1,3,4-Oxadiazole <i>N</i>-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities
The reaction of 5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3<i>H</i>)-thione <b>3</b> with formaldehyde solution and primary aromatic amines or 1-substituted piperazines, in ethanol at room temperature yielded the corresponding <i>N</i>-Mannich bases 3-arylaminome...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-04-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/8/2110 |
| _version_ | 1797538629425299456 |
|---|---|
| author | Lamya H. Al-Wahaibi Ahmed A. B. Mohamed Samar S. Tawfik Hanan M. Hassan Ali A. El-Emam |
| author_facet | Lamya H. Al-Wahaibi Ahmed A. B. Mohamed Samar S. Tawfik Hanan M. Hassan Ali A. El-Emam |
| author_sort | Lamya H. Al-Wahaibi |
| collection | DOAJ |
| description | The reaction of 5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3<i>H</i>)-thione <b>3</b> with formaldehyde solution and primary aromatic amines or 1-substituted piperazines, in ethanol at room temperature yielded the corresponding <i>N</i>-Mannich bases 3-arylaminomethyl-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3<i>H</i>)-thiones <b>4a</b>–<b>l</b> or 3-[(4-substituted piperazin-1-yl)methyl]-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3<i>H</i>)-thiones <b>5a</b>–<b>d</b>, respectively. The in vitro inhibitory activity of compounds <b>4a</b>–<b>l</b> and <b>5a</b>–<b>d</b> was assessed against pathogenic Gram-positive, Gram-negative bacteria, and the yeast-like pathogenic fungus <i>Candida albicans</i>. The piperazinomethyl derivatives <b>5c</b> and <b>5d</b> displayed broad-spectrum antibacterial activities the minimal inhibitory concentration (MIC) 0.5–8 μg/mL) and compounds <b>4j</b>, <b>4l</b>, <b>5a,</b> and <b>5b</b> showed potent activity against the tested Gram-positive bacteria. In addition, the anti-proliferative activity of the compounds was evaluated against prostate cancer (PC3), human colorectal cancer (HCT-116), human hepatocellular carcinoma (HePG-2), human epithelioid carcinoma (HeLa), and human breast cancer (MCF7) cell lines. The optimum anti-proliferative activity was attained by compounds <b>4l</b>, <b>5a</b>, <b>5c,</b> and <b>5d</b>. |
| first_indexed | 2024-03-10T12:33:06Z |
| format | Article |
| id | doaj.art-b2d98eb3030e4bc6a9ed3e7ae77b848f |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T12:33:06Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b2d98eb3030e4bc6a9ed3e7ae77b848f2023-11-21T14:28:25ZengMDPI AGMolecules1420-30492021-04-01268211010.3390/molecules260821101,3,4-Oxadiazole <i>N</i>-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative ActivitiesLamya H. Al-Wahaibi0Ahmed A. B. Mohamed1Samar S. Tawfik2Hanan M. Hassan3Ali A. El-Emam4Department of Chemistry, College of Sciences, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi ArabiaDepartment of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptDepartment of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptDepartment of Pharmacology and Biochemistry, Faculty of Pharmacy, Delta University for Science and Technology, International Costal Road, Gamasa City, Mansoura 11152, EgyptDepartment of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptThe reaction of 5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3<i>H</i>)-thione <b>3</b> with formaldehyde solution and primary aromatic amines or 1-substituted piperazines, in ethanol at room temperature yielded the corresponding <i>N</i>-Mannich bases 3-arylaminomethyl-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3<i>H</i>)-thiones <b>4a</b>–<b>l</b> or 3-[(4-substituted piperazin-1-yl)methyl]-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3<i>H</i>)-thiones <b>5a</b>–<b>d</b>, respectively. The in vitro inhibitory activity of compounds <b>4a</b>–<b>l</b> and <b>5a</b>–<b>d</b> was assessed against pathogenic Gram-positive, Gram-negative bacteria, and the yeast-like pathogenic fungus <i>Candida albicans</i>. The piperazinomethyl derivatives <b>5c</b> and <b>5d</b> displayed broad-spectrum antibacterial activities the minimal inhibitory concentration (MIC) 0.5–8 μg/mL) and compounds <b>4j</b>, <b>4l</b>, <b>5a,</b> and <b>5b</b> showed potent activity against the tested Gram-positive bacteria. In addition, the anti-proliferative activity of the compounds was evaluated against prostate cancer (PC3), human colorectal cancer (HCT-116), human hepatocellular carcinoma (HePG-2), human epithelioid carcinoma (HeLa), and human breast cancer (MCF7) cell lines. The optimum anti-proliferative activity was attained by compounds <b>4l</b>, <b>5a</b>, <b>5c,</b> and <b>5d</b>.https://www.mdpi.com/1420-3049/26/8/21101,3,4-oxadiazoles<i>N</i>-Mannich basesantimicrobial activityanti-proliferative activity |
| spellingShingle | Lamya H. Al-Wahaibi Ahmed A. B. Mohamed Samar S. Tawfik Hanan M. Hassan Ali A. El-Emam 1,3,4-Oxadiazole <i>N</i>-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities Molecules 1,3,4-oxadiazoles <i>N</i>-Mannich bases antimicrobial activity anti-proliferative activity |
| title | 1,3,4-Oxadiazole <i>N</i>-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities |
| title_full | 1,3,4-Oxadiazole <i>N</i>-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities |
| title_fullStr | 1,3,4-Oxadiazole <i>N</i>-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities |
| title_full_unstemmed | 1,3,4-Oxadiazole <i>N</i>-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities |
| title_short | 1,3,4-Oxadiazole <i>N</i>-Mannich Bases: Synthesis, Antimicrobial, and Anti-Proliferative Activities |
| title_sort | 1 3 4 oxadiazole i n i mannich bases synthesis antimicrobial and anti proliferative activities |
| topic | 1,3,4-oxadiazoles <i>N</i>-Mannich bases antimicrobial activity anti-proliferative activity |
| url | https://www.mdpi.com/1420-3049/26/8/2110 |
| work_keys_str_mv | AT lamyahalwahaibi 134oxadiazoleinimannichbasessynthesisantimicrobialandantiproliferativeactivities AT ahmedabmohamed 134oxadiazoleinimannichbasessynthesisantimicrobialandantiproliferativeactivities AT samarstawfik 134oxadiazoleinimannichbasessynthesisantimicrobialandantiproliferativeactivities AT hananmhassan 134oxadiazoleinimannichbasessynthesisantimicrobialandantiproliferativeactivities AT aliaelemam 134oxadiazoleinimannichbasessynthesisantimicrobialandantiproliferativeactivities |