The pasty mass obtained was diluted with 50ml of water and treated with aqueous sodium bicarbonate solution. A highly efficient, simple and rapid method for the preparation of various 2aminobenzoxazoles and other benzoxazole derivatives using a catalytic amount of poly ethylene glycolbound sulfonic acid pegso 3 h is described. A series of some novel benzoxazoles were synthesized and evaluated for anti. The parent benzoxazole scaffold has a planar geometry and is found to be a constituent of several naturally occurring molecules. Aug 12, 2018 the designing, synthesis, antimicrobial activity and spectral analysis of the prepared benzoxazole derivatives was done by the authors bn, sk and st. Being a heterocyclic compound, benzoxazole finds use in research as a starting material for the synthesis of larger, usually bioactive structures.
Efficient onepot synthesis of benzoxazole derivatives catalyzed by zinc triflate srinivasulu raminenia, ravi kumar kannasanib and v. Acetyl derivatives 4 and 6 were prepared by acetylation of compounds 3 and 5 with acetic anhydride. Synthesis of piperazinylsubstituted oxazolopyridine and benzoxazole was achieved in three steps starting from aminophenol and carbon disulfide. Aug 25, 2019 design, synthesis, molecular docking, and anticancer activity of benzoxazole derivatives as vegfr. Synthesis and preliminary pharmacological evaluation.
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. Novel 2substituted phenylbenzimidazole derivatives with. Pdf on jan 1, 2020, kamiar zomorodian and others published synthesis and antifungal activity of benzoxazole derivatives with their sar analysis by sasmap find, read and cite all the research. Satyanarayana peruric adepartment of chemistry, chalapathi institute of engineering and technology, guntur, india. Mohsin department of chemistry, college of science, baghdad university, baghdad, iraq abstract this research, involved a series of some new compounds containing different heterocyclic atoms, through. 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. All authors read and approved the final manuscript.
Synthesis of some novel quinazoline derivatives having anticancer activity. An experimentally simple, general, efficient, and ligandfree synthesis of substituted benzimidazoles, 2aminobenzimidazoles, 2aminobenzothiazoles, and benzoxazoles via intramolecular cyclization of obromoaryl derivatives is catalyzed by copperii oxide nanoparticles in dmso under air. Pdf synthesis of some novel benzoxazole derivatives and their. Benzoxazole is used primarily in industry and research, and has no household use. A new series of benzoxazole analogues was synthesized and checked for their in vitro antibacterial, antifungal and anticancer. Based on this result, the replacement of the benzothiazole scaffold with benzimidazole and benzoxazole moieties afforded 1f and 1g, whose activities were fundamentally retained. These ionic liquids are in the solid state at room temperature and the synthesis is carried out via the onepot condensation reaction of various ophenylenediamine with 1,2diketone derivatives. Five 3,4,5trimethoxyphenyl benzoxazole derivatives iiiaiiie were synthesized and evaluated for their antibacterial and antiinflammatory activity.
Jcprc5 2988 synthesis, characterization and biological evaluation of benzoxazole derivatives a p. Design, synthesis and biological evaluation of benzimidazole. This approach was also successfully applied to the synthesis of nformyl benzo 1,4thiazocine from the benzothiazole scheme 16, section 14. The invention provides novel 5 and 6benzoxazolyl alkanoic acids, optionally substituted in the 2position, and derivatives thereof which possess anti. Condensation of aminophenols with carbon disulfide in ethanol using potassium hydroxide as catalyst gave the required benzoxazole thiol in one step. Biologically active benzoxazole derivatives have been known for long time, they are the isosteres of cyclic. When the effervescence ceased, the precipitate obtained was filtered and washed with water. Synthesis and antimicrobial activity of benzoxazole derivatives 3 rd international conference on past and present research systems of green chemistry september 1921, 2016 las vegas, usa.
Synthesis and characterization of new 1, 2, 4 triazine. Synthesis, antimicrobial and cytotoxic activity of 2azetidinone derivatives of pyridyl benzimidazoles. Synthesis and antimicrobial activity of benzoxazole derivatives. Synthesis of benzoxazole sulfanilamide derivatives springerlink. Efficient onepot synthesis of benzoxazole derivatives. Synthesis, antifungal activities and molecular docking studies of benzoxazole and benzothiazole derivatives bo luo 1,2, ding li 2, anling zhang 2 and jinming gao 2, 1 college of life sciences, xinyang normal university, tea plant biology key laboratory of henan province, xinyang 464000, china. Based on these findings, a series of benzoic acid substituted benzoxazole were synthesized by refluxing cs 2 and oaminophenol. Synthesis, characterization and biological study of new benzoxazole. 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. It is a mancude organic heterobicyclic parent and a member of 1,3benzoxazoles.
