Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents
[Display omitted] Metronidazole and its derivatives are widely used for the treatment of amoebiasis. However, metronidazole is considered as the standard drug but it has many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoeven...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2020-12, Vol.30 (23), p.127549-127549, Article 127549 |
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| container_end_page | 127549 |
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| container_issue | 23 |
| container_start_page | 127549 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 30 |
| creator | Ansari, Mohammad Fawad Inam, Afreen Ahmad, Kamal Fatima, Shehnaz Agarwal, Subhash M. Azam, Amir |
| description | [Display omitted]
Metronidazole and its derivatives are widely used for the treatment of amoebiasis. However, metronidazole is considered as the standard drug but it has many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoevenagel condensation of 4-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethoxy]benzaldehyde 1 with various thiazolidinone derivatives 2–14 to get the new scaffold (15–27) having better activity and lesser toxicity. Six compounds have shown better efficacy and lesser cytotoxicity than the standard drug metronidazole towards HM1: IMSS strain of Entamoeba histolytica. These compounds may combat the problem of drug resistance and might be effective in identifying potential alternatives for future drug discovery against EhOASS. |
| doi_str_mv | 10.1016/j.bmcl.2020.127549 |
| format | Article |
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Metronidazole and its derivatives are widely used for the treatment of amoebiasis. However, metronidazole is considered as the standard drug but it has many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoevenagel condensation of 4-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethoxy]benzaldehyde 1 with various thiazolidinone derivatives 2–14 to get the new scaffold (15–27) having better activity and lesser toxicity. Six compounds have shown better efficacy and lesser cytotoxicity than the standard drug metronidazole towards HM1: IMSS strain of Entamoeba histolytica. These compounds may combat the problem of drug resistance and might be effective in identifying potential alternatives for future drug discovery against EhOASS.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2020.127549</identifier><identifier>PMID: 32927029</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Amoebiasis ; Entamoeba histolytica ; Metronidazole ; Molecular docking ; Thiazolidinone</subject><ispartof>Bioorganic & medicinal chemistry letters, 2020-12, Vol.30 (23), p.127549-127549, Article 127549</ispartof><rights>2020 Elsevier Ltd</rights><rights>Copyright © 2020 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-80b5b250a0160046f830fb4fb6d61592ed6becf46021fe6e970367e3b404731b3</citedby><cites>FETCH-LOGICAL-c356t-80b5b250a0160046f830fb4fb6d61592ed6becf46021fe6e970367e3b404731b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X20306600$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32927029$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ansari, Mohammad Fawad</creatorcontrib><creatorcontrib>Inam, Afreen</creatorcontrib><creatorcontrib>Ahmad, Kamal</creatorcontrib><creatorcontrib>Fatima, Shehnaz</creatorcontrib><creatorcontrib>Agarwal, Subhash M.</creatorcontrib><creatorcontrib>Azam, Amir</creatorcontrib><title>Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Metronidazole and its derivatives are widely used for the treatment of amoebiasis. However, metronidazole is considered as the standard drug but it has many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoevenagel condensation of 4-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethoxy]benzaldehyde 1 with various thiazolidinone derivatives 2–14 to get the new scaffold (15–27) having better activity and lesser toxicity. Six compounds have shown better efficacy and lesser cytotoxicity than the standard drug metronidazole towards HM1: IMSS strain of Entamoeba histolytica. These compounds may combat the problem of drug resistance and might be effective in identifying potential alternatives for future drug discovery against EhOASS.</description><subject>Amoebiasis</subject><subject>Entamoeba histolytica</subject><subject>Metronidazole</subject><subject>Molecular docking</subject><subject>Thiazolidinone</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kM1LAzEQxYMoWqv_gAfZo5etk4_NdsGLFL9A8KCit5BkZ9uU3aRutkL9602pevQ0zPDeY96PkDMKEwpUXi4nprPthAFLB1YWotojIyqkyLmAYp-MoJKQTyvxfkSOY1wCUAFCHJIjzipWAqtG5O1544cFRhez0GQdDn3wrtZfocXM6Ih1NizcdnW188Fjpr1uwzxmOmarPnQuOj9Px8HpLqBxNtNz9EM8IQeNbiOe_swxeb29eZnd549Pdw-z68fc8kIO-RRMYVgBOvUBELKZcmiMaIysJS0qhrU0aBshgdEGJVYlcFkiN6lIyanhY3Kxy03PfKwxDiq9ZLFttcewjooJwaaCl0wmKdtJbR9i7LFRq951ut8oCmoLVC3VFqjaAlU7oMl0_pO_Nh3Wf5ZfgklwtRNgavnpsFfROvQWa9ejHVQd3H_53-J9h4s</recordid><startdate>20201201</startdate><enddate>20201201</enddate><creator>Ansari, Mohammad Fawad</creator><creator>Inam, Afreen</creator><creator>Ahmad, Kamal</creator><creator>Fatima, Shehnaz</creator><creator>Agarwal, Subhash M.</creator><creator>Azam, Amir</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20201201</creationdate><title>Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents</title><author>Ansari, Mohammad Fawad ; Inam, Afreen ; Ahmad, Kamal ; Fatima, Shehnaz ; Agarwal, Subhash M. ; Azam, Amir</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-80b5b250a0160046f830fb4fb6d61592ed6becf46021fe6e970367e3b404731b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amoebiasis</topic><topic>Entamoeba histolytica</topic><topic>Metronidazole</topic><topic>Molecular docking</topic><topic>Thiazolidinone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ansari, Mohammad Fawad</creatorcontrib><creatorcontrib>Inam, Afreen</creatorcontrib><creatorcontrib>Ahmad, Kamal</creatorcontrib><creatorcontrib>Fatima, Shehnaz</creatorcontrib><creatorcontrib>Agarwal, Subhash M.</creatorcontrib><creatorcontrib>Azam, Amir</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ansari, Mohammad Fawad</au><au>Inam, Afreen</au><au>Ahmad, Kamal</au><au>Fatima, Shehnaz</au><au>Agarwal, Subhash M.</au><au>Azam, Amir</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2020-12-01</date><risdate>2020</risdate><volume>30</volume><issue>23</issue><spage>127549</spage><epage>127549</epage><pages>127549-127549</pages><artnum>127549</artnum><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Metronidazole and its derivatives are widely used for the treatment of amoebiasis. However, metronidazole is considered as the standard drug but it has many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoevenagel condensation of 4-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethoxy]benzaldehyde 1 with various thiazolidinone derivatives 2–14 to get the new scaffold (15–27) having better activity and lesser toxicity. Six compounds have shown better efficacy and lesser cytotoxicity than the standard drug metronidazole towards HM1: IMSS strain of Entamoeba histolytica. These compounds may combat the problem of drug resistance and might be effective in identifying potential alternatives for future drug discovery against EhOASS.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>32927029</pmid><doi>10.1016/j.bmcl.2020.127549</doi><tpages>1</tpages></addata></record> |
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| source | Elsevier ScienceDirect Journals |
| subjects | Amoebiasis Entamoeba histolytica Metronidazole Molecular docking Thiazolidinone |
| title | Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents |
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