Synthesis, characterization, DFT and photophysical studies of new class of 1,3,4-oxadiazole-isobenzofuran hybrids

Nayak, Swarnagowri; Sinha, Rajeev K.; Lewis, Prinston Melroy; Kulkarni, Suresh D.; Gaonkar, Santosh L.

doi:10.1016/j.jlumin.2021.118212

Cited by 8 publications

(4 citation statements)

References 47 publications

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“…Here, an unpredicted Michael addition occurs when aromatic aldehydes have pyridine and fluoro substitution. This prediction was proved by IR, 1 H-NMR, 13 C-NMR, HMBC, HSQC and elemental analysis. [41] Cui and coworkers synthesized benzofuran derivatives in one-pot and metal-free from simple ynones and quinines via aza-Michael/Michael/annulation sequence shown in Scheme 9.…”

Section: Synthetic Strategies Of Benzofuran Derivativesmentioning

confidence: 71%

“…While standardizing the reaction conditions it was observed that in the absence of triphenylphospine, product formation was not observed even after the completion of 24 hours and increasing the amount of catalyst did not have any notable effect on the yield of the product. The structures of the compounds were elucidated from IR, 1 H-NMR, 13 C-NMR, mass spectra and elemental analysis. [35] Tang et al, synthesized novel derivatives of 2arylbenzo[b]furan built on savianolic acid (26).…”

Section: Synthetic Strategies Of Benzofuran Derivativesmentioning

confidence: 99%

“…A novel class of dyes with push-pull mechanism of isobenzofuran core has been synthesized. [13,14] Some of the benzofurans extracted from plants exhibiting biological activity are shown in Figure 1. 1 was isolated from Ageratina adenophora (Asteraceae) and exhibits antifungal activity against four different fungi.…”

Section: Introductionmentioning

confidence: 99%

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Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

Dwarakanath

Gaonkar

2022

Asian J Org Chem

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Out of the many heterocycles that exhibit pharmaceutical and therapeutic properties, benzofurans remain the most eye-catching to scientists ever since their discovery. From being present in natural products to synthetic analogs they show diverse biological properties which are used to treat various diseases. Interestingly, some of the benzofuran hybrids were docked against COVID-19 Main Protease and it showed appealing results. Apart from medicinal properties it also exhibits some non-drug applications. The structure activity relationship of benzofuran derivatives in many infections draws attention to the extent where drugs can be produced in a short time span which highlights their significance in medicinal chemistry. There are considerable reaction schemes to synthesize this moiety either simple one pot reactions or multistep. Here, we emphasize on the chemistry of benzofurans, synthesis and its derivatives in the recent years, some of which show notable anti-tumor, antifungal, anti-mycobacterial and anti-oxidant activities.

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Section: Synthetic Strategies Of Benzofuran Derivativesmentioning

confidence: 71%

Section: Synthetic Strategies Of Benzofuran Derivativesmentioning

confidence: 99%

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Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

Dwarakanath

Gaonkar

2022

Asian J Org Chem

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“…Also, hybrids were studied for antimicrobial activity against selected Gram‐negative and Gram‐positive bacteria. Recently, our group has reported the photophysical properties of isobenzofuran‐oxadiazole hybrids [29] …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking and Evaluation of 1,3,4‐Oxadiazole‐Isobenzofuran Hybrids as Antimicrobial and Anticancer Agents

Nayak

Gaonkar

Hazra

et al. 2022

Chemistry & Biodiversity

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In drug discovery, the hybridization of bioactive pharmacophores is a powerful tool for targeting enzymes involved in cancer and microbial cell growth. A combination of 1,3,4‐oxadiazole and isobenzofuran may improve the antitumor and antimicrobial properties of the hybrid molecules. A series of hybrid molecules having 1,3,4‐oxadiazole and isobenzofuran were synthesized and structural characterization was done by FT‐IR, 1H‐NMR, 13C‐NMR, and mass spectrometry. Molecular docking studies were performed to investigate binding interactions of compounds with proteins (PDB NO: 2R3J and 1GII), and the results were consistent with in vitro anticancer data. All the synthesized compounds were tested for antimicrobial activity against S. aureus, E. faecalis (Gram‐positive) and E. coli and P. aeruginosa (Gram‐negative) bacterial strains. Among the synthesized compounds, 7a and 7b displayed good activity against the tested bacterial strains. Also, compounds were tested for their anti‐tumor activity against breast cancer (MCF‐7) and colon cancer (HCT‐116) cell lines via SRB assay. In comparison to doxorubicin (1.14 μM), hybrids 7e (4.32 μM), 7f (4.15 μM), 7g (4.66 μM), and 7h (4.83 μM) demonstrated comparable IC50 value against the HCT 116 cell line.

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Synthesis, characterization and photo-physical properties of sugar hydrazones having indole and 1,3,4-oxadiazole moiety

Nayak

Gaonkar

Devadiga

et al. 2023

Journal of Luminescence

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Synthesis, characterization, DFT and photophysical studies of new class of 1,3,4-oxadiazole-isobenzofuran hybrids

Cited by 8 publications

References 47 publications

Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

Advances in Synthetic Strategies and Medicinal Importance of Benzofurans: A Review

Synthesis, Molecular Docking and Evaluation of 1,3,4‐Oxadiazole‐Isobenzofuran Hybrids as Antimicrobial and Anticancer Agents

Synthesis, characterization and photo-physical properties of sugar hydrazones having indole and 1,3,4-oxadiazole moiety

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