You are free to adapt, copy or redistribute the material, providing you attribute appropriately and do not use the material for commercial purposes. Files available from the acs website may be downloaded for personal use only. Substituted benzimidazole derivatives have found applications in diverse therapeutic areas such as antiulcer, anticancer agents, and anthelmintic species to name just a few. Synthesis, characterization, and biological evaluation of. Discovery of highly potent benzimidazole derivatives as indoleamine 2,3. Hedaitullah1, syeda farha naaz1, khalid iqbal1 and hs.
Aseries of tetrasubstitued benzimidazole derivatives were synthesized and screened for their urease inhibi tion, antixanthine oxidase xo and antioxidant activities. Benzimidazole derivatives are useful intermediatessubunits for the development of molecules of pharmaceutical or biological interest. Pdf in the last 23 decades, the broad research in the application of benzimidazole derivatives made it important for mankind. Pdf a new series of non peptide angiotensinaii receptor antagonist has been prepared. The transfer of both protons and electrons during a reaction is known as protoncoupled electron transfer pcet and is. Poornima department of pharmaceutics, sri indu institute of pharmacy, hyderabad, india. Diverse chemical and biological potentials of various. Synthesis, characterization and antimicrobial activity of some novel. The similarity between the three drugs is a benzimidazole backbone, which provides the basis for novel antiparasitic agents. Benzimidazole definition of benzimidazole by medical dictionary. Chapter 4 studies on benzimidazole derivatives 2 ph. Synthesis and characterization of novel benzimidazole derivatives by using intermediate of. A screening assay based on hostpathogen interaction models identifies a set of novel antifungal benzimidazole derivatives. Synthesis and biological evaluation of novel benzimidazole.
Benzimidazole derivatives are known to have microbial. For example benzimidazole is less potent compared to its carbamide, acid chloride and tetrazole derivatives. Some of them were found to possess significant antioxidant activity, especially, compounds 4, 5a. The affinity of synthesized derivatives towards various receptors involved in neurodegeneration was assessed through docking analysis. Previously we reported that benzimidazole derivatives are more potent than benzotriazole compounds in the point of antifungal activity. Pdf green chemistry is the new and rapidly emerging field of chemistry. Synthesis of benzimidazoles the synthesis of benzimidazole. Benzimidazole derivatives have shown hopeful activity in the treatment of several diseases, for this reason, the synthesis of novel benzimidazole remains a main focus for researchers. The synthesized compounds were characterized by using ir, 1h nmr, and mass spectral data together with elemental analysis. The purity of the compounds was ascertained by melting point and tlc. Synthesis and biological activities of some benzimidazoles.
A series of 6substituted aminocarbonyl benzimidazole derivatives were designed and synthesized as nonpeptidic angiotensin ii at 1 receptor antagonists. Selective and ecofriendly procedures for the synthesis of. Ionic liquids ils as green solvents in organic synthetic processes has gained considerable importance due to their solvating ability, negligible vapour pressure, high thermal stability, low melting points, good solvating. The antiproliferative activity of the compounds against human cervical carcinoma hela, human lung carcinoma a549, human liver carcinoma cells hepg2 and normal kidney epithelial cells hek293t. A screening assay based on hostpathogen interaction. Synthesized compounds have been characterized by 1 h and cnmr and mass spectral analysis. In search of the antimicrobial potential of benzimidazole derivatives. The results also showed that alkylbenzimidazoles are more active than alkylbenzotriazole. Synthesis and trypanocidal activity of novel benzimidazole. Benzimidazoles and its derivatives represent one of the most biologically active class.
Synthesis and antibacterial activity of some derivatives. Discovery of highly potent benzimidazole derivatives as indoleamine 2,3dioxygenase1 ido1. This enzyme is involved in the metabolism of glucose, the only source of energy for the parasite. The present study describes a simple, inexpensive, and easy method for synthesis of benzimidazole derivatives in a stipulated time, without using any drastic conditions. A novel series of 2substituted benzimidazole derivatives 3a3j were synthesized by the reaction of 2chloro methyl benzimidazole with substituted primary aromatic amines. These heterocycles have shown different pharmacological and biological activities such as antibacterial, antihypertensives, anticancers, antihistaminics, antihbv activity, anti. Cyclic voltammetric and differential pulse voltammetric measurements 2. Protoncoupled electron transfer across benzimidazole. In this study, we designed compounds carrying benzimidazole and triazole rings on the. Determination of pka of some benzimidazole derivatives using drug as active substance by different methods atih islamoglu, naciye rogan, zafer hasimoglu. Suppression of staphylococcus aureus biofilm formation and.
This account gives an overview of the benzimidazole based system and their relevance in medicinal. Among these derivatives, 4,5dihydropyridazinones possess promising activity, selectivity towards pde4 isoenzymes and are able to reduce il8 production by human primary polymorphonuclear cells barberot at al. Active class of antioxidants arfa kamil 1, shamim akhtar. Synthesis and antifungal activity of benzimidazole. Hydrolysis of benzimidazole is not expected to occur due to the lack of hydrolyzable functional groups. Determination of pka of some benzimidazole derivatives. All the compounds were characterized by uv, ir, 1 h nmr, mass spectral data and chn elemental analysis.
Lamba2 1himt college of pharmacy, gr noida, uttar pradesh, india. Fenbendazole is a benzimidazole that presents a wide spectrum anthelmintic. The purity of the compounds was ascertained by a melting point and tlc. The aim of this research is to synthesize a series of benzimidazole derivatives and to test their inhibitory effect on the enzyme unh. Green synthesis of polycyclic benzimidazole derivatives. Synthesis and evaluation of selected benzimidazole. Joshi, dstjrf inspire fellow, mnschngu, patan observed that benzimidazole derivatives are found to possess antihiv,24 anthelmintic,25. The yield of all benzimidazole derivatives was found to be in the range of 75 94%. The present work reports the synthesis and biological activity of a series of 14 benzimidazole derivatives designed to act on the enzyme triosephosphate isomerase of trypanosoma cruzi tctim. Studies on this protein are hindered as only a limited number of effective nontoxic inhibitors of this drug target are known. In the current study, we extended the utility of a previously optimized c.
The inhibition of benzimidazole derivatives on corrosion. Various irreversible acting pyridinyl methyl sulfinyl benzimidazole derivatives have been synthesized but only few of them are potent and are in current use2. A series of some novel azo derivatives of benzimidazole were prepared by. Its treatment with phydroxyacetophenone afforded the corresponding pacetyl substituted derivatives. We then synthesized 34 more derivatives and identified several anti. All the synthesized benzimidazole derivatives were assayed for antimicrobial activity using standardized tests dm and ddm against seven strains microorganisms. The benzimidazole contains a phenyl ring fused to an imidazole ring, as indicated in the structure of benzimidazole. 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.
So only the derivatives of heterocyclic compounds are only used for the pharmaceutical application. Jodeh3 1laboratory of separation processes, faculty of science, university ibn tofail, po box 242, kenitra, morocco. Benzimidazole containing acetamide derivatives attenuate. In 1991 benzimidazole derivatives were synthesized by derivatization at nh of benzimidazole by electron donating group and substitution with long chain of propyl, acetamido, thio, thiazoleamino, tetramethyl piperidine on pyridine resulting in good antiulcer activity 2,3. Antiinflammatory synthesis and antiinflammatory activity of phenyl benzimidazole 1 was reported by leonardo et al 6.
