[Trichomonacidal drugs. 6. 2,4-Dichloro derivatives of piperidino- and piperazinyl-1,3,5-triazine].
The nucleophilic substitution of one chlorine atom in cyanuric chloride (1) by piperidine derivatives (2a-c) leads to the 6-substituted 2,4-dichloro-1,3,5-triazines (3a-c). Reaction of 1 with piperazine derivatives (4a-c) yields the substituted 2,4-dichloro-6-(1-piperazinyl)-1,3,5-triazines (5a-c). Structures of type 3 and 5 may be characterized by the spectroscopic data. In the mass spectra, the degradation of 3c leading to the base peak comprises the cleavage into a 2,4-dichlorotriazinyl radical and a 3,4-dihydroquinolinium ion m/e 132. Strong activity is exhibited by 5a and 5b towards Trichomonas vaginalis. Moreover, 5a displays strong antimycotic activity towards Trichophyton mentagrophytes, Trichophyton rubrum, and Microsporum canis. Additionally, 5a and 5b are capable of exerting very strong anthelminthic activity towards Caenorhabditis elegans.
D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis; D000994:Antitrichomonal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D005658:Fungi / Q000187:drug effects; D013058:Mass Spectrometry; D008968:Molecular Conformation; D010879:Piperazines / Q000138:chemical synthesis* / Q000494:pharmacology; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D014227:Triazines / Q000138:chemical synthesis* / Q000494:pharmacology; D014246:Trichomonas vaginalis / Q000187:drug effects
D000935:Antifungal Agents; D000994:Antitrichomonal Agents; D010879:Piperazines; D010880:Piperidines; D014227:Triazines
Trichomonazide Wirkstoffe. 6. Mitteilung: 2,4-Dichlor-Derivats der Piperidino- und Piperazinyl-1,3,5-triazine.