Synthesis of 1,3,4thiadiazole derivatives redha, abdul jabar and zina 33 5 hrs. Thiadiazole having 5membered ring system contains hydrogenbinding domain, and twoelectron donor nitrogen system, sulfur atom and a wide variety of biological activity. Thiadiazole compounds have versatile activities such as antimicrobial, anti inflammatory, anticancer, etc. Sep 30, 2019 the antifungal activity of 1,3,4 thiadiazole derivatives is poorly understood.
Review on biological activities of 1,3,4thiadiazole derivatives. Anticonvulsant activity of thiadiazole derivatives. The structures of 1,3,4 thiadiazoles were confirmed by 1 h nmr, ms, and elemental analysis. Thionation of amides, 1,4diketones, n2oxoalkylamides, and n,nacylhydrazines with the use of a fluorous lawessons reagent leads to thioamides, thiophenes, 1,3thiazoles, and 1,3,4thiadiazoles in high yields. The isolation of the final products is achieved in most cases by a simple filtration. Discovery of matrinic thiadiazole derivatives as a novel. A number of 1, 2, 3 thiadiazole derivatives are best prepared by transformations of the 4 and 5substituents of a preformed thiadiazole ring. Synthetic methods, chemistry, and the anticonvulsant. The resulting 2amino5hydrazino1,3,4thiadiazole was used for the synthesis of interesting derivatives as a versatile key intermediate for the.
In particular, compounds bearing the 1, 3, 4 thiadiazole nucleus is known to have unique antibacterial and antiinflammatory activities. In particular, compounds bearing the 1, 3, 4thiadiazole nucleus is known to have unique antibacterial and antiinflammatory activities. To find novel pesticide lead compounds with highly active bioactivity, 32 novel 1,2,3thiadiazole derivatives containing 1,3,4thiadiazole ring were designed and synthesized according to the. Among them, compound 6n displayed a high activity with an inhibitory rate of. Us5597785a succinimide derivatives of 2,5dimercapto1,3. Monoazo disperse dyes based on 2amino1,3,4 thiadiazole derivatives hari r.
A chemical structure of all the new compounds was confirmed by 1 h nmr and mass spectral data. Synthesis of 1, 3, 4thiadiazole derivatives by the reaction of. Corrosion inhibition of thiourea and thiadiazole derivatives. Biological activities of 1 3 4 oxadiazole derivatives. In this paper we mention the recent derivatives of. Apr 30, 20 this paper focuses on the therapeutic importance of novel thiadiazole derivatives as anticonvulsant agents for future. Synergistic combination of dimercapto thiadiazole derivatives. Heterocyclic nucleus 1,3,4thiadiazole constitutes an important class of compounds for new drug development. Synthesis, biological evaluation, and molecular modeling. Most of the synthesized thiadiazole derivatives exert anti. Biological activities of 1 3 4 oxadiazole derivatives free biological activities of 1 3 4 oxadiazole derivatives a total of five new metal complex derivatives of 2nsalicylidene5pnitro phenyl1,3,4thiadiazole, hl with the metal ions voii, coii, rhiii, pdii and auiii have. Us5597785a succinimide derivatives of 2,5dimercapto1,3,4. A series of novel matrinic thiadiazole derivatives were designed, synthesized and evaluated for their inhibitory effect on col1a1 promotor.
The antileukemic action of two thiadiazole derivatives 12 introduced by ciotti et al, and studied on retardation the growth of leukemia l1210 and extended the survival of time in mice ciotti et al,2011. The synthesis of new pyrazine substituted 1,3,4 thiadiazole derivatives was carried out in good yield by the reaction of pyrazine substituted 1,3,4thiadiazoles with various sulfonyl chlorides. The in vitro antimicrobial activity of some new 1,3,4thiadiazole derivatives such as 12 having a d,lmethionine moiety has been evaluated against several bacterial strains by pintilie et al. None of the compounds with the 1,3,4 thiadiazole substructure were derived from dmct, although a few had the 2 or 5position occupied by a sulfur atom in a thioether or sulfonyl group. Synthesis of 1,3,4thiadiazole derivatives and microbiological. Derivatives of 1,3,4thiadiazoles are known to exhibit antibacterial and antifungal activities. The 15phenyl1,3,4thiadiazol2yl1hpyrazol5amine derivatives. The in vitro antimicrobial activity of some new 1,3,4 thiadiazole derivatives such as 12 having a d,lmethionine moiety has been evaluated against several bacterial strains by pintilie et al. Synthesis and theoretical study of 5phenyl1,3,4thiadiazole. The score of toxological comparative studies of phenytoin and 1, 3, 4 thiadiazole derivatives vr 1, vr 2, vr 3, and vr 4 are show in table iv.
Monoazo disperse dyes based on 2amino1,3,4thiadiazole derivatives hari r. The new compounds were screened for their anticonvulsant activity against maximal electroshock. A facile access and evaluation of some novel thiazole and 1,3,4thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents. For example, as an additive for engine oil, gasoline engine oil oxidation stability. Novel 1, 3, 4 thiadiazole derivatives synthesis by maos i. The synthesis of new pyrazine substituted 1,3,4thiadiazole derivatives was carried out in good yield by the reaction of pyrazine substituted 1,3,4thiadiazoles with various sulfonyl chlorides. Research article synthesis of pyrazine substituted 1,3,4 thiadiazole derivatives and their anticonvulsant activity kikkerip. Synthesis of 2,4 diphenyl5imino1,3,4thiadiazole derivatives by cyclization of. The results showed that some of them exhibited good antifungal activity. In chemistry thiadiazoles are a subfamily of azole compounds. Research article synthesis of pyrazine substituted 1,3,4. A number of 1, 2, 3thiadiazole derivatives are best prepared by transformations of the 4 and 5substituents of a preformed thiadiazole ring. Synthesis and antifungal activity of 1,3,4thiadiazole. Results and discussion schemes were summarized the synthesis of different derivatives of 1,3,4thiadiazole.
Oxidation of 5methyl1, 2, 3 thiadiazole by potassium permanganate at c in water affords 1, 2, 3 thiadiazole 5carboxylic acid in 51%yield. Disclosed the novel compounds prepared by reacting 2,5dimercapto1,3,4, thiadiazole with maleic anhydride and npolyethylene aminesubstituted succinimide. Reports on the masss pectra of some 2,5disubstituted1,3,4 thiadiazole derivatives have provided data for fragmentation patterns in the system. The hurdmori and lalezari methods were used, respectively, for the preparation of these 1,2,3 thiadiazole and 1,2,3selenadiazole derivatives. Review on substituted 1, 3, 4 thiadiazole compounds.
Molecules free fulltext toward rational design of novel. The synthesis of 1,2,4dithiazole 28a is carried out by ringclosing processes, including the dimroth rearrangement, and by the thionation of 1,3thiazol4ones 152 with lr. New 1,2,3selenadiazole and 1,2,3thiadiazole derivatives. It has attracted the attention of medicinal chemists in the development of newer compounds in the recent years at a large scale. Thiadiazole compounds have versatile activities such as antimicrobial, antiinflammatory, anticancer, etc. Twenty new 21hpyrazol1yl1,3,4thiadiazole analogs were synthetized to develop p2x7 receptor p2x7r inhibitors. This nucleus exhibits a wide variety of biological activities. Antifungal effects of a 1,3,4thiadiazole derivative. Synergistic antifungal interactions of amphotericin b with. The dimroth rearrangement of 1,2,4 thiadiazole derivatives into 1,2,4dithiazole derivatives is a typical example of the title transformation. These all parameters were calculated using molinspiration property. The compounds are dispersants or detergents, antiwear agents and antioxidants. A series of monoazo disperse dyes based on 2amino5mercapto1,3,4thiadia zole was prepared by coupling with various n. Synthesis and fungicidal activity of novel 2,5disubstituted1,3,4 thiadiazole derivatives containing 5phenyl2furan skip to main content thank you for visiting.
