Imidazole-Thiazolidine-2,4-dione Conjugated 1,2,3-Triazole Derivatives as Tubulin Aiming Antiproliferative Agents
A new series of imidazole-thiazolidine-2,4-dione coupled 1,2,3-triazoles ( VIIa–VIIm ) were synthesized using Knoevengal condensation and Cu-catalyzed azide-alkyne cycloaddition as key approaches. Out of all, ( Z )-3-(2-(4-(4-methoxyphenyl)-1 H -1,2,3-triazol-1-yl)ethyl)-5-((1-methyl-1 H -imidazol-2...
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| Veröffentlicht in: | Russian journal of bioorganic chemistry 2023-10, Vol.49 (5), p.976-987 |
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| container_title | Russian journal of bioorganic chemistry |
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| creator | Nagaraju, Ashwini Nukala, Satheesh Kumar Thirukovela, Narasimha Swamy Manchal, Ravinder |
| description | A new series of imidazole-thiazolidine-2,4-dione coupled 1,2,3-triazoles (
VIIa–VIIm
) were synthesized using Knoevengal condensation and Cu-catalyzed azide-alkyne cycloaddition as key approaches. Out of all, (
Z
)-3-(2-(4-(4-methoxyphenyl)-1
H
-1,2,3-triazol-1-yl)ethyl)-5-((1-methyl-1
H
-imidazol-2-yl)methylene)thiazolidine-2,4-dione (
VIId
) exhibited superior activity against three human cell lines like MCF-7 (breast), A549 (lung) and HeLa (cervix) than the standard drug Nocodazole with IC
50
values |
| doi_str_mv | 10.1134/S1068162023050047 |
| format | Article |
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VIIa–VIIm
) were synthesized using Knoevengal condensation and Cu-catalyzed azide-alkyne cycloaddition as key approaches. Out of all, (
Z
)-3-(2-(4-(4-methoxyphenyl)-1
H
-1,2,3-triazol-1-yl)ethyl)-5-((1-methyl-1
H
-imidazol-2-yl)methylene)thiazolidine-2,4-dione (
VIId
) exhibited superior activity against three human cell lines like MCF-7 (breast), A549 (lung) and HeLa (cervix) than the standard drug Nocodazole with IC
50
values <1 μM, while, (
Z
)-4-(1-(2-(5-((1-methyl-1
H
-imidazol-2-yl)methylene)-2,4-dioxothiazolidin-3-yl)ethyl)-1
H
-1,2,3-triazol-4-yl)benzonitrile (
VIIf
) and (
Z
)-5-((1-methyl-1
H
-imidazol-2-yl)methylene)-3-(2-(4-(pyridin-3-yl)-1
H
-1,2,3-triazol-1-yl)ethyl)thiazolidine-2,4-dione (
VIII
) displayed greater activity against MCF-7 than the Nocodazole with IC
50
values 0.81 and 0.97 μM respectively. The compounds (
VIId
), (
VIIf
) and (
VIII
) were then screened for their efficacy in inhibiting tubulin polymerization and found that compound (
VIId
) showed comparable activity (IC
50
= 1.32 μM) with the standard drug Combretastatin A-4 (CA-4) (IC
50
= 1.14 μM). Finally, molecular modeling studies for active compounds (
VIId
), (
VIIf
) and (
VIII
) on α,β-tubulin (PDB ID-1SA0) were conducted and attained free energies were observed to be covenant with corresponding IC
50
values.</description><identifier>ISSN: 1068-1620</identifier><identifier>EISSN: 1608-330X</identifier><identifier>DOI: 10.1134/S1068162023050047</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Alkynes ; Benzonitrile ; Biochemistry ; Biomedical and Life Sciences ; Biomedicine ; Bioorganic Chemistry ; Cycloaddition ; Imidazole ; Life Sciences ; Methylene ; Organic Chemistry ; Triazoles</subject><ispartof>Russian journal of bioorganic chemistry, 2023-10, Vol.49 (5), p.976-987</ispartof><rights>Pleiades Publishing, Ltd. 2023</rights><rights>Pleiades Publishing, Ltd. 2023.