Pyrrole‐Thiazolidin‐4‐one Analogues Exhibit Promising Anti‐Tuberculosis Activity
A series of pyrrole‐thiazolidin‐4‐one conjugates were synthesized and evaluated for their anti‐mycobacterial and anti‐bacterial activities. Two compounds, 10 a and 10 k, were the most effective conjugates and produced identical MICs (0.5 μg/mL) against M. tuberculosis H37Rv with a high selectivity i...
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| Veröffentlicht in: | Asian journal of organic chemistry 2024-06, Vol.13 (6), p.n/a |
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| creator | Ahmed, Shujauddin Mital, Alka Akhir, Abdul Saxena, Deepanshi Jahan, Kousar Dubey, Gurudutt Bharatam, P. V. Dasgupta, Arunava Chopra, Sidharth Jain, Rahul |
| description | A series of pyrrole‐thiazolidin‐4‐one conjugates were synthesized and evaluated for their anti‐mycobacterial and anti‐bacterial activities. Two compounds, 10 a and 10 k, were the most effective conjugates and produced identical MICs (0.5 μg/mL) against M. tuberculosis H37Rv with a high selectivity index. Upon evaluation against the ESKAP bacteria panel, compound 10 g emerged most effective against S. aureus (MIC=8.0 μg/mL) while compound 10 o produced activity against A. baumannii (MIC=4.0 μg/mL). A molecular docking study revealed that the most active compound 10 a has similar binding interactions as those of BM212 and rimonabant, with a comparable docking score against M. tuberculosis mycolic acid transporter MmpL3.
This work describes the synthesis, anti‐tuberculosis, and antibacterial activities of pyrrole‐thiazolidin‐4‐one conjugates. The best analogue exhibits an MIC of 0.5 μg/mL against the M. tuberculosis H37Rv strain and also shows promising antibacterial activities. The docking study indicates that the M. tuberculosis mycolic acid transporter MmpL3 is a possible molecular target. |
| doi_str_mv | 10.1002/ajoc.202400054 |
| format | Article |
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This work describes the synthesis, anti‐tuberculosis, and antibacterial activities of pyrrole‐thiazolidin‐4‐one conjugates. The best analogue exhibits an MIC of 0.5 μg/mL against the M. tuberculosis H37Rv strain and also shows promising antibacterial activities. The docking study indicates that the M. tuberculosis mycolic acid transporter MmpL3 is a possible molecular target.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202400054</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Bacteria ; Conjugates ; ESKAP bacteria ; Molecular docking ; Pyrroles ; Thiazolidin-4-ones ; Tuberculosis</subject><ispartof>Asian journal of organic chemistry, 2024-06, Vol.13 (6), p.n/a</ispartof><rights>2024 Wiley-VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2724-616372a42580c5ab7b12db6cb2715d5417643d22d0eee5a9088af321cd80fdcb3</cites><orcidid>0000-0002-9180-2812</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fajoc.202400054$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202400054$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Ahmed, Shujauddin</creatorcontrib><creatorcontrib>Mital, Alka</creatorcontrib><creatorcontrib>Akhir, Abdul</creatorcontrib><creatorcontrib>Saxena, Deepanshi</creatorcontrib><creatorcontrib>Jahan, Kousar</creatorcontrib><creatorcontrib>Dubey, Gurudutt</creatorcontrib><creatorcontrib>Bharatam, P. V.</creatorcontrib><creatorcontrib>Dasgupta, Arunava</creatorcontrib><creatorcontrib>Chopra, Sidharth</creatorcontrib><creatorcontrib>Jain, Rahul</creatorcontrib><title>Pyrrole‐Thiazolidin‐4‐one Analogues Exhibit Promising Anti‐Tuberculosis Activity</title><title>Asian journal of organic chemistry</title><description>A series of pyrrole‐thiazolidin‐4‐one conjugates were synthesized and evaluated for their anti‐mycobacterial and anti‐bacterial activities. Two compounds, 10 a and 10 k, were the most effective conjugates and produced identical MICs (0.5 μg/mL) against M. tuberculosis H37Rv with a high selectivity index. Upon evaluation against the ESKAP bacteria panel, compound 10 g emerged most effective against S. aureus (MIC=8.0 μg/mL) while compound 10 o produced activity against A. baumannii (MIC=4.0 μg/mL). A molecular docking study revealed that the most active compound 10 a has similar binding interactions as those of BM212 and rimonabant, with a comparable docking score against M. tuberculosis mycolic acid transporter MmpL3.
