Design, synthesis, and structureactivity relationships of. The synthesis of novel achiral and chiral amides incorporating 1,3,4oxadiazole ring are reported. Synthesis of 1,3,4oxadiazoles 1a6d under conventional heating and under microwave irradiation. The 1,3,4 oxadiazole is an aromatic heterocycle valued for its lowlipophilicity in drug development.
A practical and transitionmetalfree oxidative cyclization of acylhydrazones into 1,3,4 oxadiazoles has been developed by employing stoichiometric molecular iodine in the presence of potassium carbonate. Oxadiazole, a heterocyclic nucleus has attracted a wide attention for the chemist in search for the new therapeutic molecules. This method has a broad substrate scope and a good tolerance for diverse functional groups. For the synthesis of 1,3,4oxadiazoles using the amino acid derived from nprotected selenoamino acid 6, both methodologies allowed the preparation of the compounds with similar efficiency table 2, entries 6, 12, 18 and 24. I2mediated oxidative co bond formation for the synthesis of. In this present investigations, we report the synthesis of 1,3,4oxadiazole derivatives starting from 2phenylethylamine and benzoic acid. Design and synthesis of 3,5substituted 1,2,4oxadiazoles. A multistep protocol for the synthesis of 3,5disubstituted 1,2,4 oxadiazoles on dnachemical conjugates has been developed.
Herein, we summarized some recent strategies on the synthesis of 1,3,4thiadiazole. A literature search revealed that no such oxadiazoles derived from amino acids have yet been prepared except sebastiao et al 21 who synthesized some 3aryl1,2,4oxadiazoles carrying protected lalanine side chain. To investigate and compare reversely substituted oxadiazoles, with our synthesized oxadiazoles, docking poses and 3d structurebased pharmacophores of active compounds 10 and 11 were calculated. A literature search revealed that no such oxadiazoles derived from amino acids have yet been prepared except sebastiao et al 21 who synthesized some 3aryl1,2,4 oxadiazoles carrying protected lalanine side chain. Read online synthesis and characterization of 2, 5disubstituted1, 3.
Also 1,3,4 oxadiazoles are suitable substrates in a new process in which tmp 2 zn. Jul 24, 2014 the newly synthesized 1,3,4oxadiazoles derivatives were computationally designed and optimized to investigate the interactions between the target compounds and the amino acid residues of the e. In the present study, all synthesized compounds showed. Synthesis of 1,3,4 oxadiazoles 1a6d under conventional heating and under microwave irradiation. In a direct annulation of hydrazides with methyl ketones for the synthesis of 1,3,4oxadiazoles, the use of k 2 co 3 as a base achieves an unexpected and highly efficient cc bond cleavage. Both receptor and ligand files were changed into pdbqt format.
Synthesis of chromen4oneoxadiazole substituted analogs as. Development of oxadiazoles as treatment for schistosomiasis. Most of the preparation methods involve strong acidic conditions at elevated temperatures, which narrows the convenient access of derivatized 1,3,4oxadiazoles. The first synthesis of 1,2,4 oxadiazoles, initially named furo ab1diazoles, was achieved by tiemann and kruger in 1884 1a, b,c. Synthesis of some new 1,2,4triazoles and 1,3,4oxadiazoles as a safer antiinflammatory and analgesic agents md. Synthesis and evaluation of some novel heterocyclic compounds. We report the synthesis and biological assessment of 1,3,4oxadiazole substituted 24 derivatives as novel, potential antibacterial agents. Journal of chemical and pharmaceutical research, 2012, 45. Depending on the placement of the nitrogens in the ring, several isomers exist such as 1,2,4. A series of 2, 5disubstituted 1, 3, 4oxadiazole derivatives 4a4g have been synthesized with the help of different aromatic benzaldehyde and final.
