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Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds
The formation efficiency of hydride-induced Meisenheimer complexes of nitroaromatic compounds is consistent with their anti-TB activities exemplied by MDL860 and benzothiazol N -oxide (BTO) analogs. Herein we report that nitro cyano phenoxybenzenes (MDL860 and analogs) reacted slowly and incompletel...
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| Published in: | MedChemComm 2021-01, Vol.12 (1), p.62-72 |
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| Main Authors: | , , , , , , , , , , , |
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| cites | cdi_FETCH-LOGICAL-c469t-a090169f2662daa53b4027dcff0eeef043724afe657fa6e3726d1530e07d06033 |
| container_end_page | 72 |
| container_issue | 1 |
| container_start_page | 62 |
| container_title | MedChemComm |
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| creator | Liu, Rui Markley, Lowell Miller, Patricia A Franzblau, Scott Shetye, Gauri Ma, Rui Savková, Karin Mikušová, Katarína Lee, Bei Shi Pethe, Kevin Moraski, Garrett C Miller, Marvin J |
| description | The formation efficiency of hydride-induced Meisenheimer complexes of nitroaromatic compounds is consistent with their anti-TB activities exemplied by MDL860 and benzothiazol
N
-oxide (BTO) analogs. Herein we report that nitro cyano phenoxybenzenes (MDL860 and analogs) reacted slowly and incompletely which reflected their moderate anti-TB activity, in contrast to the instantaneous reaction of BTO derivatives to quantitatively generate Meisenheimer complexes which corresponded to their enhanced anti-TB activity. These results were corroborated by mycobacterial and radiolabelling studies that confirmed inhibition of the DprE1 enzyme by BTO derivatives but not MDL860 analogs.
The formation efficiency of hydride-induced Meisenheimer complexes of nitroaromatic compounds is consistent with their anti-TB activities exemplied by MDL860 and benzothiazol
N
-oxide (BTO) analogs. |
| doi_str_mv | 10.1039/d0md00390e |
| format | article |
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N
-oxide (BTO) analogs. Herein we report that nitro cyano phenoxybenzenes (MDL860 and analogs) reacted slowly and incompletely which reflected their moderate anti-TB activity, in contrast to the instantaneous reaction of BTO derivatives to quantitatively generate Meisenheimer complexes which corresponded to their enhanced anti-TB activity. These results were corroborated by mycobacterial and radiolabelling studies that confirmed inhibition of the DprE1 enzyme by BTO derivatives but not MDL860 analogs.
The formation efficiency of hydride-induced Meisenheimer complexes of nitroaromatic compounds is consistent with their anti-TB activities exemplied by MDL860 and benzothiazol
N
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N
-oxide (BTO) analogs. Herein we report that nitro cyano phenoxybenzenes (MDL860 and analogs) reacted slowly and incompletely which reflected their moderate anti-TB activity, in contrast to the instantaneous reaction of BTO derivatives to quantitatively generate Meisenheimer complexes which corresponded to their enhanced anti-TB activity. These results were corroborated by mycobacterial and radiolabelling studies that confirmed inhibition of the DprE1 enzyme by BTO derivatives but not MDL860 analogs.
The formation efficiency of hydride-induced Meisenheimer complexes of nitroaromatic compounds is consistent with their anti-TB activities exemplied by MDL860 and benzothiazol
N
-oxide (BTO) analogs.</description><subject>Analogs</subject><subject>Aromatic compounds</subject><subject>Chemistry</subject><subject>Complex formation</subject><subject>Derivatives</subject><subject>Hydrides</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Radiolabelling</subject><subject>Tuberculosis</subject><issn>2632-8682</issn><issn>2040-2503</issn><issn>2632-8682</issn><issn>2040-2511</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdks9PFTEQxxsjEQJcvGs28WJMVqY_trt7MSGAYgLxouemr51KyW77bLvE999bePhETvOdzCffzPRbQl5T-EiBjycWZgtVAL4gB0xy1g5yYC-f6H1ynPMtALCOUtmNr8g-FyCqGg5IuNzY5C22PtjFoG2u0WcMN-hnTI2J83rC342LadbFx9AkdBOakhttir_zZdNE1wRfUmx0iveQaXQovi3LCpNZpph9fvCJS7D5iOw5PWU8fqyH5Mfni-9nl-3Vty9fz06vWiPkWFoNI1A5OiYls1p3fCWA9dY4B4joQPCeCe1Qdr3TEmsnLe04IPQWJHB-SD5tfdfLakZrMJSkJ7VOftZpo6L26v9J8DfqZ7xTA-XVYKgG7x8NUvy1YC5q9tngNOmAccmKdVxIysUoK_ruGXoblxTqeYqJQQJjXd9X6sOWMinmXJ9xtwwFdZ-kOofr84ckLyr89un6O_RvbhV4swVSNrvpv6_A_wDWs6Vw</recordid><startdate>20210101</startdate><enddate>20210101</enddate><creator>Liu, Rui</creator><creator>Markley, Lowell</creator><creator>Miller, Patricia A</creator><creator>Franzblau, Scott</creator><creator>Shetye, Gauri</creator><creator>Ma, Rui</creator><creator>Savková, Karin</creator><creator>Mikušová, Katarína</creator><creator>Lee, Bei Shi</creator><creator>Pethe, Kevin</creator><creator>Moraski, Garrett C</creator><creator>Miller, Marvin J</creator><general>Royal Society of Chemistry</general><general>RSC</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7T5</scope><scope>7T7</scope><scope>7TO</scope><scope>7U7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-0100-4877</orcidid><orcidid>https://orcid.org/0000-0003-1104-9486</orcidid><orcidid>https://orcid.org/0000-0002-3704-8214</orcidid></search><sort><creationdate>20210101</creationdate><title>Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds</title><author>Liu, Rui ; 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N
-oxide (BTO) analogs. Herein we report that nitro cyano phenoxybenzenes (MDL860 and analogs) reacted slowly and incompletely which reflected their moderate anti-TB activity, in contrast to the instantaneous reaction of BTO derivatives to quantitatively generate Meisenheimer complexes which corresponded to their enhanced anti-TB activity. These results were corroborated by mycobacterial and radiolabelling studies that confirmed inhibition of the DprE1 enzyme by BTO derivatives but not MDL860 analogs.
The formation efficiency of hydride-induced Meisenheimer complexes of nitroaromatic compounds is consistent with their anti-TB activities exemplied by MDL860 and benzothiazol
N
-oxide (BTO) analogs.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>34046598</pmid><doi>10.1039/d0md00390e</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-0100-4877</orcidid><orcidid>https://orcid.org/0000-0003-1104-9486</orcidid><orcidid>https://orcid.org/0000-0002-3704-8214</orcidid><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | PubMed Central (Open access); Royal Society of Chemistry |
| subjects | Analogs Aromatic compounds Chemistry Complex formation Derivatives Hydrides NMR Nuclear magnetic resonance Radiolabelling Tuberculosis |
| title | Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds |
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