Synthesis and biological activity of 5substituted2amino1, 3,4oxadiazole derivatives sanjeev kumar department of chemistry, iswar saran degree college university of allahabad, allahabad211004, india email. For example, raltegravir is an hiv drug which contains an 1, 3,4oxadiazole ring. Pdf the synthesis, the chemical and photochemical reactivity, and the use of 1,2,4oxadiazoles in materials and as bioactive. A convergent synthesis of 1, 3,4oxadiazoles from acyl hydrazides.
Acid hydrazides811 have been in general use as the starting materials in some 1, 3,4oxadiazole. Various methods were reported in the literature for the synthesis of 1, 3,4oxadiazole and its derivatives wang et al. Alkylation of thiol group of 1, 3,4oxadiazole n1 by sonication using different alkyl halide methyl iodide, allyl bromide, proprgyl chloride and benzyl chloride gave compounds n2n5. Oxadiazoles are fivemembered heterocyclic aromatic compounds consisting of one oxygen atom, two nitrogen atoms and two carbon atoms. So there should be possibility of 4 oxadiazole isomers reliant on the nitrogen atom position in the ring as follows3. Synthesis of nheterocycles, synthesis of oheterocycles synthesis of 1,2,4oxadiazoles.
Novel 1,2,4oxadiazoles and 1,2,4thiadiazoles as dual 5. Synthesis and anticancer activity of 3, 5diaryl 1, 2, 4. Taylor, elsevier, london, uk, 3rd edn, 2008, vol 5. The syntheses are based mostly on the use of primary amidoximes and acylating agents as the initial reactants. N o n 1 2 4 3 5 n o n 1 2 4 3 5 n n o 1 2 4 3 5 n o n 1 2 4 3 5 isomers of oxadiazole basic information oxadiazole is a heterocyclic nucleus which gains heavy interest by many research scholars regarding inventions of novel. Design and molecular docking studies of some 1, 3,4oxadiazole derivatives 1, research article. The pathway to another large group of 1,2,4oxadiazoles proceeding from a broad spectrum of reactants is via their reactions of 1, 3 dipolar cycloaddition, in particular, with primary amidoximes. Electrochemical oxidative intramolecular ns bond formation. A new convenient synthesis of 5aryl2arylamino1,3,4oxadiazole. Fourcomponent synthesis of 1,3,4oxadiazole derivatives. Further mixture of 2, arylalkyl isothiocyanate and ethanol was refluxed and formed n124hydroxyphenyl acetyl n4alkylaryl3thiosemicarbazide 3ai.
In an effort to discover new candidates with improved antimicrobial activities we report here the synthesis and in vitro biological evaluation of various series of. Pdf 1, 3, 4oxadiazole emerged as an important heterocyclic nucleus. Energetic materials based on isocyanuric acid and 1,2,4oxadiazole. Several 3 54substitutedphenyl1, 3,4oxadiazole2yl2styryl quinazoline43hone were synthesized and screened for antibacterial activity against staphylococcus aureus, bacillus subtilis, pseudomonas aeruginosa, and escherichia coli and antifungal activity against aspergillus niger and fusariumoxysporum by the serial dilution technique. We have decided to present the main synthesis approaches used for obtaining the heterocyclic nucleus, as well as the broad spectrum of pharmacological activities such as anti. Zan yang, jiaqi zhang, liping hu, lijun li, kun liu, tao yang, congshan zhou. The refractive index n25 d of 1, 3, 4oxadiazole is 1. Ptsazncl 2 is an efficient and mild catalyst for the synthesis of 3,5disubstituted1,2,4oxadiazoles from amidoximes and organic nitriles.
Fourcomponent synthesis of 1, 3,4oxadiazole derivatives from. The main synthesis route for 5substituted1, 3,4oxadiazole2thiolthiones 29 involves an initial reaction between an acylhydrazide 8 and carbon disulfide in an basic alcohol solution, followed by acidification of the reaction mixture. Thus, we planned to combine both pharmacophores into. Synthesis and antimicrobial activity of some new 354. Biological activities of thiocarbohydrazide derivatives. The outcomes of this merger have already been the subject of attention in. Synthesis and characterization of 3,5diamino1,2,4oxadiazole daod. Paper open access synthesis, characterization and study. Synthesis of a novel class of some 1, 3, 4oxadiazole derivatives as. Department of chemistry, faculty of science, gazi university, ankara 06500 turkey. Convenient synthesis of the 2,5disubstituted 1, 3,4oxadiazole derivatives under microwave dipti l. Further these synthesized derivatives were subjected to antibacterial activity against all the selected. All the synthesized amides are characterized 1 h, c, ftir and elemental analysis techniques. Efficient and mild synthesis of substituted 2amino1,3,4.
The disubstituted oxadiazoles have executed a range of pharmacologic activities. Hydrazinecarbothioamide group in the synthesis of heterocycles. London, uk were incubated according to the suppliers references and seeded at 1. Synthetic approaches and pharmacological activity of 1,3,4. Synthesis of chromen4oneoxadiazole substituted analogs as potent glucuronidase inhibitors. In a clean, dried 250 ml round bottomed flask a stirred solution of commercial 2chlorobenzonitrile 0.
In their attempt to merge material about the synthesis and. S1 supporting information synthesis, structure activity relationships and preclinical evaluation of heteroaromatic amides and 1, 3,4oxadiazole derivatives as 5ht 4 receptor partial agonists. The most widely applicable route to the synthesis of 1, 3,4oxadiazole and its 2,5disubstituted derivatives is the thermal, acid and base catalyzed cyclization of their corresponding carbonylhydrazides. Short communication synthesis of some novel 1, 3,4oxadiazole derivatives rashidi n. Synthesis of 3 substituted 5amino1,2,4thiadiazoles.
Synthesis of oxadiazolethiadiazole hybrids and their. The conventional method of synthesis of 1, 3,4oxadiazole involves intermolecular. Search results for 1, 3,4oxadiazole at sigmaaldrich. A simple and efficient cationic feiiitempocatalyzed oxidative cyclization of aroyl hydrazones in the presence of oxygen enables the synthesis of 2,5disubstituted 1, 3,4oxadiazole derivatives in high yields. We report the synthesis and biological assessment of 1, 3,4oxadiazole substituted 24 derivatives as novel, potential antibacterial agents. The 1, 3,4oxadiazole is an aromatic heterocycle valued for its lowlipophilicity in drug development. The intermediate product iii was then cyclized in dcm in the presence of phenyliodoacetate to give methyl 45isoquinoline3yl1,3,4. Allopurinol, 2aminobenzothiazole, 5substituted2amino1, 3,4oxadiazole, antimicrobial. Synthesis, characterization and evaluation the biological. Acylthiosemicarbazides prepared from the corresponding acylhydrazides undergo efficient cyclodesulfurization by phints in good yields. Bhoya chemical research laboratory, department of chemistry, saurashtra university. Biological activity of 4thiazolidinones there are several reports in the. These observations and our interest in the pharmaceutical chemistry of heterocyclic compounds promoted us to have synthesized different.
A large number of 1, 3,4oxadiazole derivatives prepared by this route have been reported in recent years. Synthesis of chromen4oneoxadiazole substituted analogs. Most of the tested compounds exhibited antiinflammatory activity and some of them were more active than. Convenient synthesis of the 2,5disubstituted 1,3,4. The synthesis of 56methyl2substituted 4pyrimidinyloxymethyl2, 3 dihydro1, 3,4oxadiazole2thiones and their 3 morpholinomethyl derivatives and the results of antiinflammatory activity in vivo are described. Materials and methods melting points were determined on electrical melting point apparatus. Synthesis and characterization of energetic 3nitro1,2,4. Thus, in recent years scientists have developed various new methods for the synthesis of its derivatives. The 1, 3,4oxadiazole isomer is much more widely applied for its fluorescent properties. Review of synthesis of 1, 3,4oxadiazole derivatives.
Synthesized compounds are screened for microbial and cytotoxic activities. The synthesis of 3aryl5pentyl1,2,4oxadiazoles from carboxylic acid esters and arylamidoximes in the presence of potassium carbonate is described. Other pharmaceutical drugs containing the 1, 3,4oxadiazole ring include fenadiazole, zibotentan, and. Chemistry of oxadiazole ainsworth prepared 1, 3, 4oxadiazole in 1965 by the thermolysis of ethylformate formly hydrazine figure 1 at atmospheric pressure 21. Synthesis and characterization of new thebaine derivatives as potential opioid agonists and antagonists. Review of synthesis of 1,3,4oxadiazole derivatives. A simple and convenient onepot protocol for the synthesis of substituted 2amino1, 3,4oxadiazoles mediated by tosyliminophenyl. The synthesis procedure started by reacting hydrazide derivative and carbon disulfide. Nitro furan containing oxadiazole johan et al, 1972 have reported the synthesis of bis 1,2,4oxadiazole derivatives and their antimalarial activity 18. Derivatives of 1, 3,4oxadiazole with suitable substitution at 2,5position have already been reported to have possible biological activities. The reaction offers a broad scope and good functionalgroup tolerance.
Synthesis of 1,2,4oxadiazole, 1, 3,4oxadiazole, and 1,2,4triazolederived dipeptidomimetics. Unless otherwise noted, the contents of the fda website. The mass spectra showed that the base peak is the molecular ion peak. Schiff base synthesis of 1, 3,4 oxadiazole derivatives containing indole moiety bearing thiazolidinone ring were synthesized by the condensation of 2 3 4oxo 3 ptolyl 1htetrazol5yl1hindol1yl n1,1,1trifluoropropan2 ylidene acetohydrazide with acetic anhydride. Synthesis of substituted 1,3,4 oxadiazoles as antiinflammatory agent. Methods of synthesis for 5substituted1, 3,4oxadiazole2thiols the main synthesis route for 5substituted1, 3,4oxadiazole2thiolthiones 29 involves an initial reaction between an acylhydrazide 8 and carbon disulfide in an basic alcohol solution, followed by acidification of the reaction mixture scheme 8. The synthesis of 2aryl1, 3,4oxadiazoles can be accomplished using. The synthesis of novel achiral and chiral amides incorporating 1, 3,4oxadiazole ring are reported. Synthesis and characterization of new thebaine derivatives. Substituents at the 2 andor 5positions can modulate the heterocycles electronic and hydrogen bondaccepting capability, while exploiting its use as a carbonyl bioisostere. Synthesis and biological activity of 5substituted2amino.
Oxadiazole s are a class of heterocyclic aromatic chemical compound of the azole family. Synthesis of 1,2,4oxadiazole, 1,3,4oxadiazole, and 1,2. Nonspecific antispasmodic active oxadiazole derivatives later in 1969 breuer prepared a nitro furan containing oxadiazoles and studied the antimicrobial activity 17. Design and molecular docking studies of some 1,3,4. N 1 2 the two tautomeric forms of 1,2, 3 triazole and benzotriazole are in equilibrium, both in. Oxadiazoles form a major class of compounds with a heterocyclic nucleus for drug development and were among the first effective. A convergent synthesis of 1,3,4oxadiazoles from acyl. Synthesis of new isoquinolinebaseoxadiazole derivatives as. Depending on the placement of the nitrogens in the ring, several isomers exist such as 1,2,4. The structures of the newly synthesized derivatives were established by the combined practice of uv, ir, 1 h nmr, c nmr, and mass spectrometry. The synthesized compoundswere screened for antibacterial activity. Structure, properties, spectra, suppliers and links for. Oxadiazoles heterocyclic building blocks sigmaaldrich.