407. The action of benzoyl chloride and pyridine on 5-hydroxy-6-acetyl-4-methylcoumarin and reactions related thereto

Bernfeld, G. J.; Wheeler, T. S.

doi:10.1039/jr9490001915

Cited by 2 publications

(1 citation statement)

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“…We have successfully synthesized a pure salicylic acid derivate compound namely 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid. The synthesis of 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid was carried out based on modified Schotten-Baumann acylation reaction [11,12], with the use of biphasic aqueous basic conditions 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid was formed spontaneously when 3-chloromethylbenzoylchloride reacted with salicylic acid. However the esters were sensitive to acid and diminished the yield of reaction.…”

Section: Characterization Of 2-((3-(chloromethyl)benzoyl)oxy)benzoic Acidmentioning

confidence: 99%

Evaluation of analgesic and antiplatelet activity of 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid

Caroline

Foe

Esar

et al. 2019

Prostaglandins & Other Lipid Mediators

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Acetylsalicylic acid is used as a non-steroidal anti-inflammatory drugs (NSAID) and antiplatelet agents by inhibiting cyclooxygenases. However, therapy using acetylsalicylic acid could induce gastric bleeding and cause other gastrointestinal toxicity. The aim of this study was to demonstrate the synthesis of a new compound bearing salicylic acid residue namely 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid, to analyze its potential as a ligand for human cyclooxygenase-2 (COX-2) receptor, to evaluate its toxicity level and its effectiveness for analgesic and antiplatelet agent compared with acetylsalicylic acid.Synthesis of 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid was conducted by microwave irradiation. The purity of this compound was evaluated with TLC, IR, NMR, and EDS spectroscopy. The chemical characterization and docking studies against human COX-2 (PDB:5F1A) was performed in-silico. The acute oral toxicity assay was performed under OECD guidelines. The analgesic activity study was performed by plantar and writhing test on animal model. For anti-platelet activity study, we performed tail-bleeding assay and flow cytometry based platelet aggregation assay. We could successfully synthesize a pure white crystalline 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid. In-Silico G-Score result of those compounds gives us preliminary hint of the potential affinity of this compound as a ligand for COX-2 receptor (PDB: 5F1A). Acute toxicity and microscopic gastrointestinal assessments indicated non-observable harmful toxicity parameters. The plantar response time of 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid treated groups showed a significant increment (P < 0.01), and the nociceptive response in writhing test demonstrated a significant dose-dependent decrement. This indicated that its analgesic activity was better than acetylsalicylic acid. The platelet aggregation of 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid was lower than its controls, indicating an aggregation inhibition pattern. The animals treated with 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid gave a longer bleeding time. Overall, this study demonstrated a successful synthesis of pure 2-((3-(chloromethyl)benzoyl)oxy) benzoic acid. We postulated that this compound was better than acetylsalicylic acid, exhibiting excellent analgesic and antiplatelet activity with no toxicity impact.

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Section: Characterization Of 2-((3-(chloromethyl)benzoyl)oxy)benzoic Acidmentioning

confidence: 99%

Evaluation of analgesic and antiplatelet activity of 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid

Caroline

Foe

Esar

et al. 2019

Prostaglandins & Other Lipid Mediators

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Synthesis and biological activity of chromones annelated at the C(7)–C(8) bond with heterocycles (review)

Лозинский

Shokol

Khilya

2011

Chem Heterocycl Comp

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407. The action of benzoyl chloride and pyridine on 5-hydroxy-6-acetyl-4-methylcoumarin and reactions related thereto

Cited by 2 publications

References 0 publications

Evaluation of analgesic and antiplatelet activity of 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid

Evaluation of analgesic and antiplatelet activity of 2-((3-(chloromethyl)benzoyl)oxy)benzoic acid

Synthesis and biological activity of chromones annelated at the C(7)–C(8) bond with heterocycles (review)

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