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Journal articles on the topic 'Dihydrobenzofuran'

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Author: Grafiati

Published: 4 June 2021

Last updated: 20 February 2023

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1

Shinde, Rahul Ashok, Vishnu Ashok Adole, Bapu Sonu Jagdale, Thansing Bhavsing Pawar, and Bhatu Shivaji Desale. "Efficient Synthesis, Spectroscopic and Quantum Chemical Study of 2,3-Dihydrobenzofuran Labelled Two Novel Arylidene Indanones: A Comparative Theoretical Exploration." Material Science Research India 17, no. 2 (August 30, 2020): 146–61. http://dx.doi.org/10.13005/msri/170207.

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Indanone and 2,3-dihydrobenzofuran scaffolds are considered as special structures in therapeutic science and explicitly associated with various biologically potent compounds. In the present disclosure, we report the synthesis of two new 2,3-dihydrobenzofuran tethered arylidene indanones via an environmentally adequate and viable protocol. The two compounds revealed in this have been characterized well by analytical methods; proton magnetic resonance (PMR), carbon magnetic resonance (CMR). The Density Functional Theory (DFT) study has been presented for the spectroscopic, structural and quantum correlation between (E)-2-((2,3-dihydrobenzofuran-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (DBDI) and (E)-7-((2,3-dihydrobenzofuran-5-yl)methylene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (DBTI). Optimized geometry, frontier molecular orbital, global reactivity descriptors, and thermodynamic parameters have been computed for DBDI and DBTI. DFT/B3LYP method using basis set 6-311++G (d,p) has been employed for the computational study. Mulliken atomic charges are established by using 6-311G (d,p) basis set. Besides, molecular electrostatic potential for DBDI and DBTI is also explored to locate the electrophilic and nucleophilic centres.

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2

Basini, Giuseppina, Carmela Spatafora, Corrado Tringali, Simona Bussolati, and Francesca Grasselli. "Effects of a Ferulate-Derived Dihydrobenzofuran Neolignan on Angiogenesis, Steroidogenesis, and Redox Status in a Swine Cell Model." Journal of Biomolecular Screening 19, no. 9 (June 10, 2014): 1282–89. http://dx.doi.org/10.1177/1087057114536226.

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In the ongoing search for new therapeutic compounds, lignans and neolignans, which are widely distributed in plants, deserve special attention because of their interactions with several biological targets. Searching for potential antiangiogenic agents related to natural lignans/neolignans, we were attracted by a previously studied synthetic dihydrobenzofuran neolignan. We synthesized the compound by means of an eco-friendly, enzyme-mediated biomimetic coupling of the methyl ester of ferulic acid, and the present study was aimed to deeply investigate its effect in angiogenesis bioassays validated in our laboratory. In addition, a previously well-defined granulosa cell model was employed to evaluate the effect of dihydrobenzofuran neolignan on cell viability, steroidogenesis, and redox status. Present data support the antiangiogenic effect of this neolignan. Moreover, we demonstrate that, at least at the highest concentrations tested, dihydrobenzofuran neolignan affects granulosa cell viability and steroidogenesis. In addition, the compound inhibits generation of free radicals and stimulates scavenger enzyme activities. The present data, which are a further deepening of the evaluation of the biological activities of the dihydrobenzofuran lignan in well-defined cell models, are of interest and worthy of special attention.

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3

Xia, Yamu, Zhen Mo, Lin Sun, Lijia Zou, Wen Zhang, Jiahong Zhang, and Lihong Wang. "First total synthesis of quiquesetinerviusin A." Journal of Chemical Research 41, no. 5 (May 2017): 296–300. http://dx.doi.org/10.3184/174751917x14931195075599.

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The first total synthesis of the dihydrobenzofuran neolignan quiquesetinerviusin A and its related structure have been described. Phenolic coupling is the key step to constructing the dihydrobenzofuran skeleton with vanillin as the raw material. The hydroxyl group was protected with dihydropyran (DHP) and the ester group was reduced with diisobutylaluminium hydride (DIBAL-H) in order to obtain the crucial intermediate diol, which was then condensed with an acid ligand to give the desired compounds following removal of the protecting groups.

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4

Chen, Zhuang, Mallesham Pitchakuntla, and Yanxing Jia. "Synthetic approaches to natural products containing 2,3-dihydrobenzofuran skeleton." Natural Product Reports 36, no. 4 (2019): 666–90. http://dx.doi.org/10.1039/c8np00072g.

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5

Previtera, Lucio, Marina Della Greca, Antonio Molinaro, and Pietro Monaco. "Dihydrobenzofuran Neolignans from Arum italicum." HETEROCYCLES 38, no. 5 (1994): 1099. http://dx.doi.org/10.3987/com-94-6681.

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6

Sakushima, Akiyo, Maksut Coşkun, Takashi Maoka, and Sansei Nishibe. "Dihydrobenzofuran lignans from Boreava orientalis." Phytochemistry 43, no. 6 (December 1996): 1349–54. http://dx.doi.org/10.1016/s0031-9422(96)00497-9.

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7

Dias, Herbert J., Andressa B. Patrocínio, Mariana C. Pagotti, Murilo J. Fukui, Vanderlei Rodrigues, Lizandra G. Magalhães, and Antônio E. M. Crotti. "Schistosomicidal Activity of Dihydrobenzofuran Neolignans." Chemistry & Biodiversity 15, no. 7 (June 20, 2018): e1800134. http://dx.doi.org/10.1002/cbdv.201800134.

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8

Wu, Chenggui, Hong-Gang Cheng, Ruiming Chen, Han Chen, Ze-Shui Liu, Jingyang Zhang, Yuming Zhang, Yuxin Zhu, Zhi Geng, and Qianghui Zhou. "Convergent syntheses of 2,3-dihydrobenzofurans via a Catellani strategy." Organic Chemistry Frontiers 5, no. 17 (2018): 2533–36. http://dx.doi.org/10.1039/c8qo00348c.

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9

Barrios Antúnez, Diego-Javier, Mark D. Greenhalgh, Charlene Fallan, Alexandra M. Z. Slawin, and Andrew D. Smith. "Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst." Organic & Biomolecular Chemistry 14, no. 30 (2016): 7268–74. http://dx.doi.org/10.1039/c6ob01326k.

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The enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives via intramolecular Michael addition has been developed using a bifunctional tertiary amine–thiourea catalyst.

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10

Zhao, Qiang, Ji-Kang Jin, Jie Wang, Feng-Lian Zhang, and Yi-Feng Wang. "Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes." Chemical Science 11, no. 15 (2020): 3909–13. http://dx.doi.org/10.1039/d0sc01078b.

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11

Wang, Yu-Jiang, Yuan Zhang, Zou Qiang, Jia-Ying Liang, and Zili Chen. "Gold catalyzed efficient preparation of dihydrobenzofuran from 1,3-enyne and phenol." Chemical Communications 57, no. 94 (2021): 12607–10. http://dx.doi.org/10.1039/d1cc05260h.

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12

Wang, Xuefeng, Tong Liu, Danqing Zheng, Qian Zhong, and Jie Wu. "Synthesis of 3-(((2,3-dihydrobenzofuran-3-yl)methyl)sulfonyl) coumarins through the reaction of 2-(allyloxy)anilines, sulfur dioxide, and aryl propiolates." Organic Chemistry Frontiers 4, no. 12 (2017): 2455–58. http://dx.doi.org/10.1039/c7qo00787f.

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13

Zhou, Fan, Ying Cheng, Xiao-Peng Liu, Jia-Rong Chen, and Wen-Jing Xiao. "A visible light photoredox catalyzed carbon radical-mediated generation of ortho-quinone methides for 2,3-dihydrobenzofuran synthesis." Chemical Communications 55, no. 21 (2019): 3117–20. http://dx.doi.org/10.1039/c9cc00727j.

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14

Sun, Haotian, Baojian Xiong, Yuan Yang, Jiangjun Liu, Xuemei Zhang, and Zhong Lian. "gem-Difluorovinylation of alkynyl bromoarenes via dual nickel-/palladium-catalyzed cross-electrophile coupling." Organic Chemistry Frontiers 9, no. 2 (2022): 305–10. http://dx.doi.org/10.1039/d1qo01406d.

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A dual nickel-/palladium-catalyzed gem-difluorovinylation of alkynyl bromoarenes is presented. This method proceeds smoothly to afford various dihydrobenzofuran compounds containing gem-difluorovinyl fragments with excellent stereoselectivities.

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15

Monte, Aaron P., Steve R. Waldman, Danuta Marona-Lewicka, David B. Wainscott, David L. Nelson, Elaine Sanders-Bush, and David E. Nichols. "Dihydrobenzofuran Analogues of Hallucinogens. 4.1Mescaline Derivatives2." Journal of Medicinal Chemistry 40, no. 19 (September 1997): 2997–3008. http://dx.doi.org/10.1021/jm970219x.

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16

Nascimento, I. "2,3-Dihydrobenzofuran neolignans from Aristolochia pubescens." Phytochemistry 52, no. 2 (September 1999): 345–50. http://dx.doi.org/10.1016/s0031-9422(99)00176-4.

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17

Nichols, David E., Scott E. Snyder, Robert Oberlender, Michael P. Johnson, and Xuemei Huang. "2,3-Dihydrobenzofuran analogs of hallucinogenic phenethylamines." Journal of Medicinal Chemistry 34, no. 1 (January 1991): 276–81. http://dx.doi.org/10.1021/jm00105a043.

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18

Benbow, John W., and Reeti Katoch-Rouse. "A Biomimetic Approach to Dihydrobenzofuran Synthesis." Journal of Organic Chemistry 66, no. 15 (July 2001): 4965–72. http://dx.doi.org/10.1021/jo000696e.

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19

Jiang, Zhi-Hua, Yan-Ping Liu, Ze-Hao Huang, Ting-Ting Wang, Xing-Yang Feng, Hao Yue, Wei Guo, and Yan-Hui Fu. "Cytotoxic dihydrobenzofuran neolignans from Mappianthus iodoies." Bioorganic Chemistry 75 (December 2017): 260–64. http://dx.doi.org/10.1016/j.bioorg.2017.10.003.

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20

Apers, Sandra, Dietrich Paper, Jutta Bürgermeister, Slavka Baronikova, Stefaan Van Dyck, Guy Lemière, Arnold Vlietinck, and Luc Pieters. "Antiangiogenic Activity of Synthetic Dihydrobenzofuran Lignans." Journal of Natural Products 65, no. 5 (May 2002): 718–20. http://dx.doi.org/10.1021/np0103968.

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21

Pieters, Luc A. C., Dirk A. Vanden Berghe, and Arnold J. Vlietinck. "A dihydrobenzofuran lignan from Croton erythrochilus." Phytochemistry 29, no. 1 (January 1990): 348–49. http://dx.doi.org/10.1016/0031-9422(90)89073-i.

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22

Pieters, Luc, Tess De Bruyne, Alex De Groot, Gao Mei, Roger Dommisse, Guy Lemière, and Arnold Vlietinck. "NMR study of some dihydrobenzofuran lignans." Magnetic Resonance in Chemistry 31, no. 7 (July 1993): 692–93. http://dx.doi.org/10.1002/mrc.1260310717.

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23

Wootton, Timothy L., Jack A. Porter, Karmjit S. Grewal, Paula G. Chirila, Sarah Forbes, Simon J. Coles, Peter N. Horton, Alex Hamilton, and Christopher J. Whiteoak. "Merging Cu-catalysed C–H functionalisation and intramolecular annulations: computational and experimental studies on an expedient construction of complex fused heterocycles." Organic Chemistry Frontiers 7, no. 10 (2020): 1235–42. http://dx.doi.org/10.1039/d0qo00283f.

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A copper-catalysed protocol for the synthesis of fused dihydrobenzofuran-isoquinolone compounds through an intramolecular annulation of readily accessible benzamide substrates is reported, along with a full DFT study into the mechanism.

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24

Sun, Xiao-Xue, Hong-Hao Zhang, Guo-Hao Li, Li Meng, and Feng Shi. "Diastereo- and enantioselective construction of an indole-based 2,3-dihydrobenzofuran scaffold via catalytic asymmetric [3+2] cyclizations of quinone monoimides with 3-vinylindoles." Chemical Communications 52, no. 14 (2016): 2968–71. http://dx.doi.org/10.1039/c5cc09145d.

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The first catalytic asymmetric [3+2] cyclization of quinone monoimides with 3-vinylindoles has been established, which constructed a biologically important 2,3-dihydrobenzofuran framework in high stereoselectivities (up to >95 : 5 dr, 96 : 4 er).

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25

Oguma, Takuya, and Tsutomu Katsuki. "Iron-catalysed asymmetric tandem spiro-cyclization using dioxygen in air as the hydrogen acceptor." Chem. Commun. 50, no. 39 (2014): 5053–56. http://dx.doi.org/10.1039/c4cc01555j.

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A tandem combination of ortho-quinone methide (o-QM) formation/Michael addition/asymmetric dearomatization, which is catalysed by an iron–salan complex in air with high enantioselectivity, provides an efficient method for spirocyclic (2H)-dihydrobenzofuran synthesis from 2-naphthols and phenols.

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26

Gu, Qiong, Xue-Mei Zhang, Jun Zhou, Sheng-Xiang Qiu, and Ji-Jun Chen. "One new dihydrobenzofuran lignan from Vitex trifolia." Journal of Asian Natural Products Research 10, no. 6 (May 12, 2008): 499–502. http://dx.doi.org/10.1080/10286020801967359.

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27

Yagunov, S. E., S. V. Kholshin, N. V. Kandalintseva, and A. E. Prosenko. "5-Hydroxy-2,3-dihydrobenzofuran-derived polyfunctional antioxidants." Russian Chemical Bulletin 66, no. 6 (June 2017): 1024–29. http://dx.doi.org/10.1007/s11172-017-1850-4.

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28

Fukui, Murilo J., Herbert J. Dias, Marcela E. Severiano, Maria G. M. de Souza, Pollyanna F. de Oliveira, Sérgio R. Ambrósio, Carlos H. G. Martins, Denise C. Tavares, and Antônio E. M. Crotti. "Antimicrobial and Cytotoxic Activity of Dihydrobenzofuran Neolignans." ChemistrySelect 3, no. 6 (February 12, 2018): 1836–39. http://dx.doi.org/10.1002/slct.201703024.

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29

ahmad, Ateeque, Laxmi N. Misra, and Munishwar C. Nigam. "A dihydrobenzofuran from indian dill seed oil☆." Phytochemistry 29, no. 6 (1990): 2035–37. http://dx.doi.org/10.1016/0031-9422(90)85066-o.

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30

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 (August 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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31

Wang, Yuefei, Li Han, Zongjun Tang, Haiping Liu, and Wenling Li. "Enzyme-promoted oxidative cross-coupling for the synthesis of oxyresveratrol-related heterodimers." Journal of Chemical Research 46, no. 1 (January 2022): 174751982110688. http://dx.doi.org/10.1177/17475198211068803.

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Horseradish peroxidase–H2O2-mediated oxidative cross-coupling reactions of oxyresveratrol 2-methyl ether and brominated isorhapontigenin or brominated resveratrol efficiently produce two 8-5’-coupled dihydrobenzofuran-type heterodimers. The LiAlH4-catalysed reductive debrominations of these cross-coupled dimeric intermediates provided the first synthesis of two unnatural oxyresveratrol-related heterodimers.

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32

Nagashima, Tadamichi, Alexey Rivkin, and Dennis P. Curran. "On the reduction of tertiary radicals by samarium diiodide (SmI2)." Canadian Journal of Chemistry 78, no. 6 (June 1, 2000): 791–99. http://dx.doi.org/10.1139/v00-011.

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Reduction of o-iodophenyl 3-methylbut-2-enyl ether with samarium diiodide generates mixtures of 3-isopropyl-2,3-dihydrobenzofuran and 3-(2-propenyl)-2,3-dihydrobenzofuran along with a small amount of dimer. If a source of deuterium is present during the reduction, then the 3-isopropyl product predominates and this product is labeled with one deuterium. However, attempts to quench the putative tertiary organosamarium reagent by adding a deuterium source after the reduction were not very successful at room temperature. But at 0°C, the organosamarium reagent was generated (at least to the extent of about 50%, as measured by deuterium quenching), and its decomposition was followed over time by a series of quenching experiments. The results suggest that tertiary radicals are reduced to a significant extent by SmI2 to form an anionic (presumably alkylsamarium) species. This species is thermally unstable and decomposes to the corresponding reduced and eliminated products. The reduced product is consistently formed in slight excess over the eliminated one, and the mechanism of formation of these products is not yet clear.Key words: samarium diiodide, SmI2, reduction, alkyl samarium.