Nano ceria catalyzed synthesis of substituted benzimidazole, benzothiazole, and benzoxazole in aqueous media. Our team of scientists has experience in all areas of research including life science, material science, chemical synthesis, chromatography, analytical and many others. It also provides intermediate compounds useful in the process. A series of benzoxazole and derivatives of heterocyclic bearing nitrogen, oxygen and oxazole moieties constitutes the core structure of a several biological active compounds. Also provided is a process for preparing such compounds by cyclising an appropriately substituted oaminophenol and, if necessary, converting the resultant benzoxazole to the desired compound. Synthesis of benzoxazole derivatives as interleukin6. Benzoxazoles as novel herbicidal agents wiley online library. Benzimidazole, benzoxazole and benzothiazole derivatives as 5ht2b receptor ligands. Bhatt 2 1research scholar jodhpur national university, jodhpur342003, rajasthan, india 2l. Pelagia research library synthesis and characterization of. Synthesis, characterization and biological evaluation of. A green and efficient protocol for the synthesis of. Facile and efficient synthesis of benzoxazole derivatives.
Helby department of pharmaceutical chemistry, faculty of pharmacy, al. Almost all amidino derivatives showed noticeable antiproliferative effect on several tumor cell lines while cyano derivatives showed considerably less pronounced activity due to poor solubility in aqueous cell culture 31,32. Consequently, developing new methodologies for construction of benzoxazole. Synthesis and characterization of oxazolopyridine and. Benzoxazole and its derivatives like 2aminobenzoxazole find extensive therapeutic importance in medicine for indications such as neural disorders wang et al.
The synthesized benzoxazole compounds were confirmed by ir, 1hcnmr, mass and screened for their in vitro antimicrobial activity against. Synthesis and pharmacological screening of some noval. Synthesis of imidazolinone and benzoxazole derivatives, and. Synthesis and characterization of new 1, 2, 4 triazine thio benzoxazole derivatives mohammad r. A highly efficient, simple and rapid method for the preparation of various 2 aminobenzoxazoles and other benzoxazole derivatives using a catalytic amount of. Application of sbaprso3h in the synthesis of benzoxazole derivatives. Benzoxazole and benzimidazole derivatives were also synthesized by these novel catalysts via the onepot condensation from reaction orthoester with o.
Antitumor evaluation of some novel cyano and amidino benzothiazole derivatives 1. Benzoxazoles can be considered as structural isosteres of the. Reaction of compound 5 with chloroacetyl chloride produced chloroacetyl derivative 7. A number of hitherto undescribed 2paminobenzenesulfamide benzoxazoles are prepared by treating 2aminobenzoxazole or its 6substituted compounds with p.
The two step conversion of the benzoxazole, first into the benzoxazolium bromide 123 followed by ring expansion afforded the nformyl benzoxazocine 124 scheme. In addition, the benzothiazole ring is present in various marine or terrestrial natural compounds, which have useful biological activities. A simple, green, and efficient method enables the synthesis of benzoxazoles and benzothiazoles from oaminothiophenols and aldehydes using samarium triflate as a reusable acid catalyst under mild reaction conditions in aqueous medium. Initially, 2chloromethyl1hbenzod imidazole i was synthesized by the reaction of ortho phenylenediamine, chloroacetic acid and hydrochloric acid. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important. Design and synthesis of 2substituted54trifluoromethylphenylsulphonamido benzoxazole derivatives as human gst p11 inhibitors tugba ertanbolellia, kayhan bolellia, yaman musdalb, ilkay yildiza, esin akiyalcina. 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. Facile and efficient synthesis of benzoxazole derivatives using novel. In reference to scheme 3, all compounds table 4 are known and widely used for scaffold synthesis. Which are further treated with hydrazine hydrate using ethanol to get their respective substituted 2mercapto benzoxazole derivatives. To our delight, the optimized analogue 1d showed comparable antiproliferative activity in vitro with better solubility, compared with 1a.
Novel benzothiazole, benzimidazole and benzoxazole. Radheshyam shelkar, sachin sarode, jayashree nagarkar. A series of imidazolinone and benzoxazole derivatives 3 and 5 have been synthesized by condensation of oxazolinone derivatives 2ac with aniline and 2hydroxyaniline. The anticancer evaluation of synthesized compounds was carried out by the authors kr, saas, sml and vm. Synthesis, antifungal activities and molecular docking. Design, synthesis, molecular docking, and anticancer activity. Pdf on jan 1, 2020, kamiar zomorodian and others published synthesis and antifungal activity of benzoxazole derivatives with their sar analysis by. Phosphorus, sulfur, and silicon and the related elements 2004, 179 2, 305319. Synthesis of some novel quinazoline derivatives having anti.
Synthesis and characterization of some benzoxazole derivatives sunila t. The method to synthesize the designed benzoxazole derivatives is given in scheme 1. Benzoxazole finds use in research as a starting material for the synthesis of larger bioactive structures. Synthesis of benzoxazole sulfanilamide derivatives. 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. It is found within the chemical structures of pharmaceutical drugs such as flunoxaprofen. Journal of chemical and pharmaceutical research, 2015, 79. Biologically active benzoxazole derivatives have been known for long time, since benzoxazoles can be considered as structural isosteres of the naturally occurring. Due to their importance in pharmaceutical utilities, the synthesis of various benzothiazole derivatives is of considerable interests. Predicted possible mechanism for synthesis of substituted benzoxazole derivatives starting from substituted onitro phenols and substituted aldehydes. Synthesis and evaluation of new benzoxazole derivatives as. An efficient synthesis of benzimidazole derivatives were prepared by wide range of aldehydes and substituted ophenylenediamines by using versatile organocatalyst lproline in an aqueous media at.