In this work 2, 5 dimarcapto1, 3, 4thiadiazole1 was synthesized from the reaction of hydrazine hydrate with carbon disulfide and then was converted into. The synthesis of novel thiadiazole derivatives and investigation of their chemical and biological behavior have gained more importance in recent decades. Applied ijans synthesis of 2, 5 disubstituted 1, 3, 4. The resulting 2amino5hydrazino1,3,4 thiadiazole was used for the synthesis of interesting derivatives as a versatile key intermediate for the. Recently, various 1,3,4thiadiazole derivatives have been synthesized and. Popoola department of chemical and metallurgical engineering tshwane university of technology, pretoria, south africa received 20 feb 2012, revised 11 june 2012. This is in addition to the synthesis of 1,3,4thiadiazoles through ring transformation 75. The chemistry of heterocyclic compounds has been an interesting field of study for a long time.
Thiadiazole derivatives are privileged structures in medicinal chemistry and have been investigated for anticonvulsant and antimicrobial activities. The synthesis of novel thiadiazole derivatives and investigation of their chemical and. Review on biological activities of 1,3,4thiadiazole derivatives arvind k. Pdf in the present designed work, we have synthesized imidazo2,1b1,3,4 thiadiazole. Pdf on jun 30, 2017, parminder kaur and others published 1,3,4 thiadiazole and its derivatives. Synthesis of pyrazine substituted 1,3,4thiadiazole.
Structurally they are fivemembered heterocyclic compounds containing two nitrogen and a sulfur atoms, and two double bonds, to give an aromatic ring. The designed molecules were synthesized and subjected to antidiabetic activity by in vitro and in vivo method. Ep0579129a2 thiadiazole derivatives for the treatment of. A threedimensional quantitative structure activity relationship 3dqsar study was performed on a series of 1, 3, 4thiadiazole derivatives reported as anticonvulsant employing selforganizing molecular field analysis somfa techniques to investigate the structural requirements for the design of novel anticonvulsant. Research article synthesis of pyrazine substituted 1,3,4thiadiazole derivatives and their anticonvulsant activity kikkerip. Some 1,3,4thiadiazole derivatives containing pyridine group were synthesized. Mohana, 1 andlingappamallesha 2 department of studies in chemistry, university of mysore, manasagangotri, mysore, india pg department of chemistry, jss college of arts, commerce and science, ooty road.
Pdf design and synthesis of thiadiazole derivatives as. The intermediate was also trapped, separated and fully characterized. Monoazo disperse dyes based on 2amino1,3,4thiadiazole. A series of 3aryl aminoamino4aryl5iminod21,2,4 thiadiazole has been synthesized and screened for anticonvulsant activity.
Present study involves design of thiadiazole compounds as antidiabetic agent using docking studies. Jan 29, 2016 a series of 2,5disubstituted1,3,4thiadiazoles were synthesized using lawessons reagent by an efficient approach under microwave irradiation in good yields. Azo compounds of schiff bases and their derivatives have been used in preparation other compounds such as 1,3,4 thiadiazole derivatives, imidazolidine derivatives, tetrazole derivatives, oxazepine derivatives and. Novel 1, 3, 4 thiadiazole derivatives synthesis by maos. Introduction synthesis of 1,3,4thiadiazole derivatives the synthetic procedures of 1,3,4thiadiazoles could be classified by the number of ring atoms contributed by each component and by the number and types of bond generated in the last reaction step. C linear or branched alkyl, benzyl, optionally substituted at the aromatic ring with one or more groups selected on their turn from the class consisting of. Indole based thiadiazole derivatives 122 have synthesized, characterized by nmr and hreims and evaluated for. Such additives also have antioxidant and antiwear properties, and are used in a wide range of lubricant applications. Recently, various 1,3,4 thiadiazole derivatives have been synthesized and evaluated their anticonvulsant activity.
