Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Journal of Medicinal Chemistry called Nα-Imidazolylalkyl and Pyridylalkyl Derivatives of Histaprodifen: Synthesis and in Vitro Evaluation of Highly Potent Histamine H1-Receptor Agonists, Author is Menghin, Sonja; Pertz, Heinz H.; Kramer, Kai; Seifert, Roland; Schunack, Walter; Elz, Sigurd, which mentions a compound: 3724-19-4, SMILESS is OC(=O)CCC1=CC=CN=C1, Molecular C8H9NO2, Recommanded Product: 3724-19-4.
A novel series of Nα-imidazolylalkyl and pyridylalkyl derivatives of histaprodifen [i.e., 2-[2-(3,3-diphenylpropyl)imidazol-4-yl]ethanamine] was synthesized and evaluated as histamine H1-receptor agonists. The title compounds displayed partial agonism at contractile H1-receptors of guinea pig ileum and were at least equipotent with histamine. Agonist effects of the new derivatives were susceptible to blockade by the H1-receptor antagonist mepyramine (2-100 nM). In the imidazole series, suprahistaprodifen [i.e., 2-(3,3-diphenylpropyl)-N-[2-(1H-imidazol-4-yl)ethyl]-1H-Imidazole-4-ethanamine trihydrogen oxalate or [2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethyl]-[2-(1H-imidazol-4-yl)ethyl]amine, Nα-2-[(1H-imidazol-4-yl)ethyl]histaprodifen] showed the highest H1-receptor agonist potency ever reported in the literature (pEC50 8.26, efficacy Emax 96%). Elongation of the alkyl spacer from Et to Bu decreased activity from 3630% (Et substituent; suprahistaprodifen ) to 163% (Bu substituent) of histamine potency. The exchange of the terminal imidazole nucleus for a pyridine ring resulted in compounds with comparably high potency. A decrease in agonist potency and efficacy was observed when the attachment of the alkyl spacer was consecutively changed from the ortho to the meta and the para position, resp., of the pyridine ring. The pyridine series that contained a Bu chain possessed the highest potency and affinity. Nα-[4-(2-pyridyl)butyl]histaprodifen emerged as a strong partial agonist, being almost equipotent with suprahistaprodifen (pEC50 8.16, Emax 89%). Suprahistaprodifen and Nα-[4-(2-pyridyl)butyl]histaprodifen also showed potent partial agonism at contractile H1 receptors in guinea pig aorta and potently activated H1-receptor-mediated endothelium-dependent relaxation in the rat aorta. The compounds thus prepared displayed low to moderate affinity at H2, H3, and M3 receptors in functional models of guinea pig. Collectively, Nα-imidazolylalkyl- and Nα-pyridylalkyl-substituted histaprodifen derivatives represent a novel class of potent H1-receptor agonists. These compounds may be useful to define the (patho)physiol. role of the H1-receptor and refine mol. models of H1-receptor activation.
This compound(3-Pyridinepropionic acid)Recommanded Product: 3724-19-4 was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.
Reference:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem