Category: benzofurans

《Fluorinated Phenanthrenes as Aryne Precursors: PAH Synthesis Based on Domino Ring Assembly Using 1,1-Difluoroallenes》 was written by Fuchibe, Kohei; Abe, Masashi; Idate, Hiroto; Ichikawa, Junji. Synthetic Route of C20H14O And the article was included in Chemistry – An Asian Journal in 2020. The article conveys some information:

On treatment with the catalyst InBr3, 1,1-difluoroallenes e.g., [1-(3,3-difluoropropa-1,2-dien-1-yl)cyclopent-3-en-1-yl]benzene that bear a cyclopentene moiety and an aryl group underwent domino ring assembly in the presence or absence of N-bromosuccinimide or N-iodosuccinimide to afford aryne precursors such as three-ringed ortho-fluoro(halo)phenanthrenes, four-ringed ortho-fluoro(halo)tetraphenes, ortho-fluoro(halo)chrysenes and 6-fluoro-benzo[c]phenanthrene. Metalation of the aryne precursors followed by elimination of the fluoride resulted in the unprecedented systematic generation of arynes bearing π-extended systems e.g., 9,14-dihydro-9,14-diphenyl-9,14-epoxybenzo[b]triphenylene. Diels-Alder reactions of these arynes with isobenzofurans afforded the corresponding cycloadducts e.g., I, whose reductive aromatization in an SnCl2/HBr system furnished fully aromatized benzotriphenylenes e.g., 9,14-diphenylbenzo[b]triphenylene. In addition, oxidative aryl-aryl coupling (Scholl reaction) of these benzotriphenylenes facilitated the synthesis of ‘half HBCs’ (hexabenzocoronenes) II (R1 = H, n-Hex, t-Bu). In addition to this study using 1,3-Diphenylisobenzofuran, there are many other studies that have used 1,3-Diphenylisobenzofuran(cas: 5471-63-6Synthetic Route of C20H14O) was used in this study.

1,3-Diphenylisobenzofuran(cas: 5471-63-6) can be used as a fluorescent probe for detection of superoxide anion radical (O2−) inside the membrane lipid layer by DPBF fluorescence quenching method. 1,3-Diphenylisobenzofuran(DPBF) can be used as quencher during the photoinactivation of TA-3 mouse mammary carcinoma cells containing hematoporphyrin.Synthetic Route of C20H14O

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

《Spectroscopic and theoretical methods to probe protein-ligand binding》 was published in Materials Today: Proceedings in 2020. These research results belong to Sreedhanya, S.; Jeena, V. R.; Ammu, S.; Aravindakumar, C. T.; Aravind, Usha K.. Synthetic Route of C20H14O The article mentions the following:

Protein-ligand binding studies have gained considerable attention owing to its application in biomedical research. The present study discusses the application of spectroscopic and theor. methods to probe the interaction between a model ligand, 1, 3-diphenylisobenzofuran (DPBF) and bovine serum albumin (BSA). The quenching of the intrinsic fluorescence of BSA arising from tryptophan residue in the presence of DPBF is monitored to follow the nature and mechanism associated with the binding process. The binding affinity and number of binding sites have been investigated. Synchronous fluorescence and UV-Vis spectroscopic studies have been carried out to follow the changes in the fluorophore micro-environment and binding mechanism. Theor. methods such as fluorescence resonance energy transfer (FRET) and mol. docking are also employed to predict the binding mechanism, binding modes, binding sites and the distance between the tryptophan residue in BSA and DPBF. The experimental part of the paper was very detailed, including the reaction process of 1,3-Diphenylisobenzofuran(cas: 5471-63-6Synthetic Route of C20H14O)

1,3-Diphenylisobenzofuran(cas: 5471-63-6) can be used as a fluorescent probe for detection of superoxide anion radical (O2−) inside the membrane lipid layer by DPBF fluorescence quenching method. 1,3-Diphenylisobenzofuran(DPBF) can be used to study the single crystal molecular structure and solution photophysical properties of DPBF.Synthetic Route of C20H14O

