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Abstract
This work involved the synthesis of some new series of chemical compound which contain Vanillin, 1,3,4 Thiadiazole with Azetidinone or thiazolidinone moieties. In the first step reaction Vanillin and thiosemicarbazide afforded 2-(4-hydroxy-3-methoxybenzylidene) hydrazinecarbo thioamide (1). This compound on further cyclized afforded 4-(5-amino-1,3,4-thiadiazol-2-yl)-2-methoxyphenol (2). Then we synthesized the various 4-(5-((4-substituted-benzylidene)amino)-1,3,4-thiadiazol-2-yl)-2-methoxyphenol (3a-e) treating with various substitutes aldehydes. The synthesized compounds (3a-e) treated with chloroacetyl chloride to get 3-chloro-1-(5-(4- hydroxy-3-methoxyphenyl)-1,3,4-thiadiazol-2-yl)-4-(4-substituted-phenyl) azetidin-2-one (4a-e). Further compound (3a-e) is reacts with mercaptoacetic acid to afforded 3-(5-(4 hydroxy-3- methoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-(4-substituted- phenyl) thiazolidin-4-one (5a-e).
All the synthesized compounds were confirmed by FTIR, 1H NMR and Mass spectral data. Some of the synthesized compounds were screened for biological activity. The compounds showed significant antifungal and antitubercular activity and QSAR studies were carried out for all newly synthesized compounds.
Keywords: Vanillin, Thiosemicarbazide, Antibacterial activity, antifungal activity, Antitubercular activity.
Introduction
Vanillin is a phenolic aldehyde, which is an organic compound. Vanillin functional groups include aldehyde, hydroxyl, and ether[1]. Similar moiety like Eugenol and Curcumin[2,3]. It exhibits the different biological activity such as antifungal, antibacterial, anticancer and antitubercular[4-7].
Heterocyclic compounds play an important role among organic compounds with biological activity used as drugs in human and veterinary medicine or as insecticides and pesticides in agriculture[8].
Thiadiazoles belong to the classes of five membered heterocycle ring. It Contains 2- Nitrogen and 1-Sulphur which have extensive application as structural units of biologically active molecules and as useful intermediates in medicinal chemistry[9].
During the past years, substituted 1, 3, 4-thiadiazole derivatives have received significant attention and have been increasingly investigated due to their broad spectrum of pharmacological properties. It is supposed that 1,3, 4-thiadiazole derivatives exhibit various biological activities due to the presence of =N-C-S- moiety[10]. The marketed drugs such as Acetazolamide and Methazolamide proved their therapeutic potential as Glaucoma and Antiepilepsy [11-14].
Azetidinone, commonly known as ß-lactams. The activity of the famous antibiotics such as Penicillin and Cephalosporin are attributed to the presence of 2-azetidinone ring in them. Recently, some other types of biological activity besides the antibacterial activity have been reported in compounds containing Azetidinone ring. Such biological activities include antifungal, antitubercular and antitumor [15].
Thiazolidinone and its important class of five membered heterocycles moieties. It is a core structure in various synthetic pharmaceuticals, displaying a broad...