Different methods of synthesis and diverse biological activities p s yadav, devprakash, senthilkumar g p bharathi college of pharmacy, bharathinagara, mandya, karnataka 571422, india abstract substituted 1, 3benzothiazole derivatives are an important class of heterocyclic compounds. The compound, 2mercapto5methoxybenzimidazole, is an important intermediate required for the synthesis of omeprazole. Pdf synthesis and characterization of some new derivatives from. Highly efficient synthesis of 2mercaptobenzothiazole derivatives in. A number of methods for the synthesis of 2 mercaptobenzothiazoles mbts have been reported. Generally, hydrazine compounds are prepared by the replacement of mercapto, methyl mercapto or chloro by the hydrazine group. Synthesis and biological evaluation of 4thiazolidinone. The chemistry of mercapto and thione substituted 1,2,4. Metalfree c h mercaptalization of benzothiazoles and.
The clp regulation makes sure that the hazards presented by chemicals are clearly communicated to. Novel synthesis and ring closure reactions of 1 3hydrazino1. Synthesis of some new 4oxothiazolidines, tetrazole and triazole. In 2017, the dong group reported a new method for the synthesis of 2mercapto. Benzothiazole moiety has wide applications in dyes such as thio. Actually, in order to improve sar studies on,benzothiazoles, we decided to investigate the isosteric. Among them, heterocyclic compounds with the 3mercapto1,2,4triazole substructure exhibit a wide spectrum of biological activities 9,10. Focused library design and synthesis of 2mercapto benzothiazole linked 1,2,4oxadiazoles as cox2. A straightforward synthesis of 2arylbenzothiazoles from 2aminothiophenol and aryl aldehydes in airdmso oxidant system is operationally simple, proceeds without catalysts, tolerates a wide range of functionalities, and. In lieu of an abstract, this is the articles first page. Synthesis, characterization and biological evaluation of. Synthesis, characterization and biological evaluations of. Design and synthesis of some benzothiazole analogs as a2a. Synthesis and biological evaluation of 2mercapto1, 3.
The thiazole and imidazole nucleus, as well as carbohydrates are important classes of compounds found in many natural and synthetic products with a wide. Synthesis and biological evaluation of 4thiazolidinone derivatives incorporating benzothiazole moiety deepak pareek, a manish chaudhary, a pawan k. Compound 7 could be further modified as suggested by ishiguro et al. Synthesis, characterization and antimicrobial activity of. Structures of the synthesized compounds were established on the basis of 1 h nmr and mass spectral data. Benzotriazole is an effective corrosion inhibitor for copper and its alloys by preventing undesirable surface reactions. Benzothiazole derivatives as potential anticonvulsant agents. The structure of the benzothiazoles were confirmed by infrared ir, nuclear magnetic resonance nmr and mass lcms spectral data. Benzotriazole bta is a heterocyclic compound containing three nitrogen atoms, with the chemical formula c 6 h 5 n 3. Among them, heterocyclic compounds with the 3 mercapto 1,2,4triazole substructure exhibit a wide spectrum of biological activities 9,10. Thiuram accelerators fast accelerators, especially for efficient or sulfurless cure. The acid derivative 4j was synthesized by hydrolysis of 4h using lithium hydroxide monohydrate as a base in a mixture of ch 3 oh, thf and water.
Studies in the synthesis of 2mercapto5 methoxybenzimidazole. To identify compounds with a potent antimicrobial profile, we designed and synthesized low molecular weight 2mercaptobenzothiazole derivatives 2a2l and. This pathway was started by janice frias, university of minnesota, biocmice 5309, and completed by carla essenberg and jiunguo yu, university of minnesota 2mercaptobenzothiazole mbt is used primarily as a vulcanization accelerator in the production of rubber, although it is also used to inhibit the corrosion of copper in water and as an ingredient in cutting oils and petroleum products. Synthesis and biological evaluation of 2mercapto1,3 benzothiazole derivatives with potential antimicrobial activity. Rawal 1, and jitender bariwal 1 department of pharmaceutical sciences, isf college of pharmacy, moga, punjab, india 2 research scholar, punjab technical university, jalandhar, punjab, india benzothiazole is a privileged heterocyclic scaffold having a benzene ring fused with a. This is to certify that the thesis entitled, synthesis and biological evaluation of some 2. Synthesis and biological evaluation of 2mercapto1,3benzothiazole derivatives with potential antimicrobial activity. Focused library design and synthesis of 2mercapto benzothiazole linked 1,2,4oxadiazoles as cox25lox inhibitors. Mercapto benzthiazole coupled benzyl triazoles as new cox. Its fivemembered ring can exist in tautomers a and b, and the derivatives of both tautomers, structures c. Mercapto benzthiazole coupled benzyl triazoles as new.
