Synthesis of novel substituted thiourea and benzimidazole. Selective and ecofriendly procedures for the synthesis of benzimidazole. Synthesis and pharmacological profile of benzimidazoles. Synthesis of new fluorobenzimidazole derivatives as an approach. The yield of all benzimidazole derivatives were found to be in the range of 75 94%.
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. The reaction yields and product stability were significantly affected by the identity of the diamine and anhydride substituents. The structures of the synthesized compounds were characterized using different. The solution is digested for fifteen minutes with about 2 g.
Dribofuranosylbenzimidazole ring system was discovered in 1948 as an integral part of the structure of vitamin b12 download. Photoluminescent benzobisimidazolium salts 9 and their physical and photophysical properties. Synthesis of 2phenyl benzimidazole derivatives prem shankar misra et al. A series of new benzimidazole derivatives were synthesized by the solid. Synthesis of commercially available benzimidazole involves condensation of ophenylenediamine with formic acid. Iodine is a commercial and environmentally benign catalyst. Pdf a new series of non peptide angiotensinaii receptor antagonist has been prepared. 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. The synthesized benzimidazole compounds were screened for acute and chronic. The most prominent benzimidazole complex features nribosyldimethylbenzimidazole as.
Benzimidazole derivatives as antioxidant and anticholinesterase inhibitors. Elnassan pharmaceutical organic chemistry department, faculty of pharmacy, cairo university, cairo 11562, egypt corresponding author. Benzimidazoles are a class of heterocyclic, aromatic compounds which. The synthesis of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substituted benzimidazole 2thiols 4ac followed by successive. A class of antihelmintic, often used to treat nematodes and cestodes. Synthesis and evaluation of selected benzimidazole.
Synthesis of new fluorobenzimidazole derivatives as an approach towards the. Synthesis, stability, and photoreactivity of diazirinyl. The crude product filtrated and extracted by dichloro methane and water. Jan 16, 2020 the development of synthesis for these compounds, however, is hampered by the regioselectivity and atom economy. Benz imidazole is a kind of substances which have found practical applications in organic synthesis 3, and the benzimidazole nucleus are found in a variety of pharmaceuticals as cardiotonic agents, 4 potential antitumor 4 poliadpribose phosphorilase inhibitors, 5 histamine h4 receptor binders, 6 antiparasitic, 7 cardiovascular, 8 anticancers. Synthesis and antimicrobial activity of certain benzimidazole. Substituted benzimidazole derivatives have found commercial application in veterinarian medicine as anthelmintic agents and in diverse human therapeutic pharm chemistry synthesis, characterization, and biological evaluation of benzimidazole derivatives as potential anxiolytics nannapaneni dt, gupta atyam vsss1, reddy mi, sarva raidu ch1. Dec 31, 2015 imidazole and benzimidazole rings are the most important nitrogencontaining heterocycles, which are widely explored and utilized by the pharmaceutical industry for drug discovery. Facile and efficient onepot synthesis of benzimidazoles using. Due to their special structural features and electronrich environment, imidazole and benzimidazole containing drugs bind to a variety of therapeutic targets, thereby exhibiting a broad spectrum of bioactivities. Synthesis of some 6flouro5substituted benzimidazole 12 were reported by alagoz et al. The reaction mixture was stirred on magnetic stirrer for four hrs. Green chemistry is the new and rapidly emerging field of chemistry.
Wed like to understand how you use our websites in order to improve them. An improved and greener protocol for the synthesis of benzimidazole derivatives. Development and synthesis of dnaencoded benzimidazole library. Motivated by the above mentioned facts herein is reported the synthesis and antimicrobial evaluation of new benzimidazole series conjugated with 1,3,4oxadiazole, 1,2,4triazole, 1,3thiazole rings 5a,b. Synthesis, biological evaluations, and molecular docking study. Benzimidazole definition of benzimidazole by medical. Synthesis, characterization, and biological evaluation of. Synthesis of benzimidazole and benztoriazole derivatives. Benzimidazole is a heterocyclic aromatic organic compound. General procedure for the synthesis of benzimidazole series series a a solution of 590 mg benzimidazole 5 mmol, 0. It is a tautomer of a 4h benzimidazole, a 2h benzimidazole and a 3ah benzimidazole. 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.
The research presented in this thesis is centered on the design and synthesis of molecules which are derived from benzimidazoles and their applications. Benzimidazoles heterocyclic building blocks sigmaaldrich. Synthesis of benzimidazole as 1substitutedmethyl2substitutedphenyl benzimidazole 3 was reported by leonardo et al 6. Compounds 3a, 3b and 3c were screened for their antibacterial activity against s. Synthesis of benzodiazepines through ring openingring. Ligandfree coppercatalyzed synthesis of substituted. In the present study, nineteen new fluorobenzimidazole derivatives. The present study describes a simple, inexpensive, and easy method for synthesis of benzimidazole derivatives in a stipulated time, without using any drastic conditions. Coordination behavior of benzimidazole, 2substituted benzimidazoles and benzothiazoles, towards transition metal ions. The mixture is stirred vigorously and heated on a steam bath until the solution boils gently.
Synthesis and antifungal activity of benzimidazole. Please cite this article in press as singh mukesh et al. Selective and ecofriendly procedures for the synthesis of. View the article pdf and any associated supplements and figures for a period of 48 hours. Similarly, the general synthesis of benzimidazoles is by the condensation. The early 1950s was an important period regarding discovery of the biological significance of benzimidazolecontaining structures and the closelyrelated purines. It has been shown that during bacterial nucleic acid and protein synthesis. It is an important pharmacophore and a privileged structure in medicinal chemistry. Satu siri baru terbitan oksadiazol dari benzimidazol telah disintesis dengan mudah oleh. Synthesis of benzimidazoles the synthesis of benzimidazole derivatives starts from biology 35417 at interamerican san german. Ds method and their physical properties were investigated. Synthesis of 3,3diphenylcyclopropene 16 list of tables ii. Experimental procedure for the synthesis of benzimidazoles 22.
Imidazole and benzimidazole synthesis is a comprehensive survey of the known methods of syntheses and ring modification. Benz imidazole is a kind of substances which have found practical applications in organic synthesis 3, and the benzimidazole nucleus are found in a variety. The imine can be alkylated and also serves as a ligand in coordination chemistry. 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 characterization are reported. 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. Synthesis, structural elucidation and dna binding profile. The purity of the compounds were ascertained by a melting point and tlc. Benzimidazole, bulk synthesis, green synthesis, ecofriendly. Simplistic and green synthesis of various benzimidazole and benzoxazole derivatives using peg400 as a green solve nt, international letters o f chemistry, physics and astronom y vol. In the first step, 3chloropropionyl chloride and triethylamine tea were added dropwise to a solution of 2aminothiazole in 1,4dioxane and reacted at reflux temperature. Introduction to the chemistry of benzimidazoles general. Synthesis of benzimidazoles the synthesis of benzimidazole. Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of enzymes. Benzimidazole derivatives are known to have microbial.
Generally, the condensation of ophenylene diamine with carboxylic acids and their nitrile, imidates and orthoester 8 derivatives have been widely used for benzimidazole synthesis. The synthesis of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substitutedbenzimidazole2thiols 4ac followed by successive. The acetylcholinesterase ache and butyrylcholinesterase buche inhibitory activities were evaluated in vitro by using ellmans method. In the last ten years, supported reagents on polymers have become increasingly applied in organic synthesis 1, because the reactions are carried out with simple workup, easy product isolation, and mild reaction conditions 2. The synthesis of substituted benzimidazoles, 2aminobenzimidazoles, 2aminobenzothiazoles, and benzoxazoles is described via intramolecular cyclization of obromoaryl derivatives using copperii oxide nanoparticles in dmso under air. The development of synthesis for these compounds, however, is hampered by the regioselectivity and atom economy. It is a benzimidazole and a polycyclic heteroarene. Pdf synthesis of benzimidazole derivatives and study of their.
Benzimidazole definition of benzimidazole by medical dictionary. A series of mannich bases of benzimidazole derivatives having a phenolic group were designed to assess their anticholinesterase and antioxidant activities. There is a growing interest over the past years for the synthesis of benzimidazolebased heterocycles due to the crucial role of benzimidazole unit in the functions of biologically important molecules. A ring system composed of a benzene ring fused with an imidazole ring. Encoded library technology elt is an effective approach to the discovery of novel smallmolecule ligands for biological targets. Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents fatmah a. Here we report the development of dnaconjugated benzimidazoles. Imidazole and benzimidazole rings are the most important nitrogencontaining heterocycles, which are widely explored and utilized by the pharmaceutical industry for drug discovery. Benzimidazole is produced by condensation of ophenylenediamine with formic acid, or the equivalent trimethyl orthoformate. The synthesis and chemistry of certain anthelmintic. This compound is bicyclic in nature which consists of the fusion of benzene 1 and imidazole 2. A key factor for the success of the technology is the chemical diversity of the libraries. Synthesis characterization and biological activity benzimidazole derivatives dr.
The synthesis, thermal stability, and photoreactivity of trifluoromethyl diazirines installed at the heterocyclic section of n. Finally, the key intermediate 16 was alkylated with benzyl chloride in aqueous sodium hydroxide. Liquid phase synthesis of coumarino benzimidazoles for antimicrobial. Eisa et alsynthesis and antimicrobial activity of benzimidazole derivatives 1517 of the cyclized structure was obtained from the absence of ester band in ir, and by 1h nmr, mass spectrometry and elemental analysis scheme ii.
The filtrate is cooled to 1015, and the benzimidazole is filtered and washed with 50 cc. Simon associate professor, department of chemistry, dhanalakshmi srinivasan engineering college, perambalur, tamilnadu ug scholar, department of electronics and communication engineering. Coordination behavior of benzimidazole, 2substituted. 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 synthesis and chemistry of certain anthelmintic benzimidazoles lb. Synthesis of novel substituted thiourea and benzimidazole derivatives containing a pyrazolone ring as antiin. There is a growing interest over the past years for the synthesis of benzimidazole based heterocycles due to the crucial role of benzimidazole unit in the functions of biologically important molecules. The most prominent benzimidazole compound in nature is nriosyldimethylbenzimidazole, which serves as a axial ligand for cobalt in vitamin b12. It also collects nonringsynthetic approaches to classes of compounds such as nitro, halogeno. Development of drugs based on imidazole and benzimidazole. A convenient method for the synthesis of 2substituted benzimidazoles and benzothizoles offers short reaction times, largescale synthesis, easy and quick isolation of the products, excellent chemoselectivity, and excellent yields as main advantages. Synthetic routes to benzimidazolebased fused polyheterocycles.
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