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Quality Control of 7-Iodoisobenzofuran-1(3H)-oneOn September 30, 1988 ,《The internal steric push-effect: its consequences on the reactivity of carbonyl functions in 3-substituted phthalic anhydrides》 was published in Spectroscopy Letters. The article was written by Kayser, Margaret M.. The article contains the following contents:

The 13C NMR for a number of 3-substituted phthalic anhydrides and corresponding lactones were measured. Substituent effects were discussed. MM2 calculations for several 3-substituted phthalic anhydrides predict that the substituent and the neighboring carbonyl group remain coplanar and within the plane of the aromatic ring. To alleviate the imposed crowding, there is an in-plane distortion of the bond angle of the substituent and the carbonyl function. The observed angle of distortion increases with increasing steric demand of the substituent, in agreement with repulsive van der Waals interaction between those two groups. Diminished reactivity of the ortho carbonyl groups vis-a-vis nucleophiles in 3-substituted phthalic anhydrides may be linked to the internal steric push-effect which causes the displacement of electrons in the CO bond from O to C. The experimental process involved the reaction of 7-Iodoisobenzofuran-1(3H)-one(cas: 105694-46-0Quality Control of 7-Iodoisobenzofuran-1(3H)-one)

7-Iodoisobenzofuran-1(3H)-one(cas: 105694-46-0) belongs to benzofurans.Quality Control of 7-Iodoisobenzofuran-1(3H)-oneBenzofurans containing one furan ring that have been implicated as psychoactive recreational drugs include 6-(2-aminopropyl)benzofuran (6-APB), 5-(2-aminopropyl)benzofuran (5-APB), 5-(2-ethylaminopropyl)benzofuran (5-EAPB), and 5-methylaminopropylbenzofuran (5-MAPB).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

《An Ultrasound-Excitable Aggregation-Induced Emission Dye for Enhanced Sonodynamic Therapy of Tumors》 was written by Zeng, Weiwei; Xu, Yan; Yang, Weitao; Liu, Kai; Bian, Kexin; Zhang, Bingbo. Recommanded Product: 5471-63-6This research focused ontumor sonodynamic therapy ultrasound aggregation induced emission dye; aggregation‐induced emission; reactive oxygen species; sonodynamic therapy; sonosensitizers. The article conveys some information:

Ultrasound (US)-triggered sonodynamic therapy (SDT) can significantly solve the problem of tissue penetrability of light of photodynamic therapy (PDT) that has long vexed physicians in clinics. However, there is a great shortage of sonosensitizers for SDT. Currently, several photosensitizers and their derivatives have been reported for SDT but these dyes are usually quenched when aggregated due to aggregation-caused quenching (ACQ) effect. In this work, aggregation-induced emission (AIE) dye (TTMN) assembled nanoparticles (S-AIE) are synthesized and employed as sonosensitizers for enhanced SDT due to the unique properties of the AIE dye and the deep tissue penetration of ultrasound. Results show that S-AIE can generate potent singlet oxygen (1O2) under US irradiation to induce cancer cells apoptosis and clearly inhibit tumor growth in vitro and in vivo. In particular, the intrinsic fluorescence of AIE dye can guide the procedure of SDT. To the best of current knowledge, this is the first demonstration of AIE dyes being used as sonosensitizers for SDT and importantly, this work could inspire other more efficient AIE dyes for being used as sonosensitizers for SDT of deep-seated tumors. In the experiment, the researchers used many compounds, for example, 1,3-Diphenylisobenzofuran(cas: 5471-63-6Recommanded Product: 5471-63-6)

1,3-Diphenylisobenzofuran(cas: 5471-63-6) is a fluorescent dye. 1,3-Diphenylisobenzofuran is the model compound in studies of singlet fission.Recommanded Product: 5471-63-6

