Synthesis and biological screening of novel series of 2-(4-hydroxy-3-methoxy-5-nitro-phenyl)-[1,3,4]oxadiazole by conventional and non conventional techniques

Jadhav, Ranjana; Pawar, Sunayna; Khilare, Chandrakant; Nikumbh, Arun B.

doi:10.1016/j.matpr.2022.10.087

Cited by 5 publications

(4 citation statements)

References 27 publications

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“…The biological activity of some of the bioactive compounds such as 2‐pentanone, and 4‐hydroxy‐4‐methyl have been well reported in the literature [32,33] . The results of the anticancer studies are also in agreement with the cytotoxicity properties of four wild edible mushrooms; Coprinus comatus (O.F.…”

Section: Resultssupporting

confidence: 66%

Comparative Study on Biological Activities and Chemical Profiling of Mushroom (Pleurotus pulmonarius (Fr.) Quel.) Cultured on Lignocellulosic Agro Wastes

Zamakshshari

Ahmed

Nasharuddin

et al. 2023

Chemistry & Biodiversity

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The relevance of the lignocellulosic substrate in the cultivation of mushrooms has lent support to the exploration of several lignocellulosic agro wastes. This study was, thus, aimed at the evaluation of durian peel as an alternative substrate for more sustainable mushroom cultivation and climate change mitigation. The secondary metabolites and biological activities of both aqueous and organic mushroom (Pleurotus pulmonarius (Fr.) Quel.) extract cultured on durian peel and rubberwood sawdust substrate were compared using GCMS, LCMS as well as various biological assays (cytotoxicity, antimicrobial and antioxidant activities). Mushroom extracts from durian peel substrates possess remarkable biological activities. The results showed that the aqueous extracts had poor antimicrobial activities. The organic extracts were more active against cancer cells than the aqueous extracts, while the aqueous extracts were more potent as antioxidants than the organic extracts. Overall, the mushroom extract from the durian substrate was the most effective except against A549 and SW948, while the aqueous extract from the durian substrate was the most effective against the A549 cancer cell lines with 29.53±2.39 % inhibition. On the other hand, the organic mushroom extract from the sawdust substrate was the most effective against SW948 with 60.24±2.45 % inhibition. Further studies, however, are needed to elucidate the molecular mechanism of action of P. pulmonarius extracts against cancer cell proliferation and the effect of the substrates on the nutritional composition, secondary metabolites, and other biological activities of P. pulmonarius extracts.

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Section: Resultssupporting

confidence: 66%

Comparative Study on Biological Activities and Chemical Profiling of Mushroom (Pleurotus pulmonarius (Fr.) Quel.) Cultured on Lignocellulosic Agro Wastes

Zamakshshari

Ahmed

Nasharuddin

et al. 2023

Chemistry & Biodiversity

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“…The possible mechanistic perspective of using dehydrating agent POCl 3 was to first convert pyrazole‐4‐carboxylic acid 4 (a – f ) into its acid chloride derivative. The carbonyl carbon of this acid chloride was then attacked by acid hydrazide ( 3 ) to produce diacylhydrazide intermediate which further converted into an oxadiazole nucleus via dehydrative cyclization [41] . Thus, two new C−C bonds built at the 2 nd and 5 th positions of an oxadiazole ring, afforded one scaffold 5 (a – f ) possessing three heterocyclic motifs in it.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, in vitro α‐Glucosidase Inhibition, DFT Calculations, and Molecular Docking Studies of Some New Substituted 2,5‐Bis(pyrazolyl)‐1,3,4‐oxadiazoles