This work describes the synthesis, anti‐tuberculosis, and antibacterial activities of pyrrole‐thiazolidin‐4‐one conjugates. The best analogue exhibits an MIC of 0.5 μg/mL against the M. tuberculosis H37Rv strain and also shows promising antibacterial activities. The docking study indicates that the M. tuberculosis mycolic acid transporter MmpL3 is a possible molecular target.</description><subject>Bacteria</subject><subject>Conjugates</subject><subject>ESKAP bacteria</subject><subject>Molecular docking</subject><subject>Pyrroles</subject><subject>Thiazolidin-4-ones</subject><subject>Tuberculosis</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkL9qwzAQxkVpoSHN2tnQ2al0tix7NCH9RyAZUugmZFlOFBwrley2ztRH6DP2SaqQko4djrvjvt_x8SF0TfCYYAy3YmPkGDDEGGMan6EBkCwKaUro-WnG7BKNnNt4CWYsI5AN0Muit9bU6vvza7nWYm9qXerGb7Ev06ggb0RtVp1ywfRjrQvdBgtrttrpZuVvrT6AXaGs7GrjtAty2eo33fZX6KIStVOj3z5Ez3fT5eQhnM3vHyf5LJTAIA4TkkQMRAzenqSiYAWBskhkAYzQksaEJXFUApRYKUVFhtNUVBEQWaa4KmURDdHN8e_Omldvs-Ub01lv2vEIM5LRJGPgVeOjSlrjnFUV31m9FbbnBPNDgPwQID8F6IHsCLzrWvX_qHn-NJ_8sT-8m3id</recordid><startdate>202406</startdate><enddate>202406</enddate><creator>Ahmed, Shujauddin</creator><creator>Mital, Alka</creator><creator>Akhir, Abdul</creator><creator>Saxena, Deepanshi</creator><creator>Jahan, Kousar</creator><creator>Dubey, Gurudutt</creator><creator>Bharatam, P. V.</creator><creator>Dasgupta, Arunava</creator><creator>Chopra, Sidharth</creator><creator>Jain, Rahul</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-9180-2812</orcidid></search><sort><creationdate>202406</creationdate><title>Pyrrole‐Thiazolidin‐4‐one Analogues Exhibit Promising Anti‐Tuberculosis Activity</title><author>Ahmed, Shujauddin ; Mital, Alka ; Akhir, Abdul ; Saxena, Deepanshi ; Jahan, Kousar ; Dubey, Gurudutt ; Bharatam, P. V. ; Dasgupta, Arunava ; Chopra, Sidharth ; Jain, Rahul</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2724-616372a42580c5ab7b12db6cb2715d5417643d22d0eee5a9088af321cd80fdcb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Bacteria</topic><topic>Conjugates</topic><topic>ESKAP bacteria</topic><topic>Molecular docking</topic><topic>Pyrroles</topic><topic>Thiazolidin-4-ones</topic><topic>Tuberculosis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ahmed, Shujauddin</creatorcontrib><creatorcontrib>Mital, Alka</creatorcontrib><creatorcontrib>Akhir, Abdul</creatorcontrib><creatorcontrib>Saxena, Deepanshi</creatorcontrib><creatorcontrib>Jahan, Kousar</creatorcontrib><creatorcontrib>Dubey, Gurudutt</creatorcontrib><creatorcontrib>Bharatam, P. V.</creatorcontrib><creatorcontrib>Dasgupta, Arunava</creatorcontrib><creatorcontrib>Chopra, Sidharth</creatorcontrib><creatorcontrib>Jain, Rahul</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ahmed, Shujauddin</au><au>Mital, Alka</au><au>Akhir, Abdul</au><au>Saxena, Deepanshi</au><au>Jahan, Kousar</au><au>Dubey, Gurudutt</au><au>Bharatam, P. V.</au><au>Dasgupta, Arunava</au><au>Chopra, Sidharth</au><au>Jain, Rahul</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pyrrole‐Thiazolidin‐4‐one Analogues Exhibit Promising Anti‐Tuberculosis Activity</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2024-06</date><risdate>2024</risdate><volume>13</volume><issue>6</issue><epage>n/a</epage><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>A series of pyrrole‐thiazolidin‐4‐one conjugates were synthesized and evaluated for their anti‐mycobacterial and anti‐bacterial activities. Two compounds, 10 a and 10 k, were the most effective conjugates and produced identical MICs (0.5 μg/mL) against M. tuberculosis H37Rv with a high selectivity index. Upon evaluation against the ESKAP bacteria panel, compound 10 g emerged most effective against S. aureus (MIC=8.0 μg/mL) while compound 10 o produced activity against A. baumannii (MIC=4.0 μg/mL). A molecular docking study revealed that the most active compound 10 a has similar binding interactions as those of BM212 and rimonabant, with a comparable docking score against M. tuberculosis mycolic acid transporter MmpL3.
This work describes the synthesis, anti‐tuberculosis, and antibacterial activities of pyrrole‐thiazolidin‐4‐one conjugates. The best analogue exhibits an MIC of 0.5 μg/mL against the M. tuberculosis H37Rv strain and also shows promising antibacterial activities. The docking study indicates that the M. tuberculosis mycolic acid transporter MmpL3 is a possible molecular target.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202400054</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-9180-2812</orcidid></addata></record> |
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| subjects | Bacteria Conjugates ESKAP bacteria Molecular docking Pyrroles Thiazolidin-4-ones Tuberculosis |
| title | Pyrrole‐Thiazolidin‐4‐one Analogues Exhibit Promising Anti‐Tuberculosis Activity |
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