Antihypertensive and monoamine oxidase inhibitory activity of some azacycloaklyl-substituted benzaldehyde hydrazone derivatives

Abstract

hydropyridine derivative (22), however, extension of this argument to the 7-membered tetrahydroazepine (23) cannot be made due to the variability in the pretreatment averages. Experimental SectionAll melting points were determined on a Thomas-Hoover capillary melting point apparatus and are cor. Where analyses are indicated only by symbols of the elements, anal, results obtained for those elements were within ±0.4% of the theor values. Nmr and ir spectra were recorded for all the compds and are consistent with assigned structures.2-(3,4-Dimethylphenyl)amino-l-pyrroline HCl ( 16).-A soln of POClg (31.0 g, 0.2 mole) in 20 ml of PhMe was added in dropwise amts to a stirred, cooled (10°) soln of 2-pyrrolidinone (4) (34.0 g, 0.4 mole) in 20 ml of PhMe. The temp during the addn (20 min) was maintained at 10-15°, then allowed to return to room temp for 3 hr. A soln of 3,4-xylidene (24.2 g, 0.2 mole) in 20 ml of PhMe was added, and the mixt was heated to reflux overnight. It was cooled to room temp, and the PhMe layer was decanted. The residue was dissolved in 150 ml of H20 and extd with 150 ml of CeH«. NaOH (100 ml, 6 N) was then added to the aq layer. The resultant alkaline mixt was cooled and 27.65 g (73%) of a light tan solid collected, mp 150.5-152.5°. Recrystn from MeCN yielded light tan crystals, mp 151-153°. Anal. (Ci.2Hj.eN2) C, , N.The HC1 salt was prepd in Et20 by addn of Et20 satd with dry HC1. Recrystn from EtOH-EtaO gave a colorless powder, mp 222-223°. Anal. (Ci2Hi«N2-HC1) C, , N, Cl.2-(2,6-Dichlorophenyl)amino-3,4,5,6-tetrahydropyridineHCl ( 22).-A cold (-10°), stirred soln of cyclopentanone oxime (9.9 g, 0.1 mole), 2.5 N KOH (50 ml), and Me2CO (10 ml) was treated dropwise with PhS02Cl (18 g, 0.1 mole). The temp of the resultant mixt was maintained at -10°for 1 hr. The reac-

Monoamine Oxidase Inhibitors

“…, an inhibitor of rat brain M A 0 of about onethird the activity of pargyline when it was administered intraperitoneally; it was found to be devoid of in uitro activity (149).…”

Azine-Hydrazone Tautomerism of Guanylhydrazones: Evidence for the Preference Toward the Azine Tautomer

“…Guanylhydrazones also known as amidinohydrazones are a class of compounds obtained by the condensation of oxo compounds (aldehyde/ketone) with aminoguanidine, known in the literature for more than 50 years . Guanylhydrazones have been reported to possess antiprotozoal, , antibacterial, antimalarial, , trypanocidal, antisecretory, antidiarrheal, anticoagulant, , antihypertensive, − antiviral, antileukemic, cardiotonic, and anticancer − activities. Recently, guanylhydrazones have been reported to inhibit Chk, a novel target for cancer. − Apart from their medicinal importance, guanylhydrazones are also useful as building blocks for the synthesis of heterocycles, , and recently furoxan derivatives of guanylhydrazones have been reported as thermally stable energetic material …”