Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 83435-58-9, is researched, SMILESS is O=C(N1[C@@H](CO)CCC1)OC(C)(C)C, Molecular C10H19NO3Journal, Article, Journal of Medicinal Chemistry called N-Acyl-2-substituted-1,3-thiazolidines, a new class of non-narcotic antitussive agents: studies leading to the discovery of ethyl 2-[(2-methoxyphenoxy)methyl]-β-oxothiazolidine-3-propanoate, Author is Gandolfi, Carmelo A.; Di Domenico, Roberto; Spinelli, Silvano; Gallico, Licia; Fiocchi, Luigi; Lotto, Andrea; Menta, Ernesto; Borghi, Alessandra; Rosa, Carla Dalla; Tognella, Sergio, the main research direction is thiazolidine derivative antitussive structure; moguisteine antitussive.Computed Properties of C10H19NO3.
The synthesis of a novel class of antitussive agents is described. The compounds were examined for antitussive activity in guinea pigs after cough induction by elec. or chem. stimulation. Et 2-[(2-methoxyphenoxy)methyl]-β-oxothiazolidine-3-propanoate (BBR 2173), moguisteine, and other structurally related compounds showed a level of activity comparable to that of codeine and dextromethorphan. The compounds are characterized by the N-acyl-2-substituted-1,3-thiazolidine moiety, which is a novel entry in the field of antitussive agents. The serendipitous discovery of the role played by the thiazolidine moiety in determining the antitussive effect promoted extensive investigations on these structures. This optimization process on N-acyl-2-substituted-1,3-thiazolidines led to the initial identification of 2-[(2-methoxyphenoxy)methyl]-3-[2-(acetylthio)acetyl]-1,3-thiazolidine (I) as an interesting lead compound Study of the rapid and very complicated metabolism of I provided further insights for the design of newer related derivatives The observation that the metabolic oxidation on the side chain’s S atom of I to sulfoxide maintained the antitussive properties suggested the introduction of isosteric functional groups with respect to the sulfoxide moiety. Subsequent structural modifications showed that hydrolyzable malonic residues in the 3-position of the thiazolidine ring were able to assure high antitussive activity. This optimization ultimately led to the selection of moguisteine as the most effective and safest representative of the series. Moguisteine is completely devoid of unwanted side effects (such as sedation and addiction), and its activity was demonstrated also in clin. studies.
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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica