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Journal articles on the topic 'Oxepane derivatives'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Paramita, Kar, Nagaiah K. та K. Gurjar M. "Radical reaction opening of glucosyl 1,2-cyclopropane derivatives : Synthesis of α and β C-glycosides and oxepane derivatives". Journal of Indian Chemical Society Vol. 82, May 2005 (2005): 428–32. https://doi.org/10.5281/zenodo.5830068.

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Fine Chemical Laboratory (2nd Floor), Organic III ·Division, Indian Institute of Chemical Technology, Hyderabad-500 007, India <em>E-mail</em>: paramita_k@yahoo.com, paramitakar2001 @yahoo.co.in <em>Manuscript received 14 October 2003, revised 9 September 2004. accepted 31 January 2005</em> α and β C-glycosides and oxepane derivatives are prepared by radical reaction opening of glucosyl 1,2-cyclnprupane derivatives. Structures have been confirmed by NOE studies of NMR, FABMS and C-H analysis.

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2

Krawczyk, Hanna. "Dibenzo[b,f]oxepine Molecules Used in Biological Systems and Medicine." International Journal of Molecular Sciences 24, no. 15 (2023): 12066. http://dx.doi.org/10.3390/ijms241512066.

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In this short review, including 113 references, issues related to dibenzo[b,f]oxepine derivatives are presented. Dibenzo[b,f]oxepine scaffold is an important framework in medicinal chemistry, and its derivatives occur in several medicinally relevant plants. At the same time, the structure, production, and therapeutic effects of dibenzo[b,f]oxepines have not been extensively discussed thus far and are presented in this review. This manuscript addresses the following issues: extracting dibenzo[b,f]oxepines from plants and its significance in medicine, the biosynthesis of dibenzo[b,f]oxepines, th

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3

Bouché, Léa, and Hans-Ulrich Reissig. "Synthesis of novel carbohydrate mimetics via 1,2-oxazines." Pure and Applied Chemistry 84, no. 1 (2011): 23–36. http://dx.doi.org/10.1351/pac-con-11-09-20.

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The combination of lithiated alkoxyallenes with carbohydrate-derived nitrones constitutes a flexible entry to highly functionalized enantiopure 1,2-oxazine derivatives. They can be used as precursors for acyclic and cyclic carbohydrate-like products such as amino sugar alcohols, azetidine and pyrrolidine derivatives. The Lewis acid-promoted rearrangement of 1,3-dioxolanyl-substituted 1,2-oxazines to bicyclic compounds allows an efficient route to novel amino pyran and oxepane derivatives. After subsequent transformations, new carbohydrate mimetics or “real” carbohydrates were obtained in good

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4

Dey, Supriya, and Narayanaswamy Jayaraman. "Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine." Beilstein Journal of Organic Chemistry 8 (April 10, 2012): 522–27. http://dx.doi.org/10.3762/bjoc.8.59.

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This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a common bromo-oxepine intermediate, involving C–C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals, displayed a good reactivity towards several acceptor moieties in C–C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and So

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5

Li, Tuo, Xue Ma, Daniil Fedotov, et al. "Structure Elucidation of Prenyl- and Geranyl-Substituted Coumarins in Gerbera piloselloides by NMR Spectroscopy, Electronic Circular Dichroism Calculations, and Single Crystal X-ray Crystallography." Molecules 25, no. 7 (2020): 1706. http://dx.doi.org/10.3390/molecules25071706.

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Crude ethyl acetate extract of Gerbera piloselloides (L.) Cass. was investigated by dual high-resolution PTP1B/α-glucosidase inhibition profiling and LC-PDA-HRMS. This indicated the presence of a series of unprecedented prenyl- and geranyl-substituted coumarin derivatives correlated with both α-glucosidase and PTP1B inhibitory activity. Repeated chromatographic separation targeting these compounds led to the isolation of 13 new compounds, of which ten could be isolated as both enantiomers after chiral separation. The structures of all isolated compounds were characterized by HRMS and extensive

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6

Tobiasz, Piotr, Filip Borys, Marta Borecka, and Hanna Krawczyk. "Synthesis and Investigations of Building Blocks with Dibenzo[b,f] Oxepine for Use in Photopharmacology." International Journal of Molecular Sciences 22, no. 20 (2021): 11033. http://dx.doi.org/10.3390/ijms222011033.

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The synthesis of photoswitchable azo-dibenzo[b,f]oxepine derivatives and microtubule inhibitors were described. Subsequently, we examined the reaction of methoxy derivative 3-nitrodibenzo[b,f]oxepine with different aldehydes and in the presence of BF3·OEt2 as a catalyst. Our study provided a very concise method for the construction of the azo-dibenzo[b,f]oxepine skeleton. The analysis of products was run using experimental and theoretical methods. Next, we evaluated the E/Z isomerization of azo-dibenzo[b,f]oxepine derivatives, which could be photochemically controlled using visible-wavelength

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7

Tobiasz, Piotr, Filip Borys, Marta Borecka, and Hanna Krawczyk. "Synthesis and Investigations of Building Blocks with Dibenzo[b,f] Oxepine for Use in Photopharmacology." International Journal of Molecular Sciences 22, no. 20 (2021): 11033. http://dx.doi.org/10.3390/ijms222011033.

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The synthesis of photoswitchable azo-dibenzo[b,f]oxepine derivatives and microtubule inhibitors were described. Subsequently, we examined the reaction of methoxy derivative 3-nitrodibenzo[b,f]oxepine with different aldehydes and in the presence of BF3·OEt2 as a catalyst. Our study provided a very concise method for the construction of the azo-dibenzo[b,f]oxepine skeleton. The analysis of products was run using experimental and theoretical methods. Next, we evaluated the E/Z isomerization of azo-dibenzo[b,f]oxepine derivatives, which could be photochemically controlled using visible-wavelength

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8

Borys, Filip, Piotr Tobiasz, Jakub Sobel, and Hanna Krawczyk. "Synthesis and Study of Dibenzo[b, f]oxepine Combined with Fluoroazobenzenes—New Photoswitches for Application in Biological Systems." Molecules 27, no. 18 (2022): 5836. http://dx.doi.org/10.3390/molecules27185836.

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Dibenzo[b, f]oxepine derivatives are an important scaffold in natural, medicinal chemistry, and these derivatives occur in several medicinally relevant plants. Two dibenzo[b, f]oxepines were selected and connected with appropriate fluorine azobenzenes. In the next step, the geometry of E/Z isomers was analyzed using density functional theory (DFT) calculations. Then the energies of the HOMO and LUMO orbitals were calculated for the E/Z isomers to determine the HOMO-LUMO gap. Next, modeling of the interaction between the obtained isomers of the compounds and the colchicine α and β-tubulin bindi

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9

Tobiasz, Piotr, Filip Borys, Marta Kucharska, Marcin Poterała, and Hanna Krawczyk. "Synthesis and Study of Building Blocks with Dibenzo[b,f]oxepine: Potential Microtubule Inhibitors." International Journal of Molecular Sciences 25, no. 11 (2024): 6155. http://dx.doi.org/10.3390/ijms25116155.

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The synthesis of biphenylmethoxydibenzo[b,f]oxepine or photoswitchable fluorinated dibenzo[b,f]oxepine derivatives with one or three azo bonds, potential microtubule inhibitors, is described. Our studies provide a concise method for constructing derivatives containing the dibenzo[b,f]oxepine skeleton. An analysis of products was run using experimental and theoretical methods. Next, we evaluated the E/Z isomerization of azo-dibenzo[b,f]oxepine derivatives, which could be photochemically controlled using visible-wavelength light.

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10

Pal, Arani, Ashoke Bhattacharjee, Anup Bhattacharjya, and Amarendra Patra. "Synthesis of chiral pyranocyclohexane, oxepanocyclohexane, and furylpyran and -oxepane systems by the application of intramolecular nitrone and nitrile oxide cycloaddition of carbohydrate derivatives." Tetrahedron 55, no. 13 (1999): 4123–32. http://dx.doi.org/10.1016/s0040-4020(99)00105-2.

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11

Maria, López‐Ramos, Figueroa‐Valverde Lauro, Díaz‐Cedillo Francisco, et al. "Synthesis of two 2,3,4,5‐tetrahydrooxepin‐7‐ylamino)benzoate derivatives as antibacterial agents against Escherichia coli and Staphylococcus aureus." Vietnam Journal of Chemistry 59, no. 6 (2021): 923–34. http://dx.doi.org/10.1002/vjch.202100095.

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AbstractSome protocols have been used to preparation of oxepine analogs using some substances which require special conditions such as higher‐temperatures or differences in the pH. The objective of this study was to synthesize two new oxepine‐derivatives from a Bicyclo[6.1.0]‐alkyne analog. Besides, the antibacterial effect against Escherichia coli and Staphylococcus aureus was determinate. The results showed that protocols used for synthesis of two oxepine analogs do not require special conditions to give a good yielding. Other data showed that oxepine analogs decreased the growth bacterial o

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12

Rakstys, Kasparas, Sanghyun Paek, Muhammad Sohail, et al. "A highly hindered bithiophene-functionalized dispiro-oxepine derivative as an efficient hole transporting material for perovskite solar cells." Journal of Materials Chemistry A 4, no. 47 (2016): 18259–64. http://dx.doi.org/10.1039/c6ta09028a.

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Dimethoxydiphenylamine-substituted dispiro-oxepine derivative DDOF has been synthesized using a facile synthetic route and tested in perovskite solar cells as a hole transporting material exhibiting a remarkable PCE of 19.4%.

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13

Shiva Kumar, K., Meesa Siddi Ramulu, Bandari Rajesham, N. Praveen Kumar, Vani Voora, and Rama Krishna Kancha. "FeCl3 catalysed 7-membered ring formation in a single pot: a new route to indole-fused oxepines/azepines and their cytotoxic activity." Organic & Biomolecular Chemistry 15, no. 20 (2017): 4468–76. http://dx.doi.org/10.1039/c7ob00715a.

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FeCl<sub>3</sub> catalysed construction of 7 membered ring, oxepine and azepine derivatives by the reaction of 2,3-dichloro N-heterocycles with 2-(1H-indol-2-yl)phenol/aniline. Several of these compounds were found anti-proliferative properties against cancer cell lines.

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14

Li, Xin, Xiao-Ming Li, and Bin-Gui Wang. "Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis." Marine Drugs 17, no. 1 (2018): 8. http://dx.doi.org/10.3390/md17010008.

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Wentiquinone C, which was previously isolated from the marine brown alga-derived endophytic fungus Aspergillus wentii EN-48, was found to be a potent antioxidant against α,α-diphenyl-picrylhydrazyl (DPPH) radical. The structure of wentiquinone C was originally assigned as an anthraquinone derivative (1,10-dihydroxy-3-(hydroxymethyl)-8-methoxydibenzo [b,e]oxepine-6,11-dione, 1) by 1D and 2D NMR experiments. However, the minor differences of the chemical shifts between xanthones and anthraquinones were queried, leading to the structure of 1 to be revised as a xanthone analog (8-hydroxy-6-(hydrox

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15

Gharpure, Santosh J., and Santosh K. Nanda. "Stereoselective synthesis of thiazino[4,3-a]indoles using the thia-Pictet–Spengler reaction of indoles bearing N-tethered thiols and vinylogous thiocarbonates." Organic & Biomolecular Chemistry 14, no. 24 (2016): 5586–90. http://dx.doi.org/10.1039/c6ob00501b.

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Thia-Pictet–Spengler cyclization is used for stereoselective synthesis of N-fused thiazinoindole derivatives. One-pot, sequential Friedel–Crafts alkylation – Pictet–Spengler cyclization and the synthesis of thiazino-oxepino-indole is developed.

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16

Pan, Chengqian, Yutong Shi, Xuegang Chen, Chen-Tung Arthur Chen, Xinyi Tao, and Bin Wu. "New compounds from a hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4." Organic & Biomolecular Chemistry 15, no. 5 (2017): 1155–63. http://dx.doi.org/10.1039/c6ob02374f.

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Three new quinazoline derivatives (1–3), one new oxepin-containing natural product (4) and four new cyclopenin derivatives (5–7 and 9) have been isolated from an EtOAc extract of the Taiwan Kueishantao hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4.

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17

Minassian, Frédéric, Nadia Pelloux-Léon, Marie-Thérèse Averbuch-Pouchot, and Yannick Vallée. "Rearrangements in the 11-Thia-9,10-dihydro-9,10-ethanoanthracene Series. Synthesis of a Bridged Thienooxepin." Journal of Chemical Research 23, no. 2 (1999): 166–67. http://dx.doi.org/10.1177/174751989902300250.

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18

Lopez, J. Cristobal, Fernando Lobo, Silvia Miranda, Clara Uriel, and Ana M. Gomez. "Ferrier–Nicholas pyranosidic cations: application to diversity-oriented synthesis." Pure and Applied Chemistry 86, no. 9 (2014): 1357–64. http://dx.doi.org/10.1515/pac-2014-0402.

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AbstractPyranosidic allylic (Ferrier) cations that share dicobalt hexacarbonyl propargyl (Nicholas) stabilization at C-1, can be easily generated by treatment of hexacarbonyldicobalt alkynyl glycals with BF3·OEt2, and display a remarkable reactivity leading to a variety of products. The substituent at O-6 in these glycals plays a pivotal role in directing the outcome of the transformations. Accordingly, 6-O-benzyl or 6-O-allyl groups cause a series of transformations resulting in the stereoselective formation of oxepanes through a process that involves an initial hydride transfer step from the

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19

Gören, N. "Oxepine derivatives from the roots of Smyrnium rotundifolium." Phytochemistry 23, no. 12 (1985): 3051–52. http://dx.doi.org/10.1016/s0031-9422(00)80634-2.

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20

Gören, Nezhun, and Ayhan Ulubelen. "Oxepine derivatives from the roots of Smyrnium rotundifolium." Phytochemistry 24, no. 12 (1985): 3051–52. http://dx.doi.org/10.1016/0031-9422(85)80056-x.

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21

Ibrahim, Sabrin, Gamal Mohamed, and Hany Ahmed. "Aegyoxepane: A New Oxepane Derivative from the Fungus Aspergillus aegyptiacus." Letters in Organic Chemistry 13, no. 8 (2016): 560–65. http://dx.doi.org/10.2174/1570178613666160905100928.

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22

Mangina, N. S. V. M. Rao, Surisetti Suresh, Balasubramanian Sridhar, and Galla V. Karunakar. "Gold(iii)-catalyzed synthesis of aroylbenzo[b]oxepin-3-ones from ortho-O-propargyl-1-one substituted arylaldehydes." Organic & Biomolecular Chemistry 14, no. 14 (2016): 3526–35. http://dx.doi.org/10.1039/c5ob02676h.

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An efficient gold-catalyzed intramolecular cyclization of ortho-O-propargyl-1-one substituted arylaldehydes has been achieved for the generation of substituted aroylbenzo[b]oxepin-3-one derivatives in moderate to good yields.

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23

Edwards, David J., Robin G. Pritchard, and Timothy W. Wallace. "Fine-tuning of biaryl dihedral angles: structural characterization of five homologous three-atom bridged biphenyls by X-ray crystallography." Acta Crystallographica Section B Structural Science 61, no. 3 (2005): 335–45. http://dx.doi.org/10.1107/s0108768105006713.

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The homologous series of three-atom bridged biaryls comprising 5,7-dihydro-1,2,3,9,10,11-hexamethoxydibenzo[c,e]oxepine, 6,7-dihydro-1,2,3,9,10,11-hexamethoxy-6-methyl-5H-dibenzo[c,e]azepinium chloride, 5,7-dihydro-1,2,3,9,10,11-hexamethoxydibenzo[c,e]thiepine, and the 6-oxide and 6,6-dioxide derivatives of the latter have been characterized by X-ray crystal structure analysis. Within this series the endocyclic and exocyclic biaryl dihedral angles vary over 10° ranges, reflecting the changing balance of intramolecular (steric, geometric) and intermolecular (crystal packing) forces, the former

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24

Zhang, Youquan, Aimin Yu, Jiru Jia, et al. "NaH promoted [4+3] annulation of crotonate-derived sulfur ylides with thioaurones: synthesis of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines." Chemical Communications 53, no. 77 (2017): 10672–75. http://dx.doi.org/10.1039/c7cc04466f.

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The [4+3] annulation reaction of crotonic acid derivative sulfur ylides with thioaurones has, for the first time, been reported using NaH as the base. A diverse array of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines is obtained in good to excellent yields. The proposed mechanism is investigated and supported by DFT calculations.

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25

Mahesh, Kukkamudi, Kanakaraju Ravi, Praveen Kumar Rathod, and Panaganti Leelavathi. "Convenient synthesis of quinoline-fused triazolo-azepine/oxepine derivatives through Pd-catalyzed C–H functionalisation of triazoles." New Journal of Chemistry 44, no. 6 (2020): 2367–73. http://dx.doi.org/10.1039/c9nj05254b.

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26

Ulubelen, Ayhan, Ertan Tuzlaci, and Nur Atilan. "Oxepine derivatives and anthraquinones from Asphodeline tenuior and A. Taurica." Phytochemistry 28, no. 2 (1989): 649–50. http://dx.doi.org/10.1016/0031-9422(89)80076-7.

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27

Li, Ning, Binrong Yao, Chunhua Wang, Qingguo Meng, and Guige Hou. "Synthesis, crystal structure and activity evaluation of novel 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives as protein–tyrosine kinase (PTK) inhibitors." Acta Crystallographica Section C Structural Chemistry 73, no. 11 (2017): 1003–9. http://dx.doi.org/10.1107/s2053229617015145.

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Four new 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives, namely (E)-4-(5-bromo-2-hydroxybenzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (7), (E)-4-[(E)-3-(5-bromo-2-hydroxyphenyl)allylidene]-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (8), (E)-4-(5-bromo-2-hydroxybenzylidene)-6-hydroxy-8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C18H15BrO5, (9), and (E)-4-[(E)-3-(5-bromo-2-hydroxyphenyl)allylidene]-6-hydroxy-8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (10), have been synthesized and characterized by FT–IR, NMR and MS. The structure of (9) was confirmed by single-cr

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28

Zhuravleva, Olesya I., Shamil Sh Afiyatullov, Ekaterina A. Yurchenko, Vladimir A. Denisenko, Natalya N. Kirichuk, and Pavel S. Dmitrenok. "New Metabolites from the Algal Associated Marine-derived Fungus Aspergillus Carneus." Natural Product Communications 8, no. 8 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800809.

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The new oxepin-containing (1) and quinazolinone (2) alkaloids and new dihydrobenzofuran derivative (3) have been isolated from a marine strain of Aspergillus carneus KMM 4638. The structures of these metabolites were determined by HR-MS and 1D and 2D NMR, along with Marfey's method.

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29

Garbicz, Damian, Damian Mielecki, Michal Wrzesinski, et al. "Evaluation of Anti-cancer Activity of Stilbene and Methoxydibenzo[b,f] oxepin Derivatives." Current Cancer Drug Targets 18, no. 7 (2018): 706–17. http://dx.doi.org/10.2174/1568009617666170623120742.

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Background: Stilbenes, 1,2-diphenylethen derivatives, including resveratrol and combretastatins, show anticancer features especially against tumor angiogenesis. Fosbretabulin, CA-4, in combination with carboplatin, is in the last stages of clinical tests as an inhibitor of thyroid cancer. The mode of action of these compounds involves suppression of angiogenesis through interfering with tubulin (de)polymerization. Objective: We have previously synthesized five E-2-hydroxystilbenes and seven dibenzo [b,f]oxepins in Z configuration, with methyl or nitro groups at varied positions. The aim of the

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30

Garbicz, Damian, Piotr Tobiasz, Filip Borys, et al. "The stilbene and dibenzo[b,f]oxepine derivatives as anticancer compounds." Biomedicine & Pharmacotherapy 123 (March 2020): 109781. http://dx.doi.org/10.1016/j.biopha.2019.109781.

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31

Yamazaki, Hiroyuki, Henki Rotinsulu, Tsuyoshi Kaneko, et al. "A New Dibenz[b,e]oxepine Derivative, 1-Hydroxy-10-methoxy-dibenz[b,e]oxepin-6,11-dione, from a Marine-Derived Fungus, Beauveria bassiana TPU942." Marine Drugs 10, no. 12 (2012): 2691–97. http://dx.doi.org/10.3390/md10122691.

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32

Gao, Wentao, Guihai Lin, Yang Li, Xiyue Tao, Rui Liu, and Lianjie Sun. "An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives." Beilstein Journal of Organic Chemistry 8 (October 30, 2012): 1849–57. http://dx.doi.org/10.3762/bjoc.8.213.

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An efficient access to the tetracyclic-fused quinoline systems, 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives 4a–l, is described, involving the intramolecular Friedel–Crafts acylation reaction of 2-(phenoxymethyl)-4-phenylquinoline-3-carboxylic acid derivatives 3a–l aided by the treatment with PPA (polyphosphoric acid) or Eaton’s reagent. The required starting compound (2) was obtained by Friedländer reaction of 2-aminobenzophenone (1) with 4-chloroethylacetoacetate by using CAN (cerium ammonium nitrate, 10 mol %) as catalyst at room temperature. The substrates 3a–l were pre

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33

Kotha, Sambasivarao, and Rashid Ali. "Diversity Oriented Approach to Oxepine Derivatives: Further Expansion via Diels‒Alder Reaction." HETEROCYCLES 90, no. 1 (2015): 645. http://dx.doi.org/10.3987/com-14-s(k)21.

