It also provides intermediate compounds useful in the process. The heterogeneous catalyst can be recovered and recycled. New 2substituted benzoxazole derivatives were synthesized and screened for their in vitro antiproliferative activities against mcf7 and mdamb231 cell lines. Onepot synthesis of 2arylbenzimidazole, 2arylbenzothiazole and 2arylbenzoxazole derivatives using vanadiumivsalen complex as homogeneous catalyst and vanadiumivsalen complex nanoparticles immobilized onto silica as a heterogeneous nanocatalyst. Pelagia research library evaporated under diminished pressure. To solve this problem, a lead optimization was conducted through introducing nmethylpiperazine groups at the 2position and 6position. In this study, we found that k3 reduced the viability of human bcell leukemia nalm6 and lymphoma daudi cells in a dosedependent manner without affecting healthy. Pdf benzoxazole derivatives as promising antitubercular.
The synthesis of benzoxazole on a solid support is demonstrated by the synthesis of benzoxazole attached to a human islet amyloid polypeptide, hiapp2227, fragment and benzoxazole derivatives of the side chain of aspartic. Synthesis of imidazolinone and benzoxazole derivatives, and. Reaction of compound 5 with chloroacetyl chloride produced chloroacetyl derivative 7. In the current research work, the title compounds 2mercaptonsubstituted arylidine benzoxazole5carbohydrazide derivatives were synthesized by the reaction of schiff bases of 2mercapto benzoxazole5carbohydrazide with appropriate aromatic aldehydes. Facile and efficient synthesis of benzoxazole derivatives using novel catalytic activity of pegso 3 h. The title compounds were synthesized by treating the 2methyl benzoxazole5carbohydrazide with appropriate aromatic aldehydes to get a new series of 2methylnsubstituted arylidene benzoxazole5carbohydrazide vi avi f. Our team of scientists has experience in all areas of research including life science, material science, chemical synthesis, chromatography, analytical and many others. Ecofriendly syntheses of 2substituted benzoxazoles and 2. Abstract rapid and efficient condensation reactions of 2. I nterestingly,s om eo f th em had promising antitubercular activity. However, the poor solubility of 1a and 1b made difficult further in vivo studies. Investigation of the synthesis of benzoxazole via aryne. Syntheses of new benzoxazole derivatives, journal of.
The reaction of oaminothiophenol with methyl isothiocya. With the success of benzoxazole synthesis using benzaldehyde, experiments were extended to other aldehydes to synthesize various benzoxazole derivatives table 3. Benzoxazole derivatives as new generation of antibreast. The main objective of the medicinal chemistry is to synthesize the compounds that show promising activity as therapeutic agents with lower toxicity. Benzoxazole ring has provided the basis for the design of biologi. The title compounds were synthesized by treating the 2methyl benzoxazole 5carbohydrazide with appropriate aromatic aldehydes to get a new series of 2methylnsubstituted arylidene benzoxazole 5carbohydrazide vi avi f. Benzisoxazole derivatives are secondgeneration atypical antipsychotic drugs. Orally active benzoxazole derivative as 5ht3 receptor. Sep 01, 2011 read syntheses of new benzoxazole derivatives, journal of heterocyclic chemistry on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Read pyrazolylbenzoxazole derivatives as protein kinase inhibitors. Elamin i elnima et al 6 studied the in vitro antibacterial 2 and antifungal activities of six benzimidazole and benzoxazole derivatives. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important. Compounds 5a, 5b, 5h, and 5i exhibited significant antifungal activities against most of the pathogens tested. Some of these compounds showed high in vitro metabolical stability, and 6g showed marked antidiarrhetic activity with little side effect of constipation in in vivo tests.
Biologically active benzoxazole derivatives have been known for long time, since. In this paper, we introduce two nonconventional ionic liquid compounds which are composed of propane sulfonate functionalized organic cations and heteropolyanions as green solid acid catalysts for the highly efficient and green synthesis of 2,3disubstitutedquinoxaline derivatives. An environmentally benign catalyst for synthesis of benzothiazoles and benzoxazole derivatives in aqueous medium monika a patil, panchsheela a ubale, shrikrishna s karhale and vasant b helavi department of chemistry, rajaram college, kolhapur, 416004, maharashtra, india abstract. Benzoxazole derivative k3 has previously been reported to possess antiinflammatory effects in lipopolysaccharideinduced raw264.
They are structurally characterized by ir, 1hnmr, mass spectroscopy methods and further investigated for antibacterial. They are prepared by reacting 1 mol of 1,7naphthalene dicarboxylic acid or its acid chloride. A simple, economical and metal free approach to the synthesis of 2substituted benzoxazoles and 2substituted benzothiazoles from 2aminophenols, 2aminothiophenols and dmf derivatives, only using imidazolium chloride 50% mmol as promoter without any. Acetyl derivatives 4 and 6 were prepared by acetylation of compounds 3 and 5 with acetic anhydride. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. The parent benzoxazole scaffold has a planar geometry and is found to be a constituent of several naturally occurring molecules. Benzoxazole derivative an overview sciencedirect topics. Disclosed is a process for preparing 2,5dicarbonamido phenol compounds comprising a step employing a 2alkyl6nitrobenzoxazole to form a 2alkyl6aminobenzoxazole in which the 2alkyl group is unbranched at the a carbon. Synthesis, molecular docking and antimicrobial evaluation of novel benzoxazole derivatives tugba ertanbolelli1 i. These examples highlight the level of interest in new synthetic approaches to benzoxazole derivatives.
A green and efficient protocol for the synthesis of. It is a mancude organic heterobicyclic parent and a member of 1,3benzoxazoles. Synthesis and pharmacological screening of some noval benzoxazole derivatives shivendra pratap singh, navneet kumar verma, praveen kumar rai and ashok kumar tripathi kailash institute of pharmacy and management, gida, gorakhpur, u. Aug 12, 2018 a new series of benzoxazole analogues was synthesized and checked for their in vitro antibacterial, antifungal and anticancer activities.
In the current research work, the title compounds 2mercaptonsubstituted arylidine benzoxazole 5carbohydrazide derivatives were synthesized by the reaction of schiff bases of 2mercapto benzoxazole 5carbohydrazide with appropriate aromatic aldehydes. A series of benzoxazole derivatives was synthesized and evaluated as melatoninergic ligands. Design and validation of a combinatorial library, tetrahedron on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Synthesis of 2substituted benzoxazole, benzimidazole and benzothiazole derivatives. An update on the synthesis of benzoxazoles semantic. The residue was boiled with 200 mg charcoal in ethanol and filtered. The benzoxazole nucleus is an important heterocyclic moiety and their derivatives display a wide variety of important biological activities such as antimicrobial, antiinflammatory, antiviral, antihistaminic, herbicidal, anthelmintic, anticancer, hypoglycemic, 5ht 3 agonist, diuretic, and 5ht 3 antagonist, uricosuric. To date, there have been no related reports on the anticancer effects of k3.
Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to. Facile and efficient synthesis of benzoxazole derivatives using novel. 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. Benzoxazoles are formed by the action of potassium amide in liquid ammonia on. The in vitro antibacterial and antifungal activities of six benzimidazole and benzoxazole derivatives were tested against standard strains and 59 clinical isolates. Disclosed is a process for preparing 2,5dicarbonamido phenol compounds comprising a step employing a 2alkyl6nitro benzoxazole to form a 2alkyl6amino benzoxazole in which the 2alkyl group is unbranched at the a carbon.
Compounds 4b, 4d and 11c eliciting the highest activity against mcf7 cells were further assayed for their cytotoxic activities against a431 and hcc827 cancer cells in addition to their in vitro inhibition of wild and mutated. Synthesis, molecular docking and antimicrobial evaluation of novel benzoxazole derivatives. Simple workup procedure, high yield, easy availability, reusability, and. A new series of benzoxazole analogues was synthesized and checked for their in vitro antibacterial, antifungal and anticancer activities. Novel 18flabeled benzoxazole derivatives as potential. Simple workup procedure, high yield, easy availability, reusability, and use of. These compounds possess antimicrobial, central nervous system activities, antihyperglycemic potentiating activity, analgesic, and antiinflammatory activity.
Benzoxazole is an important class of heterocycle having a bicyclic structure in which an aryl ring is fused with the d site of an oxazole moiety. Benzoxazole is used primarily in industry and research, and has no. After the evaporation of the solvent in vacuo, the crude product was obtained and recrystallized from ethanol. Paper 3 dealt with the structure and ultraviolet spectra of some nalkyl and salkyl derivatives of mercaptobenzothiazole and sixmembered nitrogen heterocycles. A direct basemediated intramolecular carbonoxygen bond formation has been developed without a transitionmetal catalyst. The synthesized benzoxazole compounds were confirmed by ir, 1hcnmr, mass and screened for their in vitro antimicrobial activity against. Antiinflammatory activity of benzoxazole derivatives were also reported in the literature. It can also be used as starting material for other bioactive molecules. Synthesis, characterization and biological study of new benzoxazole. An experimentally simple, general, efficient, and ligand free synthesis of substituted benzimidazoles, 2aminobenzimidazoles, 2aminobenzothiazoles, and benzoxazoles via intramolecular cyclization of obromoaryl derivatives is catalyzed by copperii oxide nanoparticles in dmso under air. Novel 18 flabeled benzoxazole derivatives as potential positron emission tomography probes for imaging of cerebral. A ballmilling strategy for the synthesis of benzothiazole. Benzoxazoles being structurally similar to bases adenine and guanine interact with biomolecules present in living systems.
In a previous hittolead research program targeting anticancer agents, two promising lead compounds, 1a and 1b, were found. A simple, economical and metal free approach to the synthesis of 2substituted benzoxazoles and 2substituted benzothiazoles from 2aminophenols, 2aminothiophenols and dmf derivatives, only using imidazolium chloride 50% mmol as promoter without any other additive, was reported. 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. Of the six compounds, only compounds ii and iii both benzoxazoles were active, whereas the rest were devoid of any activity. Aug 12, 2018 the screening of antibacterial and antifungal activity of the synthesized derivatives was done by tube dilution method and the results are shown in table 2 as well as figs. From this series of benzoxazole derivatives, compounds 14 and 17 were identified as melatonin receptor agonists. Various novel benzoxazole derivatives were synthesized by reacting with succinic anhydride and aromatic aldehydes.
Pdf promoted solventfree synthesis of benzoxazoles. The synthesized benzoxazole compounds were confirmed by ir, 1hcnmr, mass and screened for their in vitro antimicrobial activity against grampositive bacterium. The benzoxazole scaffold is a core structure found in a wide class of natural and synthetic compounds. The reaction of 2hydrazinobenzoxazole 286 with cyanogen bromide gives 4amino1,2,4triazolo3,4bbenzoxazole hydrobromide 294 hbr. The screening of antibacterial and antifungal activity of the synthesized derivatives was done by tube dilution method and the results are shown in table 2 as well as figs. Synthesis, molecular docking and antimicrobial evaluation of. Jcprc5 2988 synthesis, characterization and biological evaluation of benzoxazole derivatives a p. Read syntheses of new benzoxazole derivatives, journal of heterocyclic chemistry on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Benzoxazole and benzothiazole synthesis from carboxylic acids. Synthesis and characterization of some benzoxazole derivatives. Synthesis and structureactivity relationship of novel. The binding affinity of these compounds for human mt 1 and mt 2 receptors was determined using 2125 iiodomelatonin as the radioligand.
Nataxazole, a new benzoxazole derivative with antitumor activity produced by streptomyces sp. Antibacterial and antifungal activities of benzimidazole. A series of imidazolinone and benzoxazole derivatives 3 and 5 have been synthesized by condensation of oxazolinone derivatives 2ac with aniline and 2hydroxyaniline. Benzoxazole derivatives are very useful compounds with well known biological activity. Benzoxazole derivatives have been prepared through the reaction of substituted 2aminophenols and acyl chlorides in the presence of catalytic amount of inotf3 under solvent free reaction. The benzoxazole nucleus is an important heterocyclic moiety and their derivatives display a wide variety of important biological activities such as antimicrobial, antiinflammatory, antiviral, antihistaminic, herbicidal, anthelmintic, anticancer, hypoglycemic, 5ht 3. Synthesis of benzoxazole and benzimidazole derivatives via. Procedure for synthesis of benzoxazole derivatives. Due to the importance of benzoxazoles for anticancer drug discovery, herein new benzoxazolebased hydrazone derivatives. The method affords environmentally friendly reaction conditions that score high on the ecoscale with the low efactor. Infrared spectroscopy the ir spectroscopy data confirmed the presence of required as shown in table i.
During our search for therapeutic agents to treat diarrheapredominant ibs, we found that 2substituted benzoxazole derivatives have a characteristic 5ht3 receptor partial agonist activity with high affinity. The process provides a simple and safe way to prepare 2,5dicarbonamido phenol compounds in good yield. Synthesis and pharmacological screening of some noval. Free the chemistry of benzotriazole derivatives pdf download. Synthesis and evaluation of new benzoxazole derivatives as. Design, synthesis and biological evaluation of 2thio. The study revealed that the prepared derivatives showed moderate to good antimicrobial activity against various microbial strains used. More specifically, the synthesis and biological activity of a new series of benzoxazole derivatives as novel and potent melatoninergic ligands are discussed. These compounds have special significance in the field of medicinal chemistry due to their remarkable pharmacological potentialities.
A new series of benzoxazole analogues was synthesized and. A convenient solvent free method for the synthesis of benzothiazole, benzimidazole, and benzoxazole derivatives has been developed using recyclable znonps via a ballmilling strategy. Also, it simplifies the reaction conditions in the synthesis of benzoxazole derivatives and is no need to use complicated chemical reagents, comparing to. In this article, we present a detailed description of the sar associated with the two termini of this parent acylic benzoxazole chemotype.
Benzoxazole derivatives are very useful compounds with wellknown biological activity. Synthesis, molecular docking and antimicrobial evaluation. Novel benzothiazole, benzimidazole and benzoxazole. Synthesis of imidazolinone and benzoxazole derivatives. All animals were allowed to free access to water and fed with standard. Journal of the iranian chemical society 2012, 9 2, 189204. They work by blocking the action of dopamine and serotonin, two brain chemicals that regulate mood. Based on benzoxazole and benzothiazole scaffold as an important pharmacophore, two series of 2aryloxymethyl benzoxazole and benzothiazole derivatives were synthesized and their antifungal effects against eight phytopathogenic fungi were evaluated.
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