Affiliation:
1. Institute of Pharmaceutical Chemistry, University of Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria
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.
Cited by
5 articles.
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1. 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;ACS Omega;2020-09-24
2. Yet another ten stories on antiviral drug discovery (part D): Paradigms, paradoxes, and paraductions;Medicinal Research Reviews;2009
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4. Pyrazolo[2′,3′:3,4][1,3]oxazino[5,6-b]quinoxaline, a novel tetracyclic ring system;Tetrahedron Letters;2003-12
5. Pyridazines. 84. Pyridazino[3,4-e]pyrido[3,2-b][1,4]diazepine, a novel tricyclic ring system;Journal of Heterocyclic Chemistry;1997-09