123772-76-9

Upstream product

• 50874-15-2 1-phenylprop-2-ynyl-1-amine 
• 407-25-0 trifluoroacetic anhydride 
• 74-88-4 methyl iodide 
• 123772-68-9 N-(1-phenyl-2-propynyl)trifluoroacetamide 
• 123772-66-7 N-(α-phenylpropargyl)acetamide 
• 76651-92-8 1-phenyl-2-propynyl methanesulfonate 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 

Downstream Products

• 123772-78-1 N-methyl-1-phenyl-2-propyn-1-ylamine 
• 123772-77-0 N-methyl-N-(1-phenyl-2-propynyl)acetamide 
• 137518-09-3 2,2,2-Trifluoro-N-methyl-N-(1-phenyl-4-pyrrolidin-1-yl-but-2-ynyl)-acetamide 

Relevant academic research and scientific papers

Phenyl-Substituted Analogues of Oxotremorine as Muscarinic Antagonists

A series of phenyl-substituted analogues of the muscarinic agent oxotremorine (1) have been prepared.The new compounds (3b-11b and 9c) were assayed for antimuscarinic activity on the isolated guinea pig ileum and in intact mice.They were also evaluated for ability to inhibit the binding of the muscarinic antagonist (-)--N-methylscopolamine to homogenates of the rat cerebral cortex.The phenyl-substituted derivatives were devoid of intrinsic muscarinic activity.Instead, they behaved as competitive muscarinic antagonists in these assays with similar or lower affinity for muscarinic receptors than the corresponding methyl-substituted analogues.The succinimide (8b) and the pyrrolidone (3b) derivatives of 1 substituted with a phenyl group at position 1 of the bytynyl chain showed the highest antimuscarinic potency with dissociation constants (KD) of 0.10 and 0.20 μM, respectively, in the ileum assay.The phenyl-substituted analogues showed an approximately 10-fold lower in vivo antimuscarinic potency than their corresponding methyl-substituted position isomers.A correlation was observed between in vitro and in vivo potency within subsets consisting of methyl- and phenyl-substituted derivatives.

Base-Catalyzed Cyclization of N-Propargylamides to Oxazoles

The base-catalyzed cyclization of some N-propargylamides to oxazoles has been studied in the presence of sodium hydride and potassium carbonate.The α-arylsubstituted propargylamides 1c-d (Ar = p-OMeC6H4 (1c), C6H5 (1d), and p-O2NC6H4 (1e)) cyclized with markedly higher rates (1e > 1d > 1c) than the unsubstituted and α-methyl substituted propargylamides 1a and 1b.A 1H nmr spectroscopic experiment demonstrated the presence of an allenic intermediate in the potassium carbonate-catalyzed ring closure of 1e.The observed rank order of reactivities correlates well withthe acidities of the respective propargylic hydrogens of the amides and with the ability of the ring closed intermediates to stabilize an oxazole anion.The results demonstrate that the base-catalyzed formation of oxazoles from propargylamides may proceed via an allenic intermediate.