Stephen w page, in small animal clinical pharmacology second edition, 2008. Benzimidazoles find several applications in different areas of chemistry. Results and discussion it is known that compound 1 is unstable in basic medium and nucleophilic substitution often leads to decomposition of the thiadiazole ring. Crossresistance can exist among all members of this group, because they act on the same receptor. The reaction proceeds smoothly at 0 c or ambient temperature to provide the desired products in good to excellent yields.
They concluded that a mild, manipulatable procedure, ecofriendly and green aspects avoiding hazardous solvents, shorter reaction times and high yields of the products are the advantages of this method25. A number of routes exist for the efficient synthesis of either 2benzimidazole. Pulla reddy college of pharmacy, mehdipatnam, hyderabad 500. Synthesis and antimicrobial studies of substituted 2. When the mole ratio of ophenylenediamine and aldehyde are taken in 1.
As shown in table2, different aldehydes and ophenylenediamine react without any significant difference to give the corresponding benzimidazoles in good yield. It is an important pharmacophore and privileged structure in medicinal chemistry. Because of resistance problems, use of benzimidazole fungicides has declined. Benzimidazole derivatives are versatile nitrogen containing heterocyclic compounds which have long been known as a promising class of biologically active compounds possessing wide variety of biological and pharmacological activities like antibacterial, antiinflammatory, antiulcer, antidiabetic etc. They can control many ascomycetes and basidiomycetes, but not oomycetes. Benzimidazoles anthelmintics drugs various poultrymed. Benzimidazole definition of benzimidazole by merriamwebster. Hedaitullah1, syeda farha naaz1, khalid iqbal1 and hs. However, with the widespread development of resistance and the availability of more efficient and easier to administer compounds, their use has decreased in ruminants. Lamba2 1himt college of pharmacy, gr noida, uttar pradesh, india. Facile, novel twostep syntheses of benzimidazoles, bis.
Benzimidazole definition of benzimidazole by medical dictionary. Benzimidazole moieties are a very important class of heterocyclic compounds that have many applications in pharmaceutical chemistry. The most prominent benzimidazole compound in nature is nribosyldimethylbenzimidazole, which serves as an axial ligand for cobalt in vitamin b 12. They are applied to cereals, fruits, vegetables and vines, and are also used in postharvest handling of crops the solubility of benzimidazole fungicides is low at physiological ph. Alfa aesar has extended its comprehensive range of heterocyclic compounds with the following benzimidazoles.
In the past decades, the literature seems to brim over with research work on nitrogen containing heterocycles, as they are present in nucleic acids, vitamins, proteins and biologically important molecular systems. 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. It will be interesting to observe that these modifications can be utilized as potent therapeutic agents in future. It is known that the reaction of ophenylenediamine opda with carbonyl compounds, under strong acidic conditions, gives benzimidazoles, whereas, opda in the presence of. This compound is bicyclic in nature which consists of the fusion of benzene and imidazole. 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. Various benzimidazoles 12 were prepared and evaluated by mane et al. Benzimidazole definition of benzimidazole by medical. Synthesis and biological activity of novel benzimidazoles. Benzimidazole is a heterocyclic aromatic organic compound. Author links open overlay panel salahuddin a mohammad shaharyar b avijit.
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. The benzimidazoles are a large chemical family used to treat nematode and trematode infections in domestic animals. Benzimidazole derivatives are among the top frequently used ring systems for small molecule drugs listed by the us fda. Mechanisms of action of anthelmintics pharmacology. Antibacterial agentschemical synthesis bacteriadrug effects.
Synthesis and antimicrobial studies of novel benzimidazole. Alfa aesar has extended its comprehensive range of heterocyclic compounds with the following. All content on this website, including dictionary, thesaurus, literature, geography, and other reference data is for informational purposes only. 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. Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of enzymes. Predicted data is generated using the us environmental protection agencys episuite. Volume 10, supplement 1, february 2017, pages s157s173. Alkylative coupling of enaminones and benzimidazole.
Introduction to the chemistry of benzimidazoles general. Synthesis and pharmacological evaluation of new benzimidazole derivatives srinivas bethi, matta vidyasagar, rajamanohar. 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. A ring system composed of a benzene ring fused with an imidazole ring. Journal of chemical and pharmaceutical research, 2015, 77. Diverse pharmacological aspects of benzimidazole derivatives. Synthesis, characterization, and biological evaluation of. The standard synthesis for benzimidazoles is the cyclocondensation of ophenylenediamine or substituted ophenylenediamines with carboxylic acids or their derivatives. Benzimidazoles molecules closely based on the structure of h51845 are useful for bradykinin b1 receptor antagonists.
The most prominent benzimidazole compound in nature is nribosyldimethylbenzimidazole, which serves as an. Benzimidazole fungicides are a class of fungicides including benomyl, carbendazim mbc, thiophanatemethyl, thiabendazole and fuberidazole. Neutralization of the reaction mixture gave a small amount of from which 6% crude product. In the first step of the present study, different substituted benzimidazoles figure 1 were evaluated for in vivo antiparasitic benzimidazole drugs derivatives. Benzimidazole derivatives an overview ramanpreet walia1, md. Benzimidazoles interrupt parasite energy metabolism by binding to tubulin, thereby disrupting microtubular cell structure and preventing nutrient uptake and other functions. The logp ow effects of compounds 1 28, expressed as logp ow, are summarized in table 2. Benzimidazoles are remarkably effective compounds, extensive biochemical and. The synthesis and chemistry of certain anthelmintic benzimidazoles lb. Synthesis of 2phenylbenzimidazole ophenylenediamine 0. It is a tautomer of a 4hbenzimidazole, a 2hbenzimidazole and a 3ahbenzimidazole.
Benzimidazoles represent the only class of truly broadspectrum anthelmintics, however, they also show activity against fungi and mammalian cells. Tubulin is a protein subunit of the microtubules that have a fundamental and ubiquitous role in the mitotic spindle. Screening in vitro antimicrobial activity with various. Synthesis of substituted benzimidazo1,2c1,2,3thiadiazoles. All the chemicals and reagents used were of analytical grade and were procured from nice chemicals.
It is a benzimidazole and a polycyclic heteroarene. Pdf green chemistry is the new and rapidly emerging field of chemistry. Chemistry benzimidazole is a heterocyclic aromatic organic compound. Simple, mild, and highly efficient synthesis of 2substituted. A correlation of the drug activities antibacterial in. Mild and efficient synthesis of 2aryl benzimidazoles in.
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. Mild and efficient synthesis of 2aryl benzimidazoles in water using sds s. The position and type of substituents on the benzimidazole ring are responsible for a variety of biological activity. Benzimidazoles drugs are widely used for prevention and treatment of parasitic infections. 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. 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 nheterocyclic carbenes, usually used as ligand for transition metal complexes.
Nahso sio promoted synthesis of benzimidazole derivatives. This bicyclic compound consists of the fusion of benzene and imidazole. It plays a very important role with plenty of rational therapeutic activities such as antiulcer, antihypertensive, analgesic. The synthesis and chemistry of certain anthelmintic. General papers arkivoc 2012 viii 1726 page 18 arkatusa, inc. K, venkateshwar rao j and sandeep gummudavelly department of pharmaceutical chemistry, talla padmavathi college of pharmacy, orus. It indicated that silica supported sodium hydrogen sulphate catalyzed reaction has a favorable selectivity for the synthesis of 2substituted benzimidazoles.
They are suspected to be toxic to animals, including humans. 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. Udc multicomponent reactions mcrs benzimidazoles bis benzimidazoles bisbenzimidazoledihydroquinoxalines electronic supplementary material the online version of this article doi. Benzimidazoles heterocyclic building blocks sigmaaldrich. General procedure for the synthesis of 2substituted benzimidazoles and bis benzimidazoles.
Recent advances in the synthesis of benzimidazoles. A class of antihelmintic, often used to treat nematodes and cestodes. Substituted ophenylenediamine for benzimidazoles, 2 mmol. Mutant pathogens resistant to one benzimidazole fungicide are usually resistant to all of them. Alkylative coupling of enaminones and benzimidazole milena staykova, stela statkovaabeghe, plamen angelov, and iliyan ivanov department of organic chemistry, university of plovdiv, 24 tzar asen str. Budding uninhibited by benzimidazoles 3 how is budding.