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34

Kakehi, A., K. Kitajima, S. Ito, and N. Takusagawa. "Structure of an oxepino[2,3-b]indolizine derivative." Acta Crystallographica Section C Crystal Structure Communications 50, no. 1 (1994): 139–41. http://dx.doi.org/10.1107/s0108270193006778.

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Borys, Filip, Piotr Tobiasz, Marcin Poterała, Hanna Fabczak, Hanna Krawczyk, and Ewa Joachimiak. "Systematic Studies on Anti-Cancer Evaluation of Stilbene and Dibenzo[b,f]oxepine Derivatives." Molecules 28, no. 8 (2023): 3558. http://dx.doi.org/10.3390/molecules28083558.

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Cancer is one of the most common causes of human death worldwide; thus, numerous therapies, including chemotherapy, have been and are being continuously developed. In cancer cells, an aberrant mitotic spindle—a microtubule-based structure necessary for the equal splitting of genetic material between daughter cells—leads to genetic instability, one of the hallmarks of cancer. Thus, the building block of microtubules, tubulin, which is a heterodimer formed from α- and β-tubulin proteins, is a useful target in anti-cancer research. The surface of tubulin forms several pockets, i.e., sites that ca

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36

Bhutia, Tshering Doma, Karin M. Valant-Vetschera, and Lothar Brecker. "Orphan Flavonoids and Dihydrochalcones from Primula Exudates." Natural Product Communications 8, no. 8 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800812.

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Two orphan flavonoids containing an oxepin structure in ring A and named as Primcortusin (1) and 3’-OH-Primcortusin (2) were isolated from leaf exudates of Primula cortusoides, while P. glutinosa exudates yielded two dihydrochalcone derivatives (3,4). These novel structures have not been detected in other species of Primula so far. Chemical structures were elucidated by 2D NMR and mass spectrometry. The nature of compounds 1 and 2 is discussed, and ideas about their possible origin and that of unsubstituted flavone and other irregular substituted Primula flavones are presented.

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37

Adak, Arup Kumar, Arabinda Mandal, Susanta Kumar Manna, et al. "Pd(0)-catalyzed intramolecular Heck reaction: A general route for fused oxepine derivatives." Synthetic Communications 46, no. 5 (2016): 452–59. http://dx.doi.org/10.1080/00397911.2016.1142566.

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38

Boyd, Derek R., Narain D. Sharma, John S. Harrison, et al. "Enzyme-catalysed synthesis and reactions of benzene oxide/oxepine derivatives of methyl benzoates." Organic & Biomolecular Chemistry 6, no. 7 (2008): 1251. http://dx.doi.org/10.1039/b718375e.

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Krawczyk, Hanna, Michał Wrzesiński, Damian Mielecki, Przemysław Szczeciński, and Elżbieta Grzesiuk. "Synthesis of derivatives of methoxydibenzo[ b, f ]oxepine in the presence of sodium azide." Tetrahedron 72, no. 27-28 (2016): 3877–84. http://dx.doi.org/10.1016/j.tet.2016.05.005.

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Kotha, Sambasivarao, and Rashid Ali. "ChemInform Abstract: Diversity Oriented Approach to Oxepine Derivatives: Further Expansion via Diels-Alder Reaction." ChemInform 46, no. 20 (2015): no. http://dx.doi.org/10.1002/chin.201520217.

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Qi, Changxing, Xiaosheng Tan, Zhengyi Shi, et al. "Discovery of an Oxepine-Containing Diketopiperazine Derivative Active against Concanavalin A-Induced Hepatitis." Journal of Natural Products 83, no. 9 (2020): 2672–78. http://dx.doi.org/10.1021/acs.jnatprod.0c00558.

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Kluess, Brigitte, Wolfgang Kreiser, Tony Sukri, Wolfgang Poll, and Hartmut Wunderlich. "(R)-5-[(1R,2R)-1-Ethyl-2- (4-oxocyclohexyl)butyl]oxepan-2-one, an Enantiopure ‘Pseudosteroid′." Zeitschrift für Naturforschung B 61, no. 1 (2006): 111–12. http://dx.doi.org/10.1515/znb-2006-0122.

