Based on the known antitb benzothiazole pharmacophore, in the present study, we described the synthesis, structural elucidation, and antitubercular screening of a series of novel benzothiazole bntz derivatives bntz 17 and bntz 8. Benzothiazole and benzotriazole derivates were determined in the textile sample and benzothiazole derivatives determined in the tire sample with good analytical performance. Activity of benzothiazoles and chemical derivatives on. Firefly luciferin can be considered a derivative of benzothiazole.
Determination of benzotriazoles and benzothiazoles in. Pyridine conataining piperazine benzothiazole derivative 18. V is selected from hydrogen and halogen, or u and v taken together are c 4 h 4 joining. Design, synthesis and evaluate in vitro antifungal activity of novel benzamide derivatives nitro substitution on the benzothiazole ring was engaged in pipi interactions with phe161. The purpose of the current study was to determine the immunosuppressive 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. Oct 17, 20 stetrazine based molecules were prepared for visiblelightdriven organic transformations. The benzothiazole ring is an important scaffold for the preparation of dyes used in the identification of lanthanide metal ions in aqueous media. Free mobility of molecules in liquid state undergoes le to tict state conversion and shows redshifted fluorescence. Synthesis and biological evaluation of sulfonamide thiazole and benzothiazole derivatives as antimicrobial agents iro argyropoulou,a athina geronikaki,a paola vicini,b and franca zanib adepartment of pharmaceutical chemistry, school of pharmacy, aristotelian university of thessaloniki, thessaloniki 54006, greece. Benzothiazole derivatives are known for antitb properties.
Two superior compounds have been further evaluated for the ic50 values against pi3ksmtor. August 29, 2017 3446 1hpyrano2,3dpyrimidin6yl3oxopropanenitrile 6 in 87% yield figure 3. The myriad spectrum of medicinal properties associated with benzothiazole related drugs has encouraged the medicinal chemists to synthesize a large number of novel therapeutic agents. Catalystfree synthesis of benzimidazole and benzothiazole derivatives by the cleavage of the cc double bond of 5arylidenepyrimidine2,4,6 1h,3h,5h. Benzothiazole derivatives as anticancer agents download pdf info. Convenient route synthesis of some new benzothiazole. This s 8 mediated directed decarboxylative redoxcyclization strategy is operationally simple, ligandfree, and compatible with a wide range of functional groups.
The extraction recoveries ranged between 69% and 102% and the matrix effects between 75% and 101%. Coupling was observed between c2 of the benzothiazole and position c2 on the thiophene 171 or c5 of the thiazole moiety 172 using standard dehydrogenative conditions of pdoac 2, agno 3, and the 1,10phenanthroline monohydrate phen ligand. Synthesis and structural elucidation of novel benzothiazole. Molecules free fulltext design, synthesis and biological. Some common routes to synthesis of substituted benzothiazole derivatives. Wen and coworkers also synthesized 2aryl benzothiazoles, using a solventfree, copper ii chloridemediated. It has a role as a plant metabolite, a xenobiotic and an environmental contaminant. Benzothiazole derivatives have attracted a great deal of interest due to their anticancer6, antitumor7, anticonvulsant8, antiviral9, antibacterial0, antimicrobial11 and fungicidal activities12. Iodinated benzothiazole derivatives radiolabeled with either c 11 or i 125 i 123 have also been developed for dual modal in vivo imaging of amyloid deposits in mice using pet or spect wang et al. Benzothiazole is a sulfur containing compound used chiefly as a flavoring substance in foods or as an antimicrobial agent. The 3,6dipyridin2yl1,2,4,5tetrazine pytz derivative shows visible light absorption and reversible oneelectron reduction behavior.
A series of benzothiazol2yldithiocarbamates 3ad along with their copper complexes 4ac were synthesized via the reaction of suitable alkyl, aralkyl or heteroaryl halides with the sodium salt of benzothiazol2yldithiocarbamic acid, followed by complexation with copper sulphate. Benzothiazole is an organic heterobicyclic compound that is a fusion product between benzene and thiazole. Malaria is a major health concern particularly in africa which has about 90% of the worldwide annual clinical cases. Simple workup procedure, high yield, easy availability, reusability, and use of. Recent advances in the chemistry and biology of benzothiazoles rupinder k. Extraction and analysis of various benzothiazoles from. Synthesis and biological evaluation of sulfonamide thiazole. Benzothiazole is among the usually occurring heterocyclic nuclei in many marine as well as natural plant products. Substituted benzothiazole and benzoxazole derivatives useful as inhibitors of dpp1 15 wo2010066357 a1. Determination of benzothiazole and benzotriazole derivates. The increasing number of drugresistant plasmodium falciparum justifies the search for new drugs in this field.
