Gotowe bibliografie tematyczne / [3.3.0]furofuranone

Gotowa bibliografia na temat „[3.3.0]furofuranone”

Autor: Grafiati
Data publikacji: 8 czerwca 2024

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Artykuły w czasopismach na temat "[3.3.0]furofuranone"

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Peng, Xiao-Shui, Ridge Michael P. Ylagan, Yuk Ming Siu i Henry N. C. Wong. "Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis". Chemistry - An Asian Journal 10, nr 10 (20.07.2015): 2070–83. http://dx.doi.org/10.1002/asia.201500288.

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Peng, Xiao-Shui, Ridge Michael P. Ylagan, Yuk Ming Siu i Henry N. C. Wong. "ChemInform Abstract: Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis". ChemInform 46, nr 46 (27.10.2015): no. http://dx.doi.org/10.1002/chin.201546255.

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Kojic, Vesna, Milos Svircev, Sanja Djokic, Ivana Kovacevic, Marko Rodic, Bojana Sreco-Zelenovic, Velimir Popsavin i Mirjana Popsavin. "Synthesis and antiproliferative activity of new thiazole hybrids with [3.3.0]furofuranone or tetrahydrofuran scaffolds". Journal of the Serbian Chemical Society, nr 00 (2023): 2. http://dx.doi.org/10.2298/jsc221130002k.

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New thiazole hybrids were synthesized and evaluated for their in vitro cytotoxicity against a panel of human malignant cell lines. The key steps in the synthesis of hybrids 3-7 involved the initial condensation of appropriate aldononitriles with cysteine ethyl ester hydrochloride, followed by subsequent treatment of resulting thiazolines with DBU to form the thiazole ring. Bioiso-steres 8 and 14 have been prepared after the stereoselective addition of 2-(tri-methylsilyl)thiazole to the hemiacetals obtained by periodate cleavage of terminal diol functionality in the suitably protected D-glucose derivatives. The obtained analogues showed various antiproliferative activities in the cultures of several tumour cell lines. Hybrid 6 was the most potent in HeLa cells, exhibiting more than 10 and 4 times stronger activity than both leads 1 and 2, respectively. The most active compound in Raji cells was hybrid 12, which was nearly 2-fold more potent than the clinical antitumour drug doxorubicin. All analogues were more potent in A549 cells with respect to lead 1, while compounds 6 and 7 were slightly more active than DOX. Preliminary SAR analysis revealed that the presence of a cinnamate group at the C-3 position in analogues of type 7 increases the activity of resulting molecular hybrids.
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Ariztia, Julen, Alicia Chateau, Cédric Boura, Claude Didierjean, Sandrine Lamandé-Langle i Nadia Pellegrini Moïse. "Synthesis of anti-proliferative [3.3.0]furofuranone derivatives by lactonization and functionalization of C-glycosyl compounds". Bioorganic & Medicinal Chemistry 45 (wrzesień 2021): 116313. http://dx.doi.org/10.1016/j.bmc.2021.116313.

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Rios, María Y., Yordin D. Ocampo-Acuña, M. Ángeles Ramírez-Cisneros i María E. Salazar-Rios. "Furofuranone Lignans from Leucophyllum ambiguum". Journal of Natural Products 83, nr 5 (2.04.2020): 1424–31. http://dx.doi.org/10.1021/acs.jnatprod.9b00759.

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Swain, Nigel A., Richard C. D. Brown i Gordon Bruton. "An efficient synthesis of endo,exo-furofuranone derivatives". Chemical Communications, nr 18 (13.08.2002): 2042–43. http://dx.doi.org/10.1039/b206150c.

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Marchand, Patrice A., Norman G. Lewis i Jaroslav Zajicek. "Oxygen insertion in Sesamumindicum furanofuran lignans. Diastereoselective syntheses of enzyme substrate analogues". Canadian Journal of Chemistry 75, nr 6 (1.06.1997): 840–49. http://dx.doi.org/10.1139/v97-102.

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The furofuran lignans in sesame seed have an unusual oxygen insertion between their furan and aryl rings. In our continuing investigations on the isolation and characterization of the enzyme(s) involved, the diastereoselective syntheses of various substrate analogues for the oxygen insertion step were developed for future substrate specificity and inhibitor studies. This synthetic strategy also provided entry to so-called furofuranone epoxy-lignans, such as salicifoliol from Bupleurum sp., and acuminatolide from Helichrysum sp. Keywords: furofuran lignans, sesame, epimers, salicifoliol, acuminatolide.
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Zhang, Wen, Lingzi Li i Chuang-Chuang Li. "Synthesis of natural products containing highly strained trans-fused bicyclo[3.3.0]octane: historical overview and future prospects". Chemical Society Reviews 50, nr 17 (2021): 9430–42. http://dx.doi.org/10.1039/d0cs01471k.

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Molecules with highly strained trans-fused bicyclo[3.3.0]octanes are very difficult to synthesize. This review provides a systematic and comprehensive discussion on the synthesis of natural products with trans-fused bicyclo[3.3.0]octanes.
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Yates, Peter, D. Jean Burnell, Vernon J. Freer i Jeffery F. Sawyer. "Synthesis of cedranoid sesquiterpenes. III. Functionalization at carbon 4". Canadian Journal of Chemistry 65, nr 1 (1.01.1987): 69–77. http://dx.doi.org/10.1139/v87-012.

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Dimethyl 6,6-dimethyl-5,7-dioxobicyclo[2.2.2]oct-2-ene-2,3-dicarboxylate (8) on irradiation in acetophenone gives dimethyl 6,6-dimethyl-4,7-dioxotricyclo[3.2.1.02,8]octane-1,8-dicarboxylate (13), which on treatment with lithium dimethylcuprate followed by monodecarbomethoxylation gives methyl 4,4-endo-8-trimethyl-3,6-dioxo-cis-bicyclo[3.3.0]octane-1-carboxylate (17). Similar irradiation of dimethyl 4,6,6-trimethyl-5,7-dioxobicyclo[2.2.2]oct-2-ene-2,3-dicarboxylate (24) and its 7,7-ethylenedioxy derivative (25) followed by treatment with DBU and concentrated H2SO4, respectively, gives dimethyl 3-hydroxy-4,4,8-trimethyl-6-oxo-cis-bicyclo[3.3.0]-octa-2,7-diene-1,2-dicarboxylate (30). This, on acetylation, reduction with NaBH4/CeCl3, methanolysis, monodecarbomethoxylation, and hydrogenation, gives methyl endo-6-hydxoxy 4,4-endo-8-trimethyl-3-oxo-cis-bicyclo[3.3.0]octane-1-carboxylate (38), while on reduction with Li/NH3 followed by monodecarbomethoxylation it gives a methyl 6-hydroxy-4,4-exo-8-trimethyl-3-oxo-cis-bicyclo[3.3.0]octane-1-carboxylate (33).
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Yates, Peter, Rupinder S. Grewal, Peter C. Hayes i Jeffery F. Sawyer. "Synthesis of cedranoid sesquiterpenes. V. The biotols". Canadian Journal of Chemistry 66, nr 11 (1.11.1988): 2805–15. http://dx.doi.org/10.1139/v88-434.

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Reduction of dimethyl 3-hydroxy-4,4,8-trimethyl-6-oxo-cis-bicyclo[3.3.0]octa-2,7-diene-1,2-dicarboxylate (8) with lithium and ammonia gives dimethyl 3-hydroxy-4,4,exo-8-trimethyl-6-oxo-cis-bicyclo[3.3.0]oct-2-ene-1,2-dicarboxylate (9), which on acetylation, reduction with sodium borohydride, and methanolysis gives dimethyl 3,exo-6-dihydroxy-4,4,exo-8-trimethyl-cis-bicyclo[3.3.0]oct-2-ene-1,2-dicarboxylate (12). This on 2-decarbomethoxylation followed by treatment with lithium acetylide in the presence of cerium trichloride gives methyl 3-ethynyl-3,exo-6-dihydroxy-4,4,exo-8-trimethyl-cis-bicyclo[3.3.0]octane-1-carboxylate (21), which on hydration, diacetylation, and treatment with tri-n-butyltin hydride and azoisobutyronitrile is converted to methyl exo-6-acetoxy-3-acetyl-4,4,exo-8-trimethyl-cis-bicyclo[3.3.0]octane-1-carboxylate (31). Methanolysis of 31. tert-butyldimethylsilylation, and reaction with potassium tert-butoxide in tert-butyl alcohol gives exo-4-tert-butyldimethylsilyloxy-exo-2,6,6-trimethyl[5.3.11,5]undecane-8,10-dione (35). This on treatment with lithium aluminum hydride followed by oxidation and hydrogenation provides the corresponding 10-deoxo compound, 39. Reaction of this with methyllithium, dehydration, and desilylation with hydrogen fluoride in acetonitrile gives a mixture of (±)-α-biotol (1) and (±)-β-biotol (2); desilylation with hydrogen chloride in methanol gives solely (±)-1.
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Rozprawy doktorskie na temat "[3.3.0]furofuranone"

