Synthesis of 1,2,4oxadiazole, 1,3,4oxadiazole, and 1,2. Thus, in tables 2 and 3, all the dihedral angles belonging the ring range from 0. 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. Journal of chemical and pharmaceutical research, 2012, 48.
Chandrakantha, b 2014 synthesis, characterization and pharmacological activity of some new substituted 1,2,4triazole, pyrazole, 1,3,4 oxadiazole and 1,3,4thiadiazole derivatives. 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. Synthesis of some 1,3,4thia, oxadiazol and 1,2,4 triazole incorporated the biologically active and the pyrazolopyridine derivative. A general method for the synthesis of bissubstituted 1,2,4oxadiazoles 146 from readily available aryl nitriles, hydroxylamine, and acyl chlorides has been applied in a single continuous microreactor sequence. Most of the tested compounds exhibited antiinflammatory activity and some of them were more active than. Synthesis and antimicrobial studies of 25substituted1, 3. Jul 24, 2014 we report the synthesis and biological assessment of 1, 3, 4 oxadiazole substituted 24 derivatives as novel, potential antibacterial agents. The 1,2,3isomer is unstable and ringopens to form the diazo ketone tautomer.
We report the synthesis and biological assessment of 1, 3, 4 oxadiazole substituted 24 derivatives as novel, potential antibacterial agents. Fourcomponent synthesis of 1,3,4oxadiazole derivatives from. Review article biological importance of 1, 3, 4oxadiazole. All the synthesized compounds were characterized by spectral analysis ir, h1 synthesis of 4substitutedbenzaldehyde semicarbazone 2a 2f nmr. In conclusion, compound 2 is used for the synthesis of 1, 3, 4 oxadiazole tetrahydropyrimidine 3 using i 2 ki and naoh, similarly 1, 3, 4 thiadiazole tetrahydropyrimidine using h 2so 4 nh 3 for the first time and yields are excellent. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from fda. Othman department of industrial chemistry, faculty of science, university of sciences and. Synthesis of nheterocycles, synthesis of oheterocycles synthesis of 1,2, 4 oxadiazoles. A useful method for the synthesis of 2acylamino1,3,4oxadiazoles was developed. A series of derivatives of 1, 3, 4oxadiazole having verities of biological activities can be synthesised by various methods. 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. A common route to the synthesis of 1,3,4oxadiazole 2thione and 1,2,4triazole 3thiols derivatives of trioses and pentoses as models for acyclic cnucleosides mohamed belkadi and adil a. Compounds with 1,3,4oxadiazole and azinane appendages to. Hydrazones, hydrazides, cyclization, 1,3,4oxadiazoles, biological tests.
Oxadiazoles form a major class of compounds with a heterocyclic nucleus for drug development and were among the first effective. Oxadiazoles is a fivemember heterocyclic compound having two carbon atoms, two nitrogen atoms, one oxygen atom and two double bonds. Synthesis, characterization and pharmacological activity of. In conclusion, compound 2 is used for the synthesis of 1,3,4oxadiazole tetrahydropyrimidine 3 using i 2 ki and naoh, similarly 1,3,4thiadiazole tetrahydropyrimidine using h 2so 4 nh 3 for the first time and yields are excellent. Unless otherwise noted, the contents of the fda website. An object of the present invention is to develop an efficient, scalable, and cost effective procedure for preparing multigram quantities of 1,2,4 and 1,3,4oxadiazole carboxylates from. 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. Synthesis and biological activity of some new 1,3,4oxadiazole derivatives. We report the synthesis and biological assessment of 1, 3,4oxadiazole substituted 24 derivatives as novel, potential antibacterial agents. By far the most widespread method for the synthesis of the 1,3,4oxadiazole ring involves closure of a diacylhydrazine derivative, which provides all five ring atoms. Studies of 1,3,4oxadiazole derivatives 10 parti studies of 1,3,4oxadiazole derivatives 2. Improved synthesis and characterisation of 1,3,4oxadiazole. Depending on the placement of the nitrogens in the ring, several isomers exist such as 1,2,4.
Jun 12, 2018 chhater singh, reeta karal and bijander kumar. Synthesis, characterization and biological activity studies. We report the synthesis and biological assessment of 1,3,4oxadiazole substituted 24 derivatives as novel, potential antibacterial agents. Synthesis of nheterocycles, synthesis of oheterocycles synthesis of 1, 3, 4 oxadiazoles. The disubstituted oxadiazoles have executed a range of pharmacologic activities. Apr 09, 2014 construction of 1, 3, 4 oxadiazole and 1, 3, 4 thiadiazole library with a high level of skeletal diversity based on branching diversityoriented synthesis on solidphase supports. The reaction of pbromoanilino acetohydrazideii with aromatic aldehydes in alcohol yielded 24bromo aniline nsubstituted benzylidine hydrazides iiiaiiij, which in presence of yellow mercuric oxide and iodine in dmf, yielded corresponding 4bromon5substituted 1,3,4 oxadiazole2. The reactions were completed in neutral conditions at room temperature and the corresponding disubstituted 1,3,4oxadiazole derivatives were produced in excellent yields33.
All the synthesized amides are characterized 1 h, c, ftir and elemental analysis techniques. The synthesis of 56methyl2substituted 4 pyrimidinyloxymethyl2, 3 dihydro 1, 3, 4 oxadiazole 2thiones and their 3 morpholinomethyl derivatives and the results of antiinflammatory activity in vivo are described. 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. Oxadiazoles heterocyclic building blocks sigmaaldrich. Oxadiazoles are fivemembered heterocyclic aromatic compounds consisting of one oxygen atom, two nitrogen atoms and two carbon atoms. This has been exploited in the preparation of 1,3,4oxadiazole therapeutic molecules for various applications. The pharmacological potential of 1,3,4oxadiazole nucleus is cleared from the literature and clinically used drugs.
The 1,3,4 oxadiazole derivatives reported showed good antimicrobial and antiinflammatory activities. They are also useful as antiviral agents, neuroprotectants, and antiinflammatory agents. Synthesis of 1,2,4oxadiazole, 1, 3,4oxadiazole, and 1,2,4triazolederived dipeptidomimetics. Some new synthesized drugs have shown better activities for the anti inflammation.
Synthesis of some novel 1,3,4oxadiazole derivatives rashidi n. This method can be extended largely for the synthesis of more substituted compounds. Synthesis and biological activity of 1,2,4oxadiazole derivatives. The literature revealed that 1,3,4oxadiazole possess diverse biological potential, easy synthetic routes for the synthesis and taken the attention of researchers. Synthesis of a novel class of some 1, 3, 4oxadiazole derivatives as. Fourcomponent synthesis of 1,3,4oxadiazole derivatives. Synthesized compounds are screened for microbial and cytotoxic activities. Compounds containing 1, 3, 4oxadiazole nucleus also find unique place in medicinal chemistry and play significant role as they are associated with immense biological activity. Nonspecific antispasmodic active oxadiazole derivatives later in 1969 breuer prepared a nitro furan containing oxadiazoles and studied the antimicrobial activity 17. The 1,2,4oxadiazole system is commonly found in bioactive molecules.
The structures of the newly synthesized derivatives were established by the combined practice of uv, ir, 1 h nmr, c nmr, and mass spectrometry. A useful synthesis of 2acylamino1,3,4oxadiazoles from. Studies of 1, 3,4oxadiazole derivatives 10 parti studies of 1, 3,4oxadiazole derivatives. General procedure for the synthesis of 1,3,4oxadiazole derivatives 4ah an equimolar mixture of acid hydrazide 3, 0. The reactions were completed in neutral conditions at room temperature and the corresponding disubstituted 1, 3, 4 oxadiazole derivatives were produced in excellent yields33. Synthesis and biological activity of some new 1,3,4.
Synthesis of some novel 1, 3, 4 oxadiazole derivatives rashidi n. Compounds ive, ivf, ivh, respectively, showed better antibacterial activity, whereas all the compounds showed good antiinflammatory activity. Derivatives of 1, 3, 4oxadiazole have been found to possess a wide spectrum of pharmacological, medical and biological activities 3334. Docking studies, synthesis, and evaluation of antioxidant. Literature reveals that 1, 3, 4oxadiazole is a highly privileged structure the derivatives of which exhibit a wide range of biological activities including antibacterial, antitubercular. Fourcomponent synthesis of sterically congested 1,3,4oxadiazole derivatives5 see table. Some new synthesized drugs have shown better activities for the antiinflammation.
Nitro furan containing oxadiazole johan et al, 1972 have reported the synthesis of bis 1,2, 4 oxadiazole derivatives and their. The 1,2, 3 isomer is unstable and ringopens to form the diazo ketone tautomer. The activities include anticancer, antimicrobial, anti inflammatory, anti hiv, anti tubercular, anti diabetic, antifungal. Improved synthesis and characterisation of 1,3,4oxadiazole kati m. Synthesis and biological activity of 1,2, 4 oxadiazole derivatives. Depending on the placement of the nitrogens in the ring, several isomers exist such as 1,2, 4. The synthesis of 56methyl2substituted 4pyrimidinyloxymethyl2,3dihydro1,3,4oxadiazole2thiones and their 3morpholinomethyl derivatives and the results of antiinflammatory activity in vivo are described. Ptsazncl 2 is an efficient and mild catalyst for the synthesis of 3,5disubstituted1,2,4oxadiazoles from amidoximes and organic nitriles. The reaction offers a broad scope and good functionalgroup tolerance.
Thin layer chromatography tlc was run throughout the reaction to optimize. Donatella giomi, in progress in heterocyclic chemistry, 2009. It undergoes dielsalder reaction with electronrich and electronpoor dienophiles. Studies of 1, 3, 4 oxadiazole derivatives 10 parti studies of 1, 3, 4 oxadiazole derivatives 2.
The pathway to another large group of 1,2, 4 oxadiazoles proceeding from a broad spectrum of reactants is via their reactions of 1, 3 dipolar cycloaddition, in particular, with primary amidoximes. Synthesis of some 1, 3, 4 thia, oxadiazol and 1,2, 4 triazole incorporated the biologically active and the pyrazolopyridine derivative. Alan aitken eastchem school of chemistry, university of st andrews, north haugh, st andrews, fife, ky16 9st, united kingdom email. Ptsazncl 2 is an efficient and mild catalyst for the synthesis of 3,5disubstituted 1,2, 4 oxadiazoles from amidoximes and organic nitriles.
The synthesis of novel achiral and chiral amides incorporating 1,3,4oxadiazole ring are reported. All the synthesized compounds were characterized by spectroscopic techniques like 1hnmr, cnmr, eims, and ir to. Short communication synthesis of some novel 1,3,4oxadiazole. Synthesis and biological activity of 1,2,4oxadiazole. Abstract oxadiazole a heterocyclic nucleus has attracted a wide attention of the chemists in search for new therapeutic molecules. The structures of the newly synthesized derivatives were established by the combined practice of uv, ir, 1 h nmr. Synthesis of nheterocycles, synthesis of oheterocycles synthesis of 1,2,4oxadiazoles. Synthesis of some new 1,3,4oxadiazole derivatives bearing sugars. The 1, 3, 4 oxadiazole derivatives reported showed good antimicrobial and antiinflammatory activities. Synthesis and antimicrobial activity of some new 354.
Large scale synthesis of 1,2,4 and 1,3,4oxadiazole carboxylates. Molecular modeling and docking of the active compounds into akr1c3 complexed with its bound inhibitor indomethacin using molsoft icm 3. Thus, in recent years scientists have developed various new methods for the. Facile synthesis of some novel derivatives of 1,3,4,oxadiazole. Review of synthesis of 1,3,4oxadiazole derivatives. Chemistry and pharmacological importance of 1,3,4oxadiazole. The 1,2, 4 oxadiazole system is commonly found in bioactive molecules. The planarity of the oxadiazole ring is expected to enhance delocalization, which supports the conclusion of our discussion above.
Most of 1, 3,4oxadiazoles are best obtained by synthesis from acyclic precursors. Synthesis of some new 2, 5disubstituted 1,3,4oxadiazole. Facile synthesis of some novel 1, 3, 4 oxa diazole derivatives associated with pyrimidine core unit as a antimicrobial agents. Nitro furan containing oxadiazole johan et al, 1972 have reported the synthesis of bis 1,2,4oxadiazole derivatives and their. The synthesis of novel achiral and chiral amides incorporating 1, 3, 4 oxadiazole ring are reported. Synthesis of nheterocycles, synthesis of oheterocycles synthesis of 1,3,4oxadiazoles.
Derivatives ivb, ivc, ivd, ivg showed moderate antifungal activity. Synthesis and characterization of energetic 3nitro1,2,4. Synthesis and in vitro antimicrobial evaluation of new 1,3,4. Short communication evaluation of new 2ntert butyl5aryl. Structure, properties, spectra, suppliers and links for. Review of synthesis of 1, 3,4oxadiazole derivatives. Synthesis and biological activity of some new 1, 3, 4 oxadiazole derivatives. A general method for the synthesis of bissubstituted 1,2, 4 oxadiazoles 146 from readily available aryl nitriles, hydroxylamine, and acyl chlorides has been applied in a single continuous microreactor sequence. Synthesis, characterization and antiinflammatory activity of some 1. Construction of 1,3,4oxadiazole and 1,3,4thiadiazole library with a high level of skeletal diversity based on branching diversityoriented synthesis on solidphase supports. N 2 post graduate department of chemistry, shri shivaji science college amravati, m. A common route to the synthesis of 1,3,4oxadiazole 2thione. The syntheses are based mostly on the use of primary amidoximes and acylating agents as the initial reactants.
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