Benzimidazole is not readily metabolized by isolated soil microbial strains that metabolize benzimidazole based fungicides, and is inhibitory to some microbes at concentrations ranging from 500 to ugg. Pdf an efficient and green synthesis of benzimidazole. A highly versatile synthetic route was created for the development of sar, which led to the discovery of potent and selective inhibitors with excellent pharmaceutical properties. Synthesis, antioxidant, xanthine oxidase and urease. The synthesis of novel benzimidazole derivatives remains a main focus of modern drug discovery. Microwaveassisted efficient and facile synthesis of tetramic acid derivatives via. Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents fatmah a. A series of new benzimidazole derivatives were synthesized by the solid. Benzimidazole derivatives an overview ramanpreet walia1, md. Polycyclic benzimidazole derivatives and organic semiconductors supporting information s9 7. Benzimidazole complexes containing halides or carboxylates derivatives are discussed, as well as the coordination chemistry of 2substituted benzimidazoles. Department of pharmaceutical chemistry, federal urdu university of arts sciences and technology, gulshane iqbal campus, karachi. The versatility of new generation benzimidazole would represent a fruitful pharmacophore for further development of better medicinal agents.
Substituted benzimidazole derivatives using ddq as an efficient oxidant at room temperature. The first one comprise methyl, the second one comprise of 2 phenyl substitution on benzimidazole moiety. Reported herein is the optimization of a nonselective scaffold into a potent and highly selective inhibitor of tie2 kinase. The files associated with this dataset are licensed. Awaad 5 and nazira karodia 2,6, 1 chemistry department, college of science, king saud university, riyadh 162, saudi arabia. The most prominent benzimidazole compound in nature is nribosyldimethylbenzimidazole, which serves as an axial ligand for cobalt in vitamin b 12. Selective and ecofriendly procedures for the synthesis of benzimidazole derivatives. Designing molecular platforms for controlling proton and electron movement in artificial photosynthetic systems is crucial to efficient catalysis and solar energy conversion. Pdf benzimidazole derivatives and its biological importance.
Benzimidazole definition of benzimidazole by merriamwebster. Original article synthesis, characterisation and evaluation of nmannich bases of 2substituted benzimidazole derivatives sekar vinoth kumara, mohan raj subramanianb, santhosh kumar chinnaiyanc adepartment of pharmaceutical chemistry, gokulakrishna college of pharmacy, andhra pradesh 524121, india b department of pharmacology, ssm college of pharmacy, tamil nadu 638312. Synthesis and antimicrobial activity of some novel n. A benzimidazole used in the treatment of strongyloides, cutaneous larva migrans, visceral larva migrans, and trichinosis infections. Determination of pka of some benzimidazole derivatives using. The most commonly used starting material is orthophenylenediamine opda. Experimental section, spectroscopical data and xyz coordinates for all compounds. Due to their special structural features and electronrich environment, imidazole and benzimidazolecontaining drugs bind to a variety of therapeutic targets, thereby exhibiting a broad spectrum of. Benzimidazole is not readily metabolized by isolated soil microbial strains that metabolize benzimidazolebased fungicides, and is inhibitory to some microbes at concentrations ranging from 500 to ugg. The versatile nature of benzimidazole nucleus and its affinity toward several receptors suggested that it could be a multistep targeting neuroprotectant.
Green route for the heterocyclization of 2mercaptobenzimidazole into. Synthesis and biological activity of novel benzimidazole derivatives. Pdf benzimidazole is a heterocyclic aromatic organic compound. Moreover, in recent times, some acetamides derived from benzimidazole attached to oxadiazole heterocycle 14, 15 or triazole heterocycle exhibited promising biological activities. Topomol reads mdl mol or sd files and provides a rapid means to calculate all 2d. Synthesis of novel substituted thiourea and benzimidazole. Journal of chemical and pharmaceutical research, 2017, 98. Synthesis of benzodiazepines through ring openingring. Development of drugs based on imidazole and benzimidazole. Nov 28, 2012 leishmanolysin gp63 is a zinc metalloprotease, expressed at the surface of leishmania promastigotes. A ring system composed of a benzene ring fused with an imidazole ring. Benzimidazole derivatives have attracted a significant attention in recent years because of their medicinal applications as antiviral, antiulcer, antifungal, antihypertensive, anticancer, and antihistamine compounds. The solvent effect on the absorption and fluorescence bands has been analyzed and supplemented by computational studies. Synthesis of some fluorescent benzimidazole derivatives.