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-e0637e56916ad1607e8fde0c2f41bcd8647708eddaa0f8796b0df442bf8be71e3</citedby><cites>FETCH-LOGICAL-c316t-e0637e56916ad1607e8fde0c2f41bcd8647708eddaa0f8796b0df442bf8be71e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1068162023050047$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1068162023050047$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27923,27924,41487,42556,51318</link.rule.ids></links><search><creatorcontrib>Nagaraju, Ashwini</creatorcontrib><creatorcontrib>Nukala, Satheesh Kumar</creatorcontrib><creatorcontrib>Thirukovela, Narasimha Swamy</creatorcontrib><creatorcontrib>Manchal, Ravinder</creatorcontrib><title>Imidazole-Thiazolidine-2,4-dione Conjugated 1,2,3-Triazole Derivatives as Tubulin Aiming Antiproliferative Agents</title><title>Russian journal of bioorganic chemistry</title><addtitle>Russ J Bioorg Chem</addtitle><description>A new series of imidazole-thiazolidine-2,4-dione coupled 1,2,3-triazoles (
VIIa–VIIm
) were synthesized using Knoevengal condensation and Cu-catalyzed azide-alkyne cycloaddition as key approaches. Out of all, (
Z
)-3-(2-(4-(4-methoxyphenyl)-1
H
-1,2,3-triazol-1-yl)ethyl)-5-((1-methyl-1
H
-imidazol-2-yl)methylene)thiazolidine-2,4-dione (
VIId
) exhibited superior activity against three human cell lines like MCF-7 (breast), A549 (lung) and HeLa (cervix) than the standard drug Nocodazole with IC
50
values <1 μM, while, (
Z
)-4-(1-(2-(5-((1-methyl-1
H
-imidazol-2-yl)methylene)-2,4-dioxothiazolidin-3-yl)ethyl)-1
H
-1,2,3-triazol-4-yl)benzonitrile (
VIIf
) and (
Z
)-5-((1-methyl-1
H
-imidazol-2-yl)methylene)-3-(2-(4-(pyridin-3-yl)-1
H
-1,2,3-triazol-1-yl)ethyl)thiazolidine-2,4-dione (
VIII
) displayed greater activity against MCF-7 than the Nocodazole with IC
50
values 0.81 and 0.97 μM respectively. The compounds (
VIId
), (
VIIf
) and (
VIII
) were then screened for their efficacy in inhibiting tubulin polymerization and found that compound (
VIId
) showed comparable activity (IC
50
= 1.32 μM) with the standard drug Combretastatin A-4 (CA-4) (IC
50
= 1.14 μM). Finally, molecular modeling studies for active compounds (
VIId
), (
VIIf
) and (
VIII
) on α,β-tubulin (PDB ID-1SA0) were conducted and attained free energies were observed to be covenant with corresponding IC
50
values.</description><subject>Alkynes</subject><subject>Benzonitrile</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Bioorganic Chemistry</subject><subject>Cycloaddition</subject><subject>Imidazole</subject><subject>Life Sciences</subject><subject>Methylene</subject><subject>Organic Chemistry</subject><subject>Triazoles</subject><issn>1068-1620</issn><issn>1608-330X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kF1LwzAUhosoOKc_wLuCt4uetGmSXZb5NRh4YQXvStqc1owt3ZJ2oL_ebBO8EK_OC-d53_MRRdcUbilN2d0rBS4pTyBJIQNg4iQaUQ6SpCm8nwYd2mTfP48uvF8CUIBMjqLtfG20-upWSIoPsxdGG4skmTCiTWcxnnV2ObSqRx3TSTJJSeEOHMb36MxO9WaHPlY-LoZqWBkb52ZtbBvntjcbF_IadAcozlu0vb-Mzhq18nj1U8fR2-NDMXsmi5en-SxfkDqlvCcIPBWY8SnlSodLBMpGI9RJw2hVa8mZECBRa6WgkWLKK9ANY0nVyAoFxXQc3RxzwxLbAX1fLrvB2TCyTGTGmGCCTwNFj1TtOu8dNuXGmbVynyWFcv_Z8s9ngyc5enxgbYvuN_l_0ze8dnrX</recordid><startdate>20231001</startdate><enddate>20231001</enddate><creator>Nagaraju, Ashwini</creator><creator>Nukala, Satheesh Kumar</creator><creator>Thirukovela, Narasimha Swamy</creator><creator>Manchal, Ravinder</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20231001</creationdate><title>Imidazole-Thiazolidine-2,4-dione Conjugated 1,2,3-Triazole