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33

Arnold, Donald R., Brian J. Fahie, Laurie J. Lamont, Jacek Wierzchowski, and Kent M. Young. "1,n-Radical ions. The photosensitized (electron transfer) formation of 1,5-radical cations." Canadian Journal of Chemistry 65, no. 12 (December 1, 1987): 2734–43. http://dx.doi.org/10.1139/v87-455.

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The photosensitized (electron transfer) reactions of 3-phenyl-2,3-dihydrobenzofuran (8a), 5-methyl-3-phenyl-2,3-dihydrobenzofuran (8b), cis and trans-2-methoxy-1-phenylindane (9, cis and trans), 3,3-diphenyltetrahydrofuran (10), and 2,2-diphenyl-1-methoxycyclopentane (11) have been studied using 1,4-dicyanobenzene as an electron-accepting photosensitizer and acetonitrile–methanol (3:1) as solvent. These reaction conditions cause carbon–carbon bond cleavage of analogous acyclic β,β-diphenylethyl ethers to give products derived from the diphenylmethyl radical and the α-oxycarbocation intermediates. The purpose of this study was to determine if this reaction could be applied to five-membered cyclic derivatives to give 1,5-radical cations.The primary products from 8a and 8b were the dehydrogenated, aromatized 3-phenylbenzofurans 14a and 14b. These products react further; continued irradiation gave the methanol adducts, cis and trans-2-methoxy-3-phenyl-2,3-dihydrobenzofuran (15a and 15b, cis and trans). The only observed reaction of the indanes (9, cis and trans) was cis-trans isomerization. Deuterium was incorporated at the bis-benzylic position of 8 and 9 when the irradiation was carried out in acetonitrilemethanol-O-d. These results are consistent with reversible deprotonation from the radical cations. There was no evidence for carbon–carbon bond cleavage with either 8 or 9. The relative rate, deprotonation faster than carbon–carbon bond cleavage, is explained in terms of the conformation of the bond that cleaves in relation to the singly occupied molecular orbital (SOMO) of the radical cation. Oxidation potential measurements support the conclusion that the SOMO of 8 and 9 is largely associated with the fused phenyl ring and is therefore orthogonal to the benzylic carbon–carbon bond. Irradiation of cis or trans-2-methoxy-3-phenyl-2,3-dihydrobenzofuran (15a, cis or trans), under these conditions, leads to cis–trans isomerization. The mechanism in this case involves the reversible loss of methanol. There is evidence that the addition of methanol to 14 involves the sensitizer radical anion – 14 radical cation pair.In contrast with the fused bicyclic systems, the monocyclic tetrahydrofuran 10 and the methoxycyclopentane 11 both cleave under these conditions; the products are the expected acetals 22 and 29 formed from the intermediate 1,5-radical cations. In 10 and 11 the SOMO, which is largely associated with the diphenylmethyl moiety, can overlap with the adjacent carbon–carbon bond and cleavage occurs as in analogous acyclic systems. Both 10 and 11 are relatively stable to irradiation under conditions that are identical except with acetonitrile as solvent (without methanol). We found no evidence for cyclization of the intermediates (1,5-radical cation or 1,5-diradical) into the terminal phenyl ring.

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34

Gu, Haining, and Wei Ming Xu. "A PRACTICAL SYNTHESIS OF 4-HYDROXYETHYL-2,3-DIHYDROBENZOFURAN." Organic Preparations and Procedures International 40, no. 5 (October 2008): 465–67. http://dx.doi.org/10.1080/00304940809458107.

