Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones
A series of twenty one N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%), containing a few drops of acetic acid. Their structures were established on the...
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| Format: | Article |
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MDPI AG
2011-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/16/8/6408/ |
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| author | Muhammad Yaqub Mohammad Saeed Iqbal Humayun Pervez Naveeda Saira Khalid Mohammed Khan |
| author_facet | Muhammad Yaqub Mohammad Saeed Iqbal Humayun Pervez Naveeda Saira Khalid Mohammed Khan |
| author_sort | Muhammad Yaqub |
| collection | DOAJ |
| description | A series of twenty one N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%), containing a few drops of acetic acid. Their structures were established on the basis of analytical (CHN) and spectral (IR, 1H-NMR, EIMS) data. All the synthesized compounds were evaluated for their toxicity potential by a brine shrimp lethality bioassay. Ten compounds i.e., 3a, 3e, 3i-3l and 3n-3q proved to be active in this assay, displaying promising toxicity (LD50 = 1.11 × 10−5 M − 1.80 × 10−4 M). Amongst these, 3k, 3n and 3o were found to be the most active ones (LD50 = 1.11 × 10−5 M − 1.43 × 10−5 M). Compound 3k showed the highest activity with a LD50 value of 1.11 × 10−5 M and can, therefore, be used as a lead for further studies. Structure-activity relationship (SAR) studies revealed that the presence of strong inductively electron-attracting trifluoromethoxy substituent at position-5 of the isatin moiety played an important role in inducing or enhancing toxic potentiality of some of the synthesized compounds. |
| first_indexed | 2024-12-13T18:14:37Z |
| format | Article |
| id | doaj.art-3ab574fbc5fd42de8e4d460197dc5db0 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-13T18:14:37Z |
| publishDate | 2011-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-3ab574fbc5fd42de8e4d460197dc5db02022-12-21T23:35:53ZengMDPI AGMolecules1420-30492011-07-011686408642110.3390/molecules16086408Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazonesMuhammad YaqubMohammad Saeed IqbalHumayun PervezNaveeda SairaKhalid Mohammed KhanA series of twenty one N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%), containing a few drops of acetic acid. Their structures were established on the basis of analytical (CHN) and spectral (IR, 1H-NMR, EIMS) data. All the synthesized compounds were evaluated for their toxicity potential by a brine shrimp lethality bioassay. Ten compounds i.e., 3a, 3e, 3i-3l and 3n-3q proved to be active in this assay, displaying promising toxicity (LD50 = 1.11 × 10−5 M − 1.80 × 10−4 M). Amongst these, 3k, 3n and 3o were found to be the most active ones (LD50 = 1.11 × 10−5 M − 1.43 × 10−5 M). Compound 3k showed the highest activity with a LD50 value of 1.11 × 10−5 M and can, therefore, be used as a lead for further studies. Structure-activity relationship (SAR) studies revealed that the presence of strong inductively electron-attracting trifluoromethoxy substituent at position-5 of the isatin moiety played an important role in inducing or enhancing toxic potentiality of some of the synthesized compounds.http://www.mdpi.com/1420-3049/16/8/6408/isatin5-trifluoromethoxyisatinthiosemicarbazones5-trifluoromethoxyisatin-3-thiosemicarbazonestoxicity |
| spellingShingle | Muhammad Yaqub Mohammad Saeed Iqbal Humayun Pervez Naveeda Saira Khalid Mohammed Khan Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones Molecules isatin 5-trifluoromethoxyisatin thiosemicarbazones 5-trifluoromethoxyisatin-3-thiosemicarbazones toxicity |
| title | Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones |
| title_full | Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones |
| title_fullStr | Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones |
| title_full_unstemmed | Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones |
| title_short | Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones |
| title_sort | synthesis and toxicity evaluation of some n4 aryl substituted 5 trifluoromethoxyisatin 3 thiosemicarbazones |
| topic | isatin 5-trifluoromethoxyisatin thiosemicarbazones 5-trifluoromethoxyisatin-3-thiosemicarbazones toxicity |
| url | http://www.mdpi.com/1420-3049/16/8/6408/ |
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