New heterocyclic oxime ethers of 1benzofuran2ylethan1one and their antimicrobial activity article pdf available in acta poloniae pharmaceutica 722. Tetrahydrofuran thf a cyclic ether, one of the most polar simple ethers that is used as a solvent. Therefore, synthesis of these compounds using new protocols is always interesting. Fragmentation of oxime and silyl oxime ether oddelectron. The protective effect of naringenin oxime on cisplatininduced toxicity in rats. Diazo oxime ethers for nheterocycle synthesis chemical. Oximes can be reduced by sodium metal, sodium amalgam, hydrogenation, or reaction with hydride reagents producing respective amines 3.
Threecomponent synthesis of some novel nheterocycle methylo oxime ethers. The journal of organic chemistry 2005, 70 24, 102104. Furthermore, optically active cyclopropyl oxime ethers could be successfully converted into the corresponding. The prototypical progestogen is progesterone, an endogenous sex hormone. She worked at novi llc as a formulation chemist for two years. Free radical acylation approaches of ch bonds with 2 chloroethylsulfonyl oxime ethers sunggak kim, namsun kim, wonjin chung, chang ho cho department of chemistry and center for molecular design and synthesis, school of molecular science, korea advanced institute of science and technology, taejon 305701, korea. Advertise with us journal and book catalog media pack 2019.
Introduction oximes and osubstituted oxime ethers are important compounds in medicinal chemistry as potent pharmacophores1 3 and building blocks of drug. Heterocyclic derived oxime ethers in asymmetric synthesis. Synthesis and evaluation of novel coumarinoxime ethers as. Organic chemistry jonathan clayden, nick geeves, stuart warren.
Antihepatitis b virus hbv activities of all synthesized compounds were evaluated with hepg2. Author bios yves chapleur is the author of carbohydrate mimics. Oxime ether derivatives were synthesized by the reaction of various alkyl halides with 12 naphthyl2pyrazol1ylethanone oxime. An efficient onepot synthesis of oxime ethers from alcohols using triphenylphosphinecarbon tetrachloride mohammad navid soltani rad, ali khalafinezhad, fatemeh karimitabar, somayeh behrouz department of chemistry, faculty of basic sciences, shiraz university of technology, shiraz 715553, iran, email. Invitro antituberculosis activityagainstmtbh 37 rv strain was established for the coumarin oxime ether 1a1j. Catalytic asymmetric carbene transfer reactions of diazo. A series of capsidbinding compounds was screened against human rhinovirus hrv using a cpe based assay. Oxime ethers 14, 7, 8, 10 were prepared by our standard method as described in the literature. Abstract a novel series of benzophenone oxime ether derivatives with tertiary amine groups were synthesized and their herbicidal activities of 24 compounds against oryza sativa, sorghum sudanense, brassica chinensis, and amaranthus mangostanus l. Identification of antitumor activity of pyrazole oxime ethers. They also serve, unlike other classes of imines, as primary aminomethylating reagents ch 2 nh 2, since the formaldehyde adducts for the introduction of ch 2 nh 2 ch 2 nor are resistant to polymerization.
Oxime ethers 5, 6 and 9 were prepared by condensation with a new hydroxylamine sophea, so2hydroxy1phenylethylhydroxylamine 11. Thioaryl naphthylmethanone oxime ether analogs as novel. Oximes are also called nitrogen possessing organic compounds which are obtained from the hydroxylamine, a ketone, and an aldehyde these compounds are also derived from the reaction of hydrogendonating reagents with the nitro compounds or by another way is by the process of isomerization of the nitroso compounds. Synthesis of some novel oxime ether derivatives and their. The aryloxy acetophenone 9a was prepared from the 2chloro or 2bromoacetophenone with different bases naoh, nah, and k 2 co 3.
Synthesis and microbiological evaluation of some nmethyl piperidone oxime. An efficient onepot synthesis of oxime ethers from. The journal of organic chemistry 2019, 84 21, 794806. Medicinal chemistry research, volume 14, issue 8 springer. Oxime ethers as versatile precursors in organic synthesis. Asap, published on web 04192006 presented by zhenyu zhong lead reference. Pdf new heterocyclic oxime ethers of 1benzofuran2yl. Sundae kim, nurul ain bte kamaldin, sol kang, sunggak kim. Free radical acylation approaches of ch bonds with. Pdf synthesis, stereochemistry and antimicrobial studies. Synthesis and evaluation of coumarinoxime analogs as potent antitubercular agents. The phase transfercatalyzed alkylation of oppolzers camphorsultam derivative of oxime ether proceeded smoothly to give the alkylated n. Synthesis and c nmr studies of a series of novel oxime ethers article pdf available in synthetic communications 4020.
Heteroaromatic systems are not only prevalent in a wide variety of important classes of natural products and synthetic pharmaceuticals but are also used as a building block in organic synthesis. Reduction of oximes, oxime ethers, and oxime esters with diborane. Esterification is frequently employed to improve the pharmacokinetics of steroids, including oral bioavailability, lipophilicity, and elimination halflife. Taelim kim, hyein kim, jiyoung an, jun lee, narae lee, jinyuk heo, jieun kim, jihyun yu, yong sup lee, kyungsoo inn, namjung kim. Lenaour m, leclerc v, farce a, caignard dh, hennuyer n, staels b et al.
The ethyl oxime ether 14 was found to have outstanding antihrv activity median ic50 4. Nitriles, amides via beckmann rearrangement, nitro compounds, nitrones, amines, and azaheterocycles can be synthesised from oximes. They are used in organic synthesis, providing valuable reagents to obtain cis. Carbenes derived from diazo oxime ethers show unique reactivity towards no and ch bond activation, in which the proximity of the two functionalities, carbene and oxime ether, dictates the preferred reaction pathways toward pyridines, pyrroles, and 2hazirines. Rebecca rowe received her bs degree in chemistry from california polytechnic state university in 2014. Biao xiong, shi chen, peng zhu, meiling huang, weijie gao, rui zhu, jianqiang qian, yanfu peng, yanan zhang, hong dai and yong ling, design, synthesis, and biological evaluation of novel thiazolyl substituted bispyrazole oxime derivatives with potent antitumor activities by selectively inducing apoptosis and ros in cancer cells, medicinal chemistry. Synthesis, anticonvulsant and antimicrobial activities of. Yeon tae jeong, stereocontrolled facile synthesis and antimicrobial activity of oximes and oxime ethers of diversely substituted bispidines. A series of oxime ethers with c6c4 fragment was designed and virtually bioactively screened by docking with a target, then provided by a friedelcrafts reaction, esterification or amidation, and oximation from psubstituted phenyl derivatives methylbenzene, methoxybenzene, chlorobenzene. Review of the synthesis of acyclic and cyclic oxime ethers rsc. Synthesis of polyfunctionalized piperidone oxime ethers. New oxime ethers and oxime esters of diphenyl ethers according to the formula wherein q a in the description defined in detail aliphatic or araliphatic ether or esterrest, r 1 is halogen or one of the groups nitro, cyano or trifluoromethyl, r 2 and r 3 are each hydrogen, halogen or one of the groups nitro or cyano, r 4 is hydrogen or halogen and x is hydrogen, halogen or one of the groups. Purchase the practice of medicinal chemistry 4th edition.
Inonu university, faculty of pharmacy, department of pharmaceutical chemistry, 44280 malatya, turkey. Addition reactions a carboncentered radical adds preferentially to the carbon atom in the carbonnitrogen double bond of an oxime ether scheme 1. An oxime is a chemical compound belonging to the imines, with the general formula rrcn o h, where r is an organic sidechain and r may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. Molecules free fulltext discovery of oxime ethers as. The condensation of ketones 1 with hydroxylamine ethyl ether derivatives 4 9 ho14 and pol6 was the most convenient way of correspondence and reprints obtaining oxime ethers of the butyrophenone series. The use of mcpba as an oxidant in ethyl acetate enables an efficient, rapid oxidation of various aliphatic amines to oximes in high conversion with 90% oxime selectivity at room temperature under catalystfree conditions. The practice of medicinal chemistry 4th edition elsevier. A variety of important enantiopure thionyl and arylalkyl primary amines were afforded by the boranemediated enantioselective reduction of obenzyl ketoximes using 10% of catalyst 10 derived from sdiphenylvalinol and ethylene glycol. Oxime ethers are compounds that are becoming increasingly popular. Article pdf available in european journal of medicinal chemistry. Once again, were starting with cyclohexanone, but this time, were dealing with hydroxyl amine, so this guy right here, once again, with an acid catalyst. Inonu university, faculty of pharmacy, department of pharmaceutical chemistry, 44280 malatya. Katherine matasci received her bs degree in chemistry from california polytechnic state university in 20. Nov 04, 2011 the use of oxime ether linkages for applications in chemical biology and medicinal chemistry research has increased dramatically in the past several years as the benefits of chemoselectivity have become better understood.
Oxime ethers as useful synthons in the synthesis of a number of key medicinal heteroaromatic compounds. Effect of oxime ether incorporation in acyl indole. Osubstituted oximes form a closely related family of compounds. Mar 29, 2016 heteroaromatic systems are not only prevalent in a wide variety of important classes of natural products and synthetic pharmaceuticals but are also used as a building block in organic synthesis. Oximino carbenes are useful synthons for nheterocycles, and can be easily prepared from. Oxime, oxime ether, keto ester, dna binding, antibacterial activity, antifungal activity 1. Synthesis of oximes is an important reaction in organic chemistry, because these versatile oximes are used for protection, purification, and characterization of carbonyl compounds.
The ethyl oxime ether 14 was found to have outstanding antihrv activity median ic 50 4. Oxime ethers are alternatives to nsilylimines for the synthesis of nunsubstituted. New oxime ethers and oxime esters of diphenyl ethers according to the formula wherein q a in the description defined in detail aliphatic or araliphatic ether or esterrest, r 1 is halogen or one of the groups nitro, cyano or trifluoromethyl, r 2 and r 3 are each hydrogen, halogen or one of the groups nitro or cyano, r 4 is hydrogen or halogen and x is hydrogen, halogen or one of the. Pericyclic reactions, cycloaddition reactions, reactive dienophiles, reactive dienes, electrocyclic reactions, synthetic strategy, metalcatalyzed couplings, synthetic polymers, carbohydrates or erpines, terpines, alkaloids, carbohydrates, peptides and proteins, nucleotides and nucleic acids, synthetic polymers. Unsaturated carbonylbased compounds, oxime and oxime ether analogs as potential anticancer agents for overcoming cancer multidrug resistance by modulation of efflux pumps in tumor cells. Reduction of oximes, oxime ethers, and oxime esters with. Novel radical reaction of phenylsulfonyl oxime ethers. After optimization, it was found that treatment of 2bromoacetophenone with k 2 co 3 1. A greener and onepot synthesis of novel oximes as potential cytotoxic agents. European journal of medicinal chemistry 2010, 45 1, 2537. In addition, with intramuscular injection, steroid esters are.
Synthesis, herbicidal evaluation, and structureactivity. This study provides, on the other hand, a global vision of the family starting for their fortuitous discovery, the synthesis of their derivatives, their mechanism of action widely known nowadays, the actual classification according to the chemical structure and pharmacokinetic properties, and their uses and. In the absence of tives aol9 were obtained from their oxime 2 by using methods a and b. The use of oxime ether linkages for applications in chemical biology and medicinal chemistry research has increased dramatically in the past several years as the benefits of chemoselectivity have become better understood. The majority of such reactions involve oxime ethers and usually result in formation of a new ring. This is particularly true if an oisopropylidene group is near the reactive center, in which case the nitrogencontaining substituent and the oisopropylidene group in the product are on. As a contribution to the development of novel coumarin oxime ether conjugates with therapeutically interesting properties, a series of coumarin oxime ether 1a1j was synthesised using s n 2 reaction of bromomethyl coumarins with butane2,3dione monoxime. Structural chemistry of oximes connecting repositories. An orally bioavailable oxime ether capsid binder with. The diastereoselective alkyl radical addition to chiral oxime ethers was studied with a view to preparing enantiomerically pure.
Radical addition to oxime ethers for asymmetric synthesis of. Journal of the iranian chemical society 2016, 7, 12351256. Synthesis and fungicidal activities of novel benzothiophenesubstituted oxime ether strobilurins synthesis and fungicidal activities of novel benzothiophenesubstituted oxime ether strobilurins tu, song. The regioselectivity of this reaction is consistent with a radical adding to the oxime ether to produce the more stable of the two possible adduct radicals. But lets look into the formation of oximes and hydrazones here. The literature on the structural chemistry of oxime containing compounds is prolific, as shown by an examination of the cambridge structural database csd. Oximes have numerous advantages in organic synthesis which are used for isolation, purification and characterization of aldehydes and ketones. In the presence of a ruiipheox catalyst, various optically active cyclopropyl oxime derivatives were obtained in high yields up to 99% with high enantioselectivities up to 98% ee. Chemical introduction of the oxime ether functionality in analogue 4b was successful via direct oximation of an intact vitamin d conjugated triene system.
