It is a benzimidazole and a polycyclic heteroarene. Benzimidazoles are regarded as a promising class of bioactive heterocyclic compounds that exhibit a range of biological activities. Files are available under licenses specified on their description page. Pdf synthesis of benzimidazole derivatives and study of their.
Some areas of the world, such as india, have seen cases where worms were resistant to this type of treatment. In the course of our search for therapeutically useful antifungal azoles, we synthesized some new derivatives of benzimidazole, benzotriazole and aminothiazole table 1. The synthesis of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substituted benzimidazole 2thiols 4ac followed by successive. An iridiummediated ch activation mechanism is suggested. The grafting of the bronsted acidic ionic liquid to the surface of teos has increased the catalytic activity of the material and also simplified catalyst recovery from the reaction mixture.
Benzimidazole definition of benzimidazole by merriamwebster. Benzimidazoles, thin layer chromatography, phenylene diamine. Cambendazole 5 was the first which was claimed to be effective against cestodes in sheep. Pdf a new series of non peptide angiotensinaii receptor antagonist has been prepared. Boric acid catalyzed convenient synthesis of benzimidazoles. The standard synthesis for benzimidazoles is the cyclocondensation of ophenylenediamine or substituted ophenylenediamines with carboxylic acids or their derivatives. Benzimidazole drugs are quite effective, but their usage may be declining. They show selective neuropeptides yy 1 receptor antagonists, 1 potent inhibitors of tie2 and vegfer2 tyrosine kinase receptors, 2 antitumor agents, 3. The synthesized benzimidazoles compounds were prepared from the condensation reaction between ophenylenediamine and various carbonyl compounds, in. This was later replaced by more effective benzimidazole anthelmintics such as mebendazole 14, fenbendazole 18, oxfendazole 19 and albendazole.
Here, the synthesis of both classes of compounds starting from aromatic diamines and alcohols benzimidazoles or diols quinoxalines is reported. Certain reactions of nalkylation and nacylation of these compounds have been studied. The synthesis of benzimidazoles and quinoxalines from. Antiparasiticagents, benzimidazoles, mebendazole, atovaquone, thiabendazole, albendazole benzimidazoles. Mild and efficient synthesis of 2aryl benzimidazoles in water using sds s. 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. Synthesis of benzimidazoles virtually starts with benzene derivatives having nitrogencontaining functions ortho to each other like ophenylenediamines 7 opd and reacting with different carboxylic acids 8 to give 2substituted benzimidazole derivatives 9, generally in good yield. Mild and efficient synthesis of 2aryl benzimidazoles in. A new series of 2, 5 disubstituted benzimidazole derivatives have been synthesized. Triethylamine promoted the formation of benzimidazoles, whereas 2aminopyridine promoted the formation of n arylindazoles.
This reaction led to the formation of benzimidazoles new derivatives in good yields. Synthesis and biological evaluation of benzimidazolelinked 1, 2, 3. Benzimidazole derivatives have attracted a significant attention in recent years because of their medicinal applications as antiviral, antiulcer, antifungal, antihypertensive, anticancer, and antihistamine compounds. General procedure for the synthesis of 2substituted benzimidazoles and bis benzimidazoles. Benzimidazole article about benzimidazole by the free. A number of benzimidazoles were prepared in good yields. Various n aryl1 h indazoles and benzimidazoles were synthesized from common arylamino oximes in good to excellent yields depending upon the base used in the reaction. The discovery of thiabendazole in 1961 further spurred chemists around the world to design and synthesize several thousand benzimidazoles for screening for anthelmintic activity but less than twenty of them have reached commercial use. Benzimidazoles and its derivatives represent one of the most biologically active class of compounds, possessing a wide spectrum of activities and these are welldocumented in literature. Substituted benzimidazoles, antimicrobial activity. Synthesis of benzimidazoles has been developed by the o phenylenediamine with aldehydes using boric acid an efficient catalyst under mild reaction conditions in aqueous media.
Benzimidazole is a heterocyclic aromatic organic compound. The research presented in this thesis is centered on the design and synthesis of molecules which are derived from benzimidazoles and their applications. The reaction mixture was cooled and poured on t o the crushed ice. Synthesis of benzimidazoles the synthesis of benzimidazole. The reaction is carried out by heating the reactants. Wed like to understand how you use our websites in order to improve them. Coordination behavior of benzimidazole, 2substituted. May 11, 2020 benzimidazole drugs are quite effective, but their usage may be declining. Benzimidazoles heterocyclic building blocks sigmaaldrich. Synthesis, characterization, and biological evaluation of.
