ChemInform Abstract: BASICITY, LIPOPHILICITY, AND LACK OF RECEPTOR INTERACTION OF N‐AMINOALKYLBENZAMIDES AND N‐AMINOALKYL‐O‐ANISAMIDES AS MODEL COMPOUNDS OF DOPAMINE ANTAGONISTS

Abstract

Summary N-Aminoalkylbenzamides and N-aminoalkyl-o-methoxybenzamides have been prepared and examined for their pK,, log P and dopamine receptor affinity. The pK, values range from ca. 7.5 for the derivatives having a one-C-atom side-chain, to ca.

The CON−H…+NH2 Blue-Shifting H-Bond Stabilizing Effect on Z Secondary Amides and Cyclic System Conformational Rearrangement through an Alkylamine-Chain Migration Pathway

“…e literature studies yield only limited information on the conformational behavior of related compounds investigated [10]. e compounds 5-6 have strong structural resemblance but differ in the position of the N-methylamino group.…”

“…ese agents can hydrogenbond with the major groove and thereby recognize base pairs. Compounds whose structures contain cationic groups usually exhibit useful activities, [10,11] and such groups are present in many synthetic drugs. Orthopramides and substituted benzamides are capable of acting as selective dopamine D 2 -receptor antagonists, antiemetics, antispasmodics, antidepressants, antipsychotics, and digestive aids (e.g., clebopride, metoclopramide, and sulpiride) [10].…”

“…Compounds whose structures contain cationic groups usually exhibit useful activities, [10,11] and such groups are present in many synthetic drugs. Orthopramides and substituted benzamides are capable of acting as selective dopamine D 2 -receptor antagonists, antiemetics, antispasmodics, antidepressants, antipsychotics, and digestive aids (e.g., clebopride, metoclopramide, and sulpiride) [10]. Hence, studies concerning the conformational aspects of ammonium units in complexes are a very actual research eld in gaining a better understanding of the mechanism of action of drugs.…”

“…is paper highlights a new stereoselective strategy to prepare the isomeric Z secondary amides. Mechanistic pictures on structurally related benzamides have already provided some conformational insight [10].…”