N-(omega-Aminoalkyl)-2,2,5,5-tetramethyl-3-pyrroline- or -pyrrolidine-3-carboxamides were acylated on the primary amino group of the side chain by means of reactive acid derivatives (acid chlorides, activated esters, phthalic anhydrides, phthalimide, 2-alkyl-4H-3,1-benzoxazin-4-ones) or they were alkylated by forming the Schiff bases and subsequent sodium borohydride reduction. Other tetramethyl-3-pyrrolinecarboxamide compounds were synthesized by acylating the aminoalkyl compounds with 2,2,6,6-tetramethyl-3,5-dibromo-4-piperidinone in a reaction involving Favorskii rearrangement. Saturation of the double bond of some pyrroline derivatives furnished the pyrrolidinecarboxamides. The new compounds of each type were active against aconitine-induced arrhythmia and several of them had higher activity and better chemotherapeutic index than quinidine. A few selected examples from each type of the active new compounds showed strong activity against ouabain-induced arrhythmia; for comparison known drugs such as lidocaine, mexiletine, and tocainide were selected. The most potent compounds were oxidized to the paramagnetic nitroxides and the latter were reduced to the N-hydroxy derivatives; these products had no or only decreased antiarrhythmic effect.
2 , 3 -D i h y d r o -2 , 2 -d i m e t h y l -1 , 4 -b e n z o x a~c p i n -S~4~~-o n e s and 2 , 3 -d i h y d r o -2 , 2 -d i n e t h y l -1 , 5 -b e n z o~a~e p i -4 5 -have been synthesized by the Schmidt reaction of 2,2-dimethyl-4-chromanones. 2,2-Oimethylbenzoxazepinthiones have been prepared by the reaction of 2,2-dimethylbenzoxazepinones with Lawesson's Reagent. 7. C, 67.53; H, 5.62. Found: C, 67.66; H, 5.74 H-Nmr:d 1.50 (5, 6H), 2.70 (5, ZH), 4.52 ( 5 , 2H), 6.41 -7.88 ( m , 3 aromat.).
2-Chloro-3-(2-nitro)ethyl-and (2-nitro)vinylquinolines have been synthesized and tested in vitro for their antimycotic activity against Aspergillus fumigatus, Trichophyton mentagrophytes, Microsporum gypseum, Epidermophyton floccosum and Candida albicans. Several compounds exhibited strong inhibition to microorganisms.
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