Adamantane-isothiourea hybrid derivatives

Synthesis, characterization, in vitro antimicrobial, and in vivo hypoglycemic activities

Lamya H. Al-Wahaibi, Hanan M. Hassan, Amal M. Abo-Kamar, Hazem A. Ghabbour, Ali A. El-Emam

Research output: Contribution to journalArticleResearchpeer-review

9 Citations (Scopus)

Abstract

A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl (Z)-N1-(adamantan-1-yl)-morpholine-4-carbothioimidates 7a-e and 4-arylmethyl (Z)-N0-(adamantan-1-yl)-4 -phenylpiperazine-1-carbothioimidates 8a-e 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.

Original languageEnglish
Article number710
JournalMolecules
Volume22
Issue number5
DOIs
Publication statusPublished - 1 May 2017

Fingerprint

Adamantane
Hypoglycemic Agents
Bacteria
Nuclear magnetic resonance
Gliclazide
Derivatives
Electrospray ionization
bacteria
Candida
Gram-Positive Bacteria
synthesis
Streptozocin
Acetone
Fungi
Candida albicans
Yeast
Rats
nuclear magnetic resonance
fungi
Yeasts

Keywords

  • Adamantane
  • Antimicrobial activity
  • Carbothioimidate
  • Hypoglycaemic activity
  • Isothiourea
  • Synthesis

Cite this

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title = "Adamantane-isothiourea hybrid derivatives: Synthesis, characterization, in vitro antimicrobial, and in vivo hypoglycemic activities",
abstract = "A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl (Z)-N1-(adamantan-1-yl)-morpholine-4-carbothioimidates 7a-e and 4-arylmethyl (Z)-N0-(adamantan-1-yl)-4 -phenylpiperazine-1-carbothioimidates 8a-e 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.",
keywords = "Adamantane, Antimicrobial activity, Carbothioimidate, Hypoglycaemic activity, Isothiourea, Synthesis",
author = "Al-Wahaibi, {Lamya H.} and Hassan, {Hanan M.} and Abo-Kamar, {Amal M.} and Ghabbour, {Hazem A.} and El-Emam, {Ali A.}",
year = "2017",
month = "5",
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doi = "10.3390/molecules22050710",
language = "English",
volume = "22",
journal = "Molecules",
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publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
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Adamantane-isothiourea hybrid derivatives : Synthesis, characterization, in vitro antimicrobial, and in vivo hypoglycemic activities. / Al-Wahaibi, Lamya H.; Hassan, Hanan M.; Abo-Kamar, Amal M.; Ghabbour, Hazem A.; El-Emam, Ali A.

In: Molecules, Vol. 22, No. 5, 710, 01.05.2017.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Adamantane-isothiourea hybrid derivatives

T2 - Synthesis, characterization, in vitro antimicrobial, and in vivo hypoglycemic activities

AU - Al-Wahaibi, Lamya H.

AU - Hassan, Hanan M.

AU - Abo-Kamar, Amal M.

AU - Ghabbour, Hazem A.

AU - El-Emam, Ali A.

PY - 2017/5/1

Y1 - 2017/5/1

N2 - A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl (Z)-N1-(adamantan-1-yl)-morpholine-4-carbothioimidates 7a-e and 4-arylmethyl (Z)-N0-(adamantan-1-yl)-4 -phenylpiperazine-1-carbothioimidates 8a-e 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.

AB - A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl (Z)-N1-(adamantan-1-yl)-morpholine-4-carbothioimidates 7a-e and 4-arylmethyl (Z)-N0-(adamantan-1-yl)-4 -phenylpiperazine-1-carbothioimidates 8a-e 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.

KW - Adamantane

KW - Antimicrobial activity

KW - Carbothioimidate

KW - Hypoglycaemic activity

KW - Isothiourea

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=85020166087&partnerID=8YFLogxK

U2 - 10.3390/molecules22050710

DO - 10.3390/molecules22050710

M3 - Article

VL - 22

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 5

M1 - 710

ER -