Derivatives as Tubulin Aiming Antiproliferative Agents</title><author>Nagaraju, Ashwini ; Nukala, Satheesh Kumar ; Thirukovela, Narasimha Swamy ; Manchal, Ravinder</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-e0637e56916ad1607e8fde0c2f41bcd8647708eddaa0f8796b0df442bf8be71e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alkynes</topic><topic>Benzonitrile</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Bioorganic Chemistry</topic><topic>Cycloaddition</topic><topic>Imidazole</topic><topic>Life Sciences</topic><topic>Methylene</topic><topic>Organic Chemistry</topic><topic>Triazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nagaraju, Ashwini</creatorcontrib><creatorcontrib>Nukala, Satheesh Kumar</creatorcontrib><creatorcontrib>Thirukovela, Narasimha Swamy</creatorcontrib><creatorcontrib>Manchal, Ravinder</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of bioorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nagaraju, Ashwini</au><au>Nukala, Satheesh Kumar</au><au>Thirukovela, Narasimha Swamy</au><au>Manchal, Ravinder</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Imidazole-Thiazolidine-2,4-dione Conjugated 1,2,3-Triazole Derivatives as Tubulin Aiming Antiproliferative Agents</atitle><jtitle>Russian journal of bioorganic chemistry</jtitle><stitle>Russ J Bioorg Chem</stitle><date>2023-10-01</date><risdate>2023</risdate><volume>49</volume><issue>5</issue><spage>976</spage><epage>987</epage><pages>976-987</pages><issn>1068-1620</issn><eissn>1608-330X</eissn><abstract>A new series of imidazole-thiazolidine-2,4-dione coupled 1,2,3-triazoles (
VIIa–VIIm
) were synthesized using Knoevengal condensation and Cu-catalyzed azide-alkyne cycloaddition as key approaches. Out of all, (
Z
)-3-(2-(4-(4-methoxyphenyl)-1
H
-1,2,3-triazol-1-yl)ethyl)-5-((1-methyl-1
H
-imidazol-2-yl)methylene)thiazolidine-2,4-dione (
VIId
) exhibited superior activity against three human cell lines like MCF-7 (breast), A549 (lung) and HeLa (cervix) than the standard drug Nocodazole with IC
50
values <1 μM, while, (
Z
)-4-(1-(2-(5-((1-methyl-1
H
-imidazol-2-yl)methylene)-2,4-dioxothiazolidin-3-yl)ethyl)-1
H
-1,2,3-triazol-4-yl)benzonitrile (
VIIf
) and (
Z
)-5-((1-methyl-1
H
-imidazol-2-yl)methylene)-3-(2-(4-(pyridin-3-yl)-1
H
-1,2,3-triazol-1-yl)ethyl)thiazolidine-2,4-dione (
VIII
) displayed greater activity against MCF-7 than the Nocodazole with IC
50
values 0.81 and 0.97 μM respectively. The compounds (
VIId
), (
VIIf
) and (
VIII
) were then screened for their efficacy in inhibiting tubulin polymerization and found that compound (
VIId
) showed comparable activity (IC
50
= 1.32 μM) with the standard drug Combretastatin A-4 (CA-4) (IC
50
= 1.14 μM). Finally, molecular modeling studies for active compounds (
VIId
), (
VIIf
) and (
VIII
) on α,β-tubulin (PDB ID-1SA0) were conducted and attained free energies were observed to be covenant with corresponding IC
50
values.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1068162023050047</doi><tpages>12</tpages></addata></record> |
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| subjects | Alkynes Benzonitrile Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Cycloaddition Imidazole Life Sciences Methylene Organic Chemistry Triazoles |
| title | Imidazole-Thiazolidine-2,4-dione Conjugated 1,2,3-Triazole Derivatives as Tubulin Aiming Antiproliferative Agents |
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