Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives
The reaction of 1-adamantyl isothiocyanate 4 with the various cyclic secondary amines yielded the corresponding N-(1-adamantyl)carbothioamides 5a–e, 6, 7, 8a–c and 9. Similarly, the reaction of 4 with piperazine and trans-2,5-dimethylpiperazine in 2:1 molar ratio yielded the corresponding N,N'-...
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MDPI AG
2015-05-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/5/8125 |
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| author | Ebtehal S. Al-Abdullah Hanaa M. Al-Tuwaijri Hanan M. Hassan Monirah A. Al-Alshaikh Elsayed E. Habib Ali A. El-Emam |
| author_facet | Ebtehal S. Al-Abdullah Hanaa M. Al-Tuwaijri Hanan M. Hassan Monirah A. Al-Alshaikh Elsayed E. Habib Ali A. El-Emam |
| author_sort | Ebtehal S. Al-Abdullah |
| collection | DOAJ |
| description | The reaction of 1-adamantyl isothiocyanate 4 with the various cyclic secondary amines yielded the corresponding N-(1-adamantyl)carbothioamides 5a–e, 6, 7, 8a–c and 9. Similarly, the reaction of 4 with piperazine and trans-2,5-dimethylpiperazine in 2:1 molar ratio yielded the corresponding N,N'-bis(1-adamantyl)piperazine-1,4-dicarbothioamides 10a and 10b, respectively. The reaction of N-(1-adamantyl)-4-ethoxycarbonylpiperidine-1-carbothioamide 8c with excess hydrazine hydrate yielded the target carbohydrazide 11, in addition to 4-(1-adamantyl)thiosemicarbazide 12 as a minor product. The reaction of the carbohydrazide 11 with methyl or phenyl isothiocyanate followed by heating in aqueous sodium hydroxide yielded the 1,2,4-triazole analogues 14a and 14b. The reaction of the carbohydrazide 11 with various aromatic aldehydes yielded the corresponding N'-arylideneamino derivatives 15a–g. The compounds 5a–e, 6, 7, 8a–c, 9, 10a, 10b, 14a, 14b and 15a–g were tested for in vitro antimicrobial activity against certain strains of pathogenic Gram-positive and Gram-negative bacteria and the yeast-like fungus Candida albicans. The compounds 5c, 5d, 5e, 6, 7, 10a, 10b, 15a, 15f and 15g showed potent antibacterial activity against one or more of the tested microorganisms. The oral hypoglycemic activity of compounds 5c, 6, 8b, 9, 14a and 15b was determined in streptozotocin (STZ)-induced diabetic rats. Compound 5c produced significant reduction of serum glucose levels, compared to gliclazide. |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-12T08:44:53Z |
| publishDate | 2015-05-01 |
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| spelling | doaj.art-3e5d210d17a5479db8e2dab1b66f50312022-12-22T00:30:34ZengMDPI AGMolecules1420-30492015-05-012058125814310.3390/molecules20058125molecules20058125Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide DerivativesEbtehal S. Al-Abdullah0Hanaa M. Al-Tuwaijri1Hanan M. Hassan2Monirah A. Al-Alshaikh3Elsayed E. Habib4Ali A. El-Emam5Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaDepartment of Pharmaceutical Sciences, College of Pharmacy, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi ArabiaDepartment of Chemistry, College of Sciences, King Saud University, Riyadh 11451, Saudi ArabiaDepartment of Microbiology, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, EgyptDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaThe reaction of 1-adamantyl isothiocyanate 4 with the various cyclic secondary amines yielded the corresponding N-(1-adamantyl)carbothioamides 5a–e, 6, 7, 8a–c and 9. Similarly, the reaction of 4 with piperazine and trans-2,5-dimethylpiperazine in 2:1 molar ratio yielded the corresponding N,N'-bis(1-adamantyl)piperazine-1,4-dicarbothioamides 10a and 10b, respectively. The reaction of N-(1-adamantyl)-4-ethoxycarbonylpiperidine-1-carbothioamide 8c with excess hydrazine hydrate yielded the target carbohydrazide 11, in addition to 4-(1-adamantyl)thiosemicarbazide 12 as a minor product. The reaction of the carbohydrazide 11 with methyl or phenyl isothiocyanate followed by heating in aqueous sodium hydroxide yielded the 1,2,4-triazole analogues 14a and 14b. The reaction of the carbohydrazide 11 with various aromatic aldehydes yielded the corresponding N'-arylideneamino derivatives 15a–g. The compounds 5a–e, 6, 7, 8a–c, 9, 10a, 10b, 14a, 14b and 15a–g were tested for in vitro antimicrobial activity against certain strains of pathogenic Gram-positive and Gram-negative bacteria and the yeast-like fungus Candida albicans. The compounds 5c, 5d, 5e, 6, 7, 10a, 10b, 15a, 15f and 15g showed potent antibacterial activity against one or more of the tested microorganisms. The oral hypoglycemic activity of compounds 5c, 6, 8b, 9, 14a and 15b was determined in streptozotocin (STZ)-induced diabetic rats. Compound 5c produced significant reduction of serum glucose levels, compared to gliclazide.http://www.mdpi.com/1420-3049/20/5/8125adamantane derivativescarbothioamidesantimicrobial activityhypoglycemic activity |
| spellingShingle | Ebtehal S. Al-Abdullah Hanaa M. Al-Tuwaijri Hanan M. Hassan Monirah A. Al-Alshaikh Elsayed E. Habib Ali A. El-Emam Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives Molecules adamantane derivatives carbothioamides antimicrobial activity hypoglycemic activity |
| title | Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives |
| title_full | Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives |
| title_fullStr | Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives |
| title_full_unstemmed | Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives |
| title_short | Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives |
| title_sort | synthesis antimicrobial and hypoglycemic activities of novel n 1 adamantyl carbothioamide derivatives |
| topic | adamantane derivatives carbothioamides antimicrobial activity hypoglycemic activity |
| url | http://www.mdpi.com/1420-3049/20/5/8125 |
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