Microwave-assisted synthesis of a series of 4,5-dihydro-1H-pyrazoles endowed with selective COX-1 inhibitory potency

Altıntop, Mehlika Dilek; Temel, Halide Edip; Özdemir, Ahmet

doi:10.2298/jsc220907001a

Cited by 3 publications

(2 citation statements)

References 39 publications

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“…The precipitate was filtered and washed with water. After drying, the product was crystallized from ethanol …”

Section: Methodsmentioning

confidence: 99%

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Design, Synthesis, and In Vivo Evaluation of a New Series of Indole-Chalcone Hybrids as Analgesic and Anti-Inflammatory Agents

Baramaki,

Altıntop,

Arslan

et al. 2024

ACS Omega

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Indole-chalcone hybrids have burst into prominence as potent weapons in the battle against pain and inflammation due to their unique features, allowing these ligands to form pivotal interactions with biological targets. In this context, the basecatalyzed Claisen−Schmidt condensation of 3′,4′-(methylenedioxy)acetophenone with heteroaromatic aldehydes carrying an indole scaffold yielded new chalcones (1−7). The central and peripheral antinociceptive activities of all chalcones (compounds 1−7) at the dose of 10 mg/kg (i.p.) were evaluated by hot plate (supraspinal response), tail immersion (spinal response), and acetic acid-induced writhing tests in mice. The anti-inflammatory activities of compounds 1−7 were also investigated by means of a carrageenan-induced mouse paw edema model. The results revealed that compounds 1−7 extended the latency of response to thermal stimulus significantly in a hotplate test similar to dipyrone (300 mg/kg; i.p.), the positive control drug. However, only compounds 2−7 were found to be significantly effective in the tail-immersion test. Compounds 1−7 also significantly showed analgesic effect by reducing the number of writhes and anti-inflammatory activity by inhibiting edema formation at different time intervals and levels. 1-(1,3-Benzodioxol-5yl)-3-(1-methyl-1H-indol-2-yl)prop-2-en-1-one (4) drew attention by providing the highest efficacy results in both acute analgesia and inflammation models. Based on the in silico data acquired from the QikProp module, compound 4 was predicted to possess favorable oral bioavailability and drug-like properties. Taken together, it can be concluded that chalcones (1−7), especially compound 4, are outstanding candidates for further research to investigate their potential use in the management of pain and inflammation.

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“…The precipitate was filtered and washed with water. After drying, the product was crystallized from ethanol …”

Section: Methodsmentioning

confidence: 99%

“…After drying, the product was crystallized from ethanol. 52 Within each experimental set, a group of mice was injected with a solution containing 10% dimethyl sulfoxide (DMSO) in distilled water and served as the control group. The intraperitoneal (i.p.)…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and In Vivo Evaluation of a New Series of Indole-Chalcone Hybrids as Analgesic and Anti-Inflammatory Agents

Baramaki,

Altıntop,

Arslan

et al. 2024

ACS Omega

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Design, Synthesis, and Evaluation of a New Series of 2-Pyrazolines as Potential Antileukemic Agents

Altıntop,

Cantürk,

Özdemir

2023

ACS Omega

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In an attempt to identify small molecules for the treatment of leukemia, 12 new pyrazolines (2a−l) were synthesized efficiently. WST-1 assay was performed to examine their cytotoxic features on HL-60 human acute promyelocytic leukemia (APL), K562 human chronic myeloid leukemia (CML), and THP-1 human acute monocytic leukemia cells. Four compounds (2e, 2f, 2g, and 2h) were determined as promising antileukemic agents on HL-60 and K562 cells. IC 50 values of compounds 2f, 2h, 2e, 2g, and bortezomib for the HL-60 cell line were found as 33.

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COX inhibitory profiles of a series of thiadiazole-benzothiazole hybrids

Özdemir,

Temel

2024

Eur J Life Sci

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In an endeavour to identify small molecule COX-1 inhibitors, a colorimetric assay protocol was applied for the in vitro evaluation of COX-1 and 2 inhibitory potential of a series of thiadiazole-benzothiazole hybrids. The most potent and selective COX-1 inhibitor in this series was found as 2-[(5-amino-1,3,4-thiadiazol-2-yl)thio]-N-(6-chlorobenzothiazol-2-yl)acetamide (7) (51.36 ± 3.32% at 100 µM) compared to SC-560 (83.64 ± 3.76% at 1 µM). Compound 7 exerted weaker inhibitory effect on COX-2 (11.05 ± 1.69% at 100 µM). To explore its binding interactions at the active site of human COX-1 (PDB ID: 6Y3C), molecular docking studies were conducted. Compound 7 could establish hydrogen bonds with proper residues thanks to its amide C=O group. In silico studies were employed to shed light on their pharmacokinetic properties. Taken together, compound 7 can be considered as a potential lead compound for the generation of selective COX-1 inhibitors with enhanced efficacy.

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Microwave-assisted synthesis of a series of 4,5-dihydro-1H-pyrazoles endowed with selective COX-1 inhibitory potency

Cited by 3 publications

References 39 publications

Design, Synthesis, and In Vivo Evaluation of a New Series of Indole-Chalcone Hybrids as Analgesic and Anti-Inflammatory Agents

Design, Synthesis, and In Vivo Evaluation of a New Series of Indole-Chalcone Hybrids as Analgesic and Anti-Inflammatory Agents

Design, Synthesis, and Evaluation of a New Series of 2-Pyrazolines as Potential Antileukemic Agents

COX inhibitory profiles of a series of thiadiazole-benzothiazole hybrids

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