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Dubbert, Robert Allen. "Iron carbonyl assisted cyclocarbonylation of 1,6-enynes to bicyclo(3.3.0)octenones". Case Western Reserve University School of Graduate Studies / OhioLINK, 1993. http://rave.ohiolink.edu/etdc/view?acc_num=case1060615827.

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Hewitt, Jacqueline Diane. "Enantioselective preparation of cis-bicycolo[3.3.0]octane derivatives using chiral lithium amide bases". Thesis, University of Salford, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.292871.

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Atalar, Taner. "Synthetic Strategy Directed Towards The Synthesis Of Bicyclo[3.3.0]octa-3,5,8-triene-2,7-dione". Master's thesis, METU, 2004. http://etd.lib.metu.edu.tr/upload/12605089/index.pdf.

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Although the chemistry of benzenoid and nonbenzenoid quinones have been the subject of extensive theoretical and experimental studies, the extent of our present understanding regarding the geometries and stabilities of quinones of pentalene is meager. After studying the existence of cyclopentadienone and its reactivity as a diene and dienophile in the literature, the study of some related species, particularly the ones with fully unsaturated pentalenic structures were started. In this thesis, the elusive compound bicyclo[3.3.0]octa-3,5,8-triene-2,7-dione was tried to synthesize by using the synthetic strategy which was developed by us. We used cycloheptatriene as the starting material. The bicyclic endoperoxiedes mixture obtained by the photooxygenation of cycloheptatriene was v treated with triethylamine to give tropone in high yield. Selective reduction of tropone afforded cyclohepta-3,5-dione which was converted by the way of photochemistry to the bicyclo[3.2.0]hept-6-en-3-one. After protection of the carbonyl group, dibromocarbene was added to the double bond to give desired bicyclic compound with pentalene skeleton. Substitution of the allylic bromide with hydroxyl group followed by PCC oxidation resulted in the formation of a diketone. All efforts to convert this diketone into fully conjugated system failed.
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Bennett, Lisa Ruth. "Enantioselective synthetic approaches to natural products based on functionalised cis-bicyclo[3.3.0]octane synthons". Thesis, University of Salford, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.262622.

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Pazinatto, Mariane. "Síntese de compostos 4-azabiciclo[3.3.0]octano intermediários avançados para a preparação de alcalóides hiacintacina". reponame:Biblioteca Digital de Teses e Dissertações da UFRGS, 2012. http://hdl.handle.net/10183/37802.

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Neste trabalho desenvolveu-se uma rota curta e convergente para a obtenção de esqueletos 4-azabiciclo[3.3.0]octano, intermediários avançados que contém todos os carbonos existentes na estrutura dos alcalóides pirrolizidínicos hiacintacina. Inicialmente foram realizadas reações de Michael entre alcinos ativados e o éster etílico da prolina, em condições brandas, gerando adutos enaminocarbonílicos de forma estereosseletiva para o isômero E, com rendimentos superiores a 80%. A posterior redução destes compostos enaminocarbonílicos, por hidrogenação ou por adição de hidreto, forneceu os aminodiésteres correspondentes com rendimentos entre 75 e 85%. Para o composto (2S)-1- benzilóximetil-3-etóxi-3-oxopropilpirrolidina-2-carboxilato de etila essa redução se mostrou estereosseletiva, com uma proporção de 3:1. Estes aminodiésteres foram submetidos a condensações de Dieckmann, através de duas metodologias sintéticas distintas: com a utilização de sódio metálico em refluxo de THF, e com hidreto de potássio a temperatura ambiente, e proporcionaram a obtenção de compostos enolésteres bicíclicos, com rendimentos entre 60 e 65%. Paralelamente, reações de redução com LiAlH4 destes aminodiésteres foram realizadas e proporcionaram a obtenção dos dióis correspondentes, com rendimentos entre 75 e 80%. Um derivado a-hidroxiéster foi obtido a partir da oxidação do enoléster bicíclico promovida por CeCl3.7H2O, com rendimento de 95%. A importância desta metodologia se dá ao fato de que ela proporcionou a inserção de um grupo hidroxila na posição a-éster, substituinte este, presente nos compostos-alvo.
In this work it was developed a short and convergent route for obtention of 4- azabicyclo[3.3.0]octane skeleton, advanced intermediates that possesses all existent carbons in the structure of hiacintacine pirrolizidinic alkaloids. Initially Michael reactions between activated alkynes and proline ethyl ester were performed, in mild conditions, leading to enaminocarbonylic adducts stereoselectively for isomer E, with yields higher than 80%. Further reduction of these enaminocarbonyl compounds, by hydrogenation or hydride addition, furnished the corresponding aminodiesters with yields between 75 and 85%. For the (2S)-1-benziloximethyl-3-ethoxi-3- oxopropylpirrolidine-2-ethyl carboxylate reduction has shown to be stereoselective in a 3:1 ratio. These aminodiesters were submitted to Dieckmann condensations through two distinct methodologies: using metallic sodium in refluxing THF, and with potassium hydride at ambient temperature, affording the obtention of bicyclic enolesters, with yields between 60 and 65%. In parallel, reduction reactions with LiAlH4 of these aminodiesters were performed leading to obtention of the corresponding diols, with yields between 75 and 80%. An a-hydroxyester was obtained from oxidation of the bicyclic enolester promoted by CeCl3.7H2O, in 95% yield. The importance of this methodology is the fact that it provided the insertion of an hydroxyl group in the a-ester position, a substituent present in the target compounds.
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Mannchen, Fabian [Verfasser]. "Übergangsmetall-katalysierte Vinylcyclopropan-Umlagerung und Studien zur Struktur-Wirkungsbeziehung von Bicyclo[3.3.0]octan-Derivaten / Fabian Mannchen". München : Verlag Dr. Hut, 2015. http://d-nb.info/1075409160/34.

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Spieler, Jan. "Synthese chiraler Liganden mit [3.3.0]- und [3.3.1]-bicyclischem Grundgerüst und ihre Anwendung in der enantioselektiven Übergangsmetall-Katalyse". [S.l. : s.n.], 2000. http://deposit.ddb.de/cgi-bin/dokserv?idn=961741309.

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Jacquet, Fabienne. "Obtention de l'hydroxy-4 dioxa-2,6 bicyclo (3.3.0) octanone-8 (1S,4S,5R) par voie catalytique, et selon un procédé d'électrosynthèse organique". Grenoble 2 : ANRT, 1986. http://catalogue.bnf.fr/ark:/12148/cb37598417t.

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Pisoni, Diego dos Santos. "Preparação e funcionalização da (5R)-4,8-dimetilbiciclo[3.3.0]octa-1(8),3-dien-2-ona: um bloco de construção para a síntese de terpenóides". reponame:Biblioteca Digital de Teses e Dissertações da UFRGS, 2006. http://hdl.handle.net/10183/24007.

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A partir do (-)-epoxilimoneno (127) desenvolveu-se a preparação enantiosseletiva da dienona (5R)-4,8-dimetilbiciclo[3.3.0]octa-1(8),3-dien-2-ona (128), que representa um bloco de construção versátil para a síntese de produtos naturais e não-naturais opticamente ativos. A etapa-chave da síntese corresponde à conversão do aldeído quiral 163 na cianoidrina bicíclica 165, através da alquilação intramolecular da cianoidrina TMS-éter 164, conforme metodologia de Stork-Takahashi. A hidrogenação estereosseletiva da dienona 128 conduziu ao produto monossaturado 20, um intermediário avançado na preparação do ent-kelsoeno. Da mesma forma, a hidrogenação catalítica das duas ligações duplas C=C de 128 produziu o intermediário 129a, que representa a síntese formal do iridóide cis,cis-dihidronepetalactona (13). Além da preparação e funcionalização da dienona 128, investigou-se a cloração alílica de olefinas terminais, através de uma nova metodologia que emprega InCl3 na presença de NaClO. Este novo método de cloração alílica foi aplicado a diferentes substratos e forneceu cloretos alílicos com bons rendimentos.
This work describes the enantioselective preparation of (5R)-4,8-dimethylbicyclo[3.3.0]oct-1(8),3-dien-2-one (128) from (-)-limonene oxide (127). This compound holds the prospect of serving as useful building block or intermediate to prepare a variety of compounds having a bicyclo[3.3.0]octane framework. The key step is the conversion of the chiral aldehyde 163 to bicyclic cyanohydrin 165, through intramolecular alkylation of cyanohydrin TMS eter 164, according to Strok-Takahashi protocol. The stereoselective hydrogenation of dienone 128 led to monosaturated product 20, which is a important intermediate on the ent-kelsoene preparation. Also, catalytic hydrogenation of the two carbon-carbon double bonds of 128, produced 129a, which is a intermediate to formal synthesis of iridoid cis,cis-dihydronepetalactone 13. Further, a new methodology to allylic chlorination of terminal olefins which employ InCl3 in the presence of NaClO was developed. This method was applied to different compounds and furnished allylic chlorides in satisfactory yields.
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鍾慧容. "Synthesis of 2,3,7-triazabicyclp[3.3.0]oct-2-enes and 2,3,7-triazabicyclo[3.3.0]oct-3-ene derivatives". Thesis, 1997. http://ndltd.ncl.edu.tw/handle/34001478867006978412.

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碩士
中原大學
化學學系
85
Michael addition and Substitution reaction of 1-methoxycarbonyl-2,3,7-triaza bicyclo[3.3.0]oct-2-enes 2a to electron-deficient dipolarphiles(vinyl ketone、ester)、 alkyl halides , give 7-substituted 1- methoxycarbonyl-2,3,7-triaza bicyclo[3.3.0]oct-2-enes 5. 6. in good yields. Furthermore, 1-methoxycarbonyl-2,3,7-triaza bicyclo[3.3.0] oct-3-enes 7. 8. 9. , are prepared by isomerization of 1-methoxycarbonyl-2,3,7-triaza bicyclo[3.3.0]oct-2-enes 2. 5. 6. .
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Książki na temat "[3.3.0]furofuranone"

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Hewitt, Jacqueline Diane. Enantioselective preparation of CIS-Bicyclo [3.3.0] octane derivatives using chiral lithium amide bases. Salford: University of Salford, 1990.

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Bennett, Lisa Ruth. Enantioselective synthetic approaches tp natural products based on functionalised CIS-bicyclo[3.3.0]octane synthons. Salford: University of Salford, 1995.

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Freer, Vernon John. The synthesis of bicyclo (3.3.0) octane derivatives related to the biotols. 1985.

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Części książek na temat "[3.3.0]furofuranone"

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Whitesell, James K., i Mark A. Minton. "Bicyclo[3.3.0]octanes". W Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy, 137–50. Dordrecht: Springer Netherlands, 1987. http://dx.doi.org/10.1007/978-94-009-3161-9_13.

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"2-Oxa-4-azabicyclo[3.3.0]oct-3-ene to 3,7-Diferrabicyclo[3.3.0]oct-1(5)-ene". W Substance Index, redaktorzy Backes, Fröhlich i Padeken. Stuttgart: Georg Thieme Verlag, 2000. http://dx.doi.org/10.1055/b-0035-114015.

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"5-Ethyl-3,7-dioxa-1-azabicyclo[3.3.0]octan". W Gesundheitsschädliche Arbeitsstoffe, 1–4. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA, 2005. http://dx.doi.org/10.1002/3527603441.ch34.

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"2,4,6-Trioxabicyclo[3.3.0]octane to Thieno[3,4-d]-1,3-dithiol-1-ium". W Substance Index, redaktorzy Backes, Fröhlich i Padeken. Stuttgart: Georg Thieme Verlag, 2000. http://dx.doi.org/10.1055/b-0035-114016.

