Synthesis, Antimicrobial Evaluation and Hemolytic Activity of 2-[[5-alkyl/aralkyl substituted-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamide derivatives
2,5-Disubstituted 1,3,4-oxadiazole compounds are one of the most attractive classes for researchers due to their pharmacological activities. In the current research, a new series of 2-[[5-alkyl/aralkyl-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamides (6a–m) were prepared by convertin...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2017
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| Subjects: | |
| Online Access: | http://umpir.ump.edu.my/id/eprint/7986/1/fist-2017-nadeem-Synthesis%2C%20antimicrobial%20evaluation%20and%20hemolytic.pdf |
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| author | Akhtar, Muhammad Nadeem Gul, Samreen Rehman, Aziz-ur Abbasi, M. Athar Khan, Khalid Mohammed Nafeesa, Khadija Siddiqa, Asia Shahid, Muhammad Subhani, Zinayyera |
| author_facet | Akhtar, Muhammad Nadeem Gul, Samreen Rehman, Aziz-ur Abbasi, M. Athar Khan, Khalid Mohammed Nafeesa, Khadija Siddiqa, Asia Shahid, Muhammad Subhani, Zinayyera |
| author_sort | Akhtar, Muhammad Nadeem |
| collection | UMP |
| description | 2,5-Disubstituted 1,3,4-oxadiazole compounds are one of the most attractive classes for researchers due to their pharmacological activities. In the current research, a new series of 2-[[5-alkyl/aralkyl-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamides (6a–m) were prepared by converting different aryl/aralkyl organic acids (1a–m) successively into corresponding esters (2a–m), hydrazides (3a–m) and 5-aryl/aralkyl-1,3,4-oxadiazol-2-thiols (4a–m). Finally, the target compounds 6a–m were synthesized by stirring 5-aryl/aralkyl-1,3,4-oxadiazol-2-thiols (4a–m) with 2-bromo-N-[4-(4-morpholinyl)phenyl]acetamide (5) in the presence of N,N-dimethylformamide (DMF) and sodium hydride (NaH). The structures of the synthesized compounds were elucidated through IR, 1H-NMR, 13C-NMR and mass spectral data. The compounds were also screened for antimicrobial and hemolytic activity and most of them were found to be active against the selected microbial species at variable extent relative to reference standards. The compounds, 6d and 6f were active against the selected panel of microbes and the former was the most potent one. This series showed less toxicity and may be considered for further biological screening and application trial except 6h and 6l, possessing higher cytotoxicity. |
| first_indexed | 2024-03-06T11:50:34Z |
| format | Article |
| id | UMPir7986 |
| institution | Universiti Malaysia Pahang |
| language | English |
| last_indexed | 2024-03-06T11:50:34Z |
| publishDate | 2017 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | UMPir79862018-04-18T04:10:58Z http://umpir.ump.edu.my/id/eprint/7986/ Synthesis, Antimicrobial Evaluation and Hemolytic Activity of 2-[[5-alkyl/aralkyl substituted-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamide derivatives Akhtar, Muhammad Nadeem Gul, Samreen Rehman, Aziz-ur Abbasi, M. Athar Khan, Khalid Mohammed Nafeesa, Khadija Siddiqa, Asia Shahid, Muhammad Subhani, Zinayyera QD Chemistry 2,5-Disubstituted 1,3,4-oxadiazole compounds are one of the most attractive classes for researchers due to their pharmacological activities. In the current research, a new series of 2-[[5-alkyl/aralkyl-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamides (6a–m) were prepared by converting different aryl/aralkyl organic acids (1a–m) successively into corresponding esters (2a–m), hydrazides (3a–m) and 5-aryl/aralkyl-1,3,4-oxadiazol-2-thiols (4a–m). Finally, the target compounds 6a–m were synthesized by stirring 5-aryl/aralkyl-1,3,4-oxadiazol-2-thiols (4a–m) with 2-bromo-N-[4-(4-morpholinyl)phenyl]acetamide (5) in the presence of N,N-dimethylformamide (DMF) and sodium hydride (NaH). The structures of the synthesized compounds were elucidated through IR, 1H-NMR, 13C-NMR and mass spectral data. The compounds were also screened for antimicrobial and hemolytic activity and most of them were found to be active against the selected microbial species at variable extent relative to reference standards. The compounds, 6d and 6f were active against the selected panel of microbes and the former was the most potent one. This series showed less toxicity and may be considered for further biological screening and application trial except 6h and 6l, possessing higher cytotoxicity. Elsevier 2017 Article PeerReviewed application/pdf en cc_by_nc_nd http://umpir.ump.edu.my/id/eprint/7986/1/fist-2017-nadeem-Synthesis%2C%20antimicrobial%20evaluation%20and%20hemolytic.pdf Akhtar, Muhammad Nadeem and Gul, Samreen and Rehman, Aziz-ur and Abbasi, M. Athar and Khan, Khalid Mohammed and Nafeesa, Khadija and Siddiqa, Asia and Shahid, Muhammad and Subhani, Zinayyera (2017) Synthesis, Antimicrobial Evaluation and Hemolytic Activity of 2-[[5-alkyl/aralkyl substituted-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamide derivatives. Journal of Saudi Chemical Society, 21 (Suppl. 1). pp. 425-433. ISSN 1319-6103. (Published) https://doi.org/10.1016/j.jscs.2014.04.005 DOI: 10.1016/j.jscs.2014.04.005 |
| spellingShingle | QD Chemistry Akhtar, Muhammad Nadeem Gul, Samreen Rehman, Aziz-ur Abbasi, M. Athar Khan, Khalid Mohammed Nafeesa, Khadija Siddiqa, Asia Shahid, Muhammad Subhani, Zinayyera Synthesis, Antimicrobial Evaluation and Hemolytic Activity of 2-[[5-alkyl/aralkyl substituted-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamide derivatives |
| title | Synthesis, Antimicrobial Evaluation and Hemolytic Activity of 2-[[5-alkyl/aralkyl substituted-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamide derivatives |
| title_full | Synthesis, Antimicrobial Evaluation and Hemolytic Activity of 2-[[5-alkyl/aralkyl substituted-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamide derivatives |
| title_fullStr | Synthesis, Antimicrobial Evaluation and Hemolytic Activity of 2-[[5-alkyl/aralkyl substituted-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamide derivatives |
| title_full_unstemmed | Synthesis, Antimicrobial Evaluation and Hemolytic Activity of 2-[[5-alkyl/aralkyl substituted-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamide derivatives |
| title_short | Synthesis, Antimicrobial Evaluation and Hemolytic Activity of 2-[[5-alkyl/aralkyl substituted-1,3,4-oxadiazol-2-yl]thio]-N-[4-(4-morpholinyl)phenyl]acetamide derivatives |
| title_sort | synthesis antimicrobial evaluation and hemolytic activity of 2 5 alkyl aralkyl substituted 1 3 4 oxadiazol 2 yl thio n 4 4 morpholinyl phenyl acetamide derivatives |
| topic | QD Chemistry |
| url | http://umpir.ump.edu.my/id/eprint/7986/1/fist-2017-nadeem-Synthesis%2C%20antimicrobial%20evaluation%20and%20hemolytic.pdf |
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