Therapeutic advancement of benzothiazole derivatives in the last. Benzoxazole is an aromatic organic compound with a molecular formula c 7 h 5 no, a benzenefused oxazole ring structure, and an odor similar to pyridine. In this study, based on the antidepressant activity potential of benzothiazolebased compounds, we searched for potential antidepressantlike effects of the newly synthesized benzothiazole derivatives 3a3h through tst and modified forced swimming tests mfst. Some new hydrazino group substituted benzothiazole derivatives have been synthesized and their characterization was done by ir, nmr and mass spectral data. Substituted 1, 3benzothiazole derivatives are an important class of heterocyclic compounds. Benzothiazole derivatives have been studied extensively and found to have diverse chemical reactivity and broad spectrum of biological activity such as antitumor agents, antimicrobial,46 analgesics, 7 antiinflammatory, 79 anti hiv, 10 antileishmanial,11 etc. All synthesized compounds were evaluated for antiinflammatory activity and 3. Benzothiazole derivatives as anticancer agents us7928140 b277 us 12221,416 apr 19, 2011 shon booker benzothiazole pi3 kinase modulators for cancer treatment 14 wo2011075631 a178 pctus2010 060981 jun 23, 2011 alfonzo d.
Phosphatidylinositol3kinases beta subunit inhibitors with the structure of benzothiazole scaffold have been designed and synthesized. A series of 20 novel benzimidazole and benzothiazole derivatives linked to a 1,2. Citric acid catalyzed microwave irradiated solvent free. G is an unsubstituted or substituted pyrimidinyl group. Synthesis, computational studies and anticonvulsant.
Accurately weighed quantities of molecular iodine 0. It is also a byproduct of 2thiocyanomethylthiobenzothiazole and 2mercaptobenzothiazole degradation. Furthermore, this reagent is a cheap and waste product of the. Catalystfree synthesis of benzimidazole and benzothiazole. The presence of the inhibitors in the concentration range of 2 to 10.
In recent years heterocyclic compounds analogues and derivatives have attracted strong interest due to their biological and pharmacological properties. In recent years heterocyclic compounds analogues and derivatives have attracted wide attention due to their useful biological and pharmacological properties. Under the established conditions, the reaction produces synthetically significant yields with a. Allam, synthesis of some new benzothiazole derivatives as potential antimicrobial and antiparasitic agents. Extraction and analysis of various benzothiazoles from industrial wastewater oliver fiehn, thorsten reemtsma, martin jekel department. August 29, 2017 3346 found that compound 3 will lead to an excellent building block for the synthesis of target.
Denisony ydepartment of environmental toxicology, university of california, davis, california, usa. Simple workup procedure, high yield, easy availability, reusability, and. The maximum activity may be due to presence of f and och 3 groups. Benzotriazole btr and benzothiazole bth derivatives are used in a wide variety of industrial and consumer products and have been reported to occur in the environment. A new series of 2substituted benzothiazole derivatives was prepared by shashank and coworkers. The most important industrial applications of benzothiazole derivatives are recognized as corrosion inhibitors and surfaceactive chelating agents for mineral processing. Synthesis, characterization and antibacterial activity of.
An efficient strategy for the synthesis of various 2mercaptobenzothiazole derivatives proceeds from ohaloaniline derivatives and carbon disulfide via a tandem reaction in the presence of 1,8diazabicyclo5. For example, riluzole is used for the treatment of amyotrophic lateral sclerosis. In this manuscript, we report the synthesis of tpabenzothiazole derivatives, n4benzodthiazol2yl. The antimicrobial activities of these synthesized compounds was done by cupplate diffusion method in dmso against some gram positive and gram negative bacteria. Synthesis of some new biologically active benzothiazole. Yuans group also developed a rhodiumcopper catalyst system rh oac 2 2, cu oac 2, pph 3, cui capable of crosscoupling 2aryl pyridines and benzothiazoles 173 174 2014tet6474. Synthesis, characterization and biological evaluation of some. Benzothiazole is an aromatic heterocyclic compound with the chemical formula c 7h 5ns. The first step is to select effective compounds by simple, rapid and. Promoted solvent free synthesis of benzoxazoles, benzimidazoles, and benzothiazole derivatives article pdf available september 2012 with 150 reads how we measure reads. Antibacterial benzothiazole derivatives 5 us8691185.