The aim of this work is devoted to study the inhibition. Synthesis and analgesic activity of novel derivatives of 1,2. In conclusion, two series of benzimidazole derivatives and analogs were designed, synthesized, and their in vitro antiinflammatory activities were evaluated. Similarly, the general synthesis of benzimidazoles is by the condensation reaction of 1,2phenylenediamine with carboxaldehydes, carboxylic acids,6,7 or their derivatives 8,9 such as, chlorides, nitriles, and orthoesters, under strong acidic conditions, with high temperatures. Benzimidazole is a heterocyclic aromatic organic compound. Taking orostanal a compound from a japanese marine sponge, stelletta hiwasaensis as a lead compound, some novel bnorcholesteryl benzimidazole and benzothiazole derivatives were synthesized. The structure of the compounds had been established on the basis of ir, 1h nmr and ms spectral data. These metrics are regularly updated to reflect usage leading up to the last few days. The reaction yields and product stability were significantly affected by the identity of the diamine and anhydride substituents. 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. Discovery of highly potent benzimidazole derivatives as. These derivatives are more biological and pharmacologically active.
Synthesis and antimicrobial studies of novel benzimidazole. International journal of pharmacy and biological sciences eissn. Flubendazole is an anthelmintic that is used to treat worm infection in humans. This account gives an overview of the benzimidazole based system and. From the first series of compounds, we identified three compounds, tbz09, tbz11 and tbz21, as lead compounds. Corrosion inhibition potentiality of some benzimidazole derivatives for mild steel in hydrochloric acid.
Monitor ecgin patients witha historyof prolongation of the qtc interval or a. Benzimidazole nucleus is also found in a variety of naturally occurring compounds such as, vitamin b 12 and its derivatives, and it is structurally similar to purine bases. Some fluorescent benzimidazole derivatives have been designed and synthesized using cobaltii hydroxide as highly efficient catalyst. The preliminary pharmacological evaluation revealed nanomolar at 1 receptor binding affinity and good at 1 receptor selectivity over at 2 receptor for all compounds of the series, a potent antagonistic activity in isolated rabbit aortic strip.
The purity of the compounds were ascertained by a melting point and tlc. The results have been interpreted based on the variation of acidic properties and powder xrd phases of zirconia on incorporation of movi or ptso 4 2 ions. Synthesis and characterization of oxadiazole derivatives from benzimidazole 1516 in the present study, a series of novel oxadiazoles were synthesized from benzimidazole and their physical. A class of antihelmintic, often used to treat nematodes and cestodes. The new 2substituted derivatives of 2,3dihydrobenzimidazole are interesting both from synthetic point of view and as potential bioactive compounds. Novel benzimidazole derivatives as potent and isoform selective tumor. Imidazole and benzimidazole rings are the most important nitrogencontaining heterocycles, which are widely explored and utilized by the pharmaceutical industry for drug discovery. Gal files allow the assignment of genes to the corresponding spots on the array. In the benzimidazole category 1a and 2a affected all species of fungi. However there is a great need to study the various pharmacological actions derived from benzimidazole nucleus through research work.
Selective small molecule inhibitors of tie2 kinase are important tools for the validation of tie2 signaling in pathological angiogenesis. The benzimidazole nucleus is an important pharmacophore in medicinal chemistry. Benzimidazole derivatives are one of the most important classes of heterocyclic molecules that occur widely in natural products. Benzimidazoles are widely used as drugs such as, omeprazole, pantoprazole, lansoprazole. Two series of novel benzimidazole derivatives were synthesized. Searching the literature indicated that analogous benzimidazole derivatives might exhibit antiin. Benzimidazole is prepared from ophenylenediamine which is treated with formic acid in presence of alkali. Benzimidazoles heterocyclic building blocks sigmaaldrich. Ds method and their physical properties were investigated. Synthesis and biological evaluation of benzimidazole. Further details on data analysis are given in data analysis below. Corrosion inhibition potentiality of some benzimidazole. Coordination behavior of benzimidazole, 2substituted.