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Shih, Yi-Fan; Lee, Hsin-Yi; Huang, Ying-Hsuan; Chuang, Fu-Yu; Lee, Gon-Ann published their research in Journal of Fluorine Chemistry in 2021. The article was titled 《Study of properties of 3-fluorinated cyclopropene derivatives》.Recommanded Product: 1,3-Diphenylisobenzofuran The article contains the following contents:

Treatment of 1-bromo-2,2-dichloro-3-trimethylsilylcyclopropane with 5 equiv of CsF resulted in the formation of a chlorocyclopropenyl cation, which, under different conditions, further reacted with fluoride ion selectively to generate 3,3-difluorocyclopropene or 1-chloro-3-fluorocyclopropene. The Diels-Alder reactions of fluorinated cyclopropene derivatives with DPIBF yielded only exo or exo-anti adducts. On treatment of fused tricyclic cis-1-chloro-3-fluorocyclopropane derivative with n-BuLi, 3-fluorocyclopropene derivative was formed, which underwent Diels-Alder reaction with DPIBF to give an endo-endo adduct. Addnl., fused tricyclic 3,3-difluorocyclopropane and cis-1-chloro-3-fluorocyclopropane derivatives underwent ring-opening reaction of cyclopropane by BF3·Et2O, resp., and 1,4-diphenylnaphthalene derivatives were obtained. The results came from multiple reactions, including the reaction of 1,3-Diphenylisobenzofuran(cas: 5471-63-6Recommanded Product: 1,3-Diphenylisobenzofuran)

1,3-Diphenylisobenzofuran(cas: 5471-63-6) can be used as a fluorescent probe for detection of superoxide anion radical (O2−) inside the membrane lipid layer by DPBF fluorescence quenching method. 1,3-Diphenylisobenzofuran(DPBF) can be used to study the single crystal molecular structure and solution photophysical properties of DPBF.Recommanded Product: 1,3-Diphenylisobenzofuran

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

《Unsymmetrical zinc(II) phthalocyanine and zinc(II) naphthalocyanine with 2,3-Dicyano-1,4-diphenylnaphthalene precursor》 was written by de Souza, Thalita F. M.; Torres Antonio, Felipe Cesar; Homem-de-Mello, Paula; Ribeiro, Anderson O.. Electric Literature of C20H14OThis research focused onunsym zinc phthalocyanine naphthalocyanine preparation photophys photochem; dicyanodiphenylnaphthalene precursor preparation; Diels Alder diphenylisobenzofuran fumaronitrile. The article conveys some information:

The synthesis, photophys. and photochem. properties of an unsym. zinc(II) phthalocyanine and zinc(II) naphthalocyanine derivative are described. The precursor 2,3-Dicyano-1,4-diphenylnaphthalene was synthesized by Diels-Alder reaction with 1,3-diphenylisobenzofuran and fumaronitrile. The macrocycles were characterized by MALDI-TOF, FTIR, 1H NMR and UV-vis. On their spectroscopy, the impact of the added aromatic moiety was investigated in solution, observing a bathochromic shift in UV-vis absorption, emission and excitation spectra. The structural and electronic properties indicated that the geometry reorganization during the excitation and relaxation processes, and the dipole moment of the ground state, increases the generation of singlet oxygen in solution The results came from multiple reactions, including the reaction of 1,3-Diphenylisobenzofuran(cas: 5471-63-6Electric Literature of C20H14O)

1,3-Diphenylisobenzofuran(cas: 5471-63-6) is a fluorescent dye. 1,3-Diphenylisobenzofuran is the model compound in studies of singlet fission.Electric Literature of C20H14O

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Xing, Enyun; Du, Yingying; Yin, Juanjuan; Chen, Minghui; Zhu, Mengyao; Wen, Xiaona; Xu, Jialiang; Feng, Yaqing; Meng, Shuxian published their research in Advanced Healthcare Materials in 2021. The article was titled 《Multi-functional Nanodrug Based on a Three-dimensional Framework for Targeted Photo-chemo Synergetic Cancer Therapy》.Application In Synthesis of 1,3-Diphenylisobenzofuran The article contains the following contents:

