Murakoze gusura nature.com. Verisiyo ya mushakisha ukoresha ifite ubufasha buke bwa CSS. Kugira ngo ubone uburambe bwiza, turakugira inama yo gukoresha verisiyo igezweho ya mushakisha (cyangwa kuzimya uburyo bwo guhuza na interineti muri Internet Explorer). Byongeye kandi, kugira ngo ukomeze gushyigikira, uru rubuga ntiruzaba rurimo imiterere cyangwa JavaScript.
Ubu bushakashatsi bugaragaza uburyo bwiza cyane bwo gukora benzoxazole hakoreshejwe catechol, aldehyde na ammonium acetate nk'ibiribwa binyuze mu guhuza ethanol na ZrCl4 nk'umusemburo. Uruhererekane rwa benzoxazole (ubwoko 59) rwakozwe neza n'ubu buryo ku musaruro ugera kuri 97%. Izindi nyungu z'ubu buryo zirimo gukora cyane no gukoresha ogisijeni nk'ikintu gitanga ogisijeni. Imiterere yoroheje y'ibikorwa ituma habaho imikorere myiza, ibyo bikaba byoroshya gukora ibintu bitandukanye bifite imiterere ijyanye n'ibinyabuzima nka β-lactam na quinoline heterocycles.
Iterambere ry'uburyo bushya bwo gukora imvange y'ibinyabuzima bushobora gutsinda imbogamizi mu kubona imvange z'agaciro kanini no kongera ubudasa bwazo (kugira ngo haboneke ahantu hashya hashobora gukoreshwa) byakuruye ibitekerezo byinshi mu mashuri makuru no mu nganda1,2. Uretse imikorere myiza y'ubu buryo, uburyo burimo gukorwa buzaba bwiza ku bidukikije nabwo buzaba inyungu ikomeye3,4.
Benzoxazole ni ubwoko bw'ibinyabutabire bitagira ikirere byakuruye abantu benshi bitewe n'ibikorwa byabyo byinshi bya biyoloji. Ibinyabutabire nk'ibi byavuzwe ko bifite ibikorwa byo kurwanya mikorobe, kurinda ubwonko, kurwanya kanseri, kurwanya virusi, kurwanya bagiteri, kurwanya mikorobe, no kurwanya ububyimbirwe5,6,7,8,9,10,11. Binakoreshwa cyane mu nganda zitandukanye harimo imiti, sensorics, agrochimie, ligands (yo guhindura metal catalysis), na materials science12,13,14,15,16,17. Bitewe n'imiterere yabyo yihariye ya shimi n'uburyo butandukanye bwo gukora, benzoxazole zabaye ingenzi mu gukora molekile nyinshi zikomeye za organic18,19,20. Igishimishije ni uko zimwe muri benzoxazole ari ibintu by'ingenzi karemano kandi bifite akamaro mu mikorere ya farumasi, nka nakijinol21, boxazomycin A22, calcimycin23, tafamidis24, cabotamycin25 na neosalvianene (Ishusho ya 1A)26.
(A) Ingero z'ibikomoka ku bimera karemano bishingiye kuri benzoxazole n'ibinyabutabire bikora ku buzima. (B) Amwe mu masoko karemano ya katekoli.
Catechol zikoreshwa cyane mu nzego nyinshi nko mu by’imiti, ubwiza n’ubumenyi bw’ibikoresho27,28,29,30,31. Catechols nazo zagaragaye ko zifite ubushobozi bwo kurwanya uburozi n’ububyimbirwe, bigatuma zishobora kuba imiti ivura32,33. Iyi miterere yatumye zikoreshwa mu guteza imbere ubwiza burwanya gusaza n’ibicuruzwa byo kwita ku ruhu34,35,36. Byongeye kandi, catechols zagaragaye ko ari ingenzi mu gukora ubwiza bw’ibinyabuzima (Ishusho ya 1B)37,38. Zimwe muri izi catechols ziraboneka cyane. Kubwibyo, ikoreshwa ryazo nk'ibikoresho fatizo cyangwa ibikoresho byo gutangira gukora ubwiza bw’ibinyabuzima bishobora kuba ihame rya "gukoresha umutungo kamere". Hakozwe inzira zitandukanye zo gutegura imvange ya benzoxazole ikora7,39. Imikorere ya oxidative y’umugozi wa C(aryl)-OH wa catechols ni bumwe mu buryo bushimishije kandi bushya bwo gukora benzoxazoles. Ingero z'ubu buryo mu gukora benzoxazole ni uburyo catechols zirimo amines40,41,42,43,44, hamwe na aldehydes45,46,47, hamwe na alcools (cyangwa ethers)48, ndetse na ketones, alkenes na alkynes (Ishusho ya 2A)49. Muri ubu bushakashatsi, hakoreshejwe uburyo bwinshi bwo gukora benzoxazole (Ishusho ya 2B). Uburyo bwo gukora bwakoreshejwe ingano ya ZrCl4 mu gukamura ethanol. Menya ko ZrCl4 ishobora gufatwa nk'icyatsi kibisi cya Lewis acid catalyst, ni ikintu kidahumanya cyane [LD50 (ZrCl4, ikoreshwa mu kanwa ku mbeba) = 1688 mg kg−1] kandi ntifatwa nk'ikintu gifite uburozi bwinshi50. Catalysts za Zirconium nazo zakoreshejwe neza nk'uburyo bwo gukora ibintu bitandukanye by'umwimerere. Ibiciro byazo biri hasi kandi zihamye cyane ku mazi na ogisijeni bituma ziba katalysts nziza mu gukora organic synthesis51.
Kugira ngo tubone uburyo bukwiye bwo gukora, twahisemo 3,5-di-tert-butylbenzene-1,2-diol 1a, 4-methoxybenzaldehyde 2a n'umunyu wa ammonium 3 nk'icyitegererezo cy'ibikorwa kandi twakoze ibikorwa imbere y'aside zitandukanye za Lewis (LA), ibinyabutabire bitandukanye n'ubushyuhe kugira ngo dukore benzoxazole 4a (Imbonerahamwe ya 1). Nta kintu cyagaragaye mu gihe nta catalyst irimo (Imbonerahamwe ya 1, igice cya 1). Nyuma yaho, 5 mol % ya aside zitandukanye za Lewis nka ZrOCl2.8H2O, Zr(NO3)4, Zr(SO4)2, ZrCl4, ZnCl2, TiO2 na MoO3 byageragejwe nk'ibinyabutabire muri EtOH solvent maze ZrCl4 iboneka ko ari yo nziza kurusha izindi (Imbonerahamwe ya 1, igice cya 2–8). Kugira ngo kunoze imikorere, hageragejwe imiti itandukanye irimo dioxane, acetonitrile, ethyl acetate, dichloroethane (DCE), tetrahydrofuran (THF), dimethylformamide (DMF) na dimethyl sulfoxide (DMSO). Umusaruro w'imiti yose yageragejwe wari muto ugereranije n'uwa ethanol (Imbonerahamwe ya 1, inyandiko 9-15). Gukoresha andi masoko ya azote (nka NH4Cl, NH4CN na (NH4)2SO4) aho gukoresha ammonium acetate ntibyazamuye umusaruro w'ibisubizo (Imbonerahamwe ya 1, inyandiko 16-18). Ubushakashatsi bwakozwe bwagaragaje ko ubushyuhe buri munsi ya 60 °C no hejuru yayo butazamuye umusaruro w'ibisubizo (Imbonerahamwe ya 1, inyandiko 19 na 20). Igihe catalyst yahindukaga mol 2 na 10%, umusaruro wari 78% na 92%, uko bikurikirana (Imbonerahamwe ya 1, inyandiko 21 na 22). Umusaruro waragabanutse ubwo igikorwa cyakorwaga munsi y’ikirere cya azote, bigaragaza ko ogisijeni yo mu kirere ishobora kugira uruhare runini mu gikorwa (Imbonerahamwe ya 1, igice cya 23). Kongera ingano ya acetate ya ammonium ntibyazamuye umusaruro w’ibikorwa ndetse binagabanya umusaruro (Imbonerahamwe ya 1, igice cya 24 na 25). Byongeye kandi, nta ntambwe yazamutse mu musaruro w’ibikorwa byagaragaye mu kongera ingano ya catechol (Imbonerahamwe ya 1, igice cya 26).
Nyuma yo kumenya imiterere myiza y’imyanzuro, hakozwe ubushakashatsi ku buryo bwo gukora ibintu bitandukanye no gukoresha neza imyanzuro (Ishusho ya 3). Kubera ko alkynes na alkenes zifite amatsinda y’ingenzi mu gukora ibintu bikomoka ku binyabuzima kandi bikaba byoroshye kubikuramo, ibintu byinshi bikomoka kuri benzoxazole byakozwe hamwe na alkenes na alkynes (4b–4d, 4f–4g). Hakoreshejwe 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde nk'igice cya aldehyde (4e), umusaruro wageze kuri 90%. Byongeye kandi, benzoxazole zahinduwe na alkyl halo zakozwe mu musaruro mwinshi, zishobora gukoreshwa mu guhuza n’izindi molekile no kongera kuzikuramo (4h–4i) 52. 4-((4-fluorobenzyl)oxy)benzaldehyde na 4-(benzylloxy)benzaldehyde byatanze benzoxazoles 4j na 4k mu musaruro mwinshi, uko bikurikirana. Dukoresheje ubu buryo, twashoboye gukora ibikomoka kuri benzoxazole (4l na 4m) birimo quinolone moieties53,54,55. Benzoxazole 4n irimo amatsinda abiri ya alkyne yakozwe ku kigero cya 84% bivuye kuri benzaldehyde 2,4-substituted. Bicyclic compound 4o irimo indole heterocycle yakozwe neza mu buryo bwiza. Compound 4p yakozwe hakoreshejwe substrate ya aldehyde ifatanye n'itsinda rya benzonitrile, ikaba ari substrate y'ingirakamaro mu gutegura supramolecule (4q-4r)56. Kugira ngo tugaragaze uburyo ubu buryo bukoreshwa, gutegura molekile za benzoxazole zirimo β-lactam moieties (4q-4r) byagaragaye mu buryo bwiza binyuze mu buryo bwa aldehyde-functionalized β-lactams, catechol, na ammonium acetate. Ubu bushakashatsi bwerekana ko uburyo bushya bwo gukora bushobora gukoreshwa mu gukora molekile zikomeye mu cyiciro cya nyuma.
Kugira ngo turusheho kugaragaza uburyo ubu buryo bukoreshwa mu gukora ibintu bitandukanye no kwihanganira amatsinda y’imikorere, twize ku bintu bitandukanye bya aldehyde bihumura birimo amatsinda atanga electron, amatsinda akura electron, ibintu bya heterocyclic, na hydrocarbons zihumura za polycyclic (Ishusho ya 4, 4s-4aag). Urugero, benzaldehyde yahinduwe umusaruro wifuza (4s) mu musaruro wa 92% w’ibikomoka ku bintu bitandukanye. Aldehyde zihumura hamwe n’amatsinda atanga electron (harimo -Me, isopropyl, tert-butyl, hydroxyl, na para-SMe) zahinduwe neza mu musaruro ujyanye nazo mu musaruro mwiza (4t-4x). Substrates za aldehyde zikumirwa na sterile zishobora gukora ibicuruzwa bya benzoxazole (4y-4aa, 4al) mu musaruro mwiza kugeza ku musaruro mwiza. Gukoresha benzaldehyde za meta-substituted (4ab, 4ai, 4am) byatumye hategurwa ibicuruzwa bya benzoxazole mu musaruro mwinshi. Aldehydes za halogenated nka (-F, -CF3, -Cl na Br) zatanze benzoxazoles zijyanye nazo (4af, 4ag na 4ai-4an) mu musaruro ushimishije. Aldehydes zifite amatsinda akura electron (urugero -CN na NO2) nazo zakiriye neza kandi zitanga umusaruro wifuza (4ah na 4ao) mu musaruro mwinshi.
Urukurikirane rw'ibisubizo byakoreshejwe mu gukora aldehydes a na b. a Imiterere y'ibisubizo: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) na ZrCl4 (5 mol%) byasubijwe muri EtOH (3 mL) kuri 60 °C mu gihe cy'amasaha 6. b Umusaruro uhuye n'umusaruro wakuwemo.
Aldehyde zihumura neza nka 1-naphthaldehyde, anthracene-9-carboxaldehyde na phenanthrene-9-carboxaldehyde zishobora gutanga umusaruro wifuza wa 4ap-4ar mu musaruro mwinshi. Aldehyde zitandukanye zihumura neza harimo pyrrole, indole, pyridine, furan na thiophene zihanganira imiterere y’ingaruka neza kandi zishobora gutanga umusaruro ujyanye na zo (4as-4az) mu musaruro mwinshi. Benzoxazole 4aag yabonetse mu musaruro wa 52% hakoreshejwe alifatique ijyanye na yo.
Agace k'ibizamini byakoreshejwe aldehydes zo mu bucuruzi a, b. a Imiterere y'ibizamini: 1 (1.0 mmol), 2 (1.0 mmol), 3 (1.0 mmol) na ZrCl4 (5 mol %) byasubijwe muri EtOH (5 mL) kuri 60 °C mu gihe cy'amasaha 4. b Umusaruro uhuye n'umusaruro wakuwemo. c Ibizamini byakorewe kuri 80 °C mu gihe cy'amasaha 6; d Ibizamini byakorewe kuri 100 °C mu gihe cy'amasaha 24.
Kugira ngo turusheho kugaragaza uburyo ubu buryo bukoreshwa n’uburyo bukoreshwa, twagerageje kandi catechol zitandukanye zasimbuwe. Catechol zasimbuwe na mono-substituted nka 4-tert-butylbenzene-1,2-diol na 3-methoxybenzene-1,2-diol zakoze neza n’iyi protocole, zitanga benzoxazoles 4aaa-4aac ku musaruro wa 89%, 86%, na 57%. Amwe muri benzoxazoles zasimbuwe na poly-substituted nazo zakozwe neza hakoreshejwe catechols zasimbuwe na poly-substituted (4aad-4aaf). Nta bicuruzwa byabonetse igihe hakoreshwaga catechols zasimbuwe zidafite electron nka 4-nitrobenzene-1,2-diol na 3,4,5,6-tetrabromobenzene-1,2-diol (4aah-4aai).
Gukora benzoxazole mu gipimo cya garama byakozwe neza mu buryo bwiza, kandi imvange ya 4f yakozwe mu musaruro wa 85% (Ishusho ya 5).
Ikorwa rya benzoxazole 4f mu gipimo cya gram. Imiterere y'ingaruka: 1a (5.0 mmol), 2f (5.0 mmol), 3 (5.0 mmol) na ZrCl4 (5 mol%) byakozwe muri EtOH (25 mL) kuri 60 °C mu gihe cy'amasaha 4.
Hashingiwe ku makuru yavuye mu nyandiko, hatanzwe uburyo bwo gukora isuzuma rifatika mu gukora benzoxazole ziva muri catechol, aldehyde, na acetate ya ammonium imbere ya katalyst ya ZrCl4 (Ishusho ya 6). Catechol ishobora gukurura zirconium ihuza amatsinda abiri ya hydroxyl kugira ngo ikore igice cya mbere cy’uruziga rwa katalyst (I) 51. Muri iki gihe, igice cya semiquinone (II) gishobora gukorwa binyuze muri enol-keto tautomerization muri complex I58. Itsinda rya karuboneli ryakozwe mu gice cya kabiri (II) bigaragara ko rikorana na acetate ya ammonium kugira ngo rikore imine ya hagati (III) 47. Ikindi gishoboka ni uko imine (III^), ikorwa n’ihinduka rya aldehyde na acetate ya ammonium, ikorana n’itsinda rya karuboneli kugira ngo ikore imine-phenol ya hagati (IV) 59,60. Nyuma yaho, igice cya kabiri (V) gishobora gukora cyclization ya intramolecular40. Amaherezo, hagati ya V iterwa ogisijeni n'umwuka wa ogisijeni, igatanga umusaruro wifuza 4 hanyuma igasohora zirconium complex kugira ngo itangire cycle ikurikira 61,62.
Ibintu byose bihindura imiterere n'imiti byaguzwe mu masoko y'ubucuruzi. Ibicuruzwa byose bizwi byagaragaye hagereranyijwe amakuru ya spectral n'uduce dushonga tw'ibipimo byapimwe. 1H NMR (400 MHz) na 13C NMR (100 MHz) spectra byafashwe ku gikoresho cya Brucker Avance DRX. Agace gashonga kagenwe ku gikoresho cya Büchi B-545 mu muyoboro ufunguye. Ibyibandwaho byose byagenzuwe hakoreshejwe chromatography y'urwego ruto (TLC) hakoreshejwe plaque za silica gel (Silica gel 60 F254, Merck Chemical Company). Isesengura ry'ibice ryakozwe kuri PerkinElmer 240-B Microanalyzer.
Umuti wa catechol (1.0 mmol), aldehyde (1.0 mmol), acetate ya ammonium (1.0 mmol) na ZrCl4 (5 mol %) muri ethanol (3.0 mL) wagiye uvangwa mu muyoboro ufunguye mu bwogero bw'amavuta kuri 60 °C munsi y'umwuka mu gihe gisabwa. Iterambere ry'umuti ryagenzuwe hakoreshejwe chromatography y'urwego ruto (TLC). Nyuma yo kurangiza umuti, uruvange rwavuyemo rwakonjeshejwe kugeza ku bushyuhe bw'icyumba maze ethanol ikurwaho ku gitutu gito. Uruvange rw'umuti rwavanzwe na EtOAc (3 x 5 mL). Hanyuma, ibice bya organic byahujwe byamanitswe kuri Na2SO4 idafite amazi hanyuma byinjizwa mu cyuma gisukuye. Amaherezo, uruvange rw'ifu rwatunganyijwe hakoreshejwe chromatography y'inkingi hakoreshejwe peteroli ether/EtOAc kugira ngo haboneke benzoxazole 4 nziza.
Muri make, twakoze protocole nshya, yoroheje kandi y’icyatsi kibisi yo gukora benzoxazole binyuze mu gushyiraho imigozi ya CN na CO mu gihe hari catalyst ya zirconium. Mu gihe cy’imikorere myiza, benzoxazole 59 zitandukanye zakozwe. Imiterere y’imikorere irahuye n’amatsinda atandukanye y’imikorere, kandi ingingo nyinshi zikora neza zakozwe neza, bigaragaza ko zishobora gukora nyuma. Kubwibyo, twashyizeho ingamba nziza, zoroshye kandi zifatika zo gukora ku bwinshi ibintu bitandukanye bya benzoxazole biva muri catechol karemano mu gihe cy’ibidukikije hakoreshejwe catalyst zihendutse.
Amakuru yose yabonetse cyangwa yasesenguwe muri ubu bushakashatsi ari muri iyi nkuru yasohotse ndetse n'amadosiye yayo y'amakuru y'inyongera.
Nicolaou, Kansas City. Gukora organic synthesis: ubuhanga n'ubumenyi bwo kwigana molekile z'ibinyabuzima ziboneka mu bidukikije no gukora molekile zisa muri laboratwari. Proc. R Soc. A. 470, 2013069 (2014).
Ananikov VP n'abandi. Iterambere ry'uburyo bushya bwo gukora synthesis igezweho ya organic selective: kubona molekile zikora neza zifite ubushobozi bwa atome. Russ Chem. Ed. 83, 885 (2014).
Ganesh, KN, n'abandi. Ubutabire bw'icyatsi kibisi: Umusingi w'ejo hazaza harambye. Organic, Process, Research and Development 25, 1455–1459 (2021).
Yue, Q., n'abandi. Inzira n'amahirwe mu guhuza ibinyabuzima: imiterere y'ubushakashatsi ku isi n'iterambere mu buhanga, imikorere myiza, na chimie y'ibidukikije. J. Org. Chem. 88, 4031–4035 (2023).
Lee, SJ na Trost, ikorwa ry’ibinyabutabire bya BM Green. PNAS. 105, 13197–13202 (2008).
Ertan-Bolelli, T., Yildiz, I. na Ozgen-Ozgakar, S. Gukora, gufunga molekile no gusuzuma imiti mishya ikomoka kuri benzoxazole. Ubuki. Chem. Res. 25, 553–567 (2016).
Sattar, R., Mukhtar, R., Atif, M., Hasnain, M. na Irfan, A. Impinduka mu buryo bw'ubukorano no gusuzuma ibikomoka kuri benzoxazole: isuzuma. Ikinyamakuru cya Heterocyclic Chemistry 57, 2079–2107 (2020).
Yildiz-Oren, I., Yalcin, I., Aki-Sener, E. na Ukarturk, N. Isano hagati y’imikorere n’imiterere y’imiti mishya ikomoka kuri benzoxazole ikora ku buryo irwanya udukoko. Ikinyamakuru cy’Uburayi cy’Ubutabire bw’Imiti 39, 291–298 (2004).
Akbay, A., Oren, I., Temiz-Arpaci, O., Aki-Sener, E. na Yalcin, I. Gukora imiti ikomoka kuri benzoxazole, benzimidazole, benzothiazole na oxazolo (4,5-b) pyridine yasimbuwe na 2,5,6 hamwe n'imikorere yayo yo gukumira virusi ya HIV-1 reverse transcriptase. Arzneimittel-Forschung/Drug Res. 53, 266–271 (2003).
Osmanieh, D. et al. Gukora bimwe mu bikomoka kuri benzoxazole bishya no kwiga imikorere yabyo yo kurwanya kanseri. Ikinyamakuru cy’Uburayi cy’Ubutabire bw’Imiti 210, 112979 (2021).
Rida, SM, n'abandi. Hari imiti mishya ikomoka kuri benzoxazole yakozwe nk'imiti irwanya kanseri, irwanya agakoko gatera SIDA-1, n'imiti irwanya udukoko. Ikinyamakuru cy'Uburayi cy'Ubutabire bw'Imiti 40, 949–959 (2005).
Demmer, KS na Bunch, L. Gukoresha benzoxazoles na oxazolopyridines mu bushakashatsi ku buhanga mu by'imiti. Ikinyamakuru cy'Uburayi cy'Ubutabire mu by'Imiti 97, 778–785 (2015).
Paderni, D., n'abandi. Isensa nshya ya macrocyclic fluorescent ishingiye kuri benzoxazolyl yo gupima Zn2+ na Cd2+. Sensa za Chemical 10, 188 (2022).
Zou Yan n'abandi. Iterambere mu bushakashatsi ku miti ikomoka kuri benzothiazole na benzoxazole mu iterambere ry'imiti yica udukoko. Int. J Mol. Sci. 24, 10807 (2023).
Wu, Y. n'abandi. Ibice bibiri bya Cu(I) byubatswe na ligand zitandukanye za N-heterocyclic benzoxazole: synthesis, structure, na fluorescence. J. Mol. Struct. 1191, 95–100 (2019).
