Synthesis and evaluation of selected benzimidazole. Dribofuranosylbenzimidazole ring system was discovered in 1948 as an integral part of the structure of vitamin b12 download. It is a benzimidazole and a polycyclic heteroarene. Synthesis of new fluorobenzimidazole derivatives as an approach. 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.
Synthesis and pharmacological profile of benzimidazoles. Experimental procedure for the synthesis of benzimidazoles 22. Synthesis of benzimidazole and benztoriazole derivatives. The crude product filtrated and extracted by dichloro methane and water. Synthesis of some 6flouro5substituted benzimidazole 12 were reported by alagoz et al. Synthesis of 2phenyl benzimidazole derivatives prem shankar misra et al. The synthesis of benzimidazoles derivative involves subsequent synthesis of 42chloroethoxybenzaldehyde, 4 methyl benzaldehyde followed by benzimidazoles derivative by reaction between amines derivatives and ophenylenediamine in dimethyl farmamide dmf as solvent in the presence of iodine as a catalyst. View the article pdf and any associated supplements and figures for a period of 48 hours. The filtrate is cooled to 1015, and the benzimidazole is filtered and washed with 50 cc.
The structures of the synthesized compounds were characterized using different. Facile and efficient onepot synthesis of benzimidazoles using. Here we report the development of dnaconjugated benzimidazoles. Development and synthesis of dnaencoded benzimidazole library. It is a tautomer of a 4h benzimidazole, a 2h benzimidazole and a 3ah benzimidazole. Synthesis and antimicrobial activity of certain benzimidazole. 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. Synthesis of benzodiazepines through ring openingring. In the present study, nineteen new fluorobenzimidazole derivatives. Ds method and their physical properties were investigated.
Iodine is a commercial and environmentally benign catalyst. Benzimidazole is a heterocyclic aromatic organic compound. 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 yield of all benzimidazole derivatives were found to be in the range of 75 94%. Benzimidazoles heterocyclic building blocks sigmaaldrich. The solution is digested for fifteen minutes with about 2 g. Oct 20, 2009 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. 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. Synthesis, characterization, and biological evaluation of. Introduction to the chemistry of benzimidazoles general. Coordination behavior of benzimidazole, 2substituted benzimidazoles and benzothiazoles, towards transition metal ions. Please cite this article in press as singh mukesh et al. Benzimidazole is produced by condensation of ophenylenediamine with formic acid, or the equivalent trimethyl orthoformate. 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.
Benzimidazoles are a class of heterocyclic, aromatic compounds which. Synthesis of new fluorobenzimidazole derivatives as an approach towards the. It is an important pharmacophore and a privileged structure in medicinal chemistry. Synthesis of benzimidazole as 1substitutedmethyl2substitutedphenyl benzimidazole 3 was reported by leonardo et al 6. The synthesis of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substitutedbenzimidazole2thiols 4ac followed by successive. A series of new benzimidazole derivatives were synthesized by the solid. It also collects nonringsynthetic approaches to classes of compounds such as nitro, halogeno. Similarly, the general synthesis of benzimidazoles is by the condensation. The synthesis, thermal stability, and photoreactivity of trifluoromethyl diazirines installed at the heterocyclic section of n. This compound is bicyclic in nature which consists of the fusion of benzene 1 and imidazole 2. Encoded library technology elt is an effective approach to the discovery of novel smallmolecule ligands for biological targets.
Benzimidazole definition of benzimidazole by medical. Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of enzymes. Synthetic routes to benzimidazolebased fused polyheterocycles. Synthesis of commercially available benzimidazole involves condensation of ophenylenediamine with formic acid. An improved and greener protocol for the synthesis of benzimidazole derivatives.
Ligandfree coppercatalyzed synthesis of substituted. Wed like to understand how you use our websites in order to improve them. The purity of the compounds were ascertained by a melting point and tlc. 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, stability, and photoreactivity of diazirinyl. Jan 16, 2020 the development of synthesis for these compounds, however, is hampered by the regioselectivity and atom economy. 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. 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. 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. Simon associate professor, department of chemistry, dhanalakshmi srinivasan engineering college, perambalur, tamilnadu ug scholar, department of electronics and communication engineering. Synthesis of novel substituted thiourea and benzimidazole derivatives containing a pyrazolone ring as antiin. Elnassan pharmaceutical organic chemistry department, faculty of pharmacy, cairo university, cairo 11562, egypt corresponding author.