Synthesis of benzimidazoles the synthesis of benzimidazole derivatives starts from biology 35417 at interamerican san german. Benzimidazoles exhibit significant activity as potential antitumor agents, antimicrobial agents, smooth muscle cell proliferation inhibitors, a treatment for intestinal cystitis, and in diverse area of chemistry ansari et al. In the past decade, efficient methods have been described for the synthesis of heterocyclic compounds by aryl halides with copper catalysts 17. Other drugs have also been developed that are more water soluble and lack the metabolism issues that benzimidazole and its derivatives have, as well. Synthesis and antimicrobial activity of certain benzimidazole. This finding represents a novel strategy for the synthesis of benzimidazoles. 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.
Synthesis and antifungal activity of benzimidazole. Synthesis, characterization, and applications supervising professor. The product is applicable to aryl and heteroaryl aldehydes. 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. Practically all syntheses of benzimidazoles start with benzene derivatives possessing nitrogencontaining functions ortho to. Substituted ophenylenediamine for benzimidazoles, 2 mmol. Synthesis of new fluorobenzimidazole derivatives as an approach towards the discovery of novel intestinal antiseptic drug candidates. The synthesis of novel benzimidazole derivatives remains a. Simple, mild, and highly efficient synthesis of 2substituted. The structures of the synthesized compounds were confirmed by ir, 1h nmr.
It is considered as an alternative treatment for hydatid disease and is often indicated for patients who do not respond to surgery or benzimidazole. The benzimidazole nucleus is an important pharmacophore in medicinal chemistry. Synthetic routes to benzimidazolebased fused polyheterocycles. Some of the synthesized compounds showed appreciable antifungal activity. A class of antihelmintic, often used to treat nematodes and cestodes. Such reactions provide convenient strategies for synthesis of annulated benzimidazole polyheterocycles.
Benzimidazole is produced by condensation of ophenylenediamine with formic acid, or the equivalent trimethyl orthoformate. 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. In view of this, an attempt has been made to synthesize new benzimidazole derivatives containing 4chloropyridine2carbonyl and nmethyl picolinamide moieties in one side chain at 1h position of. It is a tautomer of a 4hbenzimidazole, a 2hbenzimidazole and a 3ahbenzimidazole. In view of their wide ranging activities, the synthesis of benzimidazoles and its. 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. Synthesis and antimicrobial studies of novel benzimidazole. The synthesis and chemistry of certain anthelmintic benzimidazoles lb. Pages in category benzimidazoles the following 89 pages are in this category, out of 89 total. Iridiumcatalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. It is an important pharmacophore and privileged structure in medicinal chemistry. A ring system composed of a benzene ring fused with an imidazole ring. The two nitrogens present in the imidazole ring are different from one another in their nature and this makes the properties of the ring system diverse in character. All structured data from the file and property namespaces is available under the creative commons cc0 license.
Benzimidazoles article about benzimidazoles by the free. Benzimidazoles are known for their many therapeutic applications. Much of this work has been done by pharmaceutical companies and is only reported in the patent literature. Thore 301 as a part of our continued work to develop organic reactions in aqueous media,20 we have tried to develop synthesis of 2 aryl benzimidazole in aqueous media, here we report a simple. Synthesis and anthelmintic activity of benzimidazole derivatives. Some of their polyfunctional derivatives have been proved to possess antibacterial, fungicide and antihelmintic activity. It can be used in the conditions of inflammation, anxiety and microbial infections. Introduction medicinal chemistry is a science having its roots in all branches of chemistry and biology. The synthesis and chemistry of certain anthelmintic. Synthesis and biological activity of novel 2, 5disubstituted. Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of. Synthesis and medicinal applications of benzimidazoles. Benzimidazole definition of benzimidazole by medical dictionary. Synthesis of commercially available benzimidazole involves condensation of ophenylenediamine with formic acid.
Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of enzymes. The full text of this article hosted at is unavailable due to technical difficulties. Gayathri 1, srujana 1, aary divya 2 1 department of pharmaceutical chemistry, sitha institute of pharmaceutical sciences, hyderabad, andhra pradesh. Benzimidazole definition is a crystalline base c7h6n2 that is composed of a benzene ring fused with an imidazole ring and is structurally similar to purine. New 2alkyl and 2aryl derivatives of 561adamantylbenzimidazole have been synthesized. Synthesis of 561adamantylbenzimidazoles springerlink. General procedure for the synthesis of 2substituted benzimidazoles and bisbenzimidazoles. Substituted benzimidazoles are an important class of heterocycles that exhibit a broad spectrum of pharmacological properties, for it assumes. Benzimidazole definition of benzimidazole by the free. This is a general method of preparing benzimidazoles. Synthesis and biological activities of some benzimidazoles.
The numbering in the benzimidazole ring system is done as shown below figure4. The benzimidazoles possess weaker activity against animal cestode parasites than the nematodes. Benzimidazoles are involved in a great variety of biological processes. It plays a very important role with plenty of rational therapeutic activities such as antiulcer, antihypertensive, analgesic. Synthesis of new fluorobenzimidazole derivatives as an approach. Pdf an efficient and green synthesis of benzimidazole.