Targeted synergistic therapy has broad prospects in tumor treatments. Here, a multi-functional nanodrug GDYO-CDDP/DOX@DSPE-PEG-MTX (GCDM) based on three traditional anticancer drugs (doxorubicin (DOX), cisplatin (CDDP) and methotrexate (MTX)) modified graphdiyne oxide (GDYO) is described, for diagnosis and targeted cancer photo-chemo synergetic therapy. In this system, for the first time, these three traditional anti-cancer drugs have played new roles and can reduce multidrug resistance through synergistic anti-tumor effects. Cisplatin can be hybridized with GDYO to form a multifunctional and well-dispersed three-dimensional framework, which can not only be used as nano-drug carriers to achieve high drug loading rates (40.3%), but also exhibit excellent photothermal conversion efficiency (47%) and good photodynamic effects under NIR irradiation Doxorubicin (DOX) is loaded onto GDYO-CDDP through π-π stacking, which is used as an anticancer drug and as a fluorescent probe for nanodrug detection. Methotrexate (MTX) can be applied in tumor targeting and play a role in synergistic chemotherapy with DOX and CDDP. The synthesized multi-functional nanodrug GCDM has good biocompatibility, active targeting, long-term retention, sustained drug release, excellent fluorescence imaging capabilities, and remarkable photo-chemo synergistic therapeutic effects. The experimental process involved the reaction of 1,3-Diphenylisobenzofuran(cas: 5471-63-6Application In Synthesis of 1,3-Diphenylisobenzofuran)

1,3-Diphenylisobenzofuran(cas: 5471-63-6) can be used as a fluorescent probe for detection of superoxide anion radical (O2−) inside the membrane lipid layer by DPBF fluorescence quenching method. 1,3-Diphenylisobenzofuran(DPBF) can be used to study the single crystal molecular structure and solution photophysical properties of DPBF.Application In Synthesis of 1,3-Diphenylisobenzofuran

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Aboraia, Ahmed S.; Yee, Sook Wah; Gomaa, Mohamed Sayed; Shah, Nikhil; Robotham, Anna C.; Makowski, Bart; Prosser, David; Brancale, Andrea; Jones, Glenville; Simons, Claire published an article in Bioorganic & Medicinal Chemistry. The title of the article was 《Synthesis and CYP24A1 inhibitory activity of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides》.Recommanded Product: Ethyl 6-methoxybenzofuran-2-carboxylate The author mentioned the following in the article:

A series of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides were prepared, using an efficient three- to five-step synthesis, and evaluated for their inhibitory activity against human cytochrome P450C24A1 (CYP24A1) hydroxylase. Inhibition ranged from IC50 0.3-72 μM compared with the standard ketoconazole IC50 0.52 μM, with the styryl derivative (11c) displaying enhanced activity (IC50 = 0.3 μM) compared with the standard, providing a useful preliminary lead for drug development. After reading the article, we found that the author used Ethyl 6-methoxybenzofuran-2-carboxylate(cas: 50551-57-0Recommanded Product: Ethyl 6-methoxybenzofuran-2-carboxylate)

Ethyl 6-methoxybenzofuran-2-carboxylate(cas: 50551-57-0) belongs to benzofurans.Recommanded Product: Ethyl 6-methoxybenzofuran-2-carboxylateBenzofurans containing one furan ring that have been implicated as psychoactive recreational drugs include 6-(2-aminopropyl)benzofuran (6-APB), 5-(2-aminopropyl)benzofuran (5-APB), 5-(2-ethylaminopropyl)benzofuran (5-EAPB), and 5-methylaminopropylbenzofuran (5-MAPB).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Quality Control of Ethyl 6-methoxybenzofuran-2-carboxylateOn May 26, 2015, Xue, Si-tu; Guo, Hui-fang; Liu, Mei-jie; Jin, Jie; Ju, Da-hong; Liu, Zong-ying; Li, Zhuo-rong published an article in European Journal of Medicinal Chemistry. The article was 《Synthesis of a novel class of substituted benzothiophene or benzofuran derivatives as BMP-2 up-regulators and evaluation of the BMP-2-up-regulating effects in vitro and the effects on glucocorticoid-induced osteoporosis in rats》. The article mentions the following:

