A new series of sulfonic acids were synthesized and tested for their enkephalinase inhibitory activity. Among them, the most potent was N-(2-benzyl-3-mercaptopropionyl)metanilic acid 10i with an IC50 value of 0.27 nM. Several other analogues (10a,b,j,n,o,gg,hh) showed the inhibitory activity comparable to or greater than thiorphan (IC50 = 2.6 nM), a C-terminal carboxyl-containing inhibitor of enkephalinase. Thus compounds containing a C-terminal sulfo group, instead of the C-terminal carboxyl group, were found to show a remarkably high level of inhibition of enkephalinase. The analgesic activity of 10b, (S)-10b, and (R)-10b was also evaluated by the phenylbenzoquinone writhing test.

Each geometrical isomer of various substituted phenylhydrazones of ethyl pyruvate and 2,4-dinitrophenylhydrazones of some α-keto esters was isolated in a pure state. Partial isomerizations of the E-isomers of the former hydrazones to the Z-isomers took place by keeping solutions of the hydrazones in organic solvents containing C, H, and Cl in the dark. An E- or Z-structure was assigned to each molecule on the basis of IR and 1H NMR spectra. In all cases, isomers with higher Rf-values on a silica gel TLC (using benzene as a developing solvent) involved an intramolecular hydrogen bonding between the imino hydrogen and the ester carbonyl oxygen. Thus, the Z-structure was assigned. An E-structure was assigned to other isomers with lower Rf-values. The present assignment is, thus, entirely the same as that proposed in a previous investigation.

In addition to cutaneous, gastrointestinal, hemodynamic, and respiratory symptoms, allergic reactions can induce an acute coronary syndrome in normal or atheromatous coronary arteries and can cause coronary stent thrombosis. Here, we report a case of coronary stent thrombosis due to allergic acute coronary syndrome during anaphylaxis induced by sugammadex in a female patient undergoing general anesthesia. She was emergently treated with percutaneous transluminal coronary balloon angioplasty with catecholamine, vasodilator, and intraaortic balloon support. Knowledge of perioperative allergy-triggered acute coronary syndrome is crucial for prompt and appropriate treatment.

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