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"4λ6,8,9-Trithiabicyclo[5.2.0]non-1(7)-ene to Bicyclo[3.3.0]octa-1,3-diene". W Substance Index, redaktorzy Backes, Fröhlich i Padeken. Stuttgart: Georg Thieme Verlag, 2000. http://dx.doi.org/10.1055/b-0035-114012.

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"Bicyclo[3.3.0]octa-1(5),2-diene to Bicyclo[2.2.1]heptan-7-ium". W Substance Index, redaktorzy Backes, Fröhlich i Padeken. Stuttgart: Georg Thieme Verlag, 2000. http://dx.doi.org/10.1055/b-0035-114013.

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"Bicyclo[2.2.1]heptane-2,5-bis[ium] to 2-Oxa-4-azabicyclo[3.3.0]octane". W Substance Index, redaktorzy Backes, Fröhlich i Padeken. Stuttgart: Georg Thieme Verlag, 2000. http://dx.doi.org/10.1055/b-0035-114014.

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"3-Oxa-6,7,8-triazabicyclo[3.3.0]oct-6-ene to 5H-1,2,3-Triazolo[4,5-c]-1λ4,2,5-thiadiazole". W Substance Index, redaktorzy Backes, Fröhlich i Padeken. Stuttgart: Georg Thieme Verlag, 2000. http://dx.doi.org/10.1055/b-0035-114018.

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Streszczenia konferencji na temat "[3.3.0]furofuranone"

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Levovnik, Bojan D., Aleksa P. Alargić, Miloš M. Svirčev i Goran I. Benedeković. "Building a 3D QSAR model with isopropylidene analogs of cytotoxic styryl-lactones". W 2nd International Conference on Chemo and Bioinformatics. Institute for Information Technologies, University of Kragujevac, 2023. http://dx.doi.org/10.46793/iccbi23.559l.

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Styryl-lactones are a class of natural products and related analogs that exhibit diverse biological activities, including anticancer, anti-inflammatory, and antimicrobial properties. Since these compounds are routinely obtained in our laboratory from their O-isopropylidene precursors, we envisioned the project to examine and compare their respective structures and in-vitro activities. This paper presents a basic 3D-QSAR steric model built on a small set of 11 selected O-isopropylidene and styryl-lactone (particularly [3.3.0]furofuranone) ligands and their in vitro activities against an MCF-7 cell line. It is part of a larger ongoing study that encompasses synthesis as well as in vitro and in silico testing of a growing library of natural products and their analogs, with the aim to determine their pharmacophores, molecular targets, and cellular mechanisms of action.
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Потапов, К. В., М. А. Новиков, Р. А. Новиков i Ю. В. Томилов. "КАТАЛИТИЧЕСКИЙ ЭНАНТИОСЕЛЕКТИВНЫЙ СИНТЕЗ 1,2-ДИАЗАБИЦИКЛО[3.3.0]-ОКТАНОВ. ФОРМАЛЬНОЕ [3+2]-ЦИКЛОПРИСОЕДИНЕНИЕ ДАЦ К ПИРАЗОЛИНАМ". W MedChem-Russia 2021. Издательство Волгоградского государственного медицинского университета, 2022. http://dx.doi.org/10.19163/medchemrussia2021-2022-23.

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Tanase, Constantin, Constantin Draghici i Miron Theodor Caproiu. "Key Intermediates for introducing a bulky bicyclo[3.3.0]heptane skeleton in the w-side chain to reduce the enzyme inactivation of prostaglandins". W The 24th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2020. http://dx.doi.org/10.3390/ecsoc-24-08390.

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Raporty organizacyjne na temat "[3.3.0]furofuranone"

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Moore, John B. Stereocontrolled Additions to a Rigid Bicyclo [3.3.0] Octane Ring System. Fort Belvoir, VA: Defense Technical Information Center, maj 2008. http://dx.doi.org/10.21236/ada486096.

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Stevens, E. D., J. H. Boyer, C. M. Lau, I. R. Politzer i K. Tangaraj. Bimanes (1,5-Diazabicyclo(3.3.0)Octadiendiones). Laser Activity in syn- Bimanes. Fort Belvoir, VA: Defense Technical Information Center, maj 1990. http://dx.doi.org/10.21236/ada222800.

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