Chaudhry,

Abdullah,

un‐Nisa

et al. 2024

ChemistrySelect

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A pivotal feature of present research study is the synthesis of some new 2,5‐bis(pyrazolyl)‐1,3,4‐oxadiazoles as promising α‐glucosidase inhibitors. In this regard, a facile reaction scheme was designed to afford 1,3,4‐oxadiazole ring. In search of the most favourable reaction condition, a model reaction was first carried out between 1,3‐diphenyl‐1H‐pyrazole‐4‐carbohydrazide (3) and 1,3‐diphenyl‐1H‐pyrazole‐4‐carboxylic acid (4 a) using phosphorous oxychloride (POCl3). The results emanated from this model reaction were utilized to prepare other derivatives to highlight the scope of current synthetic approach and the structures of the prepared molecules were characterized from spectroscopic techniques. These derivatives were further investigated for their α‐glucosidase inhibitory potentials. 2,5‐Bis(1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐1,3,4‐oxadiazole (5 a) and 2‐(3‐(4‐bromophenyl)‐1‐phenyl‐1H‐pyrazol‐4‐yl)‐5‐(1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐1,3,4‐oxadiazole (5 c) displayed strong in vitro inhibitory activities with IC50 73.1±1.13 μM and IC50 87.3±1.12 μM respectively with least toxicity profiles. Molecular docking and computational studies including geometry optimization of synthesized molecular systems, calculations of their orbital energies, and molecular electrostatic potential (MEP) surface maps further helped to establish structural and electronic properties contributing towards their bioactivity. The electrophilicity index significantly quantifies the biological activity. The experimental and computational data altogether facilitated in understanding the therapeutic attributes of these versatile scaffolds in relation to their α‐glucosidase inhibition.

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“…The 1,3,4-oxadiazole moiety has long been an important scaffold in drug design and synthesis with versatile biological activities, including hypoglycemic 9 , anti-fungal 10 , and anti-inflammatory activities 11 . Several 1,3,4-oxadiazole derivatives have been reported for their cytotoxic action through numerous pathways and fortunately none of them has been linked to any negative side effects 12 .…”

Section: Introductionmentioning

confidence: 99%

New oxadiazole and pyrazoline derivatives as anti-proliferative agents targeting EGFR-TK: design, synthesis, biological evaluation and molecular docking study

Serag,

Tawfik,

Badr

et al. 2024

Sci Rep

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Two new series of oxadiazole and pyrazoline derivatives were designed and synthesized as promising EGFR-TK inhibitors. The in vitro antiproliferative activity was studied against three human cancer cell lines; HCT116, HepG-2 and MCF7 using MTT assay. Compound 10c showed the most potent anticancer activity against all cancer cell lines, with IC50 range of 1.82 to 5.55 μM, while proving safe towards normal cells WI-38 (IC50 = 41.17 μM) compared to the reference drug doxorubicin (IC50 = 6.72 μM). The most active candidates 5a, 9b, 10a, 10b and 10c were further assessed for their EGFR-TK inhibition. The best of which, compounds 5a and 10b showed IC50 of 0.09 and 0.16 μM respectively compared to gefitinib (IC50 = 0.04 μM). Further investigation against other EGFR family members, showed that 5a displayed good activities against HER3 and HER4 with IC50 values 0.18 and 0.37 µM, respectively compared to gefitinib (IC50 = 0.35 and 0.58 µM, respectively). Furthermore, 5a was evaluated for cell cycle distribution and apoptotic induction on HepG-2 cells. It induced mitochondrial apoptotic pathway and increased accumulation of ROS. Molecular docking study came in agreement with the biological results. Compounds 5a and 10b showed promising drug-likeness with good physicochemical properties.

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Synthesis and biological screening of novel series of 2-(4-hydroxy-3-methoxy-5-nitro-phenyl)-[1,3,4]oxadiazole by conventional and non conventional techniques

Cited by 5 publications

References 27 publications

Comparative Study on Biological Activities and Chemical Profiling of Mushroom (Pleurotus pulmonarius (Fr.) Quel.) Cultured on Lignocellulosic Agro Wastes

Comparative Study on Biological Activities and Chemical Profiling of Mushroom (Pleurotus pulmonarius (Fr.) Quel.) Cultured on Lignocellulosic Agro Wastes

Synthesis, in vitro α‐Glucosidase Inhibition, DFT Calculations, and Molecular Docking Studies of Some New Substituted 2,5‐Bis(pyrazolyl)‐1,3,4‐oxadiazoles

New oxadiazole and pyrazoline derivatives as anti-proliferative agents targeting EGFR-TK: design, synthesis, biological evaluation and molecular docking study

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