NDLI: Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 2-[3-(1-Adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl]acetic Acids, 2-[3-(1-Adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl]propionic Acids and Related Derivatives

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Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 2-[3-(1-Adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl]acetic Acids, 2-[3-(1-Adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl]propionic Acids and Related Derivatives

Content Provider	Scilit
Author	Al-Deeb, Omar A. Al-Omar, Mohamed A. El-Brollosy, Nasser R. Habib, Elsayed E. Ibrahim, Tarek M. El-Emam, Ali A.
Copyright Year	2006
Abstract	The reaction of 3-(1-adamantyl)-4-substituted-1,2,4-triazoline-5-thiones 3a-g with sodium chloroacetate, in ethanolic sodium hydroxide yielded the corresponding $N^{1}$-acetic acid derivatives 4a-g. The interaction of 3a-g with ethyl 2-bromopropionate in acetone, in the presence of potassium carbonate, yielded the corresponding $N^{1}$-ethyl propionate derivatives 5a-g, which upon hydrolysis with aqueous sodium hydroxide afforded the corresponding propionic acid derivatives 6a-g. Similarly, the reaction of 3-(1-adamantyl)-4-amino-1,2,4-triazoline-5-thione 7 with sodium chloroacetate in ethanolic sodium hydroxide yielded the corresponding $N^{1}$-acetic acid derivative 8. On the other hand, the reaction of 2-(1-adamantyl)-1,3,4-oxadiazoline-5-thione 9 with sodium chloroacetate yielded the corresponding S-acetic acid derivative 10. Compounds 4a-g, 5b, 5c, 5g, 6a-g, 8 and 10 were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Several derivatives produced good or moderate activities particularly against Bacillus subtilis. In addition, the in vivo anti-inflammatory activities of these compounds were determined using the carrageenin-induced paw oedema method in rats. Compounds 4a, 4b, 4e, 4f, 6f, 6g and 10 produced good dose-dependent anti-inflammatory activities. Synthese sowie antimikrobielle und entzündungshemmende Wirkung neuer 2-[3-(1-Adamantyl)-4-substituierter-5-thioxo-1,2,4-triazolin-1-yl]essigsäuren, 2-[3-(1-Adamantyl)-4-substituierter-5-thioxo-1,2,4-triazolin-1-yl]propionsäuren und verwandter Derivate Die Reaktion der 3-(1-Adamantyl)-4-substituierte-1,2,4-triazolin-5-thione 3a-g mit Natriumchloracetat in ethanolischer Natriumhydroxid-Lösung führte zu den entsprechenden $N^{1}$-Essigsäure-Derivaten 4a-g. Die Reaktion von 3a-g mit 2-Brompropionsäureethylesther in Aceton in Gegenwart von Kaliumcarbonat ergab die entsprechenden $N^{1}$-Propionsäureethylester-Derivate 5a-g, aus denen durch Hydrolyse mit wäßriger Natronlauge die analogen Propionsäure-Derivate 6a-g entstanden. In gleicher Weise führte die Reaktion von 3-(1-Adamantyl)-4-amino-1,2,4-triazolin-5-thion 7 mit Natriumchloracetat in ethanolischer Natronlauge zum entsprechenden $N^{1}$-Essigsäure-Derivat 8. Andererseits entstanden bei der Reaktion von 2-(1-Adamantyl)-1,3,4-oxadiazolin-5-thion 9 mit Natriumchloracetat das entsprechende S-Essigsäure-Derivat 10. Die Verbindungen 4a-g, 5b, 5c, 5g, 6a-g, 8 und 10 wurden auf ihre In-vitro-Wirkung gegen eine Reihe Gram-positiver und Gram-negativer Bakterien und gegen den hefeähnlichen pathogenen Pilz Candida albicans getestet. Einige Derivate zeigten speziell gegen Bacillus subtilis gute bis mäßige Wirkung. Weiterhin wurde in vivo die entzündungshemmende Wirkung der Verbindungen am Modell des Carrageenin-induzierten Rattenödems bestimmt. Die Verbindungen 4a, 4b, 4e, 4f, 6f, 6g und 10 zeigten gute dosisabhängige entzündungshemmende Wirkung.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0031-1296699.pdf
Ending Page	47
Page Count	8
Starting Page	40
ISSN	00044172
e-ISSN	16167066
DOI	10.1055/s-0031-1296699
Journal	Arzneimittelforschung
Issue Number	01
Volume Number	56
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2006-01-01
Access Restriction	Open
Subject Keyword	Journal: Arzneimittelforschung Medicinal Chemistry 1-adamantyl Derivatives Anti-inflammatory Activity Antimicrobial Activity
Content Type	Text
Resource Type	Article
Subject	Drug Discovery

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