The synthesis of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substituted benzimidazole 2thiols 4ac followed by successive. The research presented in this thesis is centered on the design and synthesis of molecules which are derived from benzimidazoles and their applications. Benzimidazole, bulk synthesis, green synthesis, ecofriendly. The early 1950s was an important period regarding discovery of the biological significance of benzimidazolecontaining structures and the closelyrelated purines. 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. Selective and ecofriendly procedures for the synthesis of. It has been shown that during bacterial nucleic acid and protein synthesis. Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents fatmah a. 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.
A class of antihelmintic, often used to treat nematodes and cestodes. Synthesis and antifungal activity of benzimidazole. Development of drugs based on imidazole and benzimidazole. The imine can be alkylated and also serves as a ligand in coordination chemistry. Finally, the key intermediate 16 was alkylated with benzyl chloride in aqueous sodium hydroxide.
Synthesis, structural elucidation and dna binding profile. 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. The synthesis and chemistry of certain anthelmintic. The acetylcholinesterase ache and butyrylcholinesterase buche inhibitory activities were evaluated in vitro by using ellmans method. Photoluminescent benzobisimidazolium salts 9 and their physical and photophysical properties. 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. A key factor for the success of the technology is the chemical diversity of the libraries. 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.
Compounds 3a, 3b and 3c were screened for their antibacterial activity against s. Imidazole and benzimidazole synthesis is a comprehensive survey of the known methods of syntheses and ring modification. The synthesized compound exhibited by the significant antiinflammatory and antiviral activity. 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. This article is part of the thematic series green chemistry.
Synthesis, biological evaluations, and molecular docking study. Synthesis characterization and biological activity benzimidazole derivatives dr. Pdf synthesis of benzimidazole derivatives and study of their. 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 reaction yields and product stability were significantly affected by the identity of the diamine and anhydride substituents. The development of synthesis for these compounds, however, is hampered by the regioselectivity and atom economy. Awaad 5 and nazira karodia 2,6, 1 chemistry department, college of science, king saud university, riyadh 162, saudi arabia. 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. Synthesis of 3,3diphenylcyclopropene 16 list of tables ii. Synthesis, characterization, and applications supervising professor. Benzimidazole derivatives are known to have microbial. A series of mannich bases of benzimidazole derivatives having a phenolic group were designed to assess their anticholinesterase and antioxidant activities. The mixture is stirred vigorously and heated on a steam bath until the solution boils gently. 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.
Coordination behavior of benzimidazole, 2substituted. 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. 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 synthesized benzimidazole compounds were screened for acute and chronic. Synthesis and biological activities of some benzimidazoles. Green chemistry is the new and rapidly emerging field of chemistry. Synthesis of benzimidazoles the synthesis of benzimidazole. Satu siri baru terbitan oksadiazol dari benzimidazol telah disintesis dengan mudah oleh. Pdf a new series of non peptide angiotensinaii receptor antagonist has been prepared.
Synthesis of novel substituted thiourea and benzimidazole. Recent advances in the synthesis of benzimidazoles. Imidazole and benzimidazole rings are the most important nitrogencontaining heterocycles, which are widely explored and utilized by the pharmaceutical industry for drug discovery. Liquid phase synthesis of coumarino benzimidazoles for antimicrobial. Using 4fluoro3nitrobenzoic acid as a key synthon, we synthesized a 320 millionmember dnaencoded. A ring system composed of a benzene ring fused with an imidazole ring. The procedure is experimentally simple, general, efficient, and free from addition of external chelating ligands. Generally, the condensation of ophenylene diamine with carboxylic acids and their nitrile, imidates and orthoester 8 derivatives have been widely used for benzimidazole synthesis. Synthesis of benzimidazoles the synthesis of benzimidazole derivatives starts from biology 35417 at interamerican san german. Selective and ecofriendly procedures for the synthesis of benzimidazole. General procedure for the synthesis of benzimidazole series series a a solution of 590 mg benzimidazole 5 mmol, 0. The most prominent benzimidazole compound in nature is nriosyldimethylbenzimidazole, which serves as a axial ligand for cobalt in vitamin b12.
530 809 242 1587 1629 1645 942 1497 1604 155 194 1542 75 409 1039 718 116 745 319 1504 1064 712 1462 139 415 478 1504 1501 80 1354 363 1325 843 703 1496 708 1211 144 304 36 967 295 919 162 1001 176 696 1390 489