Archives for Chemistry Experiments of 5-Bromo-6-phenylpyridazin-3(2H)-one

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A series of 6-phenyl-3(2H)-pyridazinones with a diverse range of substituents in the 5-position have been prepared and evaluated in the search for new antiplatelet agents. A significant dependence of the substituent on the inhibitory effect has been observed. The pharmacological study of these compounds confirms that modification of the chemical group at position 5 of the 6-phenyl-3(2H)-pyridazinone system influences both variations in the antiplatelet activity and the mechanism of action.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N3135 – PubChem

 

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A series of diversely substituted 3(2H)-pyridazinones were efficiently N-methylated at position 2 by treatment with N,N-dimethylformamide dimethylacetal in DMF.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N3137 – PubChem

 

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The efficient one-pot functionalization, through palladium-catalysed reactions, of position 5 of the 6-phenyl-3(2H)-pyridazinone system has been performed using a retro-ene-assisted fragmentation. This route allows access through a short synthetic sequence to several pharmacologically useful 3(2H)-pyridazinones.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N3123 – PubChem

 

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5-Alkylidenepyridazin-3-ones with four points of diversity (R2, R6, X, Y) have been synthesized and evaluated as platelet aggregation inhibitors. Several derivatives eliciting antiplatelet activity in the low micromolar range (e.g., 14e, 14k, 14p, 14v, IC50 ? 1 mu M) were identified. Structure-activity relationships studies on these compounds revealed the key molecular determinants of this new family of antiplatelet agents: (a) two ester groups in the alkoxy moieties; (b) lipophilic substituents at the N2 position of the pyridazin-3-one. The preliminary results of a pharmacological study aimed at determining the mechanism of action of a set of representative compounds revealed that, unlike other pyridazinones, the documented antiplatelet effect is not a consequence of a PDE-III inhibitory activity.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N3122 – PubChem

 

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Several 6-phenyl-3(2H)-pyridazinones bearing different alkenyl groups at position 5 have been prepared in the search for novel antiplatelet agents. The target compounds were synthesised by a palladium-catalysed Heck cross-coupling reaction. Variable amounts of 4-phenyl-6-substituted-2-phthalazinones were isolated as by-products during these experiments. The crucial issues for successful Heck coupling in these systems concern the protection of position 2 of the heterocyclic ring and the use of tris(o-tolyl)phosphine as a ligand.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N3126 – PubChem

 

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The design and synthesis of two closely related series of prostacyclin receptor agonist compounds that showed excellent human IP receptor potency and efficacy is described. Compounds from this series showed in vivo activity after SC dosing in the monocrotaline model of PAH in rat.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N3140 – PubChem

 

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Pyridazines. Part XXIX: Synthesis and platelet aggregation inhibition activity of 5-substituted-6-phenyl-3(2H)-pyridazinones. Novel aspects of their biological actions

A series of 6-phenyl-3(2H)-pyridazinones with a diverse range of substituents in the 5-position have been prepared and evaluated in the search for new antiplatelet agents. A significant dependence of the substituent on the inhibitory effect has been observed. The pharmacological study of these compounds confirms that modification of the chemical group at position 5 of the 6-phenyl-3(2H)-pyridazinone system influences both variations in the antiplatelet activity and the mechanism of action.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N3134 – PubChem

 

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Pyridazines. Part 36: Synthesis and antiplatelet activity of 5-substituted-6-phenyl-3(2H)-pyridazinones

A convenient and efficient palladium-catalysed retro-ene-assisted method has been developed to prepare a series of 5-substituted-6-phenyl-3(2H)- pyridazinones as potential antiplatelet drugs. The most active compounds were those that contain a 3-phenyl-3-oxo-propenyl fragment or a phenylthio group at position 5 of the heterocyclic ring.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N3125 – PubChem

 

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Pyridazines. Part 25: Efficient and selective deprotection of pharmacologically useful 2-MOM-pyridazinones using Lewis acids

An efficient and selective procedure for the cleavage of a methoxymethyl group at the 2-position in acid-sensitive pyridazinones is presented. Deprotection with Lewis acids (boron tribromide or aluminium chloride) affords 3(2H)-pyridazinones under mild conditions without affecting multiple bonds in substituents.

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Reference£º
Pyridazine – Wikipedia,
Pyridazine | C4H4N3132 – PubChem

 

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Pyridazines. Part 26: Efficient and regioselective Pd-catalysed arylation of 4-bromo-6-chloro-3-phenylpyridazine

The regioselective arylation at position 4 of 4-bromo-6-chloro-3-phenylpyridazine has been performed using a Suzuki cross-coupling reaction. This route allows access to a wide-ranging series of pharmacologically useful pyridazine derivatives and confirms the usefulness of chloropyridazines as a masking group for the carbonyl moiety in cross-coupling reactions involving 5-bromo-3(2H)-pyridazinones.

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Reference£º
Pyridazine – Wikipedia,
Pyridazine | C4H4N3138 – PubChem