A new series of 4-(nitrogenous heteroaryl)-1,4-dihydropyridine antagonists II - XVI were synthesized and screened for inotropic, chronotropic and calcium antagonist properties, in order to evaluate the effect on pharmacological activity of replacement of the 4-aryl group of nifedipine-like drugs by heterocyclic moieties, such as quinoline, indole, carbazole and pyrazole. The most potent bradycardic compounds of the series (VIII - X, XII and XIII) elicited weak calcium antagonist activity and were stronger negative inotropic.

Die Reaktion von Aminoguanidinhydrochlorid (II) mit den Carbonylverbindungen (I), (IVa), (Va), (VIa) bzw. (VII) ergibt die Amidinohydrazon‐Derivate (III), (IVb) (60% Ausb.), (Vb) (60%), (VIb) (55%) bzw. (VIII), die überwiegend als Hydrate oder Dihydrate isoliert werden.

Synthesis and Calcium Antagonist Activity of Dialkyl 1,4-Dihydro-2,6-dimethyl-4-(nitrogenous heteroaryl)-3,5-pyridine Dicarboxylates. -A new series of title compounds (III) (15 examples) is prepared and screened for inotropic, chronotropic and calcium antagonist properties in order to evaluate the effect on pharmacological activity of replacing the 4-aryl group in nifedipine by heterocyclic moieties. The most active compounds (IIIa)-(IIIc) show a significant inotropic activity and a rather specific bradycardic action localized in the heart. -(BARALDI, P. G.; BUDRIESI, R.; CACCIARI, B.; CHIARINI, A.; GARUTI, L.; GIOVANNINETTI, G.; LEONI, A.; ROBERTI, M.; Collect.

211ChemInform Abstract The quinolines (I) and the isoquinoline (IV) are converted to the tetrahydro derivatives (II) or (V) by treatment with borane -pyridine. (II) and (V) are subjected to substitution reactions at the N-and O-atoms, yielding the compounds (III) and (VI). The analgesic activity of the compounds prepared is evaluated in comparison to morphine.

162ChemInform Abstract Benzylation of the indole-3-carbaldehyde derivatives (I) yields the N-protected aldehydes (III) which are converted into the oxime ethers (V). (III) is also transformed into the 3-imidazolylmethyl indole-2-carboxyaldehydes (IX) which serve as precursors for the oxyimino derivatives (X). The 5-nitro-2-methylbenzimidazole (XI) is N-protected and then oxidized to form the aldehyde (XIIa). This is converted to the amino derivative (XIIb), the dimethylamino compound (XIIc) and to the methoxy derivative (XIId). The 5-substituted benzimidazole-2-aldehydes (XII) produce the oxime ethers (XIV). The antimycotic activity of the oximino derivatives prepared are tested. The 5-nitro substituted benzimidazoles are the most active.