The bone morphogenetic protein 2 (BMP-2) pathway is a promising new target for the design of therapeutic agents for the treatment of low bone mass. To enrich our understanding of SAR and based on our previously concluded structure-effect relationship, 23 derivatives were prepared in this work. The synthesis, up-regulating activities on BMP-2 expression, and bone loss prevention efficacy of these compounds in rats with glucocorticoid-induced osteoporosis are presented. The bone histol. of the tested rats assessed through light microscopy showed that several compounds significantly increased the spongy bone (i.e., trabecular bone) compared with the model group and the trabecula of the groups treated with one compound was similar to that obtained with raloxifene and alfacalcidol. The compounds exhibited potential for development as anabolic agents.Ethyl 6-methoxybenzofuran-2-carboxylate(cas: 50551-57-0Quality Control of Ethyl 6-methoxybenzofuran-2-carboxylate) was used in this study.

Ethyl 6-methoxybenzofuran-2-carboxylate(cas: 50551-57-0) belongs to benzofurans.Quality Control of Ethyl 6-methoxybenzofuran-2-carboxylateBenzofurans containing one furan ring that have been implicated as psychoactive recreational drugs include 6-(2-aminopropyl)benzofuran (6-APB), 5-(2-aminopropyl)benzofuran (5-APB), 5-(2-ethylaminopropyl)benzofuran (5-EAPB), and 5-methylaminopropylbenzofuran (5-MAPB).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

SDS of cas: 5471-63-6In 2020 ,《Lifetime and diffusion distance of singlet oxygen in air under everyday atmospheric conditions》 was published in Physical Chemistry Chemical Physics. The article was written by Wang, Kang-Kyun; Song, Sanggeun; Jung, Seung-Jin; Hwang, Jung-Wook; Kim, Min-Goo; Kim, Ji-Hyun; Sung, Jaeyoung; Lee, Jin-Kyu; Kim, Yong-Rok. The article contains the following contents:

Singlet oxygen is a toxic chem. but powerful oxidant, exploited in many chem. and biol. applications. However, the lifetime of singlet oxygen in air under atm. conditions is yet to be known. This has limited safe usage of singlet oxygen in air, despite being a strong antimicrobial agent with the unique property of relaxing to breathable oxygen after serving its purpose. Here, we solve this long-standing problem by combining exptl. and theor. research efforts; we generate singlet oxygen using a photosensitizer at a local source and monitor the time-dependent extent of singlet oxygen reaction with probe mols. at a detector, precisely controlling the detector distance from the source. To explain our exptl. results, we employ a theor. model that fully accounts for singlet oxygen diffusion, radiative and nonradiative relaxations, and the bimol. reaction with probe mols. at the detector. For all cases investigated, our model, with only two adjustable parameters, provides an excellent quant. explanation of the experiment From this anal., we extract the lifetime of singlet oxygen in the air to be 2.80 s at 23°C under 1 atm, during which time singlet oxygen diffuses about 0.992 cm. The correctness of this estimation is confirmed by a simple mean-first-passage time anal. of the maximum distance singlet oxygen can reach from the source. We also confirm the sterilization effects of singlet oxygen for distances up to 0.6-0.8 cm, depending on the bacteria strain in question, between the bacteria and the singlet oxygen source. In the part of experimental materials, we found many familiar compounds, such as 1,3-Diphenylisobenzofuran(cas: 5471-63-6SDS of cas: 5471-63-6)

1,3-Diphenylisobenzofuran(cas: 5471-63-6) is a fluorescent dye. 1,3-Diphenylisobenzofuran is the model compound in studies of singlet fission.SDS of cas: 5471-63-6

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem