Synthesis and anti-HIV activity of 10,11-dihydropyrrolo [1,2-b][1,2,5]benzothiadiazepine-11-acetic acid 5,5-dioxide derivatives and related compounds.
The synthesis and the in vitro anti-HIV-1 activity of novel pyrrolo annulated benzothiadiazepine acetic acids and some related derivatives are reported. The new compounds share chemical features with pyrrolo[1,2-d][1,4]benzodiazepin-6-one 1 and Ro 5-3335 pyrrylbenzodiazepinone 4, two inhibitors of HIV-replication at the level of reverse transcriptase (RT) and transcriptional transactivation by Tat, respectively. Two derivatives, namely methyl 10,11-dihydropyrrolo[1,2-b][1,2,5]benzothiadiazepine-11-acetic-5,5 -dioxide (5a) and 1,12b-dihydro-2H-azeto[2,1-d]pyrrolo[1,2-b][1,2,5]benzoth iadiazepin-2-one 8,8-dioxide (7a), were found to exhibit a significant, although not very potent, activity against human immunodeficiency virus Type 1 (HIV-1).
Silvestri
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R
Dipartimento di Studi Farmaceutici, Università di Roma La Sapienza, Italy.
Artico
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M
Pagnozzi
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E
Stefancich
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G
Massa
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La Colla
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P
Loi
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AG
Spiga
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MG
Corrias
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Lichino
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D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D003588:Cytopathogenic Effect, Viral / Q000187:drug effects; D015756:Genes, tat / Q000187:drug effects; D006678:HIV / Q000187:drug effects* / Q000201:enzymology; D015497:HIV-1 / Q000187:drug effects / Q000201:enzymology; D015498:HIV-2 / Q000187:drug effects / Q000201:enzymology; D006801:Humans; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013841:Thiazepines / Q000138:chemical synthesis* / Q000494:pharmacology; D014158:Transcription, Genetic / Q000187:drug effects
D000998:Antiviral Agents; D011758:Pyrroles; D018894:Reverse Transcriptase Inhibitors; D013841:Thiazepines