Walker, KL, Dornan, LM, Zare, RN, Weymouth, RM, na Muldoon, MJ Uburyo bwo gusohora stirene hakoreshejwe peroxide ya hydrogen imbere y’ibice bya palladium (II) bya cationic. Ikinyamakuru cya American Chemical Society 139, 12495–12503 (2017).
Agag, T., Liu, J., Graf, R., Spiess, HW, na Ishida, H. Resine za Benzoxazole: Ubwoko bushya bwa polymeri zikoresha thermosetting zikomoka kuri resine za benzoxazine zigezweho. Macromolecule, Rev. 45, 8991–8997 (2012).
Basak, S., Dutta, S. na Maiti, D. Gutunganya C2-functional 1,3-benzoxazoles binyuze mu buryo bwo gukora C-H bukoresha ibyuma. Ubutabire – Ikinyamakuru cy’i Burayi 27, 10533–10557 (2021).
Singh, S., n'abandi. Iterambere riherutse mu iterambere ry'ibintu bikora mu buvuzi birimo ibisigazwa bya benzoxazole. Ikinyamakuru cya Asian Journal of Organic Chemistry 4, 1338–1361 (2015).
Wong, XK na Yeung, KY. Isuzuma ry'ipatanti ry'uko umuti wa benzoxazole uhagaze ubu. KhimMedKhim. 16, 3237–3262 (2021).
Ovenden, SPB, n'abandi. Sesquiterpenoid benzoxazoles na sesquiterpenoid quinones biva muri siponji yo mu mazi Dactylospongia elegans. J. Nat. Proc. 74, 65–68 (2011).
Kusumi, T., Ooi, T., Wülchli, MR, na Kakisawa, H. Imiterere y'imiti mishya ya antibiyotike boxazomycins a, B, na CJ Am. Chem. Soc. 110, 2954–2958 (1988).
Cheney, ML, DeMarco, PW, Jones, ND, na Occolowitz, JL Imiterere ya divalent cationic ionophore A23187. Ikinyamakuru cy’Umuryango w’Abanyamerika w’Ibinyabutabire 96, 1932–1933 (1974).
Park, J., et al. Tafamidis: umuti utuma umuntu ahora atekereza ku ndwara ya transthyretin amyloid cardiomyopathy. Annals of Pharmacotherapy 54, 470–477 (2020).
Sivalingam, P., Hong, K., Pote, J. na Prabakar, K. Streptomyces mu bihe bikomeye by’ibidukikije: Ese hari isoko ishobora gutera imiti mishya irwanya udukoko na kanseri? Ikinyamakuru Mpuzamahanga cya Microbiology, 2019, 5283948 (2019).
Pal, S., Manjunath, B., Gorai, S. na Sasmal, S. Alkaloids za Benzoxazole: kubaho, chimie na biology. Chimie na biology ya Alkaloids 79, 71–137 (2018).
Shafik, Z., n'abandi. Guhuza munsi y'amazi na Bionic no gukuraho kole igihe cyose bikenewe. Applied Chemistry 124, 4408–4411 (2012).
Lee, H., Dellatore, SM, Miller, VM, na Messersmith, PB Ubutabire bwo hejuru bwahumetswe n'ibimera byo mu bwoko bwa Mussel mu gusiga irangi ry'imikorere myinshi. Science 318, 420–426 (2007).
Nasibipour, M., Safai, E., Wrzeszcz, G., na Wojtczak, A. Guhindura ubushobozi bwa redox n'imikorere ya catalytic ya complex nshya ya Cu (II) hakoreshejwe O-iminobenzosemiquinone nk'umuyoboro w'ububiko bwa electron. Ugushyingo. Russ. Chemistry, 44, 4426–4439 (2020).
D'Aquila, PS, Collu, M., Jessa, GL na Serra, G. Uruhare rwa dopamine mu mikorere y'imiti igabanya ubukana. Ikinyamakuru cy'Uburayi cy'Imiti 405, 365–373 (2000).