However, with the widespread development of resistance and the availability of more efficient and easier to administer compounds, their use has decreased in ruminants. Simple, mild, and highly efficient synthesis of 2substituted. The purity of the compounds were ascertained by a melting point and tlc. Benomil, carbendazim, metil tiofanato, tiabendazol, fuberidazol. The synthesis and chemistry of certain anthelmintic. Benzimidazole derivatives have attracted a significant attention in recent years because of their medicinal applications as antiviral, antiulcer, antifungal, antihypertensive, anticancer, and.
Synthesis and medicinal applications of benzimidazoles. Similarly, the general synthesis of benzimidazoles is by the condensation reaction of 1,2phenylenediamine with carboxaldehydes, carboxylic acids,6,7 or their derivatives8,9 such as, chlorides, nitriles, and orthoesters, under strong acidic conditions, with high temperatures. Pdf an efficient and green synthesis of benzimidazole. Starting from 1,2diketones and urotropine in the presence of ammonium acetate, a simple and efficient solventless microwaveassisted enabled the synthesis of 4,5disubstituted imidazoles. All the chemicals and reagents used were of analytical grade and were procured from nice chemicals. It is an important pharmacophore and privileged structure in medicinal chemistry.
Wise a basis for interest in the benzimidazole ring system as a nucleus from which to develop potential chemotherapeutic agents was established in the i95os when it was found that 5,6dimethyl i. The yield of all benzimidazole derivatives were found to be in the range of 75 94%. Benzimidazoles molecules closely based on the structure of h51845 are useful for bradykinin b1 receptor antagonists. Benzimidazole and its derivatives are regarded as an important heterocyclic motif that exhibits a wide range of pharmaceutical applications including anticancers, antihypertensives, antivirals, antifungals, antihivs, anticonvulsants, and antidiabetics. The results were also compared with results of synthesis by conventional heating under reflux.
The equimolar amount of amines derivatives and ophenylenediamine were diluted in equimolar amount of dimethyl formamide dmf as solvent to a different round bottom flask and both are mixed and stirred for 30 min. I and ii represent the first benzimidazolebased liquid crystals. The benzimidazoles are a large chemical family used to treat nematode and trematode infections in domestic animals. Descargue como docx, pdf, txt o lea en linea desde scribd. Synthesis, characterization, and biological evaluation of. Benzimidazole derivatives have attracted a significant attention in recent years because of their medicinal applications as antiviral, antiulcer, antifungal, antihypertensive, anticancer, and antihistamine compounds. In view of their wide ranging activities, the synthesis of benzimidazoles and its. Benzimidazoles heterocyclic building blocks sigmaaldrich. Synthesis, reactions, and spectroscopic properties of benzimidazoles. The present study describes a simple, inexpensive, and easy method for synthesis of benzimidazole derivatives in a stipulated time, without using any drastic conditions. The most prominent benzimidazole compound in nature is nribosyldimethylbenzimidazole, which serves as an. In continuation, on the synthesis of heterocycles,14 and on the development of synthetic methodologies,1517 we herein report a facile method for the synthesis of benzimidazoles by the condensation of 1, 2phenylenediamine with carbonyl compounds, in the presence of ammonium salts in very good yields.
The synthesis and chemistry of certain anthelmintic benzimidazoles lb. A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext. Imidazole and benzimidazole synthesis best synthetic. It plays a very important role with plenty of rational therapeutic activities such as antiulcer, antihypertensive, analgesic. Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of enzymes. Benzimidazoles pharmacology merck veterinary manual. Facile, novel twostep syntheses of benzimidazoles, bis. The standard synthesis for benzimidazoles is the cyclocondensation of ophenylenediamine or substituted ophenylenediamines with carboxylic acids or their derivatives. All structured data from the file and property namespaces is available under the creative commons cc0 license. Benzimidazoles and paragonimiasis five patients, aged 738 years, with paragonimus skrjabini infections, were treated with oral triclabendazole 10 mgkg bd for 3 consecutive days, an antihelminthic benzimidazole derivative used in the treatment of fascioliasis in sheep 1 c. We have also tried to summarize the chemistry involved in the synthesis of various derivatives of benzimidazole for medicinal applications. General procedure for the synthesis of 2substituted benzimidazoles and bis benzimidazoles.
Alfa aesar has extended its comprehensive range of heterocyclic compounds with the following. Tubulin is a protein subunit of the microtubules that have a fundamental and ubiquitous role in the mitotic spindle. Alfa aesar has extended its comprehensive range of heterocyclic compounds with the following benzimidazoles. Chemistry benzimidazole is a heterocyclic aromatic organic compound. A set of benzimidazoles, 3himidazo4,5bpyridines, purines, xanthines and benzothiazoles was readily prepared from heteroaromatic orthodiamines or orthoaminothiophenol and aldehydes using chlorotrimethylsilane in dmf as a promoter and wateracceptor agent, followed by oxidation with air oxygen. In this method, ophenylenediamines were condensed with bisulfite adducts of various aldehydes and dialdehydes under neat conditions by microwave heating. It is known that the reaction of ophenylenediamine opda with carbonyl compounds, under strong acidic conditions, gives benzimidazoles, whereas, opda in the presence of. Pdf 2pentadecylbenzimidazole i and 1,1bisoctadecyl2,2 bibenzimidazole ii have been synthesized and. A number of routes exist for the efficient synthesis of either 2 benzimidazole. Benzimidazole is a heterocyclic aromatic organic compound. Benzimidazole, a heterocyclic aromatic organic compound consisting of a fusion of benzene and imidazole, in an extension of the wellelaborated imidazole system, has been used as a carbon skeleton for n heterocyclic carbenes, usually used as ligand for transition metal complexes. A new convenient method for preparation of 2substituted benzimidazoles and bis benzimidazoles is presented. The methods for the synthesis of benzimidazoles have become a focus of synthetic organic chemists, as they are useful building blocks for the development of important therapeutic compounds in medicine. It brings together the multitude of synthesis of the imidazole ring in a systemic way interms of specific bond formation, and recommends the most attractive synthetic approaches.
An additional point of diversity was accessible through functionalization of the isocyanidederived benzimidazole. This bicyclic compound consists of the fusion of benzene and imidazole. Various benzimidazoles 12 were prepared and evaluated by mane et al. Benzimidazole nucleus plays a very important role as a therapeutic. A set of benzimidazoles, 3himidazo4,5bpyridines, purines, xanthines and benzothiazoles was readily prepared from heteroaromatic orthodiamines or orthoaminothiophenol and aldehydes using chlorotrimethylsilane in dmf as a promoter and wateracceptor. Find msds or sds, a coa, data sheets and more information.
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