Novel 2,5-disubstituted-1,3,4-oxadiazoles as anti-inflammatory drugs

Durgashivaprasad, Ega; Mathew, Geetha; Sebastian, Sarine; Reddy, Shivakumar; Mudgal, Jayesh; Nampurath, Gopalan Kutty

doi:10.4103/0253-7613.140584

Cited by 20 publications

(2 citation statements)

References 21 publications

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“…The acute toxicity study was performed in rats according to the OECD guidelines (TG-420) [ 24 ]. Rats were allocated into test group and vehicle group randomly with half male and female.…”

Section: Methodsmentioning

confidence: 99%

The Anti-Inflammatory Activity of Toonaciliatin K against Adjuvant Arthritis

Gou

Wang

et al. 2017

BioMed Research International

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Toonaciliatin K is a natural limonoid purified from the Toona ciliata Roem. var. ciliata (Meliaceae). This study is to reveal the inflammatory suppression effect of toonaciliatin K and further the intrinsic mechanism. Firstly, anti-inflammatory effect of toonaciliatin K was evaluated in lipopolysaccharide- (LPS-) induced RAW264.7 cells. RT-PCR results indicated that the mRNA expressions of TNF-α, IL-6, and IL-1β were downregulated by toonaciliatin K. The toonaciliatin K inhibited TNF-α, IL-6, and IL-1β levels stimulated by LPS. Furthermore, LPS elicited the excess iNOS and COX-2 mRNA and protein production and toonaciliatin K attenuated the excess production. Western blot assay demonstrated that MAPK and NF-κB signaling pathways play critical roles in the toonaciliatin K's anti-inflammatory activity. Secondly, toonaciliatin K inhibited carrageenan-induced paw edema in rats. Thirdly, toonaciliatin K alleviated the paw swelling and improved arthritis clinical scores in the adjuvant arthritis rats. Toonaciliatin K decreased the proinflammatory cytokines levels and Mankin scores in adjuvant arthritis rats. The HE staining, safranin O-fast green, and toluidine blue staining results demonstrated that toonaciliatin K alleviated the histological changes of paw, for example, pannus formation, focal loss of cartilage, bone erosion, and presence of extra-articular inflammation. Hence, toonaciliatin K is a promising agent for treatment of arthritis.

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“…The acute toxicity study was performed in rats according to the OECD guidelines (TG-420) [ 24 ]. Rats were allocated into test group and vehicle group randomly with half male and female.…”

Section: Methodsmentioning

confidence: 99%

The Anti-Inflammatory Activity of Toonaciliatin K against Adjuvant Arthritis

Gou

Wang

et al. 2017

BioMed Research International

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“…1,3,4-Oxadiazole, a pivotal five-membered nitrogen-containing heterocycle, is an interesting pharmacophore in medicinal chemistry. In particular, 2-acylamino-1,3,4-oxadiazoles have a broad range of biological activities such as anticoagulant [1,2,3], antibacterial [4,5,6,7,8], antifungal [9,10], anticancer [11,12], anti-inflammatory [13,14,15], insecticidal [16,17], antihypertensive [18,19], etc. [20,21] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

A Useful Synthesis of 2-Acylamino-1,3,4-oxadiazoles from Acylthiosemicarbazides Using Potassium Iodate and the Discovery of New Antibacterial Compounds

Wen

et al. 2019

Molecules

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A useful method for the synthesis of 2-acylamino-1,3,4-oxadiazoles was developed. By using potassium iodate as an oxidant in water at 60 °C, a wide range of 2-acylamino-1,3,4-oxadiazoles were afforded in moderate to excellent yields within two hours. This method could provide a facile shortcut to generate a series of 2-acylamino-1,3,4-oxadiazoles in medicinal chemistry. Interestingly, some highly potent antibiotic compounds were found through this synthetic method, and some of them displayed a significant improvement in activity compared with the corresponding 1,4-diacylthiosemicarbazides. Compound 2n was the most active against Staphylococcus aureus with MIC (minimum inhibitory concentration) of 1.56 mg/mL, and compounds 2m and 2q were the most active against Bacillus subtilis with MIC of 0.78 mg/mL. The preliminary cytotoxic activities of the most potent compounds 2m, 2n, and 2q against the androgen-independent (PC-3) prostate cancer cell line were more than 30 μM (IC50 > 30 μM).

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Reagent/Substituent Switching Approach for the Synthesis of Substituted 1,3,4‐Oxadiazole/1,3,4‐Oxadiazoline and 1,2,4‐Triazole Derivatives from N‐Substituted Hydrazides

et al. 2016

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A metal‐free method for the synthesis of substituted 1,3,4‐oxadiazole/1,3,4‐oxadiazoline and 1,2,4‐triazole derivatives from a common starting material via reagent/substituent switching is reported. In the presence of 2‐fluoropyridine/triflic anhydride, 1,3,4‐oxadiazole derivatives were exclusively formed from N′‐tert‐butylhydrazides and 1,3,4‐oxadiazoline derivatives were produced from N‐phenylhydrazides. On the other hand, when using pyridine/triflic anhydride, salts of 1,2,4‐triazoles were the sole products.magnified image

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Novel 2,5-disubstituted-1,3,4-oxadiazoles as anti-inflammatory drugs

Cited by 20 publications

References 21 publications

The Anti-Inflammatory Activity of Toonaciliatin K against Adjuvant Arthritis

The Anti-Inflammatory Activity of Toonaciliatin K against Adjuvant Arthritis

A Useful Synthesis of 2-Acylamino-1,3,4-oxadiazoles from Acylthiosemicarbazides Using Potassium Iodate and the Discovery of New Antibacterial Compounds

Reagent/Substituent Switching Approach for the Synthesis of Substituted 1,3,4‐Oxadiazole/1,3,4‐Oxadiazoline and 1,2,4‐Triazole Derivatives from N‐Substituted Hydrazides

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