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

doi:10.1177/095632029700800410

Paper

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

Published Dec 1, 1996 · G. Heinisch, E. Huber, C. Leitner

Antiviral Chemistry and Chemotherapy

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Abstract

Starting from 3,6-dichloropyridazine-4-carboxylic acid chloride, a series of pyridazino[3,4-b][1,5]benzodiazepin-5-ones bearing various substituents in positions 3, 6, 8 and 11 was prepared via N-alkyl-3-alkylamino-6-chloro-N-(2-chloro-5-nitrophenyl)-pyridazine-4-carboxamides. The latter were smoothly accessible by treatment of N-alkyl-3,6-dichloro-N-(2-fluorophenyl)-pyridazine-4-carboxamides with primary aliphatic amines. The new tricyclic compounds, which are structurally related to nevirapine and congeners were screened as human immunodeficiency virus type 1 reverse transcriptase inhibitors; the influence of the substitution pattern on inhibitory potency is discussed.

Study Snapshot

Pyridazino[3,4-b][1,5]benzodiazepin-5-ones show potential as human immunodeficiency virus type 1 reverse transcriptase inhibitors, with substitution patterns influencing inhibitory potency.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

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

Pyridazino[3,4-b][1,5]benzoxazepin-5(6H)-ones show potential as nonnucleoside reverse transcriptase inhibitors, with promising inhibition of HIV-1 reverse transcriptase activity.

Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. 5. 4-Substituted and 2,4-disubstituted analogs of nevirapine.

4-substituted nevirapine derivatives show good activity against wild-type HCV reverse transcriptase and some show inhibitory effects against the Y181C mutant, but their structure-activity relationships cannot be combined easily.

Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. 4. 2-Substituted dipyridodiazepinones as potent inhibitors of both wild-type and cysteine-181 HIV-1 reverse transcriptase enzymes.

2-Substituted dipyridodiazepinones effectively inhibit both wild-type and cysteine-181 HIV-1 reverse transcriptase enzymes, offering potential as a new non-nucleoside inhibitor for HIV-1 treatment.

Synthesis and Antiviral Evaluation of Fluorinated Dipyridodiazepinones and Dipyridodiazepines (Nevirapine Derivatives)

Fluorinated dipyridodiazepinones and dipyridodiazepines show inhibitory effects on HIV-1-induced cytopathic effect in MT4 cells, offering potential as new HIV-1 inhibitors.

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Dipyrido[2,3-b:2',3'-e]diazepinone derivatives show potential as weaker inhibitors of HIV-1 reverse transcriptase, but with appropriate substitutions activity can be improved.

Citations

Regiospecific Synthesis and Structural Studies of 3,5-Dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-ones and Comparison with 1,3-Dihydro-2H-benzo[b][1,4]diazepin-2-ones

This study regiospecifically synthesized and studied nine 3,5-dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-ones, revealing structural effects and dynamic properties.

Yet another ten stories on antiviral drug discovery (part D): Paradigms, paradoxes, and paraductions

Antiviral drug discovery has led to new strategies for treating hemorrhagic fever virus infections, dengue fever, and papillomatosis, with potential for off-label use in papillomatosis treatment and HIV prevention.

Novel Aldose Reductase Inhibitors Derived from 6‐[[(Diphenylmethylene)amino]oxy]hexanoic Acid

Novel aldose reductase inhibitors with disubstituted phenyl rings show the highest inhibitory activity, with IC50 values approximating 3 M, similar to sorbinil.

Substituted pyridazino[3,4-b][1,5]benzoxazepin-5(6H)ones as multidrug-resistance modulating agents.

Substituted pyridazino[3,4-b][1,5]benzoxazepin-5(6H)ones effectively reverse multidrug resistance in vitro, with activity comparable to verapamil, without direct drug cytotoxicity.

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

Substituted tri- and tetracyclic compounds bearing a pyridazine core show potential as antimycobacterial agents, with substitution patterns influencing their activity.