Benzimidazoles and triazoles are useful structures for research and development of new pharmaceutical molecules and have received much attention in the last decade because of their highly potent medicinal activities. Compounds 1a, 1b, 1c and 1d were screened for antiinflammatory. Six derivatives of 2substituted benzimidazole were prepared out of that compounds 1a and 2 possess potent analgesic activity as shown in the aceticacidinduced writhing test. These solid acid catalysts have been used in the synthesis of various benzimidazole derivatives. Upload your research data, share with select users and make it publicly available and citable. Synthesis and biological evaluation of 2substituted. Synthesis and antimicrobial activity of certain benzimidazole. The synthesized benzimidazole compounds were screened for acute. Infrared and vcd spectra for each conformer is generated from the gaussian 03 output files using one of a variety of software programs to fit lorentzian.
Immadisetty sri krishnanjaneyulu, govindaraj saravanan. Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives. 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. An overview of bulk drug synthesis article pdf available in international journal of pharmtech research 89. A data set 27molecules of n1 aryl benzimidazole derivatives with varied chemical and biological activities, reported by monforte annamaria et al for antihiv activity, was considered for the qsar studies. The yield of all benzimidazole derivatives were found to be in the range of 75 94%. A novel series of noncovalent, benzimidazolebased inhibitors of dpp4 has been developed from a small fragment hit using structurebased drug design.
Synthesis and acheinhibitory activity of new benzimidazole. Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of enzymes. 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. Seven novel benzimidazole derivatives were synthesized successfully in appreciable yields and characterized physicochemically. Synthesis of benzimidazoles the synthesis of benzimidazole derivatives starts with the benzene derivatives having nitrogen at ortho position to each other. In view of these observations, some new compounds 2methylbenzimidazole derivatives bearing 1,3,4oxadiazole or 1,2,4triazole heterocycle have been synthesized. Rearrange individual pages or entire files in the desired order. Numerous heterocyclic compounds, cyclic anhydrates, cyclic imides, cyclic acetals of dihydroxy alcohols, the solvents, dioxanes and tetrahydrofuran, in all of these, the chemistry is essentially that of their openchain analogues. The yield of all benzimidazole derivatives were found to be in the range of 7594%. Benzimidazole is produced by condensation of ophenylenediamine with formic acid, or the equivalent trimethyl orthoformate.
Present study describes the identification of a variety of 2aryl and 5nitro2arylbenzimidazoles as new gp63 inhibitors. Synthesis and biological activity of novel benzimidazole derivatives as potential antifungal agents. Adelphi university 14 annual research student conference. The development of synthesis for these compounds, however, is hampered by the regioselectivity and atom economy. Benzimidazole derivatives exhibit antiinfective and antibiofilm activities. The reactions were smoothly preceded in excellent yields and short reaction times with an easy work. In both series, the alkyl groups selected were ethyl and butyl groups to study the effect of increasing the alkyl. Design, synthesis of novel azo derivatives of benzimidazole as. Although vitamin b12 is capable of inducing the growth of bacteria, the benzimidazole component and some of its derivatives repress the bacterial growth. Hence, the focus is on the synthesis of potent 1,2substituted benzimidazole derivatives as potential druglike scaffolds for future development. Moreover, the benzimidazole derivatives exhibit pharmacological. Among 16 obtained compounds, compound 4g has the best capability for detection of picric acid pa, having good selectivity and high sensitivity. In addition, some benzimidazole derivatives have been shown to be useful as amyloid.
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