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Molecules 2015, 20(5), 8125-8143; doi:10.3390/molecules20058125

Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives

1
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
2
Department of Pharmaceutical Sciences, College of Pharmacy, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi Arabia
3
Department of Chemistry, College of Sciences, King Saud University, Riyadh 11451, Saudi Arabia
4
Department of Microbiology, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt
5
Department of Pharmaceutics and Pharmaceutical Technology (Microbiology), College of Pharmacy, Taibah University, Almadinah Almunawwarah 11344, Saudi Arabia
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 23 April 2015 / Revised: 1 May 2015 / Accepted: 5 May 2015 / Published: 6 May 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [754 KB, uploaded 6 May 2015]   |  

Abstract

The reaction of 1-adamantyl isothiocyanate 4 with the various cyclic secondary amines yielded the corresponding N-(1-adamantyl)carbothioamides 5ae, 6, 7, 8ac 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 15ag. The compounds 5ae, 6, 7, 8ac, 9, 10a, 10b, 14a, 14b and 15ag 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. View Full-Text
Keywords: adamantane derivatives; carbothioamides; antimicrobial activity; hypoglycemic activity adamantane derivatives; carbothioamides; antimicrobial activity; hypoglycemic activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Al-Abdullah, E.S.; Al-Tuwaijri, H.M.; Hassan, H.M.; Al-Alshaikh, M.A.; Habib, E.E.; El-Emam, A.A. Synthesis, Antimicrobial and Hypoglycemic Activities of Novel N-(1-Adamantyl)carbothioamide Derivatives. Molecules 2015, 20, 8125-8143.

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