Synthesis, characterization and pharmacological evaluation of different 1,3,4-oxadiazole and acetamide derivatives of ethyl nipecotate
A new series of N-substituted derivatives of 2-[(5-{1-[(4-chlorophenyl)sulfonyl]-3-piperidinyl}-1,3,4-oxadiazol-2-yl)sulfanyl]acetamide (6a-w) has been designed and synthesized with multifunctional moieties. The synthesized compounds were evaluated for their antibacterial and anti-enzymatic potentia...
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Faculty of Pharmacy, Cairo University
2017-12-01
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| Series: | Bulletin of Faculty of Pharmacy Cairo University |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1110093117300315 |
| _version_ | 1797970078381113344 |
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| author | Khadija Nafeesa Aziz-ur-Rehman Muhammad A. Abbasi Sabahat Z. Siddiqui Shahid Rasool Syed A.A. Shah |
| author_facet | Khadija Nafeesa Aziz-ur-Rehman Muhammad A. Abbasi Sabahat Z. Siddiqui Shahid Rasool Syed A.A. Shah |
| author_sort | Khadija Nafeesa |
| collection | DOAJ |
| description | A new series of N-substituted derivatives of 2-[(5-{1-[(4-chlorophenyl)sulfonyl]-3-piperidinyl}-1,3,4-oxadiazol-2-yl)sulfanyl]acetamide (6a-w) has been designed and synthesized with multifunctional moieties. The synthesized compounds were evaluated for their antibacterial and anti-enzymatic potential supported by % hemolytic activity. The synthesized compound 5-(1-(4-chlorophenylsulfonyl)-3-piperidinyl)-1,3,4-oxadiazole-2-thiol (3) was stirred with synthesized electrophiles as N-aryl/alkyl/aralkyl-2-bromoacetamide (5a-w) in an aprotic solvent under basic conditions to acquire the target molecules, 6a-w. The spectral analytical techniques of IR, EI-MS, 1H NMR and 13C-NMR were utilized for structural elucidation of synthesized molecules. The antibacterial screening against certain bacterial strains of gram-negative and gram-positive bacteria rendered compound 6i as good inhibitor of gram-negative bacterial strains. The enzyme inhibition revealed low potential against lipoxygenase (LOX) enzyme. The hemolytic study provided valuable information about cytotoxic behavior of synthesized molecules. Keywords: 1,3,4-Oxadiazole, Acetamide, Antibacterial activity, Hemolytic activity, Lipoxygenase inhibition |
| first_indexed | 2024-04-11T03:12:19Z |
| format | Article |
| id | doaj.art-074f4df2fda143c582616f4ae3fe6edf |
| institution | Directory Open Access Journal |
| issn | 1110-0931 |
| language | English |
| last_indexed | 2024-04-11T03:12:19Z |
| publishDate | 2017-12-01 |
| publisher | Faculty of Pharmacy, Cairo University |
| record_format | Article |
| series | Bulletin of Faculty of Pharmacy Cairo University |
| spelling | doaj.art-074f4df2fda143c582616f4ae3fe6edf2023-01-02T11:18:20ZengFaculty of Pharmacy, Cairo UniversityBulletin of Faculty of Pharmacy Cairo University1110-09312017-12-01552333343Synthesis, characterization and pharmacological evaluation of different 1,3,4-oxadiazole and acetamide derivatives of ethyl nipecotateKhadija Nafeesa0 Aziz-ur-Rehman1Muhammad A. Abbasi2Sabahat Z. Siddiqui3Shahid Rasool4Syed A.A. Shah5Department of Chemistry, Government College University, Lahore 54000, PakistanDepartment of Chemistry, Government College University, Lahore 54000, Pakistan; Corresponding author.Department of Chemistry, Government College University, Lahore 54000, PakistanDepartment of Chemistry, Government College University, Lahore 54000, PakistanDepartment of Chemistry, Government College University, Lahore 54000, PakistanFaculty of Pharmacy and Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), University Technology MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, MalaysiaA new series of N-substituted derivatives of 2-[(5-{1-[(4-chlorophenyl)sulfonyl]-3-piperidinyl}-1,3,4-oxadiazol-2-yl)sulfanyl]acetamide (6a-w) has been designed and synthesized with multifunctional moieties. The synthesized compounds were evaluated for their antibacterial and anti-enzymatic potential supported by % hemolytic activity. The synthesized compound 5-(1-(4-chlorophenylsulfonyl)-3-piperidinyl)-1,3,4-oxadiazole-2-thiol (3) was stirred with synthesized electrophiles as N-aryl/alkyl/aralkyl-2-bromoacetamide (5a-w) in an aprotic solvent under basic conditions to acquire the target molecules, 6a-w. The spectral analytical techniques of IR, EI-MS, 1H NMR and 13C-NMR were utilized for structural elucidation of synthesized molecules. The antibacterial screening against certain bacterial strains of gram-negative and gram-positive bacteria rendered compound 6i as good inhibitor of gram-negative bacterial strains. The enzyme inhibition revealed low potential against lipoxygenase (LOX) enzyme. The hemolytic study provided valuable information about cytotoxic behavior of synthesized molecules. Keywords: 1,3,4-Oxadiazole, Acetamide, Antibacterial activity, Hemolytic activity, Lipoxygenase inhibitionhttp://www.sciencedirect.com/science/article/pii/S1110093117300315 |
| spellingShingle | Khadija Nafeesa Aziz-ur-Rehman Muhammad A. Abbasi Sabahat Z. Siddiqui Shahid Rasool Syed A.A. Shah Synthesis, characterization and pharmacological evaluation of different 1,3,4-oxadiazole and acetamide derivatives of ethyl nipecotate Bulletin of Faculty of Pharmacy Cairo University |
| title | Synthesis, characterization and pharmacological evaluation of different 1,3,4-oxadiazole and acetamide derivatives of ethyl nipecotate |
| title_full | Synthesis, characterization and pharmacological evaluation of different 1,3,4-oxadiazole and acetamide derivatives of ethyl nipecotate |
| title_fullStr | Synthesis, characterization and pharmacological evaluation of different 1,3,4-oxadiazole and acetamide derivatives of ethyl nipecotate |
| title_full_unstemmed | Synthesis, characterization and pharmacological evaluation of different 1,3,4-oxadiazole and acetamide derivatives of ethyl nipecotate |
| title_short | Synthesis, characterization and pharmacological evaluation of different 1,3,4-oxadiazole and acetamide derivatives of ethyl nipecotate |
| title_sort | synthesis characterization and pharmacological evaluation of different 1 3 4 oxadiazole and acetamide derivatives of ethyl nipecotate |
| url | http://www.sciencedirect.com/science/article/pii/S1110093117300315 |
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