Research article synthesis and antimicrobial evaluation of. Mercaptobenzothiazole derivatives is a record research work done by. This necessitates an easy availability of the intermediate, 2mercapto5methoxybenzimidazole. Hofmann first obtained 1mercaptobenzothiazole in an attempt to prepare the disulfhydryl derivative of thiocarbanilide by the reaction of carbon disulfide on oaminothiophenol. Synthesis of some bioactive 4thiazolidinone derivatives incorporating benzothiazole moiety deepak pareek, a manish chaudhary, a pawan k. Recent advances in the chemistry and biology of benzothiazoles. Synthesis of c6 methyl substituted benzothiazole derivatives. This aromatic compound is colorless and polar and can be used in various fields. Synthesis of nheterocycles, synthesis of sheterocycles benzofused nheterocycles, benzofused sheterocycles synthesis of benzothiazoles. Sep 25, 2009 synthesis and biological evaluation of 2. Synthesis and characterization of a linked, stacked organotin compound of 2mercapto6nitrobenzothiazolyl diphenyltin chloride with 2ethoxyl6nitrobenzothiazole. Research article synthesis and antimicrobial evaluation of a.
It is known that a passive layer, consisting of a complex between copper and benzotriazole, is formed when copper is immersed in a solution containing benzotriazole. The hazard classification and labelling section shows the hazards of a substance based on the standardised system of statements and pictograms established under the clp classification labelling and packaging regulation. It has a role as a carcinogenic agent and a metabolite. Journal of labelled compounds and radiopharmaceuticals 2011, 54 5, 229232. Solubility soluble in ethanol, diethyl ether and benzene. In this respect, it should be noted that this heterocyclic scaffold still attracts the attention of material chemists, because of its use as a che. Synthesis of some bioactive 4thiazolidinone derivatives.
Highly efficient synthesis of 2mercaptobenzothiazole derivatives in water. Request pdf 2mercaptobenzothiazole and its derivatives. The synthesis and cjun nterminal kinase jnk inhibition activity of a novel series of 2thioetherbenzothiazoles 54 and 55 figure 30 is described in literature. The anti microbial activity of the synthesized compounds was evaluated by disc diffusion method. In view to prepare parent compound 2, 3mercapto2, 3methyl mercapto and 3chloro 1,2,4triazolo3,4bbenzothiazole were heated. The red coloured compound, pdc 7 h 4 ns 2 2, is diamagnetic and is stable up to a temperature of 388 c. Review article recent advances in the chemistry and biology of benzothiazoles rupinder k. Starting from 2amino1,3mercaptobenzothiazoles recently reported 1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h, a series of the corresponding 2 mercapto 1,3 benzothiazole isosters 2a, 2b, 2c, 2d, 2e, 2f, 2g. In recent years heterocyclic compounds analogues and derivatives have attracted wide attention due to their useful biological and pharmacological properties.
The reagent 2mercaptobenzothiazole quantitatively precipitates palladium at a ph 5. Key properties mercapto accelerators very fast accelerators giving a very broad plateau and good aging resistance. Synthesis and characterization of a linked, stacked. It is produced by the reaction of 2aminothiophenol and carbon disulfide.
The synthesis of some new hydrazone derivatives containing. Pdf in this work 2mercaptobenzothiazole 2mbt and some of its derivatives1, 14,27 were prepared by using home made auto clave. Search results for 2methyl benzothiazole at sigmaaldrich. Some of the marketed drugs comprising benzothiazole are shown in fig. The anti microbial activity of the synthesized compounds was evaluated by disc. The different substitution pattern of the benzothiazole system did not significantly affect the activity. To prepare 2benzimidazolylthioaceto phenones by reacting with aromatic ketones, which is a key intermediate for the synthesis of thiazolo3,2abenzimidazoles. Synthesis and biological evaluation of 2 mercapto 1,3 benzothiazole derivatives with potential antimicrobial activity. Since the demand for omeprazole is increasing, there exists a tremendous scope for the development of its synthetic routes. Synthesis and study the biological activity of some seven.
Synthesis of novel benzothiazole compounds with an extended conjugated system peddiahgari vasu govardhana reddy, yangwei lin, and huantsung chang department of chemistry, national taiwan university, taipei106, taiwan email. A focused library of novel bisheterocycles encompassing 2mercapto benzothiazole and 1,2,3triazoles were synthesized using click chemistry approach. Verma, mohit dadheech, ram pal meena department of pharmaceutical sciences, birla institute of technology mesra, ranchi, jharkhand835215, india address for correspondence. The docking results clearly indicated that the compounds 4au shown good docking interaction towards cox2 enzyme. The molecule consists of a benzene ring fused to a 2 mercapto thiazole ring. Synthesis of novel 2 mercapto benzothiazole and 1,2,3triazole based bisheterocycles. It is disclosed that the sh moiety at the c position of the heterocyclic nucleus led to a remarkable antibacterial activity against gram positive and negative. Mercapto benzothiazole linked 1,2,4oxadiazole derivatives were designed 4au as new antiinflammatory agents using bioisosteric approach and docking studies. Predicted data is generated using the us environmental protection agencys episuite. During these reactions, hydrogen sulfide, benzothiazole, dimercaptobenzothiazole and sulfurous resins arise as byproducts.
