Green approach for the synthesis of thiophenyl pyrazoles and isoxazoles by adopting 1,3-dipolar cycloaddition methodology and their antimicrobial activity

Sowmya, Donthamsetty V; Teja, G. Lakshmi; Padmaja, A.; Prasad, V. Kamala; Padmavathi, V.

doi:10.1016/j.ejmech.2017.11.093

Cited by 62 publications

(22 citation statements)

References 30 publications

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“…Chalcones (17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31) were prepared by Claisen-Schmidt condensation reaction (Scheme 1) in the presence of aqueous potassium hydroxide as a catalyst. The 1-(isoxazole-5-yl)ethanone (1) was condensed with substituted benzaldehyde (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) under basis conditions at room temperature for 24 h. The reaction was stopped by transferring the mixture on ice. The crude precipitate was recrystallized using chloroform to afford chalcones 17-31.…”

Section: Chemistrymentioning

confidence: 99%

“…Previously published studies suggested that chalcones/heteroarylchalcones and compounds having dihydropyrazoles exhibited antimicrobial, antioxidant, and cytotoxic activity [1][2][3][4][5]. Hence, we decided to screen our compounds for antibacterial, antifungal, antioxidant, and anticancer (prostrate cell line) activities.…”

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

“…We have previously reported heterocyclic ring-appended chalcones exhibiting antitubercular, antifungal, and cytotoxic activities [9][10][11][12][13]. Based on a literature survey [1][2][3][4][5] and our previously conducted studies [9][10][11][12][13], we herein report a continuation of that work, with a goal of further evaluating isoxazole-containing chalcones and its dihydropyrazole derivatives (privileged heterocyclic compounds) ( Figure 2) for their antibacterial, antifungal, antioxidant, and anticancer activities. The results of these efforts and the structure- Chalcones, a privileged structure in medicinal chemistry [6], are a type of open chain flavonoids bearing two aryl rings connected through a three-carbon spacer, the propenone linkage.…”

Section: Introductionmentioning

confidence: 99%

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Antimicrobial, Antioxidant, and Anticancer Activities of Some Novel Isoxazole Ring Containing Chalcone and Dihydropyrazole Derivatives

et al. 2020

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Our previous work identified isoxazole-based chalcones and their dihydropyrazole derivatives as two important five-membered heterocycles having antitubercular activity. Hence, in the present study, we biologically evaluated 30 compounds, including 15 isoxazole ring-containing chalcones (17–31) and 15 dihydropyrazoles (32–46) derived from these chalcones for their antimicrobial, antioxidant, and anticancer activities. Chalcones exhibited superior antibacterial and antioxidant activities compared to dihydropyrazoles. Among the chalcones, compound 28 showed potent antibacterial (MIC = 1 µg/mL) and antioxidant activities (IC50 = 5 ± 1 µg/mL). Dihydropyrazoles, on the contrary, demonstrated remarkable antifungal and anticancer activities. Compound 46 (IC50 = 2 ± 1 µg/mL) showed excellent antifungal activity whereas two other dihydropyrazoles 45 (IC50 = 2 ± 1 µg/mL) and 39 (IC50 = 4 ± 1 µg/mL) exhibited potential anticancer activity. The compounds were also tested for their toxicity on normal human cell lines (LO2) and were found to be nontoxic. The active compounds that have emerged out of this study are potential lead molecules for the development of novel drugs against infectious diseases, oxidative stress, and cancer.

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Section: Chemistrymentioning

confidence: 99%

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antimicrobial, Antioxidant, and Anticancer Activities of Some Novel Isoxazole Ring Containing Chalcone and Dihydropyrazole Derivatives

et al. 2020

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“…reported that introduction of a 1,3,4‐oxadiazole ring into target compounds could change their polarity, binding affinity with their receptor and flexibility, effectively enhancing their bioactivity . Furthermore, thiophene groups constitute a class of scaffold in bioactive molecules that are related to a variety of activities including antifungal, antimicrobial, insecticidal and herbicidal . Over the past few years, the synthesis and bioactivity of thiophene derivatives have attracted considerable attention and some representative examples of thiophene‐derived compounds are known for their ability to protect certain plants against severe diseases …”

Section: Introductionmentioning

confidence: 99%

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Wen

Jian

Shang

et al. 2018

Pest Management Science

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BACKGROUND Natural stilbenes (especially resveratrol and its derivatives) are well‐known phytoalexins that are active against many plant diseases. However, oxidative degradation and low bioavailability limit their exogenous application as fungicides on crops. In this study, a new class of resveratrol‐inspired thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit was synthesized and the derivatives' antifungal activities against phytopathogenic fungi were investigated. RESULTS The results revealed that compounds 5h and 5j exhibited improved antifungal activity against Botrytis cinerea with median effective concentrations (EC50) of 168.5 and 155.4 µg mL−1, respectively, which were superior to the EC50 of resveratrol (263.1 µg mL−1). Compound 5j was shown to effectively control disease development in B. cinerea‐infected tomatoes in vivo. Notably, considerably abnormal mycelial morphology and increased cell membrane conductivity were observed in the presence of compound 5j. CONCLUSION A new class of thiophene‐containing stilbene derivatives was designed and synthesized. Bioassay results showed that compound 5j exhibited promising antifungal activity, suggesting practical potential for fungal disease control. © 2018 Society of Chemical Industry

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“…Thiophenes with a wide spectrum of biological activities are known, several of these derivatives possess potent analgesic [1,2], anticonvulsant, anti-inflammatory and antibacterial [3][4][5][6], antipyretics [7], antitumor [8,9], antiparasitic [10], antimicrobial [11], antihistaminic (H1) [12], antianexiety test in mice [13], antiarrhythmic [14] and serotonin antagonist [15]. In previous work we have found that certain substituted thiophenes and their heterocyclic derivatives show antitumor activities [16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxicity of novel thiophene, pyran and pyridine derivatives

Wardakhan¹,

Samir²,

El-Arab³

2018

Bull. Chem. Soc. Eth.

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ABSTRACT. The reaction of 2-amino-3-cyano-tetrahydrobenzothiophene 3 with ethyl acetoacetate gave the amide derivatives 5. The reactivity of 5 toward a variety of chemical reagents was studied to give pyrans, pyridines, thiophenes and the thiazoles and their fused derivatives. The structures of the newly synthesized products were confirmed on the basis of their respective analytical and spectral data. The antitumor evaluations of the synthesized compounds against the three cancer cell lines MCF-7, NCI-H460 and SF-268 showed that compounds 9a, 9c, 12a and 14 were of the highest potencies against the three cancer cell lines among the tested compounds.

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Green approach for the synthesis of thiophenyl pyrazoles and isoxazoles by adopting 1,3-dipolar cycloaddition methodology and their antimicrobial activity

Cited by 62 publications

References 30 publications

Antimicrobial, Antioxidant, and Anticancer Activities of Some Novel Isoxazole Ring Containing Chalcone and Dihydropyrazole Derivatives

Antimicrobial, Antioxidant, and Anticancer Activities of Some Novel Isoxazole Ring Containing Chalcone and Dihydropyrazole Derivatives

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Synthesis and cytotoxicity of novel thiophene, pyran and pyridine derivatives

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