as the most potent cytostatic compound among the tested compounds. The encouraging cytostatic data provide an adequate rationale for further modification of these molecular scaffolds.</description><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Cell Biology</subject><subject>Hydrazine</subject><subject>Hydrazines</subject><subject>Leukemia</subject><subject>Lymphocytes</subject><subject>Lymphocytes T</subject><subject>Melphalan</subject><subject>Original Research</subject><subject>Pharmacology/Toxicology</subject><subject>Substitutes</subject><subject>Tumor cells</subject><issn>1054-2523</issn><issn>1554-8120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp1kE1LxDAQhosouK7-AG8FL3qITj7bHkX8gkUP6jmkbepm6SZrkorVP2-WCnrxNC_D887Ak2XHGM4xQHERAIAxBBhQxXiJ6E42w5wzVGICuylDyoQTup8dhLACoAUwPsu-nkYblzqYkCvb5s0YXYgqmibX76ofUnI2d10e3FrnBJ1yFIY6RBOHqFtEkPtwxrauNxZRNPam1VafoYe_VL4cW68-jdV5o3zt4tI4tU7kYbbXqT7oo585z15urp-v7tDi8fb-6nKBGsqriOoSoKEFBdBQd1UtSi2wqigmTKuCClEzpnjXiqKGVghoC1IXrGxEVaZVJeg8O5nubrx7G3SIcuUGb9NLSUTFAdOkLVF4ohrvQvC6kxtv1sqPEoPcOpaTY5lguXUsaeqQqRMSa1-1_738f-kbZFV_sA</recordid><startdate>20111101</startdate><enddate>20111101</enddate><creator>Karki, Subhas S.</creator><creator>Kulkarni, Amol</creator><creator>Teraiya, Nishith</creator><creator>De Clercq, Erik</creator><creator>Balzarini, Jan</creator><general>Springer-Verlag</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>FR3</scope><scope>M7Z</scope><scope>P64</scope></search><sort><creationdate>20111101</creationdate><title>Synthesis and cytostatic evaluation of some 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide</title><author>Karki, Subhas S. ; Kulkarni, Amol ; Teraiya, Nishith ; De Clercq, Erik ; Balzarini, Jan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c359t-b800c37300e0bf9b68e61a93124ea7366b44a5fd67b0d660d72b748c69867b963</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Cell Biology</topic><topic>Hydrazine</topic><topic>Hydrazines</topic><topic>Leukemia</topic><topic>Lymphocytes</topic><topic>Lymphocytes T</topic><topic>Melphalan</topic><topic>Original Research</topic><topic>Pharmacology/Toxicology</topic><topic>Substitutes</topic><topic>Tumor cells</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Karki, Subhas S.</creatorcontrib><creatorcontrib>Kulkarni, Amol</creatorcontrib><creatorcontrib>Teraiya, Nishith</creatorcontrib><creatorcontrib>De Clercq, Erik</creatorcontrib><creatorcontrib>Balzarini, Jan</creatorcontrib><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 1</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Medicinal chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Karki, Subhas S.</au><au>Kulkarni, Amol</au><au>Teraiya, Nishith</au><au>De Clercq, Erik</au><au>Balzarini, Jan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and cytostatic evaluation of some 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide</atitle><jtitle>Medicinal chemistry research</jtitle><stitle>Med Chem Res</stitle><date>2011-11-01</date><risdate>2011</risdate><volume>20</volume><issue>8</issue><spage>1229</spage><epage>1234</epage><pages>1229-1234</pages><issn>1054-2523</issn><eissn>1554-8120</eissn><abstract>Various substituted 2-(5-substituted-2-oxoindolin-3-ylidene)-
N
-substituted hydrazine carbothioamide
4a–g
and 2-(5-substituted-1-(4-substituted benzyl)-2-oxoindolin-3-ylidene)-
N
-substituted hydrazine carbothioamide
5a–k
were synthesized. The compounds were evaluated for their cytostatic activity against human Molt4/C8 and CEM T-lymphocytes as well as murine L1210 leukemia cells. Several of these compounds were endowed with low micromolar 50%-inhibitory concentration (IC
50
) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells were also most inhibitory against human T-lymphocyte tumor cells. 2-(5-fluoro-1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-
N
-
p
-tolylhydrazine carbothioamide (
5b
) emerged as the most potent cytostatic compound among the tested compounds. The encouraging cytostatic data provide an adequate rationale for further modification of these molecular scaffolds.</abstract><cop>New York</cop><pub>Springer-Verlag</pub><doi>10.1007/s00044-010-9458-3</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | Medicinal chemistry research, 2011-11, Vol.20 (8), p.1229-1234 |
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| language | eng |
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| subjects | Biochemistry Biomedical and Life Sciences Biomedicine Cell Biology Hydrazine Hydrazines Leukemia Lymphocytes Lymphocytes T Melphalan Original Research Pharmacology/Toxicology Substitutes Tumor cells |
| title | Synthesis and cytostatic evaluation of some 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide |
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