Next Article in Journal
Non-Chromatographic Purification of Endohedral Metallofullerenes
Previous Article in Journal
Electrochemical Enhancement of Photocatalytic Disinfection on Aligned TiO2 and Nitrogen Doped TiO2 Nanotubes
Article Menu
Issue 5 (May) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(5), 710; doi:10.3390/molecules22050710

Adamantane-Isothiourea Hybrid Derivatives: Synthesis, Characterization, In Vitro Antimicrobial, and In Vivo Hypoglycemic Activities

1
Department of Chemistry, College of Sciences, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi Arabia
2
Department of Pharmaceutical Sciences, College of Pharmacy, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi Arabia
3
Department of Microbiology, Faculty of Pharmacy, Tanta University, Tanta, Egypt
4
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11671, Saudi Arabia
*
Author to whom correspondence should be addressed.
Academic Editor: Diego Muñoz-Torrero
Received: 14 April 2017 / Revised: 27 April 2017 / Accepted: 27 April 2017 / Published: 29 April 2017
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [837 KB, uploaded 29 April 2017]   |  

Abstract

A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl (Z)-N′-(adamantan-1-yl)-morpholine-4-carbothioimidates 7ae and 4-arylmethyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidates 8ae were prepared via the reaction of N-(adamantan-1-yl)morpholine-4-carbothioamide 5 and N-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioamide 6 with benzyl or substituted benzyl bromides, in acetone, in the presence of anhydrous potassium carbonate. The structures of the synthesized compounds were confirmed by 1H-NMR, 13C-NMR, electrospray ionization mass spectral (ESI-MS) data, and X-ray crystallographic data. The in vitro antimicrobial activity of the new compounds was determined against certain standard strains of pathogenic bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 7b, 7d and 7e displayed potent broad-spectrum antibacterial activity, while compounds 7a, 7c, 8b, 8d and 8e were active against the tested Gram-positive bacteria. The in vivo oral hypoglycemic activity of the new compounds was carried on streptozotocin (STZ)-induced diabetic rats. Compounds 7a, 8ab, and 8b produced potent dose-independent reduction of serum glucose levels, compared to the potent hypoglycemic drug gliclazide. View Full-Text
Keywords: synthesis; adamantane; isothiourea; carbothioimidate; antimicrobial activity; hypoglycaemic activity synthesis; adamantane; isothiourea; carbothioimidate; antimicrobial activity; hypoglycaemic activity
Figures

Figure 1

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).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Al-Wahaibi, L.H.; Hassan, H.M.; Abo-Kamar, A.M.; Ghabbour, H.A.; El-Emam, A.A. Adamantane-Isothiourea Hybrid Derivatives: Synthesis, Characterization, In Vitro Antimicrobial, and In Vivo Hypoglycemic Activities. Molecules 2017, 22, 710.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top