Contact with the eyes caused opacity or ulceration of the cornea, inflammation of the iris, redness and swelling of the conjunctiva and partial eversion of the eye lids, and destruction or irreversible tissue change in 24 hours or less rabbit. To synthesize sarylated 2mercaptobenzimidazoles via sarylation with substituted aryl iodides using cui and 1,10phenanthroline. Synthesis of novel benzothiazole compounds with an. Synthesis and biological evaluation of 2mercapto1,3. A simple, efficient, and mild method for the synthesis of substituted 1,2,4triazoles from hydrazines and formamide proceeds smoothly under microwave irradiation in the absence of a catalyst and shows excellent functionalgroup tolerance. Synthesis and study the biological activity of some six, five and fused ring heteroatome systems derived from 2 mercapto benzothiazole.
Synthesis and applications of benzothiazole containing. In silico druglike properties were also calculated for compounds 4au and exhibited significant hbond acceptor. Synthesis and antimicrobial activity ofsome new 2substituted. It is a member of benzothiazoles and an aryl thiol. Pdf in this work 2mercaptobenzothiazole 2mbt and some of its derivatives 1, 14,27 were prepared by using home made auto clave. After careful screening of various heteronuclei, benzothiazole was chosen as the focus of attention. A novel method for the synthesis of monomeric asymmetric benzothiazole derivatives, such as 7, containing mercapto and thioacetyl substituents has been reported 21. Synthesis of nheterocycles synthesis of 1,2,4triazoles.
Design and synthesis of some benzothiazole analogs as a 2a receptor antagonist s. Synthesis and biological evaluation of novel benzothiazole. Rapid synthesis of a c6benzothiazolium salt from c6aniline. The technical synthesis of mbt is carried out through the conversion of 1. The target 2 mercapto benzothiazole linked 1,2,4oxadiazole derivatives 4ju were synthesized as shown in scheme 2. The technical synthesis of mbt is carried out through the conversion of 1 aniline, carbon disulfide and sulfur. Synthesis of substituted benzothiazole 1sb synthesis of substituted benzothiazole nucleus was achieved by adding 8gm 0. Sudhakar, synthesis,characterization and biological evaluation of some novel 6fluoro benzothiazole.
Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticonvulsant agents by dachuan liu, hongjian zhang, chunmei jin and zheshan quan key laboratory of natural resources and functional molecules of the changbai mountain, affiliated ministry of education, college of pharmacy, yanbian university, yanji. Benzothiazole is among the usually occurring heterocyclic nuclei in many marine as well as natural plant products. The passive layer is insoluble in aqueous and many organic. In view to prepare parent compound 2, 3mercapto2, 3methyl mercapto and 3chloro 1,2,4triazolo3,4b benzothiazole were heated. Synthesis, characterization and biological evaluations of some 5substituted amino alkyl21, 3 benzothiazole2ylthiazolidine4 one mannich bases as potent antibacterial agents munendra mohan varshney1, asif husain2, versha percha3, neeraj fuloria4. The structure of the benzothiazoles were confirmed by infrared ir, nuclear magnetic resonance nmr and. If released to the soil, 2aminobenzothiazole is expected to adsorb to soil surfaces estimated koc of 1600. Some new 25substituted1,3,4oxadiazole2yl1,3 benzothiazole 3aj were synthesized by refluxing benzothiazolyl carboxyhydrazide with different aryl acids in phosphoryl chloride. Hofmann obtained the same substance by the action of. Compounds were synthesized by nucleophilic substitution of 2bromo5. Hofmannin an attempt to prepare the disulfhydryl derivative of thiocarbanilide by the action of carbon disulfide. Pdf synthesis and biological evaluation of 2mercapto1,3. This method was developed by the discoverer of the. Pdf synthesis and biological evaluation of 2mercapto1.
Benzothiazole is a privileged bicyclic ring system with multiple applications. Contact with moisture in the body by inhalation may yield sodium hydroxide corrosive and 2mercaptabenzothiazole, an irritant. Sulfenamide accelerators fast but very safe accelerators providing a steep slope on the rheometer curve. Hofmann first obtained 1 mercapto benzothiazole in an attempt to prepare the disulfhydryl derivative of thiocarbanilide by the reaction of carbon disulfide on oaminothiophenol. Similarly, we also demonstrated that the benzothiazole nucleus is a unique scaffold for further molecular exploration to synthesize novel compounds. Synthesis of novel 2mercapto benzothiazole and 1,2,3. Jun 18, 2012 the different substitution pattern of the benzothiazole system did not significantly affect the activity. Highly efficient synthesis of polyfluorinated 2mercaptobenzothiazole derivatives. Biological activities of 2mercaptobenzothiazole derivatives. This synthetic methodology could be used to prepare diverse. Their antiinflammatory and antinociceptive activities. Franchini c, muraglia m, corbo f, florio m, mola a, rosato a, matucci r, nesi m, bambeke f and vitali c. Synthesis and reactions of 2mercaptobenzothiazole derivatives of. The synthesized compounds have been tested for their antiinflammatory activity by using biochemical cyclooxygenase cox activity assays and carrageenaninduced hind paw edema.
195 121 690 779 1335 1410 1034 203 812 1210 1265 227 1458 926 1221 1494 1236 217 1417 123 38 43 556 1550 1155 872 1555 594 142 63 1302 710 1039 827 150 1227 579