View the article pdf and any associated supplements and figures for a period of 48 hours. Synthesis and evaluation of some novel heterocyclic. Ptsazncl 2 is an efficient and mild catalyst for the synthesis of 3,5disubstituted1,2,4 oxadiazoles from amidoximes and organic nitriles. Fourcomponent synthesis of 1,3,4oxadiazole derivatives. A simple and convenient onepot protocol for the synthesis of substituted 2amino1,3,4oxadiazoles mediated by tosyliminophenyl. Hence our prime target was to synthesize dimers of 2,5 disubstituted 1,3,4 oxadiazoles. Ptsazncl 2 is an efficient and mild catalyst for the synthesis of 3,5disubstituted1,2,4oxadiazoles from amidoximes and organic nitriles. National center for advancing translational sciences ncats, 6701 democracy boulevard, bethesda md 208924874 3015948966. Synthesis and characterization of energetic 3nitro1,2,4oxadiazoles zhanda fu, arui su,b yang wang, yaofeng wang, wei zeng, anan xiao, yukai wu, azhiming zhou, jun chen,b and fuxue chen in memory of professor haishan dong to reconcile the inherent contradiction of high energy and low sensitivity in energetic materials, the. Present paper reports the synthesis of four new biologically active 2, 5substituted oxadiazoles by oxidative cyclization of the semicarbazones obtained from the reaction of semicarbazides with corresponding aromatic aldehydes. The structures of the newly synthesized derivatives were established by the combined practice of uv, ir, 1 h nmr, c nmr, and mass spectrometry. Apr 23, 2012 synthesis and biological evaluation of novel marinederived indolebased 1,2,4 oxadiazoles derivatives as multifunctional neuroprotective agents. Basemediated onepot synthesis of 1,2,4oxadiazoles from. I 2mediated oxidative co bond formation for the synthesis of 1,3,4oxadiazoles from aldehydes and hydrazides.
Design and synthesis of 3,5substituted 1,2,4oxadiazoles as. A onepot synthesis of 3,5disubstituted 1,2,4 oxadiazoles with two identical substituents directly from the reaction of nitriles and hydroxylamine hydrochloride in the presence of potassium. The oxadiazoles prepared were extracted with chloroform, filtered it and washed precipitate 34 times with hot water and kept them in desiccator. Synthesis and evaluation of some novel heterocyclic compounds containing an. The pathway to another large group of 1,2,4 oxadiazoles proceeding from a broad spectrum of reactants is via their reactions of 1,3dipolar cycloaddition, in particular, with primary amidoximes. Synthesis and characterization of some oxadiazoles and. Amido group placed on the 5phenyl ring of the 1,2,4 oxadiazoles formed a hydrogen bond with asn120 in the atp pocket. Synthesis of nheterocycles, synthesis of oheterocycles synthesis of 1,3,4 oxadiazoles. Use of adobe reader to open and fill in the form is strongly recommended form fields may not.
Substituents at the 2 andor 5positions can modulate the heterocycles electronic and hydrogen bondaccepting capability, while exploiting its use as a carbonyl bioisostere. Further these synthesized derivatives were subjected to antibacterial activity against all. The structures of target oxadiazoles were confirmed by elemental, ir, nmr and lcms data. Efficient and mild synthesis of substituted 2amino1,3,4. If you have problems viewing pdf files, download the latest version of adobe reader. The present work deals with the synthesis and evaluation of the antiinflammatory activity of two novel 2,5disubstituted1,3,4oxadiazoles osd and opd. This paper therefore describes the synthesis of oxadiazole derivatives containing lamino acid moieties attached to the c2 of the heterocyclic ring, with the hope.
Synthesis of 1,3,4oxadiazoles organic chemistry portal. Pdf the synthesis of novel achiral and chiral amides incorporating 1,3,4oxadiazole ring are reported. Fourcomponent synthesis of sterically congested 1,3,4oxadiazole derivatives5 see table. Sample thesis pages the graduate college at illinois. So, the microwave synthesis method is better than the conventional method. Synthesis of some new 1,3,4oxadiazole derivatives bearing sugars. Result and discussion synthesis the characterization data of all compounds 17 are given in the experimental section. Oxadiazoles and their derivatives are considered as simple five membered heterocycles possessing one oxygen and two nitrogen atoms. International journal of chemical and pharmaceutical sciences. Fourcomponent synthesis of 1,3,4oxadiazole derivatives from. An external file that holds a picture, illustration, etc. Oxadiazoles are fivemembered heterocyclic aromatic compounds consisting of one oxygen atom, two nitrogen atoms and two carbon atoms. Synthesis, characterization and effect of bis1,3,4. Synthesis of nheterocycles, synthesis of oheterocycles synthesis of 1,2,4 oxadiazoles.
Review of synthesis of 1,3,4 oxadiazole derivatives. Thus, we tried to elaborate a convenient method for constructing diversely 2,5substituted 1,3,4oxadiazoles from easily accessible starting materials via ugihuisgen sequence. Design, synthesis, and structureactivity relationships of 3,4,5. Pdf various approaches for synthesis of oxadiazole derivatives. For the synthesis of 1,3,4 oxadiazoles using the amino acid derived from nprotected selenoamino acid 6, both methodologies allowed the preparation of the compounds with similar efficiency table 2, entries 6, 12, 18 and 24. Mild synthesis of substituted 1,2,5oxadiazoles using 1,1. Facile synthesis of 1,3,4oxadiazoles via iodine promoted oxidative annulation of methylazaheteroarenes and hydrazides. The newly synthesized 1,3,4oxadiazoles derivatives were computationally designed and optimized to investigate the interactions between the target compounds and the amino acid residues of the e. Synthesis, characterization and biological activities of 1,3. A onepot synthesis of 3,5disubstituted 1,2,4oxadiazoles with two identical substituents directly from the reaction of nitriles and hydroxylamine hydrochloride in the presence of potassium. Synthesis, characterization and biological activities of 1.
