Efficient synthesis of 3 H ,3′ H -spiro[benzofuran-2,1′-isobenzofuran]-3,3′-dione as novel skeletons specifically for influenza virus type B inhibition

Malpani, Yashwardhan R.; Achary, Raghavendra; Kim, So Yeon; Jeong, Hee Chun; Kim, Pilho; Han, Soo Bong; Kim, Meehyein; Lee, Chong-Kyo; Kim, Jae Nyoung; Jung, Young‐Sik

doi:10.1016/j.ejmech.2013.01.015

Cited by 54 publications

(14 citation statements)

References 33 publications

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“…[26][27][28] Many synthetic benzofuran derivatives also have many biological activities. [29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45] Previously, we reported a sensor containing a benzofuran-β-alaninamide moiety for the detection of Fe 3+ ions. [46] For better levels of detection, here we developed a benzofuran glycinamide-based chemosensor for the detection of Fe 3+ ions.…”

Section: Introductionmentioning

confidence: 99%

Highly selective and sensitive ‘on–off’ fluorescent chemosensor for Fe³⁺ ions crafted by benzofuran moiety in both experimental and theoretical methods

Madhu

Sivakumar²,

Sribalan³

et al. 2022

Luminescence

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A benzofuran glycinamide-based chemosensor, 3-(2-([4-fluorobenzyl]amino)acetamido)benzofuran-2-carboxamide (BGA) was developed and synthesized for the selective and sensitive detection of Fe 3+ ions. The photophysical properties of the probe BGA were studied using UV-visible light absorption and fluorescence spectrophotometers. The chemosensor BGA showed a marked 'on-off' fluorescence response towards Fe 3+ ions in the presence of other metal ions in DMSO/H 2 O solution (9/1, v/v). The very low limits of detection (LOD) were calculated to be 10 nM and 43 nM using UV-visible light absorption and fluorescence spectrophotometers, respectively. Job's plot analysis revealed the formation of a BGA-Fe 3+ complex with a 1:1 binding stoichiometry ratio using UV-visible light spectroscopy.The sensing mechanism was also demonstrated using density functional theory calculation.

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Section: Introductionmentioning

confidence: 99%

Highly selective and sensitive ‘on–off’ fluorescent chemosensor for Fe³⁺ ions crafted by benzofuran moiety in both experimental and theoretical methods

Madhu

Sivakumar²,

Sribalan³

et al. 2022

Luminescence

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“…Benzofuran, a well-known structural motif known for divergent medicinal properties, and its synthetic variants in the fused and spiro form also received considerable interest due to their synthetic as well as biological applications . Specifically, the benzofurans fused with an indanone skeleton exhibit antiviral properties, and the molecules that contain the spiro(benzofuran-isobenzofuran) scaffold is present in influenza virus type B inhibitors and fluorescent probes . Moreover, the spiro(benzofuran-isobenzofuran) skeleton is typically synthesized from indanone-fused benzofuran through a rearrangement reaction …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Spiro- and Fused Heterocycles via (4+4) Annulation of Sulfonylphthalide with o-Hydroxystyrenyl Derivatives

et al. 2019

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An expedient one-pot protocol for the synthesis of functionalized benzofuran containing fused and spiro-heterocycles has been accomplished by the modified Hauser–Kraus (HK) annulation of sulfonylphthalide with o-hydroxychalcones and o-hydroxynitrostyrylisoxazoles. The multicascade process involves Michael addition, Dieckmann cyclization, and a series of cyclizations, eliminations, and rearrangements to deliver the fused and spiro-heterocyclic products. An unusual transformation of fused indenofuran to naphthoquinone, the classical HK adduct, unraveled a novel pathway for the synthesis unsymmetrical naphthoquinones.

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“…[304][305][306] In addition, isobenzofurans are an important class of natural products possessing significant biological properties. [307][308][309] Pramanik's group used 2-hydroxy-2,2'-biindan-1,1',3,3'-tetrone 254 in a condensation reaction with various phenols, polyhydroxy benzenes, and α-and β-naphthols 255 in an acid medium to produce 2-aryl/alkyl-2,2'-biindan-1,1',3,3'-tetrones 256. 1 H and 13 C NMR spectra from adducts of 256, in the case of substrates such as resorcinol, orcinol, 1,3,5-trihydroxybenzene and α-and β-naphthols, indicate that such derivatives prefer the intramolecular hemi-ketal form 257 (Scheme 78).…”

Section: Benzofurans and Isobenzofuransmentioning

confidence: 99%

Ninhydrin in synthesis of heterocyclic compounds

Ziarani¹,

Lashgari²,

Azimian³

et al. 2015

Arkivoc

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Ninhydrin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of reactions that include ninhydrin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of ninhydrin as starting material in the synthesis of various organic compounds and drugs in a fully comprehensive way, from its first isolation in 1910 to the end of 2013. There is also a diversity of multi-component reactions of ninhydrin and we highlight the recent reports in this review.

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Efficient synthesis of 3 H ,3′ H -spiro[benzofuran-2,1′-isobenzofuran]-3,3′-dione as novel skeletons specifically for influenza virus type B inhibition

Cited by 54 publications

References 33 publications

Highly selective and sensitive ‘on–off’ fluorescent chemosensor for Fe³⁺ ions crafted by benzofuran moiety in both experimental and theoretical methods

Highly selective and sensitive ‘on–off’ fluorescent chemosensor for Fe³⁺ ions crafted by benzofuran moiety in both experimental and theoretical methods

Synthesis of Spiro- and Fused Heterocycles via (4+4) Annulation of Sulfonylphthalide with o-Hydroxystyrenyl Derivatives

Ninhydrin in synthesis of heterocyclic compounds

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Efficient synthesis of 3 H ,3′ H -spiro[benzofuran-2,1′-isobenzofuran]-3,3′-dione as novel skeletons specifically for influenza virus type B inhibition

Cited by 54 publications

References 33 publications

Highly selective and sensitive ‘on–off’ fluorescent chemosensor for Fe3+ ions crafted by benzofuran moiety in both experimental and theoretical methods

Highly selective and sensitive ‘on–off’ fluorescent chemosensor for Fe3+ ions crafted by benzofuran moiety in both experimental and theoretical methods

Synthesis of Spiro- and Fused Heterocycles via (4+4) Annulation of Sulfonylphthalide with o-Hydroxystyrenyl Derivatives

Ninhydrin in synthesis of heterocyclic compounds

Contact Info

Product

Resources

About

Highly selective and sensitive ‘on–off’ fluorescent chemosensor for Fe³⁺ ions crafted by benzofuran moiety in both experimental and theoretical methods

Highly selective and sensitive ‘on–off’ fluorescent chemosensor for Fe³⁺ ions crafted by benzofuran moiety in both experimental and theoretical methods