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Daim ntawv tshawb fawb no qhia txog ib txoj kev ua haujlwm zoo heev rau kev tsim cov benzoxazoles siv catechol, aldehyde thiab ammonium acetate ua cov khoom noj los ntawm kev sib txuas lus hauv ethanol nrog ZrCl4 ua catalyst. Ib qho series ntawm benzoxazoles (59 hom) tau ua tiav synthesized los ntawm txoj kev no hauv cov txiaj ntsig txog li 97%. Lwm qhov zoo ntawm txoj hauv kev no suav nrog kev tsim cov khoom loj thiab kev siv oxygen ua tus neeg sawv cev oxidizing. Cov xwm txheej tsis tshua muaj zog tso cai rau kev ua haujlwm tom qab, uas ua rau kev tsim cov derivatives ntau yam nrog cov qauv biologically xws li β-lactams thiab quinoline heterocycles.
Kev tsim cov txheej txheem tshiab ntawm kev tsim cov organic uas tuaj yeem kov yeej cov kev txwv hauv kev tau txais cov tshuaj muaj nqis siab thiab ua kom lawv muaj ntau haiv neeg (kom qhib cov chaw tshiab ntawm kev siv) tau nyiam ntau qhov kev saib xyuas hauv kev kawm thiab kev lag luam1,2. Ntxiv nrog rau qhov ua tau zoo ntawm cov txheej txheem no, qhov kev phooj ywg ib puag ncig ntawm cov txheej txheem uas tau tsim kuj tseem yuav yog qhov zoo dua3,4.
Benzoxazoles yog ib pawg ntawm cov tshuaj heterocyclic uas tau nyiam ntau qhov kev saib xyuas vim lawv cov dej num nplua nuj ntawm cov kab mob. Cov tshuaj no tau tshaj tawm tias muaj cov tshuaj tua kab mob, tiv thaiv cov hlab ntsha, tiv thaiv kab mob qog noj ntshav, tiv thaiv kab mob, tiv thaiv kab mob fungal, thiab tiv thaiv kev o5,6,7,8,9,10,11. Lawv kuj siv dav hauv ntau qhov chaw lag luam suav nrog tshuaj, sensorics, agrochemistry, ligands (rau kev hloov pauv hlau catalysis), thiab cov ntaub ntawv science12,13,14,15,16,17. Vim lawv cov khoom siv tshuaj lom neeg tshwj xeeb thiab kev hloov pauv tau yooj yim, benzoxazoles tau dhau los ua cov khoom tseem ceeb rau kev tsim ntau cov organic molecules nyuaj18,19,20. Qhov nthuav yog, qee cov benzoxazoles yog cov khoom ntuj tsim tseem ceeb thiab cov tshuaj pharmacologically cuam tshuam, xws li nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 thiab neosalvianene (Daim Duab 1A)26.
(A) Piv txwv ntawm cov khoom ntuj tsim uas muaj benzoxazole thiab cov tshuaj bioactive. (B) Qee cov khoom ntuj tsim uas muaj catechols.
Catechols siv dav hauv ntau qhov chaw xws li tshuaj, tshuaj pleev ib ce thiab cov ntaub ntawv tshawb fawb27,28,29,30,31. Catechols kuj tau pom tias muaj cov khoom antioxidant thiab anti-inflammatory, ua rau lawv muaj peev xwm ua cov neeg sawv cev kho mob32,33. Cov khoom no tau ua rau nws siv rau hauv kev tsim cov tshuaj pleev ib ce tiv thaiv kev laus thiab cov khoom saib xyuas tawv nqaij34,35,36. Ntxiv mus, catechols tau pom tias yog cov khoom ua ntej zoo rau kev tsim cov organic (Daim Duab 1B)37,38. Qee cov catechols no muaj ntau heev hauv xwm. Yog li ntawd, nws siv ua cov khoom siv raw lossis cov khoom pib rau kev tsim cov organic tuaj yeem ua lub hauv paus ntsiab lus ntsuab ntawm "siv cov peev txheej rov ua dua tshiab". Muaj ntau txoj hauv kev sib txawv tau tsim los npaj cov tshuaj benzoxazole functionalized7,39. Oxidative functionalization ntawm C (aryl) -OH bond ntawm catechols yog ib qho ntawm cov txheej txheem nthuav tshaj plaws thiab tshiab rau kev tsim cov benzoxazoles. Piv txwv ntawm txoj hauv kev no hauv kev tsim cov benzoxazoles yog cov tshuaj tiv thaiv ntawm catechols nrog amines40,41,42,43,44, nrog aldehydes45,46,47, nrog cawv (lossis ethers)48, nrog rau ketones, alkenes thiab alkynes (Daim Duab 2A)49. Hauv kev tshawb fawb no, ntau yam tshuaj tiv thaiv (MCR) ntawm catechol, aldehyde thiab ammonium acetate tau siv rau kev tsim cov benzoxazoles (Daim Duab 2B). Cov tshuaj tiv thaiv tau ua tiav siv cov tshuaj catalytic ntawm ZrCl4 hauv cov kuab tshuaj ethanol. Nco ntsoov tias ZrCl4 tuaj yeem suav hais tias yog cov tshuaj catalyst Lewis acid ntsuab, nws yog cov tshuaj lom tsawg dua [LD50 (ZrCl4, qhov ncauj rau nas) = ​​1688 mg kg−1] thiab tsis suav hais tias yog cov tshuaj lom heev50. Cov tshuaj catalysts zirconium kuj tau siv ua cov tshuaj catalysts rau kev tsim cov tshuaj sib txawv ntawm cov organic. Lawv tus nqi qis thiab kev ruaj khov rau dej thiab oxygen ua rau lawv muaj cov tshuaj catalysts zoo hauv cov organic synthesis51.
Yuav kom nrhiav tau cov xwm txheej uas tsim nyog rau kev ua tshuaj, peb tau xaiv 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a thiab ammonium ntsev 3 ua cov qauv tshuaj thiab ua cov tshuaj nyob rau hauv qhov muaj ntau yam Lewis acids (LA), ntau yam solvents thiab kub los ua benzoxazole 4a (Rooj 1). Tsis muaj khoom pom nyob rau hauv qhov tsis muaj catalyst (Rooj 1, nkag 1). Tom qab ntawd, 5 mol% ntawm ntau yam Lewis acids xws li ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 thiab MoO3 tau sim ua catalysts hauv EtOH solvent thiab ZrCl4 tau pom tias yog qhov zoo tshaj plaws (Rooj 1, nkag 2–8). Txhawm rau txhim kho qhov ua tau zoo, ntau yam tshuaj yaj tau raug sim suav nrog dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) thiab dimethyl sulfoxide (DMSO). Cov txiaj ntsig ntawm tag nrho cov tshuaj yaj uas tau sim qis dua li ntawm ethanol (Rooj 1, cov ntawv nkag 9–15). Siv lwm cov chaw nitrogen (xws li NH4Cl, NH4CN thiab (NH4) 2SO4) es tsis txhob siv ammonium acetate tsis tau txhim kho cov txiaj ntsig ntawm cov tshuaj tiv thaiv (Rooj 1, cov ntawv nkag 16–18). Cov kev tshawb fawb ntxiv qhia tau tias qhov kub hauv qab thiab siab dua 60 ° C tsis tau txhim kho cov txiaj ntsig ntawm cov tshuaj tiv thaiv (Rooj 1, cov ntawv nkag 19 thiab 20). Thaum qhov kev thauj khoom catalyst tau hloov mus rau 2 thiab 10 mol%, cov txiaj ntsig yog 78% thiab 92%, feem (Rooj 1, cov ntawv nkag 21 thiab 22). Cov txiaj ntsig tau txo qis thaum qhov kev tshuaj tiv thaiv tau ua tiav hauv qab huab cua nitrogen, qhia tias cov pa oxygen hauv huab cua yuav ua lub luag haujlwm tseem ceeb hauv qhov kev tshuaj tiv thaiv (Rooj 1, nkag 23). Kev nce ntxiv ntawm ammonium acetate tsis tau txhim kho cov txiaj ntsig ntawm kev tshuaj tiv thaiv thiab txawm tias txo qis qhov txiaj ntsig (Rooj 1, nkag 24 thiab 25). Tsis tas li ntawd, tsis muaj kev txhim kho hauv qhov txiaj ntsig ntawm kev tshuaj tiv thaiv tau pom nrog kev nce ntxiv ntawm catechol (Rooj 1, nkag 26).
Tom qab txiav txim siab qhov zoo tshaj plaws ntawm cov tshuaj tiv thaiv, qhov kev hloov pauv thiab kev siv tau ntawm cov tshuaj tiv thaiv tau kawm (Daim Duab 3). Txij li thaum alkynes thiab alkenes muaj cov pab pawg ua haujlwm tseem ceeb hauv kev tsim cov organic thiab yooj yim hloov pauv ntxiv, ntau cov benzoxazole derivatives tau tsim nrog alkenes thiab alkynes (4b–4d, 4f–4g). Siv 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde ua cov aldehyde substrate (4e), cov txiaj ntsig tau txog 90%. Tsis tas li ntawd, alkyl halo-substituted benzoxazoles tau tsim hauv cov txiaj ntsig siab, uas tuaj yeem siv rau kev sib txuas nrog lwm cov molecules thiab ntxiv derivatization (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde thiab 4-(benzyloxy)benzaldehyde tau muab cov benzoxazoles sib xws 4j thiab 4k hauv cov txiaj ntsig siab, feem. Siv txoj kev no, peb tau ua tiav synthesized benzoxazole derivatives (4l thiab 4m) uas muaj quinolone moieties53,54,55. Benzoxazole 4n uas muaj ob pawg alkyne tau synthesized hauv 84% cov txiaj ntsig los ntawm 2,4-substituted benzaldehydes. Bicyclic compound 4o uas muaj indole heterocycle tau ua tiav synthesized nyob rau hauv cov xwm txheej zoo tshaj plaws. Compound 4p tau synthesized siv cov aldehyde substrate txuas rau ib pawg benzonitrile, uas yog ib qho substrate pab tau rau kev npaj ntawm (4q-4r) supramolecules56. Txhawm rau qhia txog kev siv tau ntawm txoj kev no, kev npaj ntawm benzoxazole molecules uas muaj β-lactam moieties (4q-4r) tau pom nyob rau hauv cov xwm txheej zoo tshaj plaws los ntawm kev tshuaj tiv thaiv ntawm aldehyde-functionalized β-lactams, catechol, thiab ammonium acetate. Cov kev sim no qhia tau hais tias txoj hauv kev tsim tshiab tuaj yeem siv rau kev ua haujlwm ntawm cov molecules nyuaj.
Txhawm rau kom pom tseeb ntxiv txog qhov ua tau ntau yam thiab kev kam rau ntawm txoj kev no rau cov pab pawg ua haujlwm, peb tau kawm txog ntau yam aromatic aldehydes suav nrog cov pab pawg pub electron, cov pab pawg rho electron, cov tshuaj heterocyclic, thiab polycyclic aromatic hydrocarbons (Daim Duab 4, 4s–4aag). Piv txwv li, benzaldehyde tau hloov mus rau cov khoom xav tau (4s) hauv 92% cais tawm. Aromatic aldehydes nrog cov pab pawg pub electron (suav nrog -Me, isopropyl, tert-butyl, hydroxyl, thiab para-SMe) tau hloov pauv mus rau cov khoom sib xws hauv cov txiaj ntsig zoo heev (4t–4x). Cov khoom siv aldehyde uas raug cuam tshuam los ntawm sterically tuaj yeem tsim cov khoom benzoxazole (4y–4aa, 4al) hauv cov txiaj ntsig zoo rau cov txiaj ntsig zoo heev. Kev siv cov meta-substituted benzaldehydes (4ab, 4ai, 4am) tau tso cai rau kev npaj cov khoom benzoxazole hauv cov txiaj ntsig siab. Cov aldehydes halogenated xws li (-F, -CF3, -Cl thiab Br) tau muab cov benzoxazoles sib xws (4af, 4ag thiab 4ai-4an) hauv cov txiaj ntsig zoo. Aldehydes nrog cov pab pawg electron withdrawn (piv txwv li -CN thiab NO2) kuj tau teb zoo thiab muab cov khoom xav tau (4ah thiab 4ao) hauv cov txiaj ntsig siab.
Cov tshuaj tiv thaiv siv rau kev tsim cov aldehydes a thiab b. a Cov xwm txheej tshuaj tiv thaiv: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) thiab ZrCl4 (5 mol%) tau raug tshuaj tiv thaiv hauv EtOH (3 mL) ntawm 60 ° C rau 6 teev. b Cov txiaj ntsig sib raug rau cov khoom cais tawm.
Cov aldehydes uas muaj ntxhiab ntau xws li 1-naphthaldehyde, anthracene-9-carboxaldehyde thiab phenanthrene-9-carboxaldehyde tuaj yeem tsim cov khoom xav tau 4ap-4ar hauv cov qoob loo siab. Ntau yam heterocyclic aromatic aldehydes suav nrog pyrrole, indole, pyridine, furan thiab thiophene zam cov xwm txheej tshuaj tiv thaiv zoo thiab tuaj yeem tsim cov khoom sib xws (4as-4az) hauv cov qoob loo siab. Benzoxazole 4aag tau txais hauv 52% cov qoob loo siv cov aliphatic aldehyde sib xws.
Thaj chaw tshuaj tiv thaiv siv cov aldehydes lag luam a, b. a Cov xwm txheej tshuaj tiv thaiv: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) thiab ZrCl4 (5 mol%) tau tshuaj tiv thaiv hauv EtOH (5 mL) ntawm 60 ° C rau 4 teev. b Cov txiaj ntsig sib raug rau cov khoom cais tawm. c Cov tshuaj tiv thaiv tau ua tiav ntawm 80 ° C rau 6 teev; d Cov tshuaj tiv thaiv tau ua tiav ntawm 100 ° C rau 24 teev.
Txhawm rau piav qhia ntxiv txog qhov ua tau ntau yam thiab kev siv tau ntawm txoj kev no, peb kuj tau sim ntau yam catechols hloov pauv. Monosubstituted catechols xws li 4-tert-butylbenzene-1,2-diol thiab 3-methoxybenzene-1,2-diol tau teb zoo nrog cov txheej txheem no, ua rau benzoxazoles 4aaa-4aac hauv 89%, 86%, thiab 57% cov txiaj ntsig, raws li. Qee cov polysubstituted benzoxazoles kuj tau ua tiav synthesized siv cov polysubstituted catechols sib xws (4aad-4aaf). Tsis muaj cov khoom tau txais thaum electron-deficient substituted catechols xws li 4-nitrobenzene-1,2-diol thiab 3,4,5,6-tetrabromobenzene-1,2-diol tau siv (4aah-4aai).
Kev tsim cov benzoxazole hauv cov gram ntau tau ua tiav zoo hauv qab cov xwm txheej zoo tshaj plaws, thiab cov tshuaj 4f tau tsim ua ke hauv 85% cov txiaj ntsig cais tawm (Daim Duab 5).
Kev tsim cov benzoxazole 4f uas yog gram-scale. Cov xwm txheej ntawm cov tshuaj tiv thaiv: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) thiab ZrCl4 (5 mol%) tau raug tshuaj tiv thaiv hauv EtOH (25 mL) ntawm 60 ° C rau 4 teev.
Raws li cov ntaub ntawv sau, ib txoj kev ua kom muaj kev sib xyaw ua ke ntawm benzoxazoles los ntawm catechol, aldehyde, thiab ammonium acetate nyob rau hauv qhov muaj ZrCl4 catalyst (Daim Duab 6). Catechol tuaj yeem chelate zirconium los ntawm kev sib koom ua ke ob pawg hydroxyl los tsim thawj lub hauv paus ntawm lub voj voog catalytic (I) 51. Hauv qhov no, semiquinone moiety (II) tuaj yeem tsim los ntawm enol-keto tautomerization hauv complex I58. Pawg carbonyl tsim nyob rau hauv intermediate (II) pom tseeb reacts nrog ammonium acetate los tsim intermediate imine (III) 47. Lwm qhov ua tau yog tias imine (III ^), tsim los ntawm kev sib xyaw ua ke ntawm aldehyde nrog ammonium acetate, reacts nrog carbonyl pawg los tsim intermediate imine-phenol (IV) 59,60. Tom qab ntawd, intermediate (V) tuaj yeem dhau los ntawm intramolecular cyclization40. Thaum kawg, intermediate V yog oxidized nrog atmospheric oxygen, tsim cov khoom xav tau 4 thiab tso tawm zirconium complex los pib lub voj voog tom ntej 61,62.
Tag nrho cov tshuaj reagents thiab cov kuab tshuaj tau yuav los ntawm cov chaw lag luam. Tag nrho cov khoom paub tau txheeb xyuas los ntawm kev sib piv nrog cov ntaub ntawv spectral thiab cov ntsiab lus yaj ntawm cov qauv kuaj. 1H NMR (400 MHz) thiab 13C NMR (100 MHz) spectra tau kaw rau ntawm Brucker Avance DRX ntsuas. Cov ntsiab lus yaj tau txiav txim siab ntawm Büchi B-545 apparatus hauv qhov qhib capillary. Tag nrho cov tshuaj tiv thaiv tau saib xyuas los ntawm cov txheej txheem nyias nyias (TLC) siv cov phaj silica gel (Silica gel 60 F254, Merck Chemical Company). Kev tshuaj xyuas Elemental tau ua tiav ntawm PerkinElmer 240-B Microanalyzer.
Ib qho tshuaj catechol (1.0 mmol), aldehyde (1.0 mmol), ammonium acetate (1.0 mmol) thiab ZrCl4 (5 mol%) hauv ethanol (3.0 mL) tau raug do ua ntu zus hauv ib lub raj qhib hauv ib lub dab da dej roj ntawm 60 ° C hauv qab huab cua rau lub sijhawm xav tau. Kev nce qib ntawm cov tshuaj tiv thaiv tau saib xyuas los ntawm cov txheej txheem nyias nyias chromatography (TLC). Tom qab ua tiav qhov tshuaj tiv thaiv, cov khoom sib xyaw tau txias rau qhov kub thiab txias hauv chav tsev thiab ethanol tau raug tshem tawm hauv qab qhov siab txo qis. Cov tshuaj tiv thaiv tau diluted nrog EtOAc (3 x 5 mL). Tom qab ntawd, cov txheej organic sib xyaw tau qhuav hla anhydrous Na2SO4 thiab concentrated hauv vacuo. Thaum kawg, cov khoom sib xyaw tau purified los ntawm kem chromatography siv petroleum ether/EtOAc ua eluent kom tau txais benzoxazole 4 ntshiab.
Hauv kev xaus lus, peb tau tsim ib txoj kev cai tshiab, tsis muaj teeb meem thiab ntsuab rau kev tsim cov benzoxazoles los ntawm kev tsim cov CN thiab CO bonds ua ke hauv qhov muaj zirconium catalyst. Nyob rau hauv cov xwm txheej tshuaj tiv thaiv zoo tshaj plaws, 59 benzoxazoles sib txawv tau tsim. Cov xwm txheej tshuaj tiv thaiv tau sib xws nrog ntau pawg ua haujlwm, thiab ntau lub bioactive cores tau tsim tau zoo, qhia txog lawv lub peev xwm siab rau kev ua haujlwm tom qab. Yog li ntawd, peb tau tsim ib txoj hauv kev zoo, yooj yim thiab siv tau rau kev tsim ntau yam benzoxazole derivatives los ntawm cov catechols ntuj hauv qab cov xwm txheej ntsuab siv cov catalysts pheej yig.
Tag nrho cov ntaub ntawv tau txais lossis tshuaj xyuas thaum lub sijhawm tshawb fawb no suav nrog hauv tsab xov xwm luam tawm no thiab nws cov ntaub ntawv ntxiv.
Nicolaou, Kansas City. Kev tsim cov organic: kev kos duab thiab kev tshawb fawb ntawm kev theej cov tshuaj lom neeg uas pom muaj nyob rau hauv xwm thiab tsim cov tshuaj zoo sib xws hauv chav kuaj mob. Proc. R Soc. A. 470, 2013069 (2014).
Ananikov VP et al. Kev tsim cov txheej txheem tshiab ntawm kev tsim cov organic niaj hnub: tau txais cov molecules ua haujlwm nrog atomic precision. Russ Chem. Ed. 83, 885 (2014).
Ganesh, KN, et al. Tshuaj ntsuab: Lub hauv paus rau yav tom ntej ruaj khov. Organic, Txheej Txheem, Kev Tshawb Fawb thiab Kev Txhim Kho 25, 1455–1459 (2021).
Yue, Q., et al. Cov qauv thiab cov cib fim hauv kev tsim cov organic: lub xeev ntawm cov ntsuas kev tshawb fawb thoob ntiaj teb thiab kev nce qib hauv kev ua kom raug, kev ua haujlwm zoo, thiab tshuaj ntsuab. J. Org. Chem. 88, 4031–4035 (2023).
Lee, SJ thiab Trost, BM Green tshuaj synthesis. PNAS. 105, 13197–13202 (2008).
Ertan-Bolelli, T., Yildiz, I. thiab Ozgen-Ozgakar, S. Synthesis, molecular docking thiab antibacterial kev ntsuam xyuas ntawm cov tshiab benzoxazole derivatives. Zib ntab. Chem. Res. 25, 553–567 (2016).
Sattar, R., Mukhtar, R., Atif, M., Hasnain, M. thiab Irfan, A. Kev hloov pauv hluavtaws thiab kev tshuaj xyuas bioscreening ntawm benzoxazole derivatives: kev tshuaj xyuas. Journal of Heterocyclic Chemistry 57, 2079–2107 (2020).
Yildiz-Oren, I., Yalcin, I., Aki-Sener, E. thiab Ukarturk, N. Kev sib xyaw ua ke thiab kev sib raug zoo ntawm cov qauv thiab kev ua haujlwm ntawm cov tshuaj tua kab mob tshiab uas muaj cov tshuaj polysubstituted benzoxazole derivatives. European Journal of Medicinal Chemistry 39, 291–298 (2004).
Akbay, A., Oren, I., Temiz-Arpaci, O., Aki-Sener, E. thiab Yalcin, I. Kev tsim cov tshuaj 2,5,6-substituted benzoxazole, benzimidazole, benzothiazole thiab oxazolo (4,5-b) pyridine derivatives thiab lawv cov kev ua ub no inhibitory tiv thaiv HIV-1 reverse transcriptase. Arzneimittel-Forschung/Drug Res. 53, 266–271 (2003).
Osmanieh, D. et al. Kev tsim cov tshuaj benzoxazole tshiab thiab kev kawm txog lawv cov haujlwm tiv thaiv kab mob qog noj ntshav. European Journal of Medicinal Chemistry 210, 112979 (2021).
Rida, SM, et al. Qee cov tshuaj benzoxazole tshiab tau raug tsim los ua cov tshuaj tua kab mob qog noj ntshav, tshuaj tua kab mob HIV-1, thiab cov tshuaj tua kab mob. European Journal of Medicinal Chemistry 40, 949–959 (2005).
Demmer, KS thiab Bunch, L. Kev siv benzoxazoles thiab oxazolopyridines hauv kev tshawb fawb txog tshuaj lom neeg. European Journal of Medicinal Chemistry 97, 778–785 (2015).
Paderni, D., et al. Ib qho tshiab benzoxazolyl-based fluorescent macrocyclic chemosensor rau kev pom ntawm Zn2 + thiab Cd2 +. Chemical Sensors 10, 188 (2022).
Zou Yan et al. Kev nce qib hauv kev kawm txog benzothiazole thiab benzoxazole derivatives hauv kev tsim cov tshuaj tua kab. Int. J Mol. Sci. 24, 10807 (2023).
Wu, Y. et al. Ob lub Cu(I) complexes uas tsim los ntawm cov sib txawv N-heterocyclic benzoxazole ligands: kev sib xyaw ua ke, cov qauv, thiab cov khoom fluorescence. J. Mol. Struct. 1191, 95–100 (2019).
Walker, KL, Dornan, LM, Zare, RN, Weymouth, RM, thiab Muldoon, MJ Txoj kev ua haujlwm ntawm catalytic oxidation ntawm styrene los ntawm hydrogen peroxide nyob rau hauv lub xub ntiag ntawm cationic palladium (II) complexes. Phau ntawv xov xwm ntawm American Chemical Society 139, 12495–12503 (2017).
Agag, T., Liu, J., Graf, R., Spiess, HW, thiab Ishida, H. Benzoxazole resins: Ib chav kawm tshiab ntawm thermosetting polymers uas tau los ntawm cov ntse benzoxazine resins. Macromolecule, Rev. 45, 8991–8997 (2012).
Basak, S., Dutta, S. thiab Maiti, D. Kev tsim cov C2-functionalized 1,3-benzoxazoles los ntawm kev hloov pauv hlau-catalyzed C-H activation txoj hauv kev. Chemistry - Ib phau ntawv xov xwm European 27, 10533–10557 (2021).
Singh, S., et al. Kev nce qib tsis ntev los no hauv kev tsim cov tshuaj pharmacologically active uas muaj cov pob txha benzoxazole. Asian Journal of Organic Chemistry 4, 1338–1361 (2015).
Wong, XK thiab Yeung, KY. Kev tshuaj xyuas patent ntawm qhov xwm txheej tam sim no ntawm cov tshuaj benzoxazole. KhimMedKhim. 16, 3237–3262 (2021).
Ovenden, SPB, et al. Sesquiterpenoid benzoxazoles thiab sesquiterpenoid quinones los ntawm cov dej hiav txwv Dactylospongia elegans. J. Nat. Proc. 74, 65–68 (2011).
Kusumi, T., Ooi, T., Wülchli, MR, thiab Kakisawa, H. Cov qauv ntawm cov tshuaj tua kab mob tshiab boxazomysins a, B, thiab CJ Am. Chem. Soc. 110, 2954–2958 (1988).
Cheney, ML, DeMarco, PW, Jones, ND, thiab Occolowitz, JL Cov qauv ntawm divalent cationic ionophore A23187. Phau ntawv xov xwm ntawm American Chemical Society 96, 1932–1933 (1974).
Park, J., thiab lwm tus. Tafamidis: thawj zaug hauv chav kawm transthyretin stabilizer rau kev kho mob ntawm transthyretin amyloid cardiomyopathy. Annals of Pharmacotherapy 54, 470–477 (2020).
Sivalingam, P., Hong, K., Pote, J. thiab Prabakar, K. Streptomyces nyob rau hauv ib puag ncig hnyav: Ib qho chaw muaj peev xwm ntawm cov tshuaj tua kab mob tshiab thiab tshuaj tiv thaiv kab mob qog noj ntshav? International Journal of Microbiology, 2019, 5283948 (2019).
Pal, S., Manjunath, B., Gorai, S. thiab Sasmal, S. Benzoxazole alkaloids: qhov tshwm sim, chemistry thiab biology. Chemistry thiab Biology ntawm Alkaloids 79, 71–137 (2018).
Shafik, Z., et al. Kev sib txuas ntawm cov khoom siv bionic hauv qab dej thiab kev tshem tawm cov nplaum raws li qhov xav tau. Applied Chemistry 124, 4408–4411 (2012).
Lee, H., Dellatore, SM, Miller, VM, thiab Messersmith, PB Mussel-inspired surface chemistry rau multifunctional coatings. Science 318, 420–426 (2007).
Nasibipour, M., Safai, E., Wrzeszcz, G., thiab Wojtczak, A. Kho qhov muaj peev xwm redox thiab kev ua haujlwm catalytic ntawm ib qho tshiab Cu (II) complex siv O-iminobenzosemiquinone ua ib qho electron-storage ligand. Kaum Ib Hlis Russ. Chemistry, 44, 4426–4439 (2020).
D'Aquila, PS, Collu, M., Jessa, GL thiab Serra, G. Lub luag haujlwm ntawm dopamine hauv cov txheej txheem ntawm kev ua haujlwm ntawm cov tshuaj antidepressants. European Journal of Pharmacology 405, 365–373 (2000).