Although the parent compound, benzothiazole is not widely used, many of its derivatives are found in commercial products or in nature. Benzothiazole is a privileged bicyclic ring system with multiple applications. Pdf promoted solventfree synthesis of benzoxazoles. Therapeutic advancement of benzothiazole derivatives in the. Benzothiazole derivatives have been studied extensively and found to have diverse chemical reactivity and broad spectrum of biological activity such as antitumor. One pot, solventfree microwave assisted synthesis and their biological. Convenient route synthesis of some new benzothiazole derivatives and their pharmacological screening as antimicrobial agents published. The onepot threecomponent reaction of 2aminobenzothiazole, benzaldehyde derivatives and. Otherwise, when obtaining compound in the form of salts, known method itself or similar method can be utilized to be. A synthesis of 2substituted benzothiazoles in good yields from oiodoanilines, arylacetic acids, and elemental sulfur is catalyzed by cheap copper metal.
The method allows the determination of benzothiazole derivatives without further cleanup down to contents of about 5 pg i, with recovery rates exceeding 90% for all compounds. A new series of 6substituted 2aminobenzothiazole derivatives were synthesized and screened in vitro. Pandeya 1kmch college of pharmacy, kovai estate, kalapatti road, coimbatore,india. Novel benzothiazole derivatives with enhanced biological activity. N4acetyl5aryl4,5dihydro1,3,4thiadiazol2ylnbenzothiazol2ylacetamides 7ac were synthesized by.
Identification of benzothiazole derivatives and polycyclic aromatic hydrocarbons as aryl hydrocarbon receptor agonists present in tire extracts guochun he department of environmental toxicology, university of california, davis, california, usa. Benzothiazole, benzotriazole, and their derivates in clothing. Benzothiazole is an aromatic heterocyclic compound with the chemical formula c 7 h 5 ns. Synthesis and antidepressant activity profile of some novel. However, pet and spect, due to their low spatial resolution, are unable to detect individual plaques and earlystage amyloid deposition. Identification of benzothiazole derivatives and polycyclic aromatic hydrocarbons as aryl hydrocarbon receptor agonists present in tire extracts guochun he,y bin zhao,yzand michael s. Synthesis of 234amino phenyl benzothiazole derivatives. Article information, pdf download for synthesis of novel. Cyclic voltammetry and potentiodynamic polarization techniques were used to study the effects of 441,3benzothiazol2ylphenoxy phthalonitrile bt and tetrakisbenzodthiazol2ylphenoxy phthalocyaninato galliumiiichloride clgabtpc as aluminium corrosion inhibitors in 1. Pdf synthesis of 2substituted benzothiazole derivatives under.
Synthesis, computational studies and anticonvulsant activity. Silicon industry waste polymethylhydrosiloxanemediated. Pdf discovery of benzothiazole derivatives as novel non. Novel benzothiazole derivatives with enhanced biological activity 4 wo2016079688 a168 pctib2015 058919 nov 11, 2015 christine schmitt et al.
Synthesis of novel benzothiazole compounds with an extended. A series of benzothiazole derivatives were efficiently synthesized in good to excellent yields via the reaction of 2aminothiophenol with aromatic benzoyl chlorides under solventfree conditions. In the manufacturing chain from natural andor synthetic fibers to the final clothing products, the use of many different chemicals is ubiquitous. Interestingly, activation of more vibrational bands of tict. Beside this, a number of benzothiazole derivatives as well as derivatives of riluzole have been reported to exhibit anticonvulsant activity in preliminary experimental studies 10, 11. Abstract rapid and efficient condensation reactions of 2. Pdf a series of benzothiazole derivatives were efficiently synthesized. Synthesis of novel benzimidazole and benzothiazole derivatives. An efficient protocol has been developed for the preparation of a library of benzoxazole, benzimidazole, and benzothiazole derivatives from reactions of acyl chlorides with o substituted aminoaromatics in the presence of catalytic amount of silicasupported sodium hydrogen sulphate under solvent free conditions. Since, a wide range of methods are available for synthesizing benzothiazole nucleus and its derivatives but a real need exists for new procedures that support many kinds of structural diversity. Therapeutic advancement of benzothiazole derivatives in. Substituted benzothiazole then condensed with 2 3 or. The benzothiazole nucleus containing compounds involved in research aimed at evaluating new products that possess biological activities, such as.
Benzothiazole article about benzothiazole by the free. Besides, another benzothiazolebased drug, pramipexole, has been approved for the treatment of parkinsons disease 32. A series of benzothiazole derivatives were screened for immunosuppressive activity. Pdf benzothiazole derivatives as anticancer agents researchgate. Novel benzothiazole containing 4hpyrimido2,1bbenzothiazoles derivatives. Synthesis of novel benzothiazole compounds with an. Benzothiazole compounds of the following structural formula modify the growth and development of plants. When obtaining compound i with free compound form, known method itself or similar method can be utilized to be changed into target salt. Benzothiazole derivative an overview sciencedirect topics. Synthesis of c6 methyl substituted benzothiazole derivatives and. In the presence of pytz and aerial oxygen, aldehyde reacts with ophenylenediamine or oaminothiophenol under visible light irradiation at ambient temperature to. Furthermore, there are approved drugs that contain a benzothiazole core. Cn102300854b benzothiazole derivatives as anticancer. 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.
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. Synthesis, characterization and biological evaluation of. Pdf synthesis of 2substituted benzothiazole derivatives. A new and efficient method for the synthesis of pyrimido2,1. Design of new anticancer prodrugs is important source to the development of antitumoral agents that can be effective on resistant cancer cell types and have fewer side effects. Review article recent advances in the chemistry and biology of benzothiazoles rupinder k. Synthesis of some new biologically active benzothiazole derivatives bull. Owing to a lack of analytical methods, human exposure to btr and bth is still unknown. Activity cage tests were also incorporated into the experimental protocol to.
A new and efficient method for the synthesis of pyrimido2. Antimalarial activity of 2substituted 6nitro and 6aminobenzothiazoles and their anthranilic acids has been tested. Synthesis, characterization and antibacterial activity o f substituted benzothiazole derivatives prachi k. Pdf benzothiazole bta belongs to the heterocyclic class of.
Citric acid catalyzed microwave irradiated solvent free synthesis of 2 substituted benzothiazole derivatives from 2 aminothiophenol and aryl aldehydes rahul bhat, shrikrishna karhale, sunil kumbhar, vasant helavi department of chemistry, rajaram college, kolhapur 416004, m. All the compounds have been evaluated for inhibitory activities against pi3k. Thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29 miscellaneous substances from chemical group 30 view page or view pdf. Synthesis of substituted benzothiazole derivatives. The results of the studies revealed that the new method reduces cost by. Solvent free accelerated synthesis of 2hydrazinobenzothiazole derivatives using microwave. Us4556411a benzothiazole derivatives for plant growth. Chlorinated and fluorinated derivatives of this moiety exhibit good in vitro as well as in vivo antitumor activity. C in 60% 72% yields without using any catalyst in an optimistic time.
Us81538b2 benzothiazole and benzooxazole derivatives and. Oct 25, 2014 textiles play an important role in our daily life, and textile production is one of the oldest industries. Abstract various substituted 2aminobenzothiazoles have been synthesized cyclocondensation of various. Riluzole, a benzothiazole containing moiety, is having phenytoin like spectrum of anticonvulsant activity. Also, the importance of the benzothiazole nucleus is evident from the fact that it is a part of many clinically useful drugs. Inhibition of aluminium corrosion using benzothiazole and. Benzothiazoles have been observed to undergo a c c crosscoupling with thiophenes and thiazoles in fair to good yields 2014cc3996. They are also useful as antiallergic, antiinflammatory14and anthelmintic15 agents and as.
Synthesis and screening of benzothiazole derivatives have great importance in heterocyclic. A lot of research has focused on chemicals in textile wastewater, but the knowledge of the actual content of harmful chemicals in clothes sold. Discovery of benzothiazole derivatives as novel nonsulfamide nedd8 activating enzyme inhibitors by targetbased virtual screening. Oxidative ringopening of benzothiazole derivatives. Nov 29, 2018 benzothiazole and its derivatives show a wide range of biological activities, including anti. Conclusions in brief, we have established industrial waste pmhs pmhs as an e. Synthesis and in vitro evaluation of new benzothiazole. The present invention is related to the use of benzothiazole derivatives for the manufacture of a medicament for the treatment of metabolic disorders mediated by insulin resistance or hyperglycemia, comprising diabetes type ii, inadequate glucose tolerance, insulin resistance, obesity, polycystic ovary syndrome pcos formula i. Identification of benzothiazole derivatives and polycyclic. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important. Correspond ingly, benzothiazole and its derivatives are widely distributed and have been detected by screening analyses in industrial and municipal wastewater lo121 as well as in various environmental com. Benzothiazole and its derivatives show a wide range of biological activities, including anti. An oxidative ring opening of benzothiazole to an acylamidobenzene sulfonate ester using alcohol solvents and magnesium monoperxoyphthalate hexahydrate has been described. Recent advances in the chemistry and biology of benzothiazoles.
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