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Novel Synthesis, And Biological Evaluation of Four Co-Ordinate Co (Ii)-Complexes Derived From 5-Amino 2(4’thiazolyl)1 hbezimidazole (ATBZ) And Heterocyclic Bases

Dr.J.R.Gujarathi, Assi Prof.T.V. Rajale
Department of Chemistry, Pratap College, Amalner, Maharashtra, India
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Four coordinate Co (II) adducts were synthesized by the reaction of CoCl2.6H2O with and 5- aminothiabendazole as chelate ligand in ethanol and heterocyclic bases in the ratio 1:1:1. The synthesized compound ATBZ was elucidated by elemental analysis, 13C, 1H NMR. The synthesized adducts were characterized by elemental analysis, magnetic measurements, conductivity measurements. Screenings of antimicrobial activity of prepared metal complexes were also carried out against different bacterial species such as Pseudomonas putida, Escherichia coli, and fungal species such as Aspergillus Nigar, Candida Albicans, Yields of the synthesized compounds were found moderate and some of them also indicated potent activity against bacterial and fungal species.


5-aminothiabendazole, CoCl2.6H2O, antimicrobial assay.


Sulfur and/or nitrogen heterocycles have acquired a great importance among the heterocycles, as these possess pharmaceutical activities and pest management potency. These widely occur in the nature in the form of alkaloids, vitamins, pigments and as constituents of plant and animal cells. The utility of thiazoles in curative treatment has been firmly established. They exhibit anti-bacterial, anti-hypertensive, anti-anginal, anti-arrhythmetic, anti-histaminic, narcotic antagonist activities [1]. Thiazole nucleus is found in many antibiotics and vitamins in one or another form.The benzimidazole compounds have been proved to be the most important group of fungicides with systemic activity and are well known for their pronounced ability to control a large number of fungal diseases. Benomyl, thiabendazole and thiophanate methyl are main examples of this fungicide class. Because of their systematic activity, they can help to control some diseases after infection. Benzimidazole fungicides are also used to prevent post-harvest rots and in soildrench treatments [2].
The 2-(4-thiazolyl)-1H-benzimidazoles are structurally analogous to benzimidazoles, well known as an anthelminitic agent and systemic fungicide. Its fungicidal properties and systemic properties in plants have already been reported as a fungicide with protective and curative action. It is used to control of Aspergillus, Botrytis, Ceratocystis, Cercospora, Colletotrichum, Corticium, Diaporthe, Diplodia, Fusarium, Gibberella, Gloeosporium, Oospora, Penicillium, Phoma, Rhizoctonia, Sclerotinia, Septoria, Thielaviopsis, Verticillium spp., etc.[3] in asparagus, avocados, bananas, barley, beans, cabbage, celery, chicory, cherries, citrus, cotton, some cucurbits, flax, mangoes, mushrooms, oats, onions, ornamentals, pawpaws, pome fruit, potatoes, rice, soyabeans, strawberries, sugar beet, sweet potatoes, tobacco, tomatoes, turf, vines and wheat. Also used for control of storage diseases of fruits and vegetables and for control of Dutch elm disease. It is commonly used as an anthelminitic in human and veterinary medicine too[4]. Again thiabendazole has significant anthelmentic activity for gastrointestinal parasites in sheep, goats, cattle, horses, swine, dogs, and poultry. This compound is well-tolerated and does not stain the skin, hair or wool of animals. It may be given orally for therapeutic use or in feed or mineral supplements for the prophylactic control of parasites in domestic animals.
Benzimidazole and thiazole analogues have found applications in medicine and agriculture[5]. Therefore development of a simple, fast and flexible method to generate libraries of such compounds was desirable. The structural modification or derivatization and bioassay are highly essential to establish structure-activity relationships in order to exploit the molecules having better potency and efficacy. In continuation of our work on synthesis of biologically active compound using polymer-supported reactions, we report herein a simple, rapid and safer method for the preparation of N-alkyl and N-acyl derivatives of 2-(4-thiazolyl)-1H-benzimidazole. Easy separation of products with higher yield and purity by simple work-up, and speed are crucial features of the method. The metal complexes of thiabendazole structure, antimicrobial activity and photodynamic effects has been done [6].
5-Aminothiabendazole (ANTBZ) acts as both acid and base, thus it is possible to make compounds which are neutral, cationic or anionic in nature, as well as report biological activity of metal complexes. The potential N, N’- donor chelating agent are quite rare. In present paper we report synthesis and characterization of derivatives of 5- Aminothiabendazole, and differentiate fungi toxic activity with those of nitrothiabendazole. Nitrogen heterocycles have acquired an immense importance among the heterocycles, possessing pharmaceutical activities and widely occur in the nature in the form of alkaloids, vitamins, pigments and as constituents of plant and animal cells. The utility of thiazoles in curative treatment has been firmly established. They exhibit anti-bacterial, anti-hypertensive, anti-anginal, antiarrhythmetic, anti-histaminic, narcotic antagonist, etc. activities. Thiazole nucleus is found in many antibiotics and vitamins in one or another form. Benzimidazole and many of its derivatives exhibit a variety of biological actions, including antibacterial, antiviral, anticancer and antifungal activity [7]. Benomyl, thiabendazole and thiophnate methyl are main examples of this fungicide class. Because of their systematic activity, they can help to control some diseases after infection. In present work 5-Aminothiabendazole,is selected as chelte ligand because of structural similarity to chelating agents such as 2,2’ bipyridine and 1,10 phenanthroline.


Thiabendazole (A.R.Grade), Cobalt Chloride (A.R.Grade), zinc dust, methanol, formic acid, chloroform, sodium bicarbonate, super saturated solution of NaCl (A.R.Grade).
Synthesis of Thiabendazole to 5-Nitrothiabendazole
Ice cold conc.H2SO4 was added to thiabendazole with constant stirring .The reaction mixture was warmed at 50º C for 10 min. till thiabendazole dissolved completely. In ice bath below - 4º C. Nitrating mixture (ice cold 1.5 ml conc.H2SO4 and 10.2 ml of conc. HNO3) was added with constant stirring. After complete addition the reaction mixture was kept aside for 45 min (i.e. at R.T.25º C). The reaction mixture was then warmed at 85-90º C for 90 min. The reaction mixture was then cooled at room temperature. Crushed ice was then added with constant stirring, very faint yellowish white precipitate was then separated out. Sodium bicarbonate was then added to it till the effervesces of CO2 completely stopped and precipitate became neutral. The precipitate was then filtered off, washed with water and finally with diethyl ether and dried under IR lamp.
The chelate Co.L.Cl py showed maximum activity against bacterial and fungal species than free ligand Thus the coordination of metal ion to ligand is responsible for high biological activity. It has been observed that the % activity index decreases on dilution i.e. it is more in concentrated solution.The most probable reason for this difference might be due to chelation which reduces the polarity of the central metal atom because of the partial sharing of its positive charge with donor groups and possible π-electron delocalization within the whole chelating ring. As a result of this, the lipophilic nature of the central metal atom increases, which favors the permeation of the complexes through the lipid layer of the cell membrane [10].


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