ChemInform Abstract: 1,3-Benzimidazoles. Part 2. 2-Aryl-Substituted Benzo-Anellated 5- Membered Heterocycles as Potential Effectors in the Cardiovascular System.

2-Aryl-substituted 4H-3,1-benzoxazin-4-ones as novel active substances for the cardiovascular system

4H-3,1-Benzoxazin-4-ones of the structural types 3 and 4 are accessible by cyclization reactions. The introduction of the phosphonate group was achieved by way of Wohl-Ziegler bromination and subsequent Michaelis-Arbuzow reaction with a trialkyl phosphite. Pharmacological investigations on isolated left atria, ileum specimens, and Langendorff hearts as well as in vivo circulatory studies on anesthetized rats revealed that the phosphonates 4 exert calcium antagonistic effects. Whereas 2-(arylvinyl)benzoxazinones gave rise to pronounced negative inotropic effects, compound 3e exhibited relaxing effects on smooth musculature in particular and markedly increased the coronary flow through Langen…

Antidiabetische wirkstoffe. V Lang- und verzweigtkettig substituierte chlor-dihexylamino-1,3,5-triazine

Die nucleophile Substitution eines Chloratoms in 2,4-Dichlor-6-dihexylamino-1,3,5-triazin (1) durch Amine (2a-c) fuhrt zu den Alkylamino-chlor-dihexylamino-1,3,5-triazinen 3a-c. Fur Strukturtyp 3 typische Signale in den 1H-NMR-Spektren sind das Triplett bei 0,9 ppm fur die endstandigen Methylgruppen und das Multiplett bei 3,3-3,65 ppm fur die den Stickstoffatomen benachbarten Methylengruppen. In Verbindungsklasse 3 finden sich Vertreter mit antidiabetischer, trichomonazider, antiviraler und anthelminthischer Wirksamkeit. The nucleophilic substitution of one chlorine atom in 2,4-dichloro-6-dihexylamino-1,3,5-triazine (1) by amines 2a-c leads to the alkylamino-chlorodihexylamino-1,3,5-triazin…

ChemInform Abstract: Synthesis, Configuration, and Calcium Modulatory Properties of Enantiomerically Pure 5-Oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylates.

ChemInform Abstract: 2-Arylsubstituted Benzo-Annelated Five-Ring Heterocycles and Potential Active Agents in the Cardiovascular System. Part 1.

ChemInform Abstract: 2-Aryl-Substituted 4H-3,1-Benzoxazin-4-ones as Novel Active Substances for the Cardiovascular System.

4H-3,1-Benzoxazin-4-ones of the structural types 3 and 4 are accessible by cyclization reactions. The introduction of the phosphonate group was achieved by way of Wohl-Ziegler bromination and subsequent Michaelis-Arbuzow reaction with a trialkyl phosphite. Pharmacological investigations on isolated left atria, ileum specimens, and Langendorff hearts as well as in vivo circulatory studies on anesthetized rats revealed that the phosphonates 4 exert calcium antagonistic effects. Whereas 2-(arylvinyl)benzoxazinones gave rise to pronounced negative inotropic effects, compound 3e exhibited relaxing effects on smooth musculature in particular and markedly increased the coronary flow through Langen…

Hexahydrochinolinone mit calciummodulatorischem Effekt - Synthese und pharmakologische Wirkung

Die Hexahydrochinolinone 4a-1 lassen sich durch Knoevenagel-Reaktion zwischen Cyclohexandion (1) und den aromatischen Aldehyden 2a-1 und anschliesende cyclisierende Michael-Addition mit β-Aminocrotonsauremethylester (3) gewinnen. Zur Charakterisierung wurden IR-, 1H-NMR- und Massenspektren herangezogen. Untersuchungen von Stukturtyp 4 am elektrisch gereizten, linken Meerschweinchenvorhof ergeben positiv inotrope Wirkungen, wahrend BaCl2-induzierte Kontraktionen am Meerschweinchenileum durch einige Verbindungen mit der des Nifedipins vergleichbarer Wirkstarke gehemmt werden. Desgleichen wird die mit KCl stimulierte Aortenmuskulatur dosisabhangig relaxiert. Hexahydroquinolinones with Calcium-…

ChemInform Abstract: 5-Oxo-1,4-dihydroindenopyridines: Calcium Modulators with Partial Calcium Agonistic Activity.

The title compounds 4a-g were prepared by Knoevenagel reactions of 1,3-indandione (1) with the aromatic aldehydes 2a-g followed by cyclizing Michael addition of the products thus obtained with methyl β-aminocrotonate (3). The structures of products 4 were characterized by spectal data. Positive inotropic activities were observed on electrically stimulated, left atria of giunea pigs and these effects could be attributed to calcium agonism. On the other hand, barium chloride-induced contractions of guinea pig ileum were inhibited in a dose-dependent manner.

2-Aryl-substituted, benzo-anellated 5-membered heterocyclic compounds as potentially active substances for the cardiovascular system: 1,3-Benzothiazolyl- and 1,3-benzoxazolylbenzylphosphonates

In the course of investigations on structure-activity relationships of calcium antagonists analogous to fostedil, a series of 2-aryl- and 2-arylvinyl-substituted 1,3-henzothiazoles and 1,3-benzoxazoles bearing a phosphonate group on the phenyl ring has been synthesized by cyclization, bromination, and subsequent Michaelis-Arbuzow reaction. Pharmacological investigations on isolated organs from guinea pigs revealed both negative inotropic effects and a relaxing action on smooth musculature; these activities were particularly pronounced in the 1,3-benzothiazole compound group.

Herbizide, VI [1] kernfluorierte 2,4-dianilino-6-(dihexylamino)-1,3,5-triazine

Zusammenfassung Auf dem Wege der nucleophilen Substitution der Chloratome in 2,4-Dichlor- 6-(dihexylamino)-1,3,5-triazin durch Anilin werden das 2,4-Dianilino-6-(dihexylamino)-1,3,5-triazin und durch fluorierte Amine die (Dihexylamino)- 1,3,5-triazine mit den folgenden Resten zuganglich: (2-Fluoranilino)-, (3-Fluoranilino)-, (4-Fluoranilino)-, (2,4-Difluoranilino)-, (2,5-Difluoranilino)- und (2,6-Difluoranilino)-. Zur Charakterisierung der neuen Verbindungen sind die IR-, 1 H-NMR- und Massenspektroskopie herangezogen worden. 2,4-Bis-(2,4-difluoranilino)-6-(dihexylamino)-1,3,5-triazin vermag insbesondere herbizide und antidiabetische Wirkungen auszuuben.

Trichomonazide Wirkstoffe, 3. Mitt. Aryloxy-chlor-1,3,5-triazine

Die Umsetzung von 2,4-Dichlor-6-(dihexylamino)-1,3,5-triazin (1) mit Phenolen (2) fuhrt bei niedrigen Temperaturen zu den Monoaryloxy-chlor-1,3,5-triazinen (3a–c), unter drastischeren Reaktionsbedingungen zu den Bis-(aryloxy)-1,3,5-triazinen (4c–d). Fur die neuen Verbindungstypen ist besonders charakteristisch die massenspektroskopische Abspaltung der Aryloxygruppen, beispielsweise in 4c der Ubergang von m/z 504 nach m/z 383. Auffallende trichomonazide und blutzuckersenkende Wirkungen vermag insbesondere 3b auszulosen. Trichomonacidal Agents, III: Aryloxy chloro- 1,3,5-triazines The reaction of 2,4-dichloro-6-(dihexylamino)-1,3,5-triazine (1) with the phenols 2 leads at low temperatures to …

2-Chlor-4-(dihexylamino)-1,3,5-triazine Herbicides, IV: 2-Chloro-4-(dihexylamino)-1,3,5-triazines

Synthese de derives alkylamino-6 des composes du titre par action d'alkylamines sur la dichloro-2,4 dihexylamino-6 s-triazine

5-Oxo-1,4-dihydroindenopyridines: Calcium modulators with partial calcium agonistic activity

The title compounds 4a-g were prepared by Knoevenagel reactions of 1,3-indandione (1) with the aromatic aldehydes 2a-g followed by cyclizing Michael addition of the products thus obtained with methyl β-aminocrotonate (3). The structures of products 4 were characterized by spectal data. Positive inotropic activities were observed on electrically stimulated, left atria of giunea pigs and these effects could be attributed to calcium agonism. On the other hand, barium chloride-induced contractions of guinea pig ileum were inhibited in a dose-dependent manner.

ChemInform Abstract: 2-Aryl-Substituted, Benzo-Anellated 5-Membered Heterocyclic Compounds as Potentially Active Substances for the Cardiovascular System: 1,3- Benzothiazolyl- and 1,3-Benzoxazolylbenzylphosphonates.

In the course of investigations on structure-activity relationships of calcium antagonists analogous to fostedil, a series of 2-aryl- and 2-arylvinyl-substituted 1,3-henzothiazoles and 1,3-benzoxazoles bearing a phosphonate group on the phenyl ring has been synthesized by cyclization, bromination, and subsequent Michaelis-Arbuzow reaction. Pharmacological investigations on isolated organs from guinea pigs revealed both negative inotropic effects and a relaxing action on smooth musculature; these activities were particularly pronounced in the 1,3-benzothiazole compound group.