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Design, Synthesis and Biological Evaluation of 3-Amino-3- phenylpropionamide Derivati

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Bluelighter
Joined
Apr 12, 2013
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I've sent him a copy of the paper 'Design, Synthesis and Biological Evaluation of 3-Amino-3-phenylpropionamide Derivatives as Novel Opioid Receptor Ligands' Bioorganic & Medicinal Chemistry Letters 10 (2000) 523±526.

SMILES Oc1cc(ccc1)C(NC)C(C)(C)C(=O)NCCc2ccccc2

Anyone who inputs the SMILES and compares it with BDPC will get an interesting result. I know phenol derivatives of BDPC exist and were active but something about the p-Br or (Dan' thinks) that a p-Me will work.

μ Ki is 1.4
k Ki is 6.3
δ Ki is 176

The paper describes it as a μ Opioid receptor ligand.

An interesting compound. Obviously, the first thing you would look at is making the amine tertiary - with that in place it overlays the MDPC ligand. Interesting that while MDPC used a hydroxy as a hydrogen-bond acceptor, in this case, it's the O of the amide.

I cannot imagine anyone ever making this stuff but the MOST important features are the benzyl amine moiety. I can only think of Dr. Lednicers work and the obscure ciramadol. I remember seeing a paper in Reaxys in which the m-phenolic group of ciramadol was replaced by a p-Cl.

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