In the presence of bf 3 oet 2, radical addition to the. Oximes proceeds to hydrolysis easily by heating in the presence of inorganic acids, leading to the formation of ketonesaldehydes and hydroxylamines. An oxime is a chemical compound belonging to the imines, with the general formula rr c n o h, where r is an organic sidechain and r may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. The synthesis of 12a, as outlined in scheme 1, was selected as a model protocol. Ep0023890a1 oxime ethers and oxime esters of diphenyl. Anisole methoxybenzene an aryl ether and a major constituent of the essential oil of anise seed. Facile nucleophilic substitution of sulfonyl oxime ethers. Victor meyer, a german scientist along with alois janny, was the first scientist to synthesize acetoximsaur also known methylglyoxime. Amidoximes are oximes of amides with general structure r 1 c. As a contribution to the development of novel coumarinoxime ether conjugates with therapeutically interesting properties, a series of coumarinoxime ether 1a1j was synthesised using s n 2 reaction of bromomethyl coumarins with butane2,3dione monoxime. Design, synthesis, and biological evaluation of novel. New chemical entities 16ene25ketone 2b and the corresponding oxime 3b and oxime ether 4b, analogues of natural calcitriol 1, were rationally designed and synthesized on a milligram scale.
In our daily life important of heterocyclic compounds are of very essential. Formation of oximes and hydrazones video khan academy. The various mass spectra showed that the mclafferty rearrangement is relatively enhanced compared with other primary fragmentation reactions by the following factors. Effect of oxime ether incorporation in acyl indole derivatives on ppar subtype selectivity. Amidoximes are oximes of amides with general structure r 1 cnohnr 2 r 3 oximes are. In an organic chemistry, largest families of organic compounds are belongs in the heterocyclic compounds. Synthesis and in vitro antiprotozoan activity of new 5nitrothiophene. It has broad range of application in medicinal chemistry and in agrochemicals products. The journal of organic chemistry 2010, 75 18, 61416148. Addition of electrophilic and heterocyclic carboncentered. This feature article introduces the preparation and synthetic utility of.
She is currently a scientist with product development consulting south san francisco, ca. Employing a rational design of thioaryl naphthylmethanone oxime ether analogs containing functional properties of various anticancer drugs, a series of compounds were identified that displayed potent cytotoxicity toward various cancer cells, out of which 4methylthiophenylnaphthalen1ylmethanone o2diethylaminoethyl oxime mnd exhibited the best safety profile. These cyclization reactions often are quite stereoselective. An asymmetric synthesis for the preparation of nonracemic amines bearing heterocyclic and heteroaromatic rings is described. And so, this reaction works, of course, for oximes or hydrazones as well. Assembly of quinoline, triazole and oxime ether in a single. Asymmetric reduction of oxime ethers promoted by chiral spiroborate esters with an o 3bn framework yunbo chu, zixing shan, dejun liu, and nannan sun j. In this study, 12 new oxime ether derivatives, which were expected to show anticonvulsant and antimicrobial activities, were synthesized. Radical addition to oxime ethers for asymmetric synthesis. Synthesis, stereochemistry and antimicrobial studies of. This book should be an inspiration to scientists in organic, medicinal chemistry, biochemistry, and biology. Dolliver, southeastern louisiana university this prf grant has afforded the pi the opportunity to establish an active undergraduate research program which has resulted in numerous presentations by students five at national acs meetings, three at regional acs meetings, and one at a louisiana academy of.
A rapid, convenient, solventless green approach for the. Cyclic polyethers that are used as phase transfer catalysts. Two series of bicyclic oxime ethers viz, 2,4diaryl3azabicyclo3. Glyoxylic oxime ethers are also good radical acceptors for heterocyclic. Conceptually new lowcalcemic oxime analogues of the. Employing a rational design of thioaryl naphthylmethanone oxime ether analogs containing functional properties of various anticancer drugs, a series of compounds were identified that displayed potent cytotoxicity toward various cancer cells, out of which 4methylthiophenylnaphthalen1ylmethanone o2diethylaminoethyl oxime mnd. The first catalytic asymmetric cyclopropanation of diazo oxime ethers with olefins was developed. A useful application of an enolateoxime ether condensation, described by weeks, volkmann and coworkers, is found in the synthesis of 6aminomethylpenicillin derivative 218, a potent. Oximes definition, structure, properties along with. Oxime ethers as useful synthons in the synthesis of a. For tbutyldimethylsilyl oxime ethers with oxygen in a. Synthesis, characterization and screening for antioxidant activity, chemicobiological interactions, vol. Highly enantioselective borane reduction of heteroaryl and.
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