Histamine H2-receptor agonists. Synthesis, in vitro pharmacology, and qualitative structure-activity relationships of substituted 4- and 5-(2-aminoethyl)thiazoles

Journal of Medicinal Chemistry
1992.0

Abstract

It is well known that both histamine and dimaprit show moderate histamine H2-receptor agonistic activities on the guinea pig right atrium. Quantum chemical calculations on these two compounds showed similarities in electron distributions and molecular electrostatic potentials (MEP's), which could be extended to rigid analogues [2-amino-5-(2-aminoethyl)thiazoles] of the latter structure. On the base of these results a series of substituted 4- and 5-(2-aminoethyl)thiazoles was synthesized applying small alkyl substitution variations as reported for histamine. 2-Amino-5-(2-aminoethyl)-4-methylthiazole (Amthamine) proved to be the most potent full histamine H2-receptor agonist on the guinea pig right atrium, being with a pD2 value of 6.21 slightly more potent than histamine. This compound shows no affinity for H1-receptors and is a full but weak agonist on the histamine H3-receptor with a pD2 value of 4.70, thus showing a marked specificity for histamine H2-receptors. In the 5-(2-aminoethyl)thiazole series the presence of a 2-amino substituent proved to be not essential for stimulation of the histamine H2-receptor, leading to the important conclusion that in contrast to histamine, for this series, acceptance of a proton by the thiazole nucleus of the agonist from the active site of the receptor is sufficient for the stimulation of the histamine H2-receptor.

Knowledge Graph

Similar Paper

Histamine H2-receptor agonists. Synthesis, in vitro pharmacology, and qualitative structure-activity relationships of substituted 4- and 5-(2-aminoethyl)thiazoles
Journal of Medicinal Chemistry 1992.0
Amselamine, a new selective histamine H2-receptor agonist
Bioorganic & Medicinal Chemistry Letters 1994.0
Potential histamine H2-receptor antagonists. 3. Methylhistamines
Journal of Medicinal Chemistry 1976.0
Inhibitors of gastric acid secretion: 3,4-diamino-1,2,5-thiadiazole 1-oxides and 1,1-dioxides as urea equivalents in a series of histamine H2 receptor antagonists
Journal of Medicinal Chemistry 1982.0
Studies on histamine H2 receptor antagonists. 2. Synthesis and pharmacological activities of N-sulfamoyl and N-sulfonyl amidine derivatives
Journal of Medicinal Chemistry 1987.0
Bioisosteric prototype design of biaryl imidazolyl and triazolyl competitive histamine H2-receptor antagonists
Journal of Medicinal Chemistry 1986.0
Abolishing Dopamine D<sub>2long</sub>/D<sub>3</sub> Receptor Affinity of Subtype-Selective Carbamoylguanidine-Type Histamine H<sub>2</sub> Receptor Agonists
Journal of Medicinal Chemistry 2021.0
(Imidazolylphenyl)formamidines. A structurally novel class of potent histamine H2 receptor antagonists
Journal of Medicinal Chemistry 1984.0
Iodoaminopotentidine and related compounds: a new class of ligands with high affinity and selectivity for the histamine H2 receptor
Journal of Medicinal Chemistry 1992.0
Cardiotonic agents. 6. Histamine analogs as potential cardiovascular selective H2 agonists
Journal of Medicinal Chemistry 1990.0