Pyridazino[3,4-b][1,5]Benzoxazepin-5(6H)-ones: Synthesis and Biological Evaluation

Abstract

Starting from 3,6-dichloro-4-pyridazinecarboxylic acid chloride a series of novel pyridazino[3,4-b][1,S]benzoxazepin-S(6H)-ones as 1,2-diazine isosters of nonnucleoside reverse transcriptase inhibitors was prepared via N-(2-hydroxyphenyl)-3,6-dichloro-4-pyridazinecarboxamides. The inhibition of HIV-1 reverse transcriptase was evaluated.

Synthesis of Substituted Tri- and Tetracyclic Compounds Bearing a Pyridazine Core and their Biological Evaluation as Antimycobacterial Agents

“…The new substituted heterocyclic compounds as well as some recently described [12] pyridazino [3,4-b] [1,5]benzoxazepin-5(6H)-ones were evaluated for in vitro antituberculous activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system [14] . Rifampicin was used as the standard in the tests (MIC = 0.125 µg/mL, 94% inhibition vs. M. tuberculosis), the results obtained are summarized in Tables 1 and 2.…”

“…The tricyclic compounds were prepared as described before starting from 3,6-dichloropyridazine-4-carboxylic acid chloride (1) [13] and (substituted) 2-aminophenols via the 3,6-dichloro-N-(2-hydroxyphenyl)-pyridazine-4carboxamides (2a-d) [12] .…”

“…In view of the diversity of chemical structures of these antituberculotic agents, recently prepared pyridazino [3,4-b]- [1,5]benzoxazepin-5(6H)-ones which were found to exhibit HIV-1 reverse transcriptase inhibition [12] as well as derivatives with increased lipophilicity became an object of our interest as potential antimycobacterial agents. Here we report on the synthesis of a series of substituted tri-and tetracyclic systems containing a pyridazine core and on the evaluation of their activity against M. tuberculosis.…”

Pyridazino[3,4-b][1,5]Benzodiazepin-5-Ones: Synthesis and Biological Evaluation

“…1468 120) and Barth et al (1996). For the exact composition and concentration of the solutions and for the precise working procedure see instructions of the assay (Cat.…”

Synthesis of Certain 6-(Arylthio)uracils and Related Derivatives as Potential Antiviral Agents

“…Among the non-nucleoside derivatives, 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) and its derivatives which represent a new class of potent anti-HIV agents. [5][6][7][8][9][10][11][12] Potent antiviral activity was also reported among several tricyclic derivatives including dipyridodiazepinones, [13][14][15][16][17][18] pyridazinobenzodiazepinones, 19,20 dibenzoxazepinones and pyridobenzoxazepinones, 21 and pyrimidobenzothiazepines. 22 In addition, several bis(heteroaryl)piperazine derivatives were introduced as potent antiviral drugs.…”