Further insight into the dual COX-2 and 15-LOX anti-inflammatory activity of 1,3,4-thiadiazole-thiazolidinone hybrids: The contribution of the substituents at 5th positions is size dependent

Omar, Yasser M.; Abdel-Moty, Samia G.; Abdu-Allah, Hajjaj H.M.

doi:10.1016/j.bioorg.2020.103657

Cited by 50 publications

(34 citation statements)

References 38 publications

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“…Increasing the number of hydroxy groups decreased inhibitory activity (67f). Similar trends could be observed for derivatives with methoxy groups (67g, 67h and 67i) [65].…”

Section: Anti-inflammatory and Analgesic Propertiessupporting

confidence: 81%

“…All the tested compounds at a dose 28 µg/kg showed maximal activity 3h after administration comparable to the reference drug celecoxib. The most active compounds (65, 67q and 67r) showed percent of inhibition of edema 49.5, 60.7and 57.9%, respectively [65]. The Compound 63 with campholenic aldehyde residue in structure (Figure 27) at a dose of 100 mg/kg showed significant protection against indometacin-induced ulceration.…”

Section: Anti-inflammatory and Analgesic Propertiesmentioning

confidence: 94%

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The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

Mech

Kurowska

Trotsko

2021

IJMS

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Thiazolidin-4-ones is an important heterocyclic ring system of a pharmacophore and a privileged scaffold in medicinal chemistry. This review is focused on the latest scientific reports regarding biological activities of thiazolidin-4-ones published in 2020 and 2021. The review covers recent information about antioxidant, anticancer, anti-inflammatory, analgesic, anticonvulsant, antidiabetic, antiparasitic, antimicrobial, antitubercular and antiviral properties of thiazolidin-4-ones. Additionally, the influence of different substituents in molecules on their biological activity was discussed in this paper. Thus, this study may help to optimize the structure of thiazolidin-4-one derivatives as more efficient drug agents. Presented information may be used as a practical hint for rational design of new small molecules with biological activity, especially among thiazolidin-4-ones.

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“…Increasing the number of hydroxy groups decreased inhibitory activity (67f). Similar trends could be observed for derivatives with methoxy groups (67g, 67h and 67i) [65].…”

Section: Anti-inflammatory and Analgesic Propertiessupporting

confidence: 81%

Section: Anti-inflammatory and Analgesic Propertiesmentioning

confidence: 94%

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

Mech

Kurowska

Trotsko

2021

IJMS

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“…Compounds 74a , 74b , and 74c ( Figure 11 ) were capable of inhibiting 15-LOX at 2.74, 13.11, and 10.21 µM, respectively, and COX-2 at 0.32, 0.1, and 0.1 µM, respectively. The compounds showed in vivo anti-inflammatory activity comparable to the reference drug (celecoxib) 89 .…”

Section: Recent Development In Anti-inflammatory Agentsmentioning

confidence: 81%

“…Compounds 74a, 74b, and 74c (Figure 11) were capable of inhibiting 15-LOX at 2.74, 13.11, and 10.21 mM, respectively, and COX-2 at 0.32, 0.1, and 0.1 mM, respectively. The compounds showed in vivo anti-inflammatory activity comparable to the reference drug (celecoxib) 89 . Notably, there is a thiazolidinone ring in the structure of compound 3 (Figure 1), compounds 4a-4d (Figure 1), compounds 16a-16f (Figure 2), and compound 20b (Figure 2).…”

Section: Thiazolidinone Derivatives As Anti-inflammatory Agentsmentioning

confidence: 81%

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Bian

Wu³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Inflammation and disease are closely related. Inflammation can induce various diseases, and diseases can promote inflammatory response, and two possibly induces each other in a bidirectional loop. Inflammation is usually treated using synthetic anti-inflammatory drugs which are associated with several adverse effects hence are not safe for long-term use. Therefore, there is need for anti-inflammatory drugs which are not only effective but also safe. Several researchers have devoted to the research and development of effective anti-inflammatory drugs with little or no side effects. In this review, we studied some small molecules with reported anti-inflammatory activities and hence potential sources of anti-inflammatory agents. The information was retrieved from relevant studies published between January 2019 and May, 2021 for review. This review study was aimed to provide relevant information towards the design and development of effective and safe anti-inflammation agents.

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“…Reportedly, the binding of the test compounds with active site of COX‐2 isoenzyme depended on the bulkiness of the substituents at 5‐position, as evidenced by the in vitro enzyme immunoassay. in vivo ulcerogenic liability investigations on test compounds indicated no symptoms of ulceration edema or desquamation of epithelial cells (Omar, Moty, & Abdul‐Allah, 2020). Conjugation of thiazolidinone with pyridazine nucleus resulted in the compounds 80a–e (Figure 14) with a promising gastric safety profile.…”

Section: Selective Cox‐2 Inhibitors Based On Azole Nucleusmentioning

confidence: 99%

“Azole” as privileged heterocycle for targeting the inducible cyclooxygenase enzyme

Prasher

Sharma

2020

Drug Development Research

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An over‐expression of COX‐2 isoenzyme belonging to the Cyclooxygenase Enzyme Family triggers the overproduction of pro‐inflammatory prostaglandins that instigate the development of chronic inflammation and related disorders. Hence, the rationally designed drugs for mitigating over‐activity of COX‐2 isoenzyme play a regulatory role toward the alleviation of the progression of these disorders. However, a selective COX‐2 inhibition chemotherapy prompts several side effects that necessitate the identification of novel molecular scaffolds for deliberating state‐of‐the‐art drug designing strategies. The heterocyclic “azole” scaffold, being polar and hydrophilic, possesses remarkable physicochemical advantages for designing physiologically active molecules capable of interacting with a wide range of biological components, including enzymes, peptides, and metabolites. The substituted derivatives of azole nuclei enable a comprehensive SAR analysis for the appraisal of bioactive profile of the deliberated molecules for obtaining the rationally designed compounds with prominent activities. The comprehensive SAR analysis readily prompted the identification of Y‐shaped molecules and the eminence of bulkier group for COX‐2 selective inhibition. This review presents an epigrammatic collation of the pharmacophore‐profile of the chemotherapeutics based on azole motif for a selective targeting of the COX‐2 isoenzyme.

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Further insight into the dual COX-2 and 15-LOX anti-inflammatory activity of 1,3,4-thiadiazole-thiazolidinone hybrids: The contribution of the substituents at 5th positions is size dependent

Cited by 50 publications

References 38 publications

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

“Azole” as privileged heterocycle for targeting the inducible cyclooxygenase enzyme

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