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The title compound C18H30O3 represents an optically pure member of a class of ‘pseudosteroids’, i. e. perhydrostilbene derivatives which mimic steroidal androgens (in the way like hexestrols or stilbestrols serve to substitute natural estrogens). The molecule 2 is characterized by three consecutive chiral centers leading to eight possible stereoisomers including four diastereomers. All enantiomers have been separated and their biological profile has been determined. As the result of the crystal structure presented here the two symmetry independent molecules display the configuration R,R,R at t

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Tochtermann, Werner, and Brigit Karl. "Synthesis of Alkano-1H-imidazo-azepine Derivatives from 3,6-Alkano-oxepines." HETEROCYCLES 40, no. 2 (1995): 555. http://dx.doi.org/10.3987/com-94-s92.

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KAKEHI, A., K. KITAJIMA, S. ITO, and N. TAKUSAGAWA. "ChemInform Abstract: Structure of an Oxepino(2,3-b)indolizine Derivative." ChemInform 25, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199416039.

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Bukhvalova, S. Yu, A. A. Maleev, Yu A. Gracheva, et al. "Gold-catalyzed cyclization in the synthesis of antimitotic 2,3-dihydrobenzo[b]oxepine derivatives of colchicine." Russian Chemical Bulletin 68, no. 12 (2019): 2205–15. http://dx.doi.org/10.1007/s11172-019-2689-7.

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Wang, Yiyun, Jiaru Wang, Hui Wu, et al. "Synthesis and Cap-Dependent Endonuclease Inhibition of Baloxavir Derivatives." Crystals 13, no. 7 (2023): 988. http://dx.doi.org/10.3390/cryst13070988.

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Baloxavir marboxil is a creative antiviral drug for influenza A and B viruses with a novel mechanism of action. In this study, three series comprising a total of 21 previously unreported target compounds were designed and synthesized. The drug-likeness of these compounds was evaluated by molecular docking, PAINS-Remover and SwissADME. The inhibitory effect and affinity of the compounds on the cap-dependent endonuclease activity of the influenza virus were evaluated. Compounds I-4, II-1~II-9 and compound III-8 showed similar inhibitory activity to baloxavir (7.45 μM) on the cap-dependent endonu

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Neogi, Arpita, Tirtha Pada Majhi, Nanda Ghoshal, and Partha Chattopadhyay. "Radical cyclization of exo-methylene furanose derivatives: an expedient approach to the synthesis of chiral tricyclic nucleosides and benzannulated oxepine derivatives." Tetrahedron 61, no. 39 (2005): 9368–74. http://dx.doi.org/10.1016/j.tet.2005.07.054.

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Tsuchiya, Takashi, Naoki Kakusawa, Kiyohiro Inui, and Jyoji Kurita. "Preparation of p-Benzoquinono[b]oxepines and Their Aromatic Ring Annulated Derivatives." HETEROCYCLES 43, no. 8 (1996): 1601. http://dx.doi.org/10.3987/com-96-7500.

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Kim, Soyoung, Bao-Ning Su, Soedarsono Riswan, et al. "Edulisones A and B, two epimeric benzo[b]oxepine derivatives from the bark of Aglaia edulis." Tetrahedron Letters 46, no. 52 (2005): 9021–24. http://dx.doi.org/10.1016/j.tetlet.2005.10.107.

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Yoo, Minjin, Tae Hyun Park, Miyoun Yoo, et al. "Synthesis and Structure–Activity Relationships of Aristoyagonine Derivatives as Brd4 Bromodomain Inhibitors with X-ray Co-Crystal Research." Molecules 26, no. 6 (2021): 1686. http://dx.doi.org/10.3390/molecules26061686.

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Epigenetic regulation is known to play a key role in progression of anti-cancer therapeutics. Lysine acetylation is an important mechanism in controlling gene expression. There has been increasing interest in bromodomain owing to its ability to modulate transcription of various genes as an epigenetic ‘reader.’ Herein, we report the design, synthesis, and X-ray studies of novel aristoyagonine (benzo[6,7]oxepino[4,3,2-cd]isoindol-2(1H)-one) derivatives and investigate their inhibitory effect against Brd4 bromodomain. Five compounds 8ab, 8bc, 8bd, 8be, and 8bf have been discovered with high bindi

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