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35

Melo, Francisca N., Vanessa R. Navarro, Marcelo S. Da Silva, Emidio V. L. Da-cunha, José M. Barbosa-Filho, and Raimundo Braz-filho. "Bowdenol, a New 2,3-Dihydrobenzofuran Constituent fromBowdichia Virgilioides." Natural Product Letters 15, no. 4 (October 2001): 261–66. http://dx.doi.org/10.1080/10575630108041290.

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36

Li, Yan-Ping, Liao-Bin Dong, Duo-Zhi Chen, Hong-Mei Li, Jin-Dong Zhong, Fei Li, Xing Liu, Bei Wang, and Rong-Tao Li. "Two new dihydrobenzofuran-type neolignans from Breynia fruticosa." Phytochemistry Letters 6, no. 2 (May 2013): 281–85. http://dx.doi.org/10.1016/j.phytol.2013.03.009.

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37

Nascimento, Isabele R., and Lucia M. X. Lopes. "Erratum to “2,3-Dihydrobenzofuran neolignans from Aristolochia pubescens”." Phytochemistry 53, no. 5 (March 2000): 621. http://dx.doi.org/10.1016/s0031-9422(99)00595-6.

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38

Lee, Ik-Soo, Hong-Jin Kim, Ui-Jung Youn, Quan-Cheng Chen, Jin-Pyo Kim, Do Thi Ha, Tran Minh Ngoc, et al. "Dihydrobenzofuran Norlignans from the Leaves ofCedrela sinensisA. Juss." Helvetica Chimica Acta 93, no. 2 (February 2010): 272–76. http://dx.doi.org/10.1002/hlca.200900180.

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39

Benbow, John W., and Reeti Katoch-Rouse. "ChemInform Abstract: A Biomimetic Approach to Dihydrobenzofuran Synthesis." ChemInform 32, no. 48 (May 23, 2010): no. http://dx.doi.org/10.1002/chin.200148096.

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40

Zheng, Xiao Ke, Ke Ke Li, Yan Zhi Wang, and Wei Sheng Feng. "A new dihydrobenzofuran lignanoside from Selaginella moellendorffii Hieron." Chinese Chemical Letters 19, no. 1 (January 2008): 79–81. http://dx.doi.org/10.1016/j.cclet.2007.11.019.

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41

NICHOLS, D. E., S. E. SNYDER, R. OBERLENDER, M. P. JOHNSON, and X. HUANG. "ChemInform Abstract: 2,3-Dihydrobenzofuran Analogues of Hallucinogenic Phenethylamines." ChemInform 22, no. 23 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199123137.

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42

Haridy, Mamdouh S. A., and Abou El-Hamd H. Mohamed. "New Derivatives of Chromene and Acetoxyeudesmane Obtained by Microbial Transformation." Natural Product Communications 3, no. 5 (May 2008): 1934578X0800300. http://dx.doi.org/10.1177/1934578x0800300523.

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Microbial transformation of dihydrobenzofuran derivative 1 and 4, 6-dihydroxy-1,5(H)-guai-9-ene (2), the major isolated compounds from Chrysothamnus viscidiflorus, afforded a new chromene derivative 3 and a new acetoxyeudesmane derivative 4, respectively. The structures of the new compounds were determined by comprehensive NMR studies, including DEPT, COSY, NOE, HMQC, HMBC and HRMS.

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43

Palu, Doreen Stacy, Mathieu Paoli, Hervé Casabianca, Joseph Casanova, and Ange Bighelli. "New Compounds from the Roots of Corsican Calicotome Villosa (Poir.) Link.: Two Pterocarpans and a Dihydrobenzofuran." Molecules 25, no. 15 (July 30, 2020): 3467. http://dx.doi.org/10.3390/molecules25153467.

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Three new compounds, a dihydrobenzofuran (coumaran) derivative (compound 1) and two pterocarpans (compounds 2 and 3) were isolated from a root extract of Calicotome villosa growing wild in Corsica. Their structures were elucidated using 1D and 2D NMR spectroscopy and MS/MS as 2-(1-methylethenyl)-5-hydroxy-6-carbomethoxy-2,3-dihydro-benzofuran, 4,9-dihydroxy-3-methoxy-2-dimethylallylpterocarpan, and 4,9-dihydroxy-3′,3′-dimethyl-2,3-pyranopterocarpan.

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44

Jin, Lei, Hu Biao Fang, Nian Yu Huang, Jun Zhi Wang, and Kun Zou. "Synthesis and Structure Elucidation of Novel Oxime Ether Type H/K+-ATPase Inhibitors." Advanced Materials Research 746 (August 2013): 40–44. http://dx.doi.org/10.4028/www.scientific.net/amr.746.40.

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Six 6,6-dimethyl-2-phenyl-6,7-dihydrobenzofuran-4(5H)-one oxime derivatives were synthesized, characterized and evaluated as potential anti-ulcer agents. Most of the target compounds exhibited better H+/K+-ATPase inhibitory activity than commercial revaprazan, and both of the two O-propyl oxime ethers displayed the most potent activities with IC50˰̵̱̼͆̓ͅ˰̵̼̓̓˰̸̱̈́̾˰́̀˰μ̝˾ These compounds could be potentially used for the treatment of ulcer disease.

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45

Fang, Hu Biao, Lei Jin, Wei Chen Zai, Yu Rong Song, Jun Zhi Wang, and Nian Yu Huang. "Synthesis and H⁺/K⁺-ATPase Inhibitory Activity of 2-Phenyl-6,7-Dihydrobenzofuran-4(5H)-one Oxime Ether Derivatives." Advanced Materials Research 634-638 (January 2013): 1192–95. http://dx.doi.org/10.4028/www.scientific.net/amr.634-638.1192.

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Three pairs of 2-phenyl-6,7-dihydrobenzofuran-4(5H)-one oxime and corresponding oxime ether isomers were synthesized and separated as potential anti-ulcer agent. Their structures were characterized by NMR, IR, ESI-MS and elemental analysis. Preliminarily H+/K+-ATPase activity evaluation indicated that all the target compounds had a better inhibitory effect than the commercial omeprazole with the IC50 of 2.0~30.0 μM.

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YANO, Satoshi, Takako NAKANISHI-UEDA, Sachiko TOMOYASU, Kayo AOKI, Seiichi UCHIDA, and Hajime YASUHARA. "Dihydrobenzofuran Derivative Modulates Oxidative Stress-induced PC12 Cell Injury." Showa University Journal of Medical Sciences 20, no. 2 (2008): 89–95. http://dx.doi.org/10.15369/sujms1989.20.89.

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Wu, Tian-Shung, Ping-Chung Kuo, Chung-Ren Su, and Amooru G. Damu. "Eurycomalin A, a New Dimeric Dihydrobenzofuran from Eurycoma longifolia." HETEROCYCLES 63, no. 9 (2004): 2123. http://dx.doi.org/10.3987/com-04-10167.

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Lamaty, F., M. Szlosek-Pinaud, P. Diaz, and J. Martinez. "Synthesis of 2,3-Dihydrobenzofuran by Tandem Palladium-Catalyzed Reactions." Synfacts 2007, no. 7 (July 2007): 0695. http://dx.doi.org/10.1055/s-2007-968680.

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de Castro Oliveira, Luciano Gomes, Lucas Moreira Brito, Michel Muálem de Moraes Alves, Layane Valéria Amorim, Enoque Pereira Costa Sobrinho-Júnior, Camila Ernanda Sousa de Carvalho, Klinger Antonio da Franca Rodrigues, Daniel Dias Rufino Arcanjo, Antônia Maria das Graças Lopes Citó, and Fernando Aécio de Amorim Carvalho. "In VitroEffects of the Neolignan 2,3-Dihydrobenzofuran AgainstLeishmania Amazonensis." Basic & Clinical Pharmacology & Toxicology 120, no. 1 (September 16, 2016): 52–58. http://dx.doi.org/10.1111/bcpt.12639.

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Mino, Takashi, Yoshiaki Naruse, Shohei Kobayashi, Shunsuke Oishi, Masami Sakamoto, and Tsutomu Fujita. "Synthesis and application of atropisomeric dihydrobenzofuran-based bisphosphine (BICMAP)." Tetrahedron Letters 50, no. 19 (May 2009): 2239–41. http://dx.doi.org/10.1016/j.tetlet.2009.02.182.

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