In a direct annulation of hydrazides with methyl ketones for the synthesis of 1,3,4 oxadiazoles, the use of k 2 co 3 as a base achieves an unexpected and highly efficient cc bond cleavage. Sample thesis pages revised january 2015 the graduate college. Synthesis and evaluation of anticancer activity of 1, 3, 4oxadiazole. The course of reaction and purity were ascertained by performing tlc. Design, synthesis, and biological evaluation of novel 5. Solventfree microwaveassisted synthesis of oxadiazoles. Pdf various approaches for synthesis of oxadiazole. Files available from the acs website may be downloaded for personal use only.
A convergent synthesis of 1,3,4oxadiazoles from acyl hydrazides under semiaqueous conditions. S1 mild synthesis of substituted 1,2,5 oxadiazoles using 1,1 carbonyldiimidazole as a dehydrating agent andrew j. The 1,3,4oxadiazole is an aromatic heterocycle valued for its lowlipophilicity in drug development. Present work introduces one of possible routes for a total synthesis of compound 2.
A set of six dnaconnected aryl nitriles were converted to corresponding amidoximes with hydroxylamine followed by the oacylation with a series of aryl and aliphatic carboxylic acids. Synthesis and characterization of 1,3,4oxadiazoles. A simple basemediated onepot synthesis of 3,5disubstituted 1,2,4oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride has been developed, in which the aldehydes act as both substrates and oxidants. Also, xray crystal structure analysis will be necessary for one or two representative compounds in order to completely rule out the possibility of alternate formation of oxadiazoles. Swift synthesis of 1, 2, 4oxadiazoles employing polymersupported reagents in microwave heating. The first monosubstituted 1,3,4oxadiazoles were reported in 1955 by two independent laboratories1,2. Synthesis of 1,2,4oxadiazoles by tandem reaction of nitroalkenes. Synthesis, reactions, and applications in medicinal, agricultural, and materials chemistry yang hu, cuiyun li, xiaoming wang, yonghua yang, and hailiang zhu state key laboratory of pharmaceutical biotechnology, nanjing university, nanjing. Oxadiazoles article about oxadiazoles by the free dictionary. The conditions of this cyclization reaction also work well with crude acylhydrazone substrates obtained from the condensation of aldehydes and hydrazides. A convergent synthesis of 1,3,4oxadiazoles from acyl. The syntheses are based mostly on the use of primary amidoximes and acylating agents as the initial reactants. Synthesis and characterization of some oxadiazoles and thiadiazoles derivatives ali omairi mohammad college of science, university of tikrit. The pathway to another large group of 1,2,4oxadiazoles proceeding from a broad spectrum of reactants is via their reactions of 1,3dipolar cycloaddition, in particular, with primary amidoximes.
Pdf oxadiazole, a fivemembered heterocycle having two carbon atoms, two nitrogen atoms, one oxygen atom, and two double bonds, inclusive of inductive. The synthesis and biological evaluation of some 2,5. Further these synthesized derivatives were subjected to antibacterial activity against all the selected. Target compounds were docked into active site of pdf pdb code 1g2a using mvd version 5. The first monosubstituted 1,3,4 oxadiazoles were reported in 1955 by two independent laboratories1,2. A useful synthesis of 2acylamino1,3,4oxadiazoles from.
A new approach to 1,3,4oxadiazoles is described wherein. The alkylsubstituted1,3,4oxadiazoles are less encountered compared to their hetaryl counterparts. Melting points were determined in open capillaries and is. Recently, ajay kumar and coworkers reported the synthesis of 1,3,4oxadiazoles, in an attempt to synthesise alkenyl substituted oxadiazoles, they observed that. Synthesis of phidianidines a and b the journal of organic. In an attempt to produce heterocyclic compounds based on. Characterization of 1,3,4 oxadiazoles oxadiazole o 1 form h 1 1 ethyl 7 methyl 3 5. Amido group placed on the 5phenyl ring of the 1,2,4oxadiazoles formed a. Development of oxadiazoles as treatment for schistosomiasis and hookworm schistosomiasis and hookworm are parasitic diseases responsible for significant mortality and morbidity in developing countries, together infecting more than 1 billion people worldwide. Oxadiazoles is a fivemember heterocyclic compound having two carbon atoms, two nitrogen atoms, one oxygen atom and two double bonds. Apr 11, 2007 microwaveassisted as well as conventional synthesis of 5substituted22methyl4nitro1imidazomethyl1,3,4 oxadiazoles containing the nitroimidazole moiety is carried out and their antibacterial, antifungal and antiinflammatory activity is reported. Synthesis of compounds by the microwave method gives comparatively more yield and requires less time to complete the reaction.
