Furamizole compound 1 is a compound which is based upon 1,3,4oxadiazole ring and has strong antibacterial activity. Jcprc5 104 studies on novel 1,3,4oxadiazole derivatives darshan raol and g. In order to discover new lead compounds with high antibacterial activity, a series of new derivatives were designed and synthesized by introducing a sulfonate or carboxylate moiety into the 1,3,4 oxadiazole structure. In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4oxadiazole2thione derivatives. A series of chalconesbearing 1,3,4oxadiazole derivatives was synthesized as novel bioactive antimicrobial agents against multidrugresistant bacteria and fungi. The in vitro antitumor activity of the compounds obtained was investigated and the benzothiazol derivatives 6d and 6e showed strong effects on leukaemia cell lines ccrfcem cc 50 12 2. Studies of 1,3,4oxadiazole derivatives 10 parti studies of 1,3,4oxadiazole derivatives 2. The reactions were completed in neutral conditions at room temperature and the corresponding disubstituted 1,3,4oxadiazole derivatives were produced in excellent yields. Synthesis of novel 1,3,4 oxadiazole derivatives and their biological properties. Oxadiazoles form a major class of compounds with a heterocyclic nucleus for drug development and were among the first effective. Target compounds were docked into active site of pdf pdb code 1g2a using mvd version 5.
A series of new benzothiazole derivatives 6ah have been synthesized, in five steps, from substituted phenols via the 1,3,4oxadiazole2thiones 5ah. Out of its four possible isomers, 1,3,4 oxadiazole is widely being exploited for various biological applications. Parthsarthy akamla nehru institute of management and technology, faculty of pharmacy, sultanpur up, india. Synthesis of some new 2, 5disubstituted 1,3,4oxadiazole. The most widely applicable route to the synthesis of 1,3,4 oxadiazole and its 2,5disubstituted derivatives is the thermal, acid and base catalyzed cyclization of their corresponding carbonylhydrazides. Journal of chemical and pharmaceutical research, 2015, 78. In view of these observations, some new compounds 2methylbenzimidazole derivatives bearing 1,3,4oxadiazole or 1,2,4triazole heterocycle have been synthesized. Oxadiazole s are a class of heterocyclic aromatic chemical compound of the azole family. Oxadiazole derivatives have been found to possess broad spectrum antimicrobial activity and therefore are useful substructures for further molecular exploration 15.
Use of the furoxan 1,2,5oxadiazole 2oxide system in the. Various methods were reported in the literature for the synthesis of 1,3,4oxadiazole and its derivatives wang et al. Synthesis of 1,3,4oxadiazoles organic chemistry portal. Oxadiazoles heterocyclic building blocks sigmaaldrich. Inhibition of tobacco bacterial wilt with sulfone derivatives. The structures of the newly synthesized derivatives were established by the combined practice of uv, ir, 1 h nmr, c nmr, and mass spectrometry. We report the synthesis and biological assessment of 1,3,4 oxadiazole substituted 24 derivatives as novel, potential antibacterial agents. Various methods were reported in the literature for the synthesis of 1,3,4 oxadiazole and its derivatives wang et al. Novel 1,3,4oxadiazole derivatives containing a cinnamic acid.
This reaction is proposed to go through oxidative cleavage of csp 3 h bonds, followed by cyclization and deacylation. State key laboratory breeding base of green pesticide and. The purity of the compounds was checked by thin layer chromatography tlc. Synthesis, characterization and pharmacological activity.
For the first time, the 1,2,4 oxadiazole ring has been used as a bioisosteres of the ester group in the field of nucleotide chemistry for the production of inhibitors of. Thus, to develop highly effective and lowrisk bactericides, 31 novel 1,3,4oxadiazole derivatives containing a cinnamic acid moiety were designed and synthesized. These results could be used for the development of novel, potent, and effective antimicrobial agents. All the chemicals and solvents ethanol, dioxane used were of laboratory grade and solvents were purified by suitable methods 21. Suvorexant, a dual orexin receptor antagonist dora is approved for the treatment of primary insomnia. Oxadiazoles form a major class of compounds with a heterocyclic nucleus for drug development and were among. We report the synthesis and biological assessment of 1,3,4oxadiazole substituted 24 derivatives as novel, potential antibacterial agents. Synthesis of 1,3,4oxadiazole derivatives from amino acid. Synthesis, characterization and antiinflammatory activity of. New oxadiazole derivatives of isonicotinohydrazide in the. Moreover, in recent times, some acetamides derived from benzimidazole attached to oxadiazole heterocycle 14, 15 or triazole heterocycle exhibited promising biological activities. Derivatives of 1,3,4 oxadiazole with suitable substitution at 2,5position have already been reported to have possible biological activities. Synthesis and antimicrobial evaluation of 1,3,4oxadiazole.
Unless otherwise noted, the contents of the fda website. The key step of this protocol is the coupling between 5herteroaryl1,3,4 oxadiazole 2thione and activated sugars cyclic or acyclic sugar analogues in the presence of basic medium. Download acrobat pdf file 52kb recommended articles citing articles 0. Nitro furan containing oxadiazole johan et al, 1972 have reported the synthesis of bis 1,2,4 oxadiazole derivatives and their antimalarial activity 18. All the synthetic compounds produced a dose dependant inhibition of growth of the cells. Studies of 1,3,4 oxadiazole derivatives 10 parti studies of 1,3,4 oxadiazole derivatives 2. Synthesis of novel 1,3,4oxadiazole derivatives and their. Experimental melting points were determined in open capillary tubes and are uncorrected. Ep1234820a1 oxadiazole derivatives and drugs containing. Experimental material and methods melting points of the synthesized compounds were determined in openglass capillaries on stuart smp10 melting point apparatus and are uncorrected.
This is especially true in case of infectious diseases such as pneumonia, meningitis and tuberculosis, which would. A number of oxadiazole derivatives are very popular and common in use as potential therapeutic agents. Further these synthesized derivatives were subjected to antibacterial activity against all. An oxadiazole derivative of formula i and a nontoxic salt thereof, wherein r is hydrogen, alkyl, cyca, etc aa 1 is a single bond, amino acid residue, etc aa 2. Naphthofuran derivatives were reported to possess various biological. Oxadiazole is a very weak base because there is an inductive effect of extra heteroatom3. Currently, effective antimicrobials for rice bacterial diseases are still lacking. Chemistry and pharmacological importance of 1,3,4oxadiazole derivatives sharma r 1, kumar n 1 and yaday r 2. The number of so many synthetic compounds with oxadiazole nucleus used for antibacterial,antifungal, analgesic and antiinflammatory activities.
Synthesis and screening of new 5substituted1,3,4oxadiazole. In particular, resistance of bacterial pathogens to current antibiotic has emerged as a measure health problem. In vitro antitumor and antiviral activities of new. The hydrophobic and vander waals interactions with residues. Fluoroiodinated 1,2,4 oxadiazole derivatives were reacted with olefins in the presence of sodium dithionite to obtain the corresponding functionalised oxadiazoles. Biological activities of 1, 3, 4oxadiazole derivatives. Then disubstituted 1,3,4 oxadiazole derivatives are formed via intramolecularazawittig reaction of the iminophosphorane intermediates. Design and molecular docking studies of some 1,3,4. Abstract the orexin system plays an important role in the regulation of wakefulness. Benzimidazole and oxadiazole have received attention in recent years due to widespread applications notably in the field of medicinal chemistry due to their privileged biological activity. Various approaches for synthesis of oxadiazole derivatives article pdf available in international journal of research in ayurveda and pharmacy 22.
A new and efficient synthesis of 1,3,4oxadiazole derivatives using tbtu. N35aryl substituted aryl1,3,4oxadiazole2ylmethyl5,5disubstituted2,4 imidazolidine dione derivatives. Jul 24, 2014 the results of docking study of synthesized 1,3,4 oxadiazole derivatives table 7 figures figures6, 6,7, 7,8, 8, and and9 9 with peptide deformylase depicted the hydrogen bonding interactions with lys 150 6e, 6f, 8e, 8f, 8h, c, and e, lys 157 e, arg 97 b and c, and arg 153 e and g. In an attempt to find new molecules that can defeat microbial resistance, two new series of 22substituted ethenyl5substituted methoxy1,3,4 oxadiazole derivatives were synthesized. Recently, 1,3,4oxadiazole derivatives has been reported as antimycobacterial agents also 11. The controversy over its structure, its chemistry, and the reactivity of its sidechain. Novel 1,3,4oxadiazole derivatives containing a cinnamic. Oxadiazole derivatives were synthesized by reacting phthalic anhydride with semicarbazide and hydrazine hydrate in. Thus, to develop highly effective and lowrisk bactericides, 31 novel 1,3,4 oxadiazole derivatives containing a cinnamic acid moiety were designed and synthesized. A series of newly 1,3,4 oxadiazole 2thioglycoside derivatives were synthesized. New oxadiazole derivatives of isonicotinohydrazide in the search for antimicrobial agents. Oxadiazoles are fivemembered heterocyclic aromatic compounds consisting of one oxygen atom, two nitrogen atoms and two carbon atoms. The structures of synthesized oxadiazole derivatives and their copper complexes. Synthesis of 1,3,4 oxadiazole derivatives from amino acid and acyl hydrazides under thermal heating or microwave irradiation conditions luciano dornelles,a oscar e.
In an attempt to find new molecules that can defeat microbial resistance, two new series of 22substituted ethenyl5substituted methoxy1,3,4oxadiazole derivatives were synthesized. Fourcomponent synthesis of 1,3,4oxadiazole derivatives. State key laboratory breeding base of green pesticide and agricultural bioengineering, key. Oxadiazole derivatives as dual orexin receptor antagonists. Synthesis, characterization and biological activities of 1. Theoretical study on molecular packing and electronic. Pdf various approaches for synthesis of oxadiazole derivatives. Then disubstituted 1,3,4oxadiazole derivatives are formed via intramolecularazawittig reaction of the iminophosphorane intermediates. However, a number of researchers are working and have worked to find out more synthetic analogues for anticancer and antifungal, antihiv agents using biological and in. Antibacterial activity against two phytopathogens, xanthomonas oryzae pv. These observations and our interest in the pharmaceutical chemistry of heterocyclic compounds promoted us to have synthesized different. Mehta college of science, palanpur, gujarat, india. A series of newly 1,3,4oxadiazole2thioglycoside derivatives were synthesized.
In order to discover new lead compounds with high antibacterial activity, a series of new derivatives were designed and synthesized by introducing a sulfonate or carboxylate moiety into the 1,3,4oxadiazole structure. Original article synthesis, characterization and antiinflammatory activity of some 1, 3,4 oxadiazole derivatives arvind kumar singh a, m. The key step of this protocol is the coupling between 5herteroaryl1,3,4oxadiazole2thione and activated sugars cyclic or acyclic sugar analogues in the presence of basic medium. Crystals of 8a and 8b are remarkably stable to longterm storage under ambient conditions. Molecules free fulltext synthesis and antibacterial. The first monosubstituted 1,3,4 oxadiazoles were reported in 1955 by two independent. The newly synthesized 1,3,4 oxadiazoles derivatives were computationally designed and optimized to investigate the interactions between the target compounds and the amino acid residues of the e. Various approaches for synthesis of oxadiazole derivatives. Chemistry and pharmacological importance of 1,3,4oxadiazole. Synthesis and in vitro evaluation manav malhotra1, mohit sanduja2, abdul samad3 and aakash deep4 1department of pharmaceutical chemistry, meerut institute of. Synthesis, characterization and antiinflammatory activity.
Other pharmaceutical drugs containing the 1,3,4 oxadiazole ring include fenadiazole, zibotentan, and tiodazosin. 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. It is also well established that various derivatives of 1,3,4oxadiazole exhibit broad spectrum of pharmacological properties such as antibacterial and antifungal activities 1718. Ep1234820a1 ep00979048a ep00979048a ep1234820a1 ep 1234820 a1 ep1234820 a1 ep 1234820a1 ep 00979048 a ep00979048 a ep 00979048a ep 00979048 a ep00979048 a ep 00979048a ep 1234820 a1 ep1234820 a1 ep 1234820a1 authority ep european patent office prior art keywords oxo 2s yl methyl pentyl prior art date 19991203 legal status the legal. Review of synthesis of 1,3,4 oxadiazole derivatives. Synthesis and antifungal activities of novel nicotinamide.
However, a number of researchers are working and have worked to find out more synthetic analogues for anticancer and antifungal, antihiv agents using biological and insilico models. Biological assays revealed that most of the synthesized compounds were provided with weak to moderate activities against g. In synthesized 1,3,4oxadiazole derivatives replacement of free carboxylic group by oxadiazole nucleus enhanced the receptor interaction by formation of numerous hydrogen bonds and favourable steric interactions with peptide deformylase. A series of novel 1, 3, 4 oxadiazole analogues was synthesized from cyclization of hydrazones of substituted 1ethyl1,4dihydro7methyl4oxo1,8naphthyridine3carbohydrazides were prepared from nalidixic acid. A series of 1,3,4 oxadiazole and 1,2,4triazole derivatives of biphenyl4yloxy acetic acid were synthesized compounds activity,antiinflammatory activity, analgesic activity and lower ulcerogenic potential. For example, raltegravir is an hiv drug which contains an 1,3,4 oxadiazole ring. Synthesis and appraisal of their potential as antimicrobial agents. Further these synthesized derivatives were subjected to antibacterial activity against all the.
As we know, oxadiazole consists of the 2 pyridine type nitrogen n, hence reduction in aromaticity of oxadiazole ring and which in turn leads the oxadiazole ring to exhibit the conjugated diene character. Recently, benzimidazole derivatives have been reported as antidiabetic 1, antimicrobial 23, antiviral 46 antispasmodic 7 and antiasthmatic 8 agents. A novel series of 234bromophenylpropan3one5substituted phenyl1,3,4oxadiazoles 4an have been synthesized from 34bromobenzoylpropionic acid 3 with the aim to get better antiinflammatory and analgesic agents with minimum or without side effects ulcerogenicity. Synthesis and antibacterial activity of some derivatives. A new and efficient synthesis of 1,3,4oxadiazole derivatives. Recent advancements in biological activities of oxadiazole. A series of derivatives of 1, 3, 4 oxadiazole having verities of biological activities can be synthesised by various methods. 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. From this point of view, the objective of the present work is to prepare new derivatives of oxadiazole containing naphtho2,1bfuran moiety.
Biological activities of 1,3,4oxadiazole derivatives. The activities include anticancer, antimicrobial, anti inflammatory, anti hiv, anti tubercular, anti diabetic, antifungal. Over the past decade, drug resistance has become a growing problem in the treatment of infectious disease caused by bacteria, fungi and viruses. Literature survey reveals that 1,3,4 oxadiazole is a highly privileged structure. Depending on the placement of the nitrogens in the ring, several isomers exist such as 1,2,4. Various aromatic hydrazides were allowed to undergo cyclization to substituted oxadiazole2 amines in the presence of cyanogen bromide and further condensed with different heterocyclic aldehydes to give new oxadiazole derivatives.
In search of pharmalogically active molecules in the class of oxadiazoles, the present article deals with the synthesis of 55. Nitro furan containing oxadiazole johan et al, 1972 have reported the synthesis of bis 1,2,4oxadiazole derivatives and their antimalarial activity 18. 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. Use of the furoxan 1,2,5oxadiazole 2oxide system in. The escalating threat due to dwindling effect of antibiotics and challenge of tackling rising drugresistant infections has gathered high focus in current medicinal research. Oxadiazoles is a fivemember heterocyclic compound having two carbon atoms, two nitrogen atoms, one oxygen atom and two double bonds. Bis1,2,4 oxadiazole derivatives synthesis of isothiocyanatophenyl1,2,4 oxadiazole derivatives and its antiparasitic propeties were reported by haugwitz and coworkers 1985 19. The reactions were completed in neutral conditions at room temperature and the corresponding disubstituted 1,3,4 oxadiazole derivatives were produced in excellent yields. Nonspecific antispasmodic active oxadiazole derivatives later in 1969 breuer prepared a nitro furan containing oxadiazoles and studied the antimicrobial activity 17. Synthesis of 1,3,4oxadiazole derivatives from amino acid and acyl hydrazides under thermal heating or microwave irradiation conditions luciano dornelles,a oscar e. Synthesis of novel 1,3,4oxadiazole derivatives and their biological properties. Rice bacterial leaf blight and leaf streak are two important bacterial diseases of rice, which can result in yield loss. Based on this hypothesis, a series of novel nicotinamide derivatives containing 1,3,4oxadiazole substructure were designed and synthesized.
Dhara, deboleena and sunil, dhanya and kamath, pooja r and ananda, k and shrilakshmi, s and balaji, s 2018 new oxadiazole derivatives. 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. Among of the synthesized compounds, compounds 7, 10, 11 and were screened for. The conversion of isoniazid inh to oxadiazoles produces the corresponding 5 substituted 3h1,3,4oxadiazol2thione, 3h1,3,4,oxadiazol2one and their 3. Fourcomponent synthesis of 1,3,4oxadiazole derivatives from.
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