Synthesis of 1,3,4thiadiazoles organic chemistry portal. Many authors have determined the values of minimal inhibitory concentrations mics for newly synthesized derivatives. The new compounds were screened for their anticonvulsant activity against maximal. Sciencecollege,vallabhvidyanagar388120,gujaratstate,india received 20 november 2001, revised 27 july 2002 abstract. Recently, various 1,3,4thiadiazole derivatives have been synthesized and evaluated their anticonvulsant activity.
Synthetic methods, chemistry, and the anticonvulsant activity. In general, 1,2,4thiadiazole derivatives are prepared by appropriate intra or. Lactam derivatives, heterocyclic play an important role in biochemical processes because the side groups of the most. In silico design and computational study of novel 1, 3, 4. New 1,2,3 thiadiazole and 1,2,3selenadiazole derivatives, 1423, were prepared from the ketones 15 via the corresponding semicarbazones or hydrazones 612.
Full text 2amino1,3,4thiadiazole as a potential scaffold. The dimroth rearrangement of 1,2,4thiadiazole derivatives into 1,2,4dithiazole derivatives is a typical example of the title transformation. P2x7r inhibition in vitro was evaluated in mouse peritoneal macrophages, hek293 cells transfected with hp2x7r dye uptake assay, and thp1 cells il1. A new series of 1,3,4thiadiazole derivatives was synthesized and the. Reports on the masss pectra of some 2,5disubstituted1,3,4thiadiazole derivatives have. Oxidation of 5methyl1, 2, 3thiadiazole by potassium permanganate at c in water affords 1, 2, 3thiadiazole5carboxylic acid in 51%yield.
Compound td7 was found to show potent antidiabetic. To find novel pesticide lead compounds with highly active bioactivity, 32 novel 1,2,3 thiadiazole derivatives containing 1,3,4 thiadiazole ring were designed and synthesized according to the. Abstract 1,3,4thiadiazole nucleus is therapeutically interesting drug candidate as antiinflammatory, antimicrobial,anticonvulsant, antihypertensive, analgesic, antiepileptic. C linear or branched alkyl residues, nitro groups, halogen atoms, c. In this paper we mention the recent derivatives of 1,3. Sar study of the synthesized compounds indicated that thiadiazole ring, free thiol. The compounds are dispersants or detergents, antiwear agents and antioxidants when incorporated into lubricating compositions. A facile access and evaluation of some novel thiazole and 1,3,4 thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents. Heating of the latter in alcohol or aqueous alcohol gave the free bases. The title compounds were investigated for antifungal activities.
Four possible structures exist depending on the relative positions of the. Screening tests carried out on several dozen of synthetic 1,3,4thiadiazole derivatives allowed selection of a compound called 45methyl1,3,4thiadiazole2yl benzene1,3diol abbreviated as. None of the compounds with the 1,3,4thiadiazole substructure were derived from dmct, although a few had the 2 or 5position occupied by a sulfur atom in a thioether or sulfonyl group. The score of toxological comparative studies of phenytoin and 1, 3, 4thiadiazole derivatives vr 1, vr 2, vr 3, and vr 4 are show in table iv. Synthesis and fungicidal activity of novel 2,5disubstituted. All the synthesized compounds were screened for their anticancer potentiality over human breast carcinoma mcf7 and human lung carcinoma a549. Review on biological activities of 1,3,4 thiadiazole derivatives arvind k. Thiadiazole derivatives of general formula i wherein r. Vinit raj, amit rai, ashok k singh, amit k keshari, sudipta saha.
Differently substituted thiadiazole moieties have also been found to. Recent update on 1,3,4thiadiazole derivatives american. The antifungal activity of 1,3,4thiadiazole derivatives is poorly understood. Synthesis of some new thiadiazole derivatives and their.