Design, synthesis and biological screening of novel 1,3,4. Synthesis and evaluation of some new 1,3,4oxadiazoles bearing. Pdf the synthesis of novel achiral and chiral amides incorporating 1,3,4 oxadiazole ring are reported. A number of heterocyclic compounds was synthesized from the reaction of methyl benzoate 1 with. Synthesis of 1,3,4oxadiazole derivatives from amino acid. The synthesis of 2aryl1,3,4 oxadiazoles can be accomplished using nisocyanoiminotriphenylphosphorane 172 with benzoic acid derivatives in a clean reaction under mild conditions. Synthesis of nheterocycles, synthesis of oheterocycles synthesis of 1,2,4oxadiazoles. The in vitro antitubercular study was conducted against mycobacterium tu. All the synthesized compounds of series i was screened for the microbial activity. Rabie et al design, synthesis, and biological evaluation of novel 5substituted23,4,5trihydroxyphenyl1,3,4 oxadiazoles as potent antioxidants in order to construct a good general antioxidant.
Unlimited viewing of the articlechapter pdf and any associated supplements and figures. After cyclodehydration of the oacyl amidoximes by heating at 90 c in ph 9. Microwaveassisted as well as conventional synthesis of 5substituted22methyl4nitro1imidazomethyl1,3,4oxadiazoles containing the nitroimidazole moiety is carried out and their antibacterial, antifungal and antiinflammatory activity is reported. Synthesis and characterization of energetic 3nitro1,2,4 oxadiazoles zhanda fu, arui su,b yang wang, yaofeng wang, wei zeng, anan xiao, yukai wu, azhiming zhou, jun chen,b and fuxue chen in memory of professor haishan dong to reconcile the inherent contradiction of high energy and low sensitivity in energetic materials, the. I2mediated oxidative co bond formation for the synthesis. Download synthesis and characterization of 2, 5disubstituted1, 3. Synthesis of 1,2,4oxadiazoles organic chemistry portal. Synthesis and anticancer activity of 1,2,4oxadiazol linked benzimidazole derivatives.
Although synthesis of omeprazole 1 and its analogues is well known,810 to the best of our knowledge no data on the chemical synthesis of its primary metabolite 5hydroxyomeprazole 2 is published. Oxadiazoles form a major class of compounds with a heterocyclic nucleus for drug development and were among the first effective. Synthesis of chromene based oxadiazole derivatives 119. Synthesis and characterization of energetic 3nitro1,2,4. Russian journal of general chemistry 2018, 88 12, 26532657. Synthesized compounds are screened for microbial and cytotoxic activities. Synthesis of some new 2, 5disubstituted 1,3,4oxadiazole. Swift synthesis of 1, 2, 4 oxadiazoles employing polymersupported reagents in microwave heating.
The most often used synthetic route for 1,3,4oxadiazoles includes reactions of acid hydrazides or hydrazine with acid chloridescarboxylic acids and direct cyclization of diacylhydrazines using a variety of dehydrating agents such as phosphorous oxychloride 24, thionyl. Unlimited viewing of the articlechapter pdf and any. For language access assistance, contact the ncats public information officer. Various approaches for synthesis of oxadiazole derivatives article pdf available in international journal of research in ayurveda and pharmacy 22. Synthesis, characterization and biological activities. C3h3on a structure that consists of a fivemembered ring containing oxygen and nitrogen in the 1 and 3 position.
The first synthesis of 1,2,4oxadiazoles, initially named furo ab1diazoles, was achieved by tiemann and kruger in 1884 1a, b,c. Hence our prime target was to synthesize dimers of 2,5 disubstituted 1,3,4oxadiazoles. All the synthesized amides are characterized 1 h, c, ftir and elemental analysis techniques. All books are in clear copy here, and all files are secure so dont worry about it. Oxadiazoles heterocyclic building blocks sigmaaldrich. One of such compound of 2,5disubstituted 1,3,4oxadiazole class a204197 had been proven useful for the treatment of neoplastic diseases inin vivo studies as an antimitotic agent51.
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