Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines
The reaction of adamantane-1-carbohydrazide (1) with heterocyclic aldehydes, namely 5-(4-chlorophenyl)isoxazole-3-carboxaldehyde (2a), 5-(4-methylphenyl)isoxazole-3-carboxaldehyde (2b), 5-(4-methoxyphenyl)isoxazole-3-carboxaldehyde (2c), 1H-imidazole-2-carboxaldehyde and 2-butyl-4-chloro-1H-imidazol...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2012-03-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/17/3/3475/ |
| _version_ | 1828434658267758592 |
|---|---|
| author | Abdul-Malek S. Al-Tamimi Ali A. El-Emam Mohamed A. Al-Omar Khalid A. Alrashood |
| author_facet | Abdul-Malek S. Al-Tamimi Ali A. El-Emam Mohamed A. Al-Omar Khalid A. Alrashood |
| author_sort | Abdul-Malek S. Al-Tamimi |
| collection | DOAJ |
| description | The reaction of adamantane-1-carbohydrazide (1) with heterocyclic aldehydes, namely 5-(4-chlorophenyl)isoxazole-3-carboxaldehyde (2a), 5-(4-methylphenyl)isoxazole-3-carboxaldehyde (2b), 5-(4-methoxyphenyl)isoxazole-3-carboxaldehyde (2c), 1H-imidazole-2-carboxaldehyde and 2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde, in ethanol, yielded the corresponding N′-heteroarylidene-1-adamantylcarbohydrazides 3a, 3b, 3c, 4 and 5, respectively, in good yields. The 4-acetyl-1,3,4-oxadiazoline analogues 6a‑c were prepared in 48–55% yields by heating their corresponding N′-heteroarylidene-1-adamantylcarbohydrazides 3a–c with acetic anhydride for two hours. Compounds 3a–c, 4, 5 and 6a–c were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 4 and 5 displayed potent broad-spectrum antimicrobial activity, while compounds 3a–c showed good activity against the Gram-positive bacteria. |
| first_indexed | 2024-12-10T18:53:29Z |
| format | Article |
| id | doaj.art-49ac859cc48246eea8abc60bec2f9fc3 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T18:53:29Z |
| publishDate | 2012-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-49ac859cc48246eea8abc60bec2f9fc32022-12-22T01:37:14ZengMDPI AGMolecules1420-30492012-03-011733475348310.3390/molecules17033475Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolinesAbdul-Malek S. Al-TamimiAli A. El-EmamMohamed A. Al-OmarKhalid A. AlrashoodThe reaction of adamantane-1-carbohydrazide (1) with heterocyclic aldehydes, namely 5-(4-chlorophenyl)isoxazole-3-carboxaldehyde (2a), 5-(4-methylphenyl)isoxazole-3-carboxaldehyde (2b), 5-(4-methoxyphenyl)isoxazole-3-carboxaldehyde (2c), 1H-imidazole-2-carboxaldehyde and 2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde, in ethanol, yielded the corresponding N′-heteroarylidene-1-adamantylcarbohydrazides 3a, 3b, 3c, 4 and 5, respectively, in good yields. The 4-acetyl-1,3,4-oxadiazoline analogues 6a‑c were prepared in 48–55% yields by heating their corresponding N′-heteroarylidene-1-adamantylcarbohydrazides 3a–c with acetic anhydride for two hours. Compounds 3a–c, 4, 5 and 6a–c were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 4 and 5 displayed potent broad-spectrum antimicrobial activity, while compounds 3a–c showed good activity against the Gram-positive bacteria.http://www.mdpi.com/1420-3049/17/3/3475/adamantane derivatives1,3,4-oxadiazolesisoxazolesantimicrobial activity |
| spellingShingle | Abdul-Malek S. Al-Tamimi Ali A. El-Emam Mohamed A. Al-Omar Khalid A. Alrashood Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines Molecules adamantane derivatives 1,3,4-oxadiazoles isoxazoles antimicrobial activity |
| title | Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines |
| title_full | Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines |
| title_fullStr | Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines |
| title_full_unstemmed | Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines |
| title_short | Synthesis and Antimicrobial Activity of N′-Heteroarylidene-1-adamantylcarbohydrazides and (±)-2-(1-Adamantyl)-4-acetyl-5-[5-(4-substituted phenyl-3-isoxazolyl)]-1,3,4-oxadiazolines |
| title_sort | synthesis and antimicrobial activity of n heteroarylidene 1 adamantylcarbohydrazides and 2 1 adamantyl 4 acetyl 5 5 4 substituted phenyl 3 isoxazolyl 1 3 4 oxadiazolines |
| topic | adamantane derivatives 1,3,4-oxadiazoles isoxazoles antimicrobial activity |
| url | http://www.mdpi.com/1420-3049/17/3/3475/ |
| work_keys_str_mv | AT abdulmaleksaltamimi synthesisandantimicrobialactivityofnheteroarylidene1adamantylcarbohydrazidesand21adamantyl4acetyl554substitutedphenyl3isoxazolyl134oxadiazolines AT aliaelemam synthesisandantimicrobialactivityofnheteroarylidene1adamantylcarbohydrazidesand21adamantyl4acetyl554substitutedphenyl3isoxazolyl134oxadiazolines AT mohamedaalomar synthesisandantimicrobialactivityofnheteroarylidene1adamantylcarbohydrazidesand21adamantyl4acetyl554substitutedphenyl3isoxazolyl134oxadiazolines AT khalidaalrashood synthesisandantimicrobialactivityofnheteroarylidene1adamantylcarbohydrazidesand21adamantyl4acetyl554